2 Years of Me

The Kramer family taking a selfie in Times Square.

I’ve been meaning to write this post all summer, but in the last few months life’s really gotten away from me in some weird ways. It’s September now, and I’m watching the number of days tick away till my birthday. I’m turning 45 this year, a number which is simultaneously meaningless and momentus. When I started to think about transitioning I decided I wanted to do it when I was 42. We were watching the Hitchhiker’s Guide to the Galaxy movie recently with the oldest kiddo and I mentioned that fact when we got to the bit with Deep Thought. It doesn’t make as much sense now, just a funny anecdote, but it felt important back then. It was me making my play for a shot at Life, the Universe and Everything. Have I gotten it? Hmm.

I wrote about my first year transitioning in April of last year. The year and a half since have really just slow but steady progress feeling more comfortable in my skin, a lot of loss and sadness, work, and the joy (terror) of being trans in America (on Earth). So let’s jump in, shall we?

Life as Me

It’s a nice coincidence that I just happened to take a selfie in the same dress around the time of the last blog post update and now. The comparison isn’t perfect: The angles aren’t exact, my hair’s different and all that jazz, but there’s some change there, if you look close. I’m that girl on the right now, all the time, which is wild. Of course I still feel like nothing has changed in the last year and a half because that’s how brains work.

I’ve gotten better at being me with a year and a half of practice. I can do a red lip in like a minute now, but I still usually skip eyeliner and mascara because there’s always something else that needs doing, and I don’t think my face looks good without glasses, and I don’t understand all the eyeshadow and primer and setting spray and other products needed for a good look, and help I fell in a dysphoria hole.

So I do a red lip and throw on my just-for-style glasses and get on with it. Here’s a before and after from this morning, on the left is me with no time to get ready, on the right is if I actually get to put myself together.

I’m a housewife right now, having left my last job a month ago. I’ve achieved a bucket list goal, and it’s great, but kind of overwhelming. I know how to do a hopefully passable job at being a mom, wife, and engineering manager at the same time, but it feels like if I’m just a wife and mother the bar is higher. I’ve started bringing cold tea and lemonade to my kids when I pick them up from school, which maybe is a start.

I’m learning more about myself and my traumas and issues. One of my friends said that transition is like pulling up the carpet it an old house. Yes, that horrible carpet is gone, but now you get to figure out all the other things that are underneath. Maybe there are original pine floors, but maybe there’s plywood and awful 70’s linoleum. My plywood and linoleum are largely centered around not feeling like I was safe and understood and belonged as a kid, a fun mix of being neurodivergent, an adopted single child, and trans. I make families so I can take care of them and so someone loves needs me. That’s not healthy and I need to stop it. I need to be able to just be a girl who’s worthy of love, and who also happens to be fun and interesting and caring, too. Learning about yourself is a bear, but it’s growth, and growth is good. Hulk smash trauma!

Me and this guy, we both got problems

I’ve made some new friends since I came out, and many of my older friendships have gotten deeper now that I can be more honest about who I am. I’ve met some people in the local trans community, and more on social media. I’ve made new friends at work. I’m amazed at just how awesome and unique and interesting they all are, and that brings me so much joy. I’m trying to learn how to be a better friend, and how I can be there for people and let them be there for me. It’s a process.

I’m terrible at taking selfies with people, but here are some pictures of me and some of my amazing friends!

Jennifer and Kate, the Macintosh Librarian

I’m letting go more of the things that I used to think defined me, but things that didn’t bring me joy. I’ve been able to donate / offload a couple of chunks of my retro computer collection to the Macintosh Librarian, which makes me very happy. Kate runs an amazing YouTube channel and I know that she’ll take very good care of these relics of a bygone era. Old Jennifer had a really hard time letting things go, new Jennifer is trying to learn to accept that a cycle is important. You get things, you enjoy them, and then you can say goodbye. I’m trying to teach that to my 8 year old, too, but the lesson isn’t sticking.

A girl sitting in front of two black NeXT Station computers.
Me and some NeXt friends, now in Macintosh Librarian’s care

As far as physical changes from the last year and a half, some stuff’s different. Here’s another gratuitous selfie comparison, me in a pencil skirt in May 2021 and me in a pencil skirt in August 2022. Some of this is poise and fit and confidence, some of it is something else. You can decide for yourself how much, or if you’re trans you can ping me and I can give you the low down. Let’s just say that since starting Progesterone I’ve gained 10 pounds and it didn’t go to my tummy.

Looking at these pictures I am amazed at that girl on the left. How much confidence she had, how much she just kept plugging away. It may be a fundamental life truth, that after the fact we’re amazed at what we were capable of. I don’t think I really believed that I’d get to where I am, and lots of days I still feel awful, but today is a good brain day, and today I’m happy with the progress I’ve made.

Life in Grief

Irma and I both lost close, close friends early this year. Mentors, compatriots, supporters. Both to cancer, both in hospice, and less than two months apart. I lost Chad Neff, the guy I met when I first started working in the internet business all those years ago. Chad was an artist, a cowboy, a park ranger, and a fount of stories and humor that I was fortunate enough to experience in my youth. We drove all over San Marcos in his Toyota van connecting people to the internet. The Neffs welcomed me into their family and treated me like one of their own, and I’ll be forever grateful for that. After I moved to Austin and got busier with work and kids I didn’t see Chad as often, but our text message chats were a regular reminder of my weird, wonderful friend. I only got to see Chad once after I transitioned and before he went into hospice. COVID sucks and we didn’t know how fast he was going to decline. Spend time with the people you care about. You don’t have forever.

Jennifer and Chad Neff, sitting together on a bed.
Me and Chad

I was honored to get to give a eulogy for Chad at his memorial. It was the first time I’d gotten up in front of a crowd of mostly strangers and talked, and after it was over and I sat back down in the pew Arthur loudly whispered, “Great speech, mum!” So I guess I did ok.

Life at Work

I spent the last year and a half as an Engineering Manager and then Director of Engineering at a company called Swiftly, working on software to help make public transit better. It was really strange, being a manager at a place that hadn’t really had them before, but also coming into a startup that was starting to mature but hadn’t done so yet. I discovered that I’m prone to taking too much responsibility and I want to sacrifice to do what feels like the best thing for other people, but in the long term that’s unsustainable without really strong support. I think I did some good, encouraged people to grow, and helped make the engineering culture, organization, and technology better.

Jennifer and a few other folks in a conference room.

I was able to make some really great friends at Swiftly, and before I left I got to meet a bunch of them in person in San Francisco. I generally knew I was leaving at that point, so it was very bitter sweet, but I got to check off a lot of things off my ‘life as a woman’ bucket list. Stuff like giving a fellow co-worker who was having a breakdown a hug, being on the opposite side and having a friend watch out for me as I emotionally collapsed, closing the hotel bar down at midnight doing shots with a bunch of other girls, and navigating the city with a girl friend, watching out for each other, but also being myself in a big city and getting a yelled outfit compliment from a girl in a passing car. I’m so grateful I got to experience it.

Work-wise, I learned a ton about leading teams and making change happen in malleable organizations. I also learned about what to watch out for, including spotting traps that will drain the life from people with good intent, how the best intent can lead to dysfunctional situations, and how people are just fallible and are often helpless to do anything about it. I don’t know if I’ll want to do a startup of 100 people again, at least without good relationships with executive leadership, but I’m glad I did it.

When I left HP I didn’t miss it, and I don’t miss Swiftly, but I miss Vox Media, at least the buzzy, exciting days in Product back in 2016 or so. I think there’s something about being part of an organization that tells its own story well, that carefully curates its culture and tries to make people feel like they’re part of something wonderful that’s catnip to me. Being on the other side of that, where you’re the person at the top responsible for ensuring that culture gets crafted could be good, I suppose. Logically that’s where I would end up in my career, at some small startup that was just trying to figure culture out, but it must look different from the other side, mustn’t it? The film looks different to the director than to the caterer or the prop wrangler. In any case, that’s a problem for another time.

Life at Home

Jennifer and the kids in a store mirror

The last year and a half at home has been largely about having two kids in school during a pandemic. We’re managing the best we can. I do a lot of the traditional mom duties in our house, and have for a long time. I need to feel needed, and a house with two elementary age kids in it definitely needs someone to cook and clean and do laundry and get the kids to school.

I know it’s problematic, from a patriarchal view. I’m doing what I saw my mom and hundreds of TV and movie moms do in order to keep the house running and keep her family happy and healthy. I’m trying to work on asking for help more, but a small, scared, very sensitive to rejection part of me is terrified that if my family didn’t need me I wouldn’t have a place in it.

I didn’t care for the latest Dr. Strange movie. I didn’t like Wanda Maximoff’s heel turn, and how they used her desire to have a family to do it. She does terrible things because she wants a family to love and to care for. She uses means that the establishment consider abnormal to get it. I couldn’t enjoy that movie. It felt like a condemnation.

Jennifer and the kids in the car

The kids keep getting bigger, and it’s interesting to see how the nature and nurture aspects of upbringing reveal themselves below the surface. Irma and I’s kids are very much like us. You can pull out a trait or a gift or a quirk from us or somewhere up our family lines, and there it is. It’s amazing and weird and hilarious when they laugh at the same thing we do, or quote the same lines we used to. The older one is binge-watching shows that Irma and I watched, and now we have even more shared touchstones. It’s lovely. They’re also starting to edge towards teenagerdom, and memories of the feelings from those awful angst ridden years are surfacing. I feel every flustered, embarrassed, sobbing stomp up the stairs in my bones.

The gift I’ve gotten as a parent is to be able to be the kind of parent I needed when I was a kid. I am certainly far, far from perfect, but I am trying. When I get to tell my kids something I wish someone had told me when I was their age it’s the most gratifying thing in the world.

Jennifer and Irma in Times Square

Irma and I continue to figure out life. We both had a lot of stress this year, way more than felt fair, but we supported each other, and we have hopes for easier days ahead. We hadn’t had a babysitter since the start of the pandemic, and we both worked, which meant we had very little time together without the kids. We finally found someone a few months ago, and it’s been nice to get some time for just the two of us again.

Lots of couples where a spouse transitions don’t make it. Trans people sometimes marry people they think will fix them, or marry the people who turn out to not be accepting, or their spouse just isn’t attracted to the gender identity the trans person end up at. It’s a hard thing, rewriting your relationship story while still having all the memories and traumas and issues from before. I’m so grateful that Irma and I found each other all those years ago, and that we’re doing our best to adjust to this new normal. I’m a lucky girl.

On the fun side of things, this spring we got to go to New York for the second year in a row, which was fun. I love exploring with the family and I’m glad we can keep doing it. We’ve gotten into Only Murders in the Building so it was neat to go see the Belnord which plays the Arconia in exteriors.

Only Tourists in the Building

A Little Q & A

I asked for questions for this post and got a few, so here are some things you may be wondering.

“Are there any differences in how people treat you as a woman now?”

Yes! Women are kinder and more open or genuine, I think. They strike up conversations and it’s easy and feels natural. Sisterhood is definitely a thing. Men are often more confused or dismissive, especially when I do things like ask for a pair of needle nosed pliers at a car dealership. With a few men I feel like I’m being talked down to a lot more, or dismissed. They’ll tell me things they probably shouldn’t admit outloud, or assume they know everything and I don’t know anything any just talk at me about things I already know. In some ways it’s a relief, to not feel like I have to show that I’m smart, too, but I’m old enough and experienced enough that I don’t feel like I need to do that, and if I was younger I’m sure it would infuriate me.

People have tried to be extra nice to me in ways that start to feel insincere, which is awkward, though that may be a bit of overly performative allyship. I got an ‘I’d tap that’ comment from someone I knew professionally. I’m not young, I’m white, my style and presentation are overly femme, and I’m 5′ 10″ in flats, so I benefit greatly from the patriarchy and get a lot of respectful (presumably) “Ma’am”‘s from people.

“What I want to know is what is the most different than you thought it’d be.”

Tilly, you’re going to get a dumb answer, but an honest one.

Before I transitioned I thought having boobs for real would be amazing and I’d be constantly obsessed with them. All the magical female gender transition tropes have girls obsessed by their new cleavage, but when it actually happens, they’re just like… there. I assume it’s just like it is for other women, we may hate our boobs or love our boobs but they’re just a body part and part of life and they’re fun sometimes in the right hands and society puts a lot of value on them, but as long as they look ok, most of the time I don’t think about them. They kinda get in the way if you’re a side sleeper, I’m still envious of girls with bigger ones, but they aren’t my whole world. I will say that looking in the mirror and seeing them when I wash my hands, they are a nice reminder that I’m probably doing this transition thing ok.

“I’d love to know the unexpected and beautiful ways your life has changed! Not the big things but the tiny joys you didn’t imagine.”

I love seeing older men and knowing I won’t have to ever be that.

I love the small, spontaneous chats with other girls, like when the waitress at our local haunt showed me some cherry earrings she’d gotten that reminded her of me.

I love being able to give people compliments, and getting a ‘I love your dress’ from someone.

I love not having to pretend to be someone I’m not. There’s so much freedom in not trying to be this successful, confident, fake person you’ve cobbled together from movies and TV shows and books.

I love being sad and just feeling it, and understanding wanting to just feel it.

I love being able to let go of things that aren’t right and not being crippled by fear that I’ve made a mistake, but instead knowing that I can grieve a bit if I need to and it’s ok.

I love it when I look in the mirror and see the beautiful girl that was hiding inside for all those years.

I love not having to know everything or be perfect.

“I’d love to know more about how you found support and this glowing confidence! Did you seek any support from a mental health professional? ESP now that it seems to be less taboo.”

The confidence is it’s own mysterious force. The pain of dysphoria and living in the closet drags you forward and then you have momentum and the euphoria of new things pushing you to keep going and then your life just kinda is what it is. At least for me. I spent years and years collecting a toybox of things I loved and knew about and desperately wanted and now I get to play in it and share it with people.

As far as mental health professionals, I have a therapist who I started seeing a few months before I started hormone therapy. It’s mostly just talk therapy, but she has had a lot of other trans patients so especially in the beginning it was very comforting to have someone who could say, ‘oh yea, a lot of my patients talk about that,’ when I was dealing with new things. There’s a lot of gatekeeping in trans healthcare, so having a long term relationship with a therapist who can write me letters for surgery recommendations if I need them is really useful. I have a psychiatrist but that was for ADHD, we don’t really talk about transness.

“What are some ways people have been particularly supportive and here do you feel like people could be more supportive of you?”

I love it when people give me feedback or respond to me on social media. It can feel like I’m vogue-ing into the void sometimes, but having a group of people who encourage me and respond positively helps keep the fears away. Every once in a while someone will pop up and tell me I’m an inspiration, or they love my style choices, or something like that, and I treasure those moments. I also share when I’m feeling down sometimes, and the messages of support then may not make everything better, but they mean a ton.

I love seeing people share articles about trans rights issues, especially when it isn’t Trans Day of Visibility or Pride month. There aren’t enough of us, our allies are critical, and the fact that you took the time to read up on something or decide to share it with your likely mostly cis audience means a lot.

“Gender is part of your identity, but you are also so many other things as well. What impact if any has coming out had on other aspects of yourself?”

I’d say it has made things easier. I’ve been able to shed some baggage and some trappings of a life that I was leading because I felt I had to, but one that wasn’t real. I think I’m kinder to the rest of me now.

How should we think about there suddenly being this giant rise in trans people and our kids doing things they’ll potentially regret.

First, the statistics on gender dysphoria are pretty clear. Untreated gender dysphoria and a trans person whose gender identity is invalidated or mocked by their family will have significantly higher incidences of mental health issues and suicide than a trans person in a family where someone accepts them and validates their gender identity. Not accepting trans people or making it harder to transition or be accepted as who they are is patriarchal violence. (The only people that benefits from the enforcement of rigid, binary gender structures are the people in power in a patriarchal system. I’ll talk more about that later.)

Kids will experiment, it’s what they do, they put on identities and personas as they grow up. When a child comes to you and says that they’re actually a girl and would like to wear dresses and be called a feminine name, or says they’re a boy and never wants to wear dresses again and wants you to use a masculine name, or doesn’t feel like either and wants to use they/them pronouns, the chances are very, very, very high that that child understands themselves on a deep level and is trying to share that with you. If they do it consistently, it is almost a certainty that they have some gender issues, and the best thing you can do is support them.

The reason we have a rise in trans identification in America isn’t because it’s a fad or in vogue, it’s that the representation is finally there to the point where people are not terrified to step out of the patriarchal birth-assigned gender binary line. Everyone shares the chart of left handedness once we stopped punishing it, and it’s exactly the same. Trans people have always been here, some of us have always known ourselves, but we were terrified to speak out, either because we tried and were shoved back into the closet by someone we entrusted our secret to who wasn’t prepared or worthy of it, or because all the representation we saw was mockery.

The incidents of trans people who detransition, especially those who do so due to something other than societal or family pressure, is less than 3% and possibly less than 1% according to studies. The rate of regret from trans people who’ve had gender affirming surgeries is less than 1%, a rate lower than pretty much any other type of surgical procedure.

Transness and gender identity is a journey. The best thing you can do for someone who is on it is accept them as exactly what they say are, and assume that this is exactly who they have been their entire life unless they give you specific insight otherwise. I’ve always been a girl, the world just didn’t see me as one. If at some point in the future through learning about myself I discover that I’m non-binary, then I will have always been non-binary, I was just on a journey to discover that before then.

If you are a parent or teacher or friend of a trans person, accept and celebrate that person’s identity as much as you can without being awkward or creepy. That shy non-binary kid probably doesn’t want to stand up in front of everyone at parent-teacher night and tell a crowd about their pronouns. They just want you to use the right name and the right pronouns and see them as not a boy or a girl and not make a big deal out of it. On the other hand, the trans woman who’s constantly posting online about transness and trans joy would probably be happy to come talk to a class about gender identity and what it’s like to transition.

9 Months Out or “A Thing That Happened”

I posted my transition announcement on Twitter on July 24th, 2020, which means I’ve been out for 9 months. A lot of things have happened since my coming out post in October, and my feelings about transition and life before have changed a bit, so now seems like a good time to post an update and share how I’m doing.

There are two audiences for this post. First, the folks who know me, care about me, and want to know how my first 9 months have gone. Second, other trans women who may be thinking about transitioning or are earlier in it than I am. My answers are a little different for both, so I’m breaking this into two parts. Feel free to read one, the other, or both.

For the world: I’m Fine

Wanda in Wandavision saying 'I'm fine, I'm fine.'

I’m fine, I’m fine! Transitioning is a thing that, most days, feels like something in the past. I can’t remember the last time I had to present as a boy and can’t imagine a scenario where I would ever need to again. I haven’t been misgendered on the phone or on a drive-thru speaker in months. All the people in my life seem to be trying to get my name and pronouns right, and the moments of being accidentally mis-gendered seem to be dropping.

All of my daily identity documents have been corrected except my Passport, which I have all the stuff to update but just haven’t made time. Yesterday a very nice lady in the neighborhood came over and helped us file paperwork to get the deed for our house changed over, and our mortgage company finally updated their files. The health insurance portal helpfully reminds me about maternity options. Unless they’ve gone looking, the folks at my new job (more on that in a moment) have never even seen my deadname.

Jennifer, sitting on a restaurant.
On the patio at Torchy’s for lunch with Irma

Most days I just… exist as myself. I get up, throw something on (a dress or skirt and top if I don’t have workout, workout clothes if I do), get the kids ready for school, and drop them off. Maybe I workout with Haley, in which case then I put on real clothes after. Hopefully I moisturize, do as good a job of a lip as I can, try to find some bangles to match my outfit, and then sit down for work. Maybe Irma and I get lunch, then more work. Irma or I pick up the kids, and I figure out dinner. We do whatever it is that families do in a pandemic until bedtime. I read the kids a story and let them nod off a bit. Then it’s time with Irma and hopefully sleep. Oh, and some days I do laundry. Rinse, repeat. I’m a suburban housewife and mom, and thousands of moms in my neighborhood have the same day I do.

Sometimes I put on music, which I can dance to now. It was weird and awkward before, and I’m still terrible, but at least I think I get it now. I wish my voice was better and I could sing more songs, but I feel more free. I know I don’t move quite right. Like this comic says, I’m too big and too broad. Too many years with the wrong endocrine system. I’m grateful for what I have, though, which is a body that’s finally mine, and a life full of people who love me.

Change has happened really slowly and most days feels imperceptible until I look at old pictures. Then all of a sudden 3 months ago seems like forever and I have a hard time recognizing myself.

Here’s an example, the first picture was taken last September when my friend Maddy inspired me to wear a different dress every day for a month. The girl on the left has been out for 2 months and is still very much getting her feet under her. She hasn’t figured out makeup or that an Apple Watch isn’t really her style. Me lately, on the right, is more comfortable in her skin, has gotten over her giant fear of makeup, and has 7 months more estrogen in her.

You might think that trans women wouldn’t be transphobic, but we’re all a bit transphobic, and those of us who were in the closet for decades can have heaps of it, deeply internalized.

I’ve hated makeup for as long as I can remember. I had the excuse of having ADHD and being sensitive to textures and smells, but what it may have been, really is something else. The garishly painted face of a macho guy in drag in a college party movie, perhaps, or a painful memory I’ve buried so deep I don’t even know it’s shape.

I knew it was something I would have to get over. Something that would make me happier and my life easier once I could do it. So many of my trans friends had mastered it, or so I felt, and here I was, paralyzed. Internalized transphobia made me incredibly fearful of judgement. I couldn’t actually try makeup until the house was empty, which during a pandemic isn’t very often.

This was my first attempt, back on January 12th. I took 57 selfies. The color is Pioneer in Maybelline Super Stay Matte Ink, which is the only product I’ve tried, though now my everyday color is Savant.

Annette told me I looked like a mysterious librarian with a door to another universe, which is honestly, the best compliment ever

Last fall, after many months of lusting after them, I started picking up bangles from Splendette. Most bangles and bracelets won’t fit over my hands, but Splendette has a Duchess size that fits perfectly. I’m a vintagey girl, bangles are a vintagey look, and having something I could collect was wonderful. I’ve spent more on them than I care to admit, but being able to accessorize has been really fun, and helps me feel more put together. They have matching necklaces, which I wear regularly, and earrings, which I haven’t quite gotten to.

Splendette has a Facebook group, which is a really welcoming, inclusive place. I’ve been able to post my selfies and get wonderful, affirming feedback on them. I’ve made friends I wouldn’t have otherwise, and have been able to be an out and visible vintage-enjoying trans woman, of which there aren’t many.

I’m also in the Pinup Couture Facebook group, which is similarly inclusive. I posted my pink, blue, and white Transgender Day of Visibility outfit there and ended up with over 800 reactions and 65 comments. That was pretty lovely, but made me realize that the volume of feedback isn’t nearly as important to me as the nature of it. A single comment from another trans or queer woman is worth more than all the other likes put together.

This was the first Transgender Day of Visibility where I was out, and it was great posting on social media and liking other trans people’s posts. I probably should have taken the day off of work. It was hard to switch back and forth and try to get things done.

Trans day of visibility was the day I came out at my job, or rather, my new job. Vox was wonderful and supportive and I’m not sure if I would have transitioned if I hadn’t been there, but I’d been there for nearly 6 years, and it was starting to feel like I needed something new. I’d gotten both of my corporate jobs by nepotism, or as we say in the tech industry, through my network. I’d never applied at a place I didn’t know anyone. I hadn’t gone through an interview loop to show that I was a person worth bringing in. I wasn’t sure if I could do it, to be honest, or as a trans woman, if anyone would even want to talk to me. If you have someone on your team who doesn’t want a trans woman managing them, it’s easy to come up with reasons why I wouldn’t be a good hire. Heck, most of the time I don’t think I would be a good hire.

I decided to only apply at places where I could learn about something interesting and/or do something good. My short list of areas was fashion, transit/transport, women’s health, or public service. The second job I applied for was at Swiftly, a company that generates fixed route arrival and departure predictions (buses, trains, ferries) and insights for transit agencies. Their core mission is to help cities move better, and their work improves people’s lives on a daily basis. I wrote a cover letter in a flash, sent in my resume and crossed my fingers. They called me back, I had some good interviews, felt I really connected with their Head of Engineering, made and presented a slide deck, and even though I was sure up to the very end they wouldn’t, they gave me an offer. It’s a company of 80 people, and it’s been great being in a place where I can make things better and have a bigger, hopefully positive, influence.

Getting out of the Vox bubble I’m also realizing I’m sometimes the first trans person that people have ever knowingly interacted with, which brings me to the downer part of this update.

Wanda in Wandavision unconvincingly saying 'I'm fine'.

I’m an out trans woman in the world, and my style is middle-aged-soccer-mom femme, which is possibly the least uncomfortable trans woman presentation for cis folks to deal with. If I pass (which is a whole other topic) people I interact with may have no idea I’m trans. I generally blend and am non-threatening. If I were Black or Hispanic or Asian, or my style more androgynous, aggressive or otherwise not societally conforming, I’m sure the reaction would be different, and that things would be much, much harder. So since I have the privilege, I feel like I have to be visible.

Being visible is important, because it isn’t a great time to be trans. Not that it has ever been a good time to be trans, but last year’s massive anti-trans pushes in the UK have moved to the US and a deluge of anti-trans bills have been filed in legislatures across the country. Trans people are the GOP’s newest minority target of choice. There are bills here in Texas that would ban trans girls from playing on girls teams in school and bills that would make it legal for doctors to deny trans people any care (even critical, life-saving care) if they felt it was against their beliefs to be trans. There’s a bill proposing changing the definition of child abuse to include providing or enabling a minor to get the gender affirming care that is broadly accepted in the medical community. Imagine having a 12 year old trans child, not being able to get them care, not having the means to move out of state, and having your child take their own life. More than half of trans kids consider suicide, a number that drops by half if even just their pronouns are respected by the people around them. They are literally going to kill trans kids with these bills.

There have been regular hearings at the state house on them, with trans Texans and their allies across the state traveling to Austin in the midst of a pandemic and waiting for hours to testify. It feels like my responsibility to not look away, but it’s heartbreaking to read the testimony by those of us who are opposed, and incredibly emotionally painful to read people’s arguments in favor. People who would rather that trans people just not exist, and are happy to inflict great injury on us because they are afraid and have power.

This is a new thing for me, and I honestly am having a hard time handling it. Before last year I moved through society as a cis, white male, and in the last decade, one with a job that made things very comfortable. I experienced a level of undeserved societal privilege and comfort that is the exact thing Republicans are fighting to maintain. Now I’m part of a small minority that they’re trying to extinguish by brute legislative force. I don’t feel like I can ignore what’s going on, but it hurts so much to watch.

Someone I know was recently lamenting that trans Twitter, a normally joyful, geekish, occasionally catty place had turned mournful and distressed. What alternative is there when you see your siblings suffer at the hands of the government? What hope can we have, when we think about the fact that there will likely be a Republican-dominated US House in two years, and two years after that, who maybe the presidency? State bills could become national bills. They could outlaw trans healthcare completely. Trans people might have to flee the country for their own safety. Anything could happen.

So what can we do, but keep fighting, and be as visible as we can? The Governor of Arkansas vetoed their bill (which the legislature overrode, but it’s a start) after he met with some trans women, including the state’s only openly trans elected official. They don’t know us, so it’s easy to hate us. The most hopeful I’ve been, reading the testimony against these bills, is when I read about the lifelong Republicans and grandparents who are out there, taking their legislators to task for putting their trans children and grandchildren at risk.

It is, in the end, a race. Just like with the fight for gay rights before it the more trans people someone personally knows, the harder it is to support a bigoted position against us. When they know us it’s harder to see us as an abstract concept, and easier to see us as caring, feeling human beings who deserve the same protections and respect as they do. We are fortunate a majority of Americans don’t support anti-trans legislation, but we aren’t yet to the point where enough see it as the bigoted attack on a vulnerable, tiny minority that it is and are willing to speak out against it. To that end, I try to be visible, I try to not offend, and I try to exist.

I’m fortunate, because I’m not popular on Twitter or Instagram, I don’t get a torrent of hateful and bigoted reactions when I post a picture or story, but a lot of my friends are not as lucky. I don’t know how they keep going when so much hatred is spewed at them all the time. Like most trans women, all I get are the chasers.

So I’m fine. I’m fine. I’m fine. I’m fine…

For the Trans Girls: The 28 Day Monster

Hey girl, I hope you’re doing ok. I’m going to presume that you’re somewhere behind me on the timeline. To do a time check, I’m about 14 months into HRT. I was at 200mg/day of Spiro and 8mg a day of oral Estradiol for most of that time. I started 100mg Progesterone around last November, so I guess I’m about 6 months into that. I’ve tried both methods with P, and I felt the more effective one gave me worse cramps, so I’ve stopped. You should probably experiment and track.

A month ago I switched to injections, so now I stab myself every Sunday and push .25ml of Estradiol Valerate into one of my thighs. I think that injections have smoothed out my swings a lot. I no longer feel out of sorts at the end of the day, and doing every 1 week instead of every 2 has meant that I haven’t generally felt like I’m having awful days before an injection, though Saturdays and Sunday mornings can sometimes be rough.

I do have awful days, though. 2 days out of every 28 to be exact (the ones 2 months ago was so bad that Irma told me to start logging them), and on those days I’m a freaking monster. Like, life would be better if I was isolated from all interactions with other people. I haven’t managed to track down other changes, but there are definitely periods of the month where my voice is just garbage for days on end, and I can’t get it together. I’m still figuring out my cycle, but one of my friends Jocelyn has a great post about hers on her blog. If you’re on HRT you might want to start tracking mood and period symptoms. I ran the numbers and the next time I’m going to be a disaster is Mother’s day and after that my mom’s birthday. At least now I can prepare. Maybe buy some chocolate.

A vial of lidocaine with a drawing needle stuck in it on a medical tray.
My vial of lidocaine from my last trip to Electrology 3000

We’ve been driving to Dallas every 6 weeks recently for full face electrolysis. 16-ish sessions of laser got most of the blonde hairs on my face, but not the dark ones, so it’s zapping and plucking if I want to get rid of them. At Electrology 3000 they inject Lidocane all over to numb your face (which is super, super-awful especially around the mouth and upper lip), but it still swells up a ton afterwards. You can’t shave for a few days before, which sucks for dysphoria, and then you look like you gained 20 lbs of water weight all in your face afterwards. I seem to bruise, as well, and those take a week and a half to two weeks to go away. It isn’t fun, and it’s expensive, but hopefully I’ll only have to do it a few more times and then I can start going to someone local. Hair grows in cycles, and you can only kill the hair that’s currently in a growth cycle. In summary, testosterone puberty is dumb and I hate it, but you knew that already.

When I’m not dealing with hair, one of the weirdest things I’ve run into is that a year in, I can’t really remember what the dysphoria was like. It was obviously awful, if I was willing to upend my entire life, and I’m still super happy to be living as myself, but the little nagging thought of ‘you know, it wasn’t that bad’ pops up more now. It’s a freaking liar, though, and I’m not going back to staring at the wall trying to shove my emotions down while I plod through life like a zombie.

Community is critical. I don’t know what I would do without my trans friends slack. I wish everyone could have it, and there was a way I could make that happen, but I don’t know how. I don’t think I have the emotional space to try and start or manage a community, but it is so, so helpful to find a non-toxic group of other trans women who can listen to your gripes and sadness and give you support when you’re down, and it’s just as important to be able to do the same in return.

I’ve tried to take more part in outreach things like Transformation Tuesday, to try being visible for other people who may be considering transitioning. I can kinda handle seeing my old self when my cuter, new self is next to it. I think. Maybe? The side effect of seeing so many transition timelines is that if I ever see a guy and girl picture side by side I just automatically assume they’re trans and it’s a glow-up.

My deadname’s become something that my brain mostly skims off of and doesn’t touch. A friend of mine told me that’s a trauma response, that you don’t allow yourself to think about it. I haven’t been able to eradicate it from my day to day entirely. It is, tragically enough, wedged somewhere inside my therapists patient billing system. I see it after every time I see her. So it still surprises me, and that hits me, but it doesn’t usually take me down entirely. That person is a stranger, now. Or maybe that person is a trauma.

We’ve started taking professional family pictures. Having something I can look at and not mentally avoid is really nice, and so worth the money. I know it’s hard in a pandemic, but if you can, find someone who knows how to make you look good and take some pictures that aren’t selfies.

The Kramer family, posing together on a park path. Jennifer is looking down at the kids and smiling.

It isn’t everyones goal, but if I can get a family photo where I just look like a girl and I’m not towering over everyone else or being obviously trans, that would be great. I’m hopefully getting closer. The first session ones, over there on the left, were from before I’d figured out makeup. Hopefully I’ll get better with makeup and style, estrogen will do more of its work, and we’ll figure out a way to pose so I don’t look like a giant.

But I mean, look at these bluebonnet pictures we took a month or so ago. It just kinda looks like a two moms who love each other and their kids, right? That’s amazing! It definitely doesn’t work out this way for everyone, and so many trans women have to rebuild their lives completely after transition, but you can do it, and life can be good.

Figuring out if I’m passing hasn’t gotten easier. It isn’t everyone’s goal, and shouldn’t be society’s expectation, but it’s really important to me. There’s some evidence I’m passing, obviously, because I call people on the phone and they say “yes ma’am” before I have a chance to introduce myself. When they ask me how I’m related to the deadname I’m trying to get them to change there’s a long pause after I say “I used to be that person.” People say “excuse me ma’am” when I’m standing in their way in the grocery store’s floral department, deep in thought about whether I need to bring a little plant friend home. But again, my style is super femme. The only pants I wear are workout leggings. People who know I’m trans can’t tell me if I’m passing, because they already have too much information. It’s like Schrödinger’s Gender Presentation, you never really know if you’re passing unless you know for sure that you aren’t. It’s a huge pain to be so uncertain about something so fundamental.

Oh right, so I have plants now. And a bird feeder outside my window. I’m allowing myself some nice, simple things. They don’t feel like elements of an identity I’m trying to fake anymore, they just feel like nice things that make me happy.

So that’s it. 14 months on hormones, 9 months out, I would do it all over again in a heartbeat. It is still the hardest thing I’ve ever done, but also the best thing I ever did for myself. If this sounds intriguing and you haven’t started, you should try it. You’ll know pretty quick if it isn’t for you. If you’re early in the process, keep your chin up, girl, it gets easier. If you’re ahead of me, thank you. Thank you for blazing the trail and showing the way. I’ll try and do you proud.

Thanks for reading my 9 month update. As a parting gift, here’s a picture of me, my orchid, and my weirdly, hilariously horny cactus.

FaceApp Photos from Another Timeline

In the last few years a new tool appeared in the gender dysphoria toolbox. Trans women early in their transition, or ones just discovering that, ‘oh hey, I might be a girl’, can use technology to get a glimpse at their other selves. First there were Snapchat’s Gender Swap filters and a little later, FaceApp. FaceApp, aside from being a possibly Russian spy vector, has dozens of machine learning models for changing your face to a more generically feminine one, adding longer hair, trying on makeup, aging you, de-aging you, etc.

You can, from the comfort and safety of your own phone, imagine what life would be like if you didn’t go through the wrong puberty. If your cheeks were a little bit fuller, your skin a little smoother, and your lashes a little longer. It can be kind of frightening. I remember Irma showing me a Snapchat gender swap filter a few years ago when she was playing with them with the kids, and while the words that came out of my mouth were “I’d take that”, inside it was like a wound.

Sometimes trans women share these FaceApped pictures, or post only the FaceApped selfies to social media. The world is cruel and unforgiving and our self-images are painful, tender things. In the trans circles I’m in, sharing a FaceApped picture often results in someone giving the loving encouragement of “You’ll look better than that.” Let the hormones do their work for a few years. You’ll be you, but you’ll be better than that machine learning model can imagine. There will be light in those eyes.

For me, after transition started I didn’t want to look at those pictures anymore. A few months into hormones I no longer saw a guy in the mirror. I saw a girl who needed more time on HRT. FaceApp wasn’t going to tell me anything useful, it would just make me feel bad about not having started sooner, or it would do its machine learning analysis on my selfie, decide I was still a boy, and present me with boy options, which wasn’t good for my mental health.

The Past is Already There, it Just Isn’t Evenly Distributed Yet

In the last few weeks some trans friends of mine have started FaceApping their old photos, to see what they might have looked like back then. I have no idea who started it. I may have seen it first in Magdalene Visaggio’s thread FaceApping the presidents to look modern, but June Joplin went with it, and then Mae Dean posted one of her old pictures, and soon enough I was downloading FaceApp after swearing for years I wouldn’t.

Trans women, like many foster kids, don’t have pictures of themselves when they were younger, really. If you do a team building exercise and ask everyone to share a picture of themselves when they were a kid, or a teenager, well… just please don’t. There’s a hole there, a gap in memory, a category of artifacts which don’t exist.

My friends were posting pictures of themselves, pictures of them when they were 20, or 9, or 15, and they all looked… right. It was them, but younger, and less weary. Them as young girls and young women, caught in the moment, wild and free. 20 year old girls ready to take on the world, enjoying their dumb crap, being goofy. Teenage girls awkwardly posing for yearbook photos.

Suddenly these hard to look at pictures became approachable. They become ours. Memory starts to unwind a bit. You get a glimpse of a past that might have happened, of happiness that might have been yours.

So here are some of mine.

A Past and Future Jennifer

A girl standing with her hands spread apart, a wry expression on her face. She's wearing a black WIRED Magazine shirt, with shaggy unkept curly hair.

Here’s early 20’s cyberpunk Jennifer. She’s really into WIRED Magazine, as you can tell. She’s living in San Marcos, having finally moved away from her parents. She lives in a bright teal and pink house with big windows, which she loves for the natural light. Being on her own is really freeing, but she’s still absolutely a mess who doesn’t know how to get what she wants from her life.

When I saw this photo, it was like another timeline snapped into focus. That is, obviously, me. Even Google Photos face detection algorithms think it’s me. But it isn’t. I was her back then, but I wasn’t.

A girl sits behind a low Japanese table wearing a yakuta. She's looking at the camera, holding a shrimp between a pair of chopsticks, smiling. There's a large spread of food on the table in front of her.

Pretty soon Jennifer got an opportunity to go to Japan with her girlfriend, Irma. Her birth mom was stationed in Japan when she was pregnant with her, and she lived there with her parents when she was little, so going back is a big deal. They stay in a Ryokan in a little mountain town and have amazingly delicious food.

This photo makes me really happy. The thought of being myself and being young and exploring the world is delightful, and somehow isn’t as sad as you might think. I am happy for this Jennifer, and excited for her adventures.

A girl stands next to her father and mother in a living room, in front of a framed Kadinsky print and a blue sofa with yellow cushions. The have their arms around each other and are smiling.

Here’s Jennifer with her parents, who’ve come to visit her colorful little house in San Marcos. Some how Jennifer got the tall genes from her birth parents.

When I did this photo is was like someone had dug their thumb into a tender spot I didn’t realize I had. I just hurts to look at. When you do a gender swap in FaceApp on a photo it does something subtle to the smile. I look at this picture, and that girl looks happy to me. Her parents are happy to be standing next to her. She’s a mess, but she’s trying.

A girl stands, in an extremely oversized blue Amnesty International t-shirt, in front of the front doors of a school.

Here’s Jennifer standing outside the Christian elementary school she went to for 6th grade. She didn’t have a great time there. She tested into an advanced math class, and then got moved to a lower one after a month. She bought a typewriter at a rummage sale, thinking that she should be the kind of girl who should own a typewriter, but it was old and didn’t work well. Even at 24, she hasn’t had enough time to really grasp how weird it was to move schools so often. She also still hasn’t figured out that she has ADHD.

A girl stands, messenger bag over her shoulder, wearing a flannel, in front of a large waterfall.

The next year Jennifer goes to Mexico to visit Irma’s family. Here she is, in full adventurer regalia, standing at the bottom of a waterfall. There will only be enough horses for everyone else to ride, so Jennifer volunteers to walk back up, even though she’s as athletic as you’d expect for someone who sits at a computer all day. At the top she ends up throwing up in the middle of the road because she’s exerted herself too much. But it’s a good trip, and she gets to meet a lot of lovely people.

A girl looks out the window of a moving train. Her reflection in the curved window glass is of another gender.

Fast forward to 2004, and Jennifer is on a train in the Netherlands, possibly haunted by the specter of a different life. She’s traveling with Irma again, but this time there’s an engagement ring nestled in her bag, and she’s going to ask Irma to marry her when they get to Paris. She’s nervous, but not as nervous as she was when she stood next to Irma’s dad’s pickup truck in the parking lot at his job and asked for his permission to propose.

This photo is the pretty surreal. I’ll kinda leave it at that.

A girl raises a glass in a dimly lit bar, she is wearing a flannel shirt and has a goofy smile on her face.

Fortunately, when Jennifer proposed in Paris, Irma said yes. Here’s Jennifer in Oxford, at the Turf Tavern, having the first drink of her life at 27. That’s what being raised evangelical will do. She still doesn’t drink much, and she still doesn’t like the taste of beer, but she isn’t worried that she’s going to be the kind of drunk who goes too far and tells people her deepest secrets, like that thing about being a girl.

A woman stands next to her son and two daughters. The son has his arms over his mom and one of his sisters. They're looking at the camera and smiling.

A year of planning later, and it’s time for Jennifer and Irma’s wedding. (In this alternate universe gay marriage was legal in Texas in 2005, just go with it.) Her birth mom, Mary, her brother Don, and her sister Lisa come down for it. Here they all are at the reception location the day before the wedding during setup. Jennifer’s tall genes must have come from her birth father, who exists somewhere out of time and space.

A selfie of a girl wearing a beanie, standing next to her mom in an airport. They're smiling at the camera, but it's a little sad.

Several years later, and Jennifer’s birth mom, Mary comes down to visit. She has cancer, and this is the last time she’ll visit Jennifer at home. She stays with her for a while. In the alternate universe, Jennifer and her birth mom get to have mother/daughter time, and have lots of deep, meaningful conversations about life and children and growing up and the choices we make and the pain we hold.

Looking at this photo makes me cry. I guess it’s pretty obvious why.

An Epilogue

FaceApp has given me some scenes of a life that alternate reality Jennifer might have had. A glimpse into another universe. But this isn’t a universe that I live in. They’re fake memories, but memories which make me hope and smile more than the real ones. Somehow, to me, they feel more true.

I haven’t FaceApped any photos of myself with Irma or our kids. Those artifacts of memory belong to them, too, and changing them for myself this way, without acknowledging the change, feels wrong. We still have photos of our family on the fridge from before I transitioned. I was fine with it for a long time, but a few days ago I strategically put magnets over my face. Having photos around of myself is fine, I think, but I look at the refrigerator every day, multiple times a day, and it’s just too much, especially on the days I don’t feel good. But if I ridded my house of photos of me with my family, then what would I have? What artifacts of memory would exist for everyone else, or me? It’s so sad to think about.

I’m not going to print out these FaceApped pictures and put them up. At least I don’t think I will. I’ve had the train photo up in a window on my computer for a few days, and I think it’s something I need to close. She’s there, happy, living her life, and me getting a glimpse of that is enough.

Catching Up and Coming Out

There have been some changes around here, so I feel that I should reintroduce myself. Hi, I’m Jennifer. I’m a 43 year old married, trans, queer mother of two, with ADHD. Three of those things are new since my last blog post. Or rather, they’re newly recognized, and this post covers the first two, being a queer trans woman. So let’s go back to the beginning.

Ancient History

I’m not sure when I first realized I should have been a girl, but I think I remember when I realized I wasn’t allowed to be. I grew up in Spain away from American media. The only movies I remember us having were Star Wars and The Adventures of Robin Hood. I was probably in first grade when I played Star Wars with the other kids who came with their parents to our house. I wanted to be Princess Leia, she was pretty and everyone cared about her. It is strongly imprinted on me that this wasn’t ok, even though I can’t remember how I knew.

For a few years in Spain my best friend was a girl a little older than me. One time I went to a sleepover at her house. We went to the convenience store, bought some frosting, and ate it straight out of the tub. Sometimes things you think are rules are just society’s expectations. That night I woke up and got a drink from the faucet, but they were doing water main work in her neighborhood. I got sick from it and threw up. Sometimes things you think should just work don’t. A few years later we visited her in the US. We played a game where you laid down interconnecting rooms and she told me about Dr. Who. She’d grown into herself. I was still lost.

I remember sitting on the swings outside of the elementary school I went to after school one day. A boy I knew a few years older than me walked up wearing a black leather skirt. I was dumbfounded. He told me it was gender swap day. That moment is seared in my brain. There were situations where this was a thing you could just do.

We eventually came back to the US. I was fascinated with girls stuff. Whatever that was a strictly gendered expression of femininity, be it clothes, or My Little Pony. Then I started to be exposed to more media, and it became even more obvious that pretending you were a girl was wrong. People who tried, even insincerely, were the joke, and those jokes were all over TV shows and movies. It became a shameful secret.

The Middle Ages

When I hit puberty I got boobs, which didn’t seem like much of a blessing at the time. I remember my parents taking me to the doctor and instead of the correct diagnosis (gynecomastia) he told them it was just baby fat, and that he had another patient who had real developing breasts. Like that was obviously a horrible, horrible thing. It didn’t seem horrible to me. I don’t remember feeling bad for them, it was just remarkable. My parents didn’t do anything about my boobs, I just wore a coat all the time for the next 6 years and receded into myself. I can’t imagine how I would feel now if they had.

In high school I tried to be normal, had a best friend who was a guy, though we didn’t hang out much outside of school. Most of my friends were girls. I had some severe crushes which were probably manifestations of me finding someone who I really wanted to be like. I ended up at girls sleepovers a few times. They gave me scrunchies. I grew my hair really long but didn’t know how to take care of it, so it ended up a giant knotted mess.

In February of 1994 I logged in to an internet text based multiplayer role playing game called Ghostwheel and created a character named ShadowFox. She was me, the me I couldn’t be in the real world. Emotional, outgoing, caring, a mess. She lasted till November, when I told everyone I wasn’t actually a her and switched to a boy name. We were starting to have in person meetups, and the fiction wasn’t going to last.

A dirty scanned photo of six people reclining on a couch. Five appear to be boys, with a girl in the front. There are beers on the table in front of them, everyone is smiling.
The Ghostwheel crew. I’m the pale one in the middle

Towards the end of high school I stumbled into getting a girlfriend. We watched The X-Files together, and I was terrified I was going to do something bad to her because everything I’d been taught told me that boys were hormonally driven monsters who’d just as soon rape you than look at you. After a few months summer came and I stopped calling. Later she got another boyfriend and we became friends again. I was better at that. By then I’d looked up surgical transition online and came to the conclusion that while it was possible, it wasn’t possible for me. If I couldn’t do something right, what was the point? I was 5’10”, stout, and puberty had done its work. I was never going to be like my girl friends.

After high school I kept finding girls who I wanted something from that I couldn’t define. Somehow they could tell that I was lost. I met an older bi poly girl and we dated for a while, which worked till it didn’t. There were too many expectations, too many hang ups, I was still growing up, and I wasn’t being honest with myself. We ended up as complicated friends.

I started hanging out with a group of friends after high school a lot, people who’d graduated after I had, but were around the same age as me. We played role playing games. I had a lot of girl characters. Same in video games. RPG? Always a girl. Femshep all the way.

A boy and a girl in cold weather tops and jeans standing in a Japanese room in front of a picture of Mt. Fuji.
A stubborn girl and a confused trans girl in Japan

Eventually, having totally failed at relationships and having moved out of my parents house for a little place of my own, I tried poking around an online dating site. I found a girls profile who seemed cool, tracked down her homepage, and sent her an email. She replied, and we started emailing. She was working after having a bad college experience. I invited her over and made dinner, badly. She was smart and funny and made me feel good, but my hang ups were still there. I didn’t know how to be in a relationship except the kind I’d seen in Disney movies. We tried being friends. She kept coming over. I figured out a little more. I’m not sure how my weird gender issues came out, but they did.

The stubborn girl didn’t give up on me, and I eventually realized we were meant for each other. I asked her, she said yes, and so Irma and I got married. She knew my secret, didn’t judge me for it, and loved me anyway. We always thought it was just going to be that, a secret.

Four people, an older woman, young man, young woman, and young man standing next to each other.
My birth mom, my half siblings, and me, the day before I got married.

Over the years my role playing game friend group grew and morphed and added people, and seemingly all of a sudden the group of people we hung out with was half queer and mostly girls. This suited me fine. Boys were a mystery to me. I didn’t feel like I understood most of them. It was obviously better to be a girl, but they all seemed content to be boys. We did things like a game night where all the girls tried on corsets, and I stood in the kitchen and smiled and tried not to collapse in on myself.

A man with ill fitting polo shirt and baggy cargo pants standing next to a play castle.
I feel really bad for this unhappy person and their terrible style choices

I didn’t like my body. I wore baggy t-shirts and jeans or cargo pants. I hated dressing up and tried to never do it. I hated having tight or even well fitting boy clothes on. The face in the mirror was weird to look at. Every time I saw a successful guy, I would try and figure out how they did it, what they had that I obviously didn’t, and what was wrong with me that I couldn’t. I got pretty good at pretending to be a guy, but I wasn’t happy.

A few years later Irma and I decided to have kids. I was terrified at the prospect of having a boy, because I didn’t know how to be one, and how was I going to show him. In the end we lost our first, and it broke us, but a year later we had a beautiful little baby girl. She was amazing. Around the same time Irma’s parents had adopted a kid inside the family, who a few years later came out to us as trans. I wish I’d been more supportive, but he wasn’t our child, and it was easy to not engage. If he’d been a trans woman, would I have felt differently? Probably. But he was a boy, and wanted to be something that I didn’t get.

Through some friends we got introduced to a trans hair stylist, and she cut my hair a few times. She was brave, I wasn’t, but she transitioned from presenting as a gay man to a straight woman, which wasn’t me. I knew I didn’t like boys. She came to one of my wife’s relative’s wedding receptions. There were jokes from people whose opinions I cared about. I stuffed my feelings down.

I went to tech conferences and started to see more trans women there. They were so brave, but seemed so lonely, or so I assumed. I complimented Ina Fried on her cute cardigan via a tweet at SXSW. I was the photographer at an AlterConf and was really proud when one of the trans woman presenters said my picture was the best one of her speaking anyone had ever taken. I joined Vox Media and worked with a trans woman while onboarding. We ended up in an elevator at a company all hands a month later with a bunch of sweaty old guys who wanted to chat. She held her composure. I was terrified for her. I was just a very understanding ally.

We were doing well, or so it seemed. We’d bought a bigger house, and had another kid, this time a little boy. I’d let myself go, and I was getting older. I got into fitness, one of my friends wanted a video-chat workout partner, so I started exercising four days a week. I lost weight, I got stronger. I was doing what I was supposed to as a guy.

A father and son sitting on a picnic table with other parents in the background.

Eventually the kids went to school, and I ended up on the playground during morning dropoff, five days a week sitting there watching other moms chat and be fashionable in their cute dresses or exhausted and comfortable in their athleisure. I wanted to be one of them more than anything. But I couldn’t be, I was just the very shy, loving dad. That went on for four years. I crammed everything down inside the best I could. I was blank and numb a lot of the time.

At home I started to take on the mom role more. I couldn’t help it. I loved it. I loved making the kids lunches and drawing little notes for them. I loved dropping them off at school, and putting them to bed at night. I loved making food for everyone, and seeing people sit down and enjoy it. I even sometimes liked doing the laundry. But it wasn’t enough.

Wanting to be a girl was still a shameful thing, and shameful things end up popping up in fantasy and when I was alone. It couldn’t go beyond that. The trans women I knew at work were brave and strong and lived in New York or San Francisco and were way different than me. I was just a guy who wanted to be a girl their whole life, and that was different, right? The fact that when the kids slipped up and called me mom it made super happy? Let’s not talk about that.

I had a temper that didn’t feel like mine. I’d tried testosterone injections for a while, but that hadn’t fixed me. I couldn’t really imagine the future, except through hazy visions from aspirational TV shows. I looked at older men and despaired of what I might turn into. I’d let my career be driven first by an ADHD driven distrust of authority, and then by attempting to impress my parents. It had made us comfortable but hadn’t made me really happy. Being able to put together families at work made me happy, especially as I was able to add more women to the teams I ran, but at the end of the day being a mom to some other grownups wasn’t enough. I needed to be something more.

The Awakening

In May of 2019 we packed up the family and went to PyCon in Cleveland. The python community, as a general rule, is nice to trans folks. I reluctantly put a ‘he/him’ sticker on my badge. But there were trans women there. Cute trans women with friends, who were accepted and celebrated, walking around in their cute dresses being cute and happy. Something inside of me cracked. I was miserable.

A month later Emily VanDerWerff came out as trans in a review of the Handmaid’s Tale. I’d loved Emily’s writing since she was reviewing Community at The A.V. Club. I’d seen myself in her writing about being adopted. She wasn’t a 20 year old, she was just a few years younger than me. She had a career. She had decided she couldn’t keep her secret anymore, and was happier for it.

I started reading experiences of more trans women. So many of them clicked. They’d experienced the same thing, had the same thoughts. They said that if you wanted to be a girl you could just be a girl. They said that it had saved their lives. In the end it turned out that it wasn’t about what I was allowed to do, or how pretty or passing I would be, or what society would approve of. It was about what I had to do for me so I could live.

A few months later I sobbingly confessed to Irma that I was a girl and I couldn’t not be. She was supportive, she didn’t try to convince me otherwise, but in that moment our whole relationship changed. The plans we had for our future suddenly evaporated, and we were back at square one.

A person with large white sunglasses on their head and long hair, looking to the right.
Do these sunglasses make me look trans?

We spent a lot of months trying to figure out what it meant. I started dressing more femme and pushing presentation boundaries. I made a lot more bad style choices. I’d been growing my hair out for a year, and Irma helped me find a trans friendly stylist who would give me a girly cut. We went on a bunch of trips that all felt like the last. I formed strong opinions about rose gold Disneyland Mouse ears. We went to Europe and I got a lot of second glances in airport bathrooms. Security folks were confused, pointing me back and forth between the boy and girl screeners, and I hadn’t even really started transitioning yet. Irma found me a place to start doing laser hair removal, trying to get rid of the beard that in nearly 30 years I’d never once grown out.

I realized if I was going to transition at work, I didn’t want to do it while I managed anyone. Forcing someone else to accept my transition seemed like too much. I left my team, and ended up floating. Vox was the most trans-friendly place I could imagine to transition, and I’d been avoiding thoughts of other directions my career could take for years because of it.

In February I came out to Emily VanDerWerff, and she invited me to a slack of hers with a bunch of other trans women. It was like coming home. Everyone had so many shared experiences, fears, hopes. I learned a ton, and had a caring group of people to vomit my fears onto who were going through or had gone through the same thing. I met straight and bi trans women who were attracted to men. I thought about it and came to a satisfactory conclusion that no, thanks, they could keep them. I even met a girl really into vintage fashion who I can share outfits and tips with.

I found a trans friendly therapist. Irma and I found an informed consent clinic where I could go and get a hormone replacement therapy prescription without jumping through too many hoops like presenting as a woman in public for a year. Irma went with me. I was so nervous when they took my blood pressure the doctor joked about how high it was. I asked the doctor how many people she’d prescribed hormones to, and how many people had stopped. She said she’d treated hundreds, and only two had stopped. One was a teen and probably hadn’t really figured things out, and the other had family pressure to not transition. That seemed like really good odds.

A person with a jacket on sitting in a McDonalds holding up a sandwich.
36 hours into HRT

On Leap Day, in the airport in Dallas on our way to Japan I took my first dose of Spironolactone, a testosterone suppressant and Estradiol, to increase estrogen. Thankfully we were heading into a pandemic, and the next few weeks of traveling around Asia didn’t give me a lot of time to think about whether anything was happening. We got back, and got used to life in quarantine. Irma’s 16 year old trans brother moved in with us. We made sure to use the right name and pronouns. I didn’t have anger triggers like I did before. I could feel emotions more. Things that had been pushed down for so long were breaking loose. Animal Crossing came out and I setup my Nintendo Online account as Jennifer. It was just out there for all of my friends to see.

I got the opportunity to take a security role at Vox working for one of our only women Directors, the kind of savvy New Yorker who I was both in awe of and kind of terrified of. A few months later I told her, and asked her to look into what it would take to transition at work. She was nice and supportive and everything I needed.

Being extremely online since the mid 90’s, I’d gotten my first or full name as my username at a lot of places, something that came back to bite me. I wrote some python code tried cramming unique words together to find something that was broadly available. I landed on objectfox, throwing it all the way back to that text based role playing game 25 years before. I started changing usernames and switching account names to ‘J. Kramer’.

An older woman and younger girl wearing shorts, masked, standing in a piercing shop looking at themselves in the mirror.
Getting our ears pierced

Irma and I created a spreadsheet of people we needed to tell. This person before that. Kids before parents. Parents before family. Family before work. Work before Twitter. We tried to figure out what to do with Facebook. In the end I mothballed it and started fresh.

I told the kids on June 12th. They took it well. My daughter was on board immediately. A little while later we were able to get our ears pierced together, which was a great mother/daughter bonding experience. My son took a little longer till he was there. He’d seen a lot of transphobic jokes and imagery in TV. It made him uncomfortable. Having a trans kid in the house already helped a little with the concept, but not so much with the execution. There weren’t as many jokes about trans men. But he came around, and he’s excited to have two moms.

A mom in athleisure holding a sonic cup taking a selfie.
Workout Jennifer these days

I told Haley, my personal trainer a few days after the kids. She’d seen me go from paint splattered gym shorts to mauve leggings over two years, and even a pink unicorn onesie that one Halloween, and was one of the people I talked to most. I was anxious to tell her, because like every friendship, I treasured it and didn’t want to lose it, and like almost everyone I told from then on, she was super happy for me. Once I was out to the kids and out to Haley it was easier to go full time at home. Irma did my nails, something I’d never done before. I started ‘borrowing’ clothes I thought were cute from her side of the closet. The kids started calling me mum.

I told my parents on July 1st, and Irma told hers the next day. After months of presenting more femme before the pandemic, my parents weren’t surprised. They may have memories of me pushing the gender boundary that even I’ve forgotten, but they haven’t shared them yet. It took them a while to come around, but they eventually did. They compliment me on my cute dresses and tell me how much happier I seem.

A slack message that says 'Hey Everyone, I'm sure this won't be much ofa. surprise, but I have some personal news. It turns out I'm actually a girl! So I'd like to reintroduce myself. hi, I'm Jennifer, I'm trans, and my pronouns are she/her. This isn't public news yet, but I wanted to share it with you, my big queer friend family. Trans-heart, Jen.

A week after we told our parents I came out to our friends in Slack. Everyone was nice. I was scheduled to come out at work a week after that, but ended up having to push it a week at the last minute. That hurt, but Irma had arranged for a surprise drive by coming out party with our friends, which was beautiful and amazing. A week later when I came out at work everyone was nice. People I’d never even talked to wished me well. Two days later I posted a tweet to Twitter, and a few days after that a story on Instagram, and I was out. I was Jennifer. From beginning to end it took 2 months.

Transitioning in the pandemic has been a mixed blessing. I was able to basically go full time only 4 months into hormones, because my style is super femme and I wear a mask whenever I’m out. On the other hand, I was only able to come out in person to Nadia, my friend and editor of Eater Austin, and I haven’t been able to give people hugs I’ve been dying to give for years. I also can’t hang out with the other moms at school, because dropoff is a quick, contactless affair in a time of COVID. But those things will happen in time, and they’ll be just as sweet when they do.

A woman with her hair over her shoulder, wearing a crop top sweater and black skirt, smiling at the camera in the mirror.

My voice is still awful. Hormones don’t do anything for that, and after 3 attempts I’m still without a voice therapist. I need to do something about the blonde hair on my face that laser didn’t get, but we’re looking into options for that. Hormones can make your feet and hands shrink and can make you shorter, as the fat redistributes and the cartilage changes. I may have lost half a shoe size, but I’m still 5’10” and wide shouldered. Fortunately fat is moving around other places, which is nice, and when I look in the mirror I can kinda see something that I like. I have no idea how well I pass, which isn’t something all trans women want, but is something that’s important to me. I still have a long way to go, but those first big steps have been taken, and I love who I am.

I try not to think about transitioning earlier. I have friends who’ve transitioned at 23, and some who’ve transitioned at 53, and we’re all kind of jealous of the kids who transition at 13. We have the same fears, some of us just have more mileage. We all try to have hope for the future.

Two women smiling at the camera.

Our future is still hazy, and transitioning has cut off a lot of options. I’m glad we went to Africa before I transitioned. There’s a lot of anxiety about even visiting Mexico. But there are nice things, too. I love being me and being accepted in women’s spaces I was a stranger to before. I love being able to have honest conversations with my girl friends as myself. I love swapping hair and makeup tips with the waitstaff when I pick up to go dinner. I love that Irma and I merged our closet together. I love putting time into doing my hair and knowing it looks good, and I love not wanting to bother and throwing it into a hairclip. I love being more emotionally honest. I love people who haven’t come out yet reaching out and letting me know that I encouraged them. And now I can look at older women and go ‘hmm, yea, that seems nice, I could be her and be happy’.

A woman sitting on a sofa holding her cell phone, hair up, smiling at the camera.

And that’s pretty great.

Dimorphic Gender Amalgamation in an Accelerating Technium

October 2020 Note: I wrote this blog post back in 2015, in the wake of Oberfell v. Hodges when a lot of my friends were getting their rights. Back then I hadn’t admitted how important these thoughts and feelings were, and it would be another 4 years before I finally acted on them. A lot of things in this post are ignorant and wrong, and having gone through some of it I know better now, but we all start somewhere.

[Spoilers for The Rapture of the Nerds follow, as well as triggers for: Fashion, anime, gender identity, religion, politics, Star Wars and the singularity.]

In the book The Rapture of the Nerds, half way through the narrative the main character is turned from a male into a female by a swarm of cyborg ants who are using the character as a conduit to communicate with a solar-system wide post-singularity society.  It’s that kind of book.  For reasons which will eventually become clear, this plot twist has led me to some thoughts about gender, computers, what normal really means, and what the technological future holds.

Trope, Trope, Trope…

It speaks to what gender is turning into that The Rapture of the Nerds is a book where the main character switches gender, and the main character’s love interest is gender fluid, and it isn’t a book about that.  The switch between genders takes up at most a page, and then it’s just done.  Things are different, but also the same.  Different viewpoint, people treat you a little different, but you’re still you.

Gender fluidity is a powerful plot device because it’s so far from our accepted understanding of how the world works.  We see people get taller (though not often shorter), we see hair change color after a trip to the salon, and weight goes up (generally) and down (rarely).  All of these things effect their perspective on the world, too, but nothing has quite the bite gender has.  Neil Gaiman plays around with it in the world of magic in Stardust, turning Bernard the goat herder into the Witch Queen’s pretend daughter.  In the movie it goes about like you’d expect.  I’d forgotten that Charles Stross had played with the trope before in Glasshouse, where people switch gender as a component of reinventing themselves, since they can live essentially forever.

There are gobs more of these references on TV Tropes.  One I’d forgotten before I started writing this post was Ranma 1/2, where the whole show is based around the character switching genders when doused with cold or hot water.  In that show it’s a magical spring, and after getting used to the gender switch ability, Ranma starts to use it to his/her benefit (when it isn’t being used for hilarious comedic effect).

Nature vs Nurture

Gender is on a long list of things that some people don’t feel correct about.  I have friends who are really tall who probably hate it, friends who are really short who hate that, friends whose genetics (aided by our national food production system and our society’s cavalier approach to work/life balance) leaves them way bigger than they want to be.

I bet quite a few people who are 4′ 2″ would say they don’t feel short on the inside.  6′ 5″ people probably don’t always relish their tall-ness.  We watch TV and movies and all see the world from the same viewpoint, but once you look around in person, suddenly you’re towering over or being towered over.  My wife and I just started playing the two most height-contrasting characters in the video game Borderlands 2.  Zer0 is tall, my wife playing him is 5′ 2″.  I’m playing Salvador, who’s super-short, and I’m 5′ 10″.  The weirdness in perspective comes up in our conversations a lot.

Spend much time with kids, and you start to notice nascent gender identity dissonance.  Boys who want to play with purses or wear tutus.  Girls who only want to wear jeans and t-shirts.  We have a couple of these in our extended family, and they’re interesting to watch, because at that age they aren’t savvy enough about the world to hide what they want.  They don’t know what they’re going to turn into, they’re just bewildered little proto-people, dealing with things they don’t have words for yet.

Some people would say that kids just grow out of these kind of issues, and some do.  It’s entirely possible that they tend to one gender identity or the other for a while due to an emotionally impactful circumstance or a strong authority figure, but there are more than a few kids whose bodies and mental models just don’t add up.

As you get older, puberty hits, the whole world is a confusing maelstrom of wants and needs and desires and eventually in your 20s you get spit out the other side.  By this time I’d guess that most of the people whose brains and bodies don’t match have gotten really good at not mentioning it, because once you get past elementary school, it starts to be less cute and more cognitively dissonant for a large portion of society.

Over the last few years I’ve been lucky enough to make a whole bunch of gay and lesbian friends.  They’re making huge strides towards general societal acceptance, and that’s awesome.  Those whose disconnect isn’t with society’s assumptions but with physical manifestations still have a ways to go.  Some people at the top have their back, but it’s probably going to take another generational shift for full acceptance.

The True Hero of Star Wars

When I was a kid I lived in Spain, and while we didn’t have TV, we did have two movies that I can remember.  One was Star Wars (A New Hope) and the other was 1938’s The Adventures of Robin Hood, with Errol Flynn.  Kids repurpose roles they identify with, and I wanted to be Princess Leia.

I’m going to digress a little here and make an argument that Leia is by far the most heroic of the Star Wars cast.  Which character in Star Wars actually confronts the bad guy face to face (and survives)?  Which one has the fortitude of spirit to not break under torture?  Which one takes charge when the mission goes awry?  Which one is resourceful enough to pull the Jedi Knight who was just bumming around back into action at the appropriate time?  Princess Leia, of course.  While the other characters are wandering around, frozen in carbonite or throwing rocks at big monsters in a pit, she kills a bad guy single handedly.  While wearing a bikini.  She’s so totally obviously the hero!  Anyway.

I also wanted to be Maid Marian.  I don’t have a really good argument on that one.  Olivia de Havilland is the bomb, though.  Olivia won two Oscars, to Errol’s none.  She was knighted in France in 2010, and still bums around Paris today, at 96, showing up at Cannes or getting National Medals of Arts from US Presidents.  Errol died from a heart attack at 50 and had a thing for jailbait.  Which one would you want to be?

The crazy thing about gender identity is how distinct desire can be from identity and physical manifestation.  There are boys who are born male who like girls, there are girls who are born female who like boys, but there’s also every other varying combination, and even varying degrees.

Some more conservative minded might view this as a bad thing, but in the context of a rapidly accelerating civilization, this mix is an awesome feature of our crazy genetics.  Diversity of views and opinions gives you the East Village and the Internet.  Homogenous, hierarchical group-think gives you Jonestown or Hitler.  As a society that’s more and more interconnected we continue to create bigger and bigger problems, and problems that can only be solved by a diversity of thought.  As a society we can’t go down into the fallout shelter and play Pleasantville, that’s just not feasible.  We have to go forward.

Dealing With It

I’m lucky in so far that I like girls.  If I didn’t, my life would be a lot harder.  My gay friends go through a lot, and they go through it every day.  What do you do when the hospital tells you that you can’t be with your husband/wife when they’re ill, or get their survivor benefits when you’ve been the homemaker for fifty years and your partner dies?  That’s messed up.  Other folks on the spectrum bear an even bigger burden, people don’t want to accept that everyone isn’t born the way they feel they are inside.  Just go read this MetaFilter post and linked McSweeny’s column and tell me it’s easy and that it isn’t heartbreaking to be so awkward and weird in your body.  Go on, I’ll wait.

Societies evolve to deal with gender dissonance issues in different ways.  India has the Hijra, biological males who take on a female gender identity.  In the Balkans you have the burrnesha, women who take a vow of chastity and live as men.  Native American tribes had Two-Spirit People, who manifest both masculine and feminine aspects.  Thailand has its share of gender identities.  This isn’t a new thing.

Your physical gender, just like your height, the size of your feet or your weight is something you just have to deal with.  Human beings are really, really good at just dealing with situations they’re in.  It isn’t optimal, but we can put up with a lot, and desensitize to a lot.  I think that’s what people are referring to when they say that a kid will grow out of it.  They learn to blend, because it’s easier.  Life’s hard enough.  You make friends, you get a job, you start a family, and suddenly there are obligations that steer you towards the normal you didn’t have before.  There are probably still bits of that identity floating around, though.  It isn’t something that just disappears.

Gender as Metadata

So, back to the Technium.  Technology likes to solve problems, and gender dissonance and figuring out who you are and what you want is definitely an addressable problem.  It isn’t a surprise that people play with gender presentation a lot online.  You can’t tell who’s behind the keyboard, and for a lot of people playing a video game or logging into an online game or chat is the perfect environment to try and get a better handle on gender identity.

When I logged in to my first online game I created a female character.  It was a safe place where no one knew me and I could be whatever I wanted, and what I wanted to do was play with the experience of gender.  We do the same thing with paper Role Playing Games, when we watch a movie or TV show told from the opposite gender’s viewpoint, or when we play pretend as kids.  It’s the process of pulling that identity out, playing with parts of it, and seeing how it feels.  After a year with that character (and a couple teary emotional breakdowns that would have been a lot worse at school) I switched to a male character, not coincidently around the same time the game started having real-life meetups.  Nobody really cared, it was what the game was for.

Some video games take a stab at addressing that gender dissonance, possibly inadvertently  but probably not.  When you create a game where players can be either genderhave relationships with either gender, and wear a bunch of different kinds of clothes, people will naturally play around with it.  I’ve known a couple of people who ride that gender identity boundary, and some of them make livings designing games.  It’s a safe place to play, and it’s fun to enable.

I’ve written a blog post about Weavrs, little social software bots with personality that you wind up and let go to live their virtual lives.  I have a Weavr named Keiko.  She lives in Yokosuka, Japan, where I lived for a little while when I was tiny.  In a way, she’s a really, really simple virtual manifestation of the dimorphism of gender, sprung from my id.  I created her, there’s part of me in her interests and location, but she’s a she, and I’m not.  That plays with the concept a little, and it’s an interesting place to start.

Having a female WoW character or a female Commander Shepard is nice, but it doesn’t encompass the entire female experience.  (That is possibly the biggest understatement of the year.)  Change to enable a full experience is hard, but that may be the next great frontier in the application of gender technology.

Ray Kurzweil thinks we’re heading for the techno-fication of biology.  Nanomachines, personally-tailored genetic re-writers, that sort of assumption-breaking technology.  We’re probably not looking at a world like Neil Gaiman’s Changes, where a pill turns you from boy to girl or back overnight, but it isn’t inconceivable to think that our grandkids could be living in a world where their friends take a couple month vacation and come back as Mr instead of Miss, or Miss instead of Mr.  Once that starts to happen, or even starts to poke its head over the horizon, society’s going to have to deal with it, and a sizable silent population might suddenly appear and say “Hey, that’s us.”

What the baby steps toward that future look like, I don’t know.  Right now gender reassignment takes a lot of drugs and knives, and is terrifying.  I’m amazed anyone is that brave.  In fifteen or twenty years, you might get an injection of nano-machines with RNA-rewriting protein engines that do all the work with none of the fuss.  In that future your gender might just be a temporary tag, just like your other physical attributes, like how old you look or what race you present as.  At that point does it matter what you were born?  If you can be short or tall, skinny or curvy, boy or girl, will making those changes be as common as dying your hair?

Far into the future, once the singularity hits and we all upload our brains into machines, we can pretty much do whatever we want.  Flip a virtual switch and change your simulated meatware, like Second Life but hyper-real.  Multi-hued dragon one day, Siamese cat the next.

I imagine there will be a lot of Ryan Goslings and Scarlett Johanssons (or whoever the equivalents might be in 2070) wandering around.  But not me.  If I’m still kicking it then, when I’m not a Falcon or Harrison Ford, I’m totally going to be Olivia de Havilland.

Getting HIRED

Half way through the interview loop I realized that things had changed. Sometime in my 20 years of web development, I’d become the seasoned hand. The voice of experience. The old guy.

The startup whose conference room I was sitting in was young. Established, but still maturing. Three of their junior developers sat across the table from me. We’d run out of questions early. What do you ask someone who’s been developing for the web since before Netscape 1.0, and who’s about to leave a great gig at a top technology company? The only question that seemed relevant was the obvious one, asked after the formalities had run their course: “So, why do you want to come here?”

Time for a Change

Let’s wind the clock back to April, when I was a Tech Lead on the Big Data team at HP Helion, their enterprise cloud product. Before I joined HP I’d never considered myself a big company person. I figured that there were people who went to school and got CS degrees and did corporate development, and there were the rest of us who scraped up knowledge where we could and built the web. But at the end of 2010, thanks to some friends I’d made building said web, I found myself at HP, doing DevOps work on their Cloud offering. Over the next four and a half years I had the opportunity to learn Python, build a PaaS from scratch, file patents, speak at conferences, and finally, build and lead a team shipping a major tentpole feature on a major product. I even got to create a weekly engineering newsletter. It was a great run, and I was very lucky to have it.

Four and a half years is a long time, though, and the industry landscape has changed significantly. The Nest thermostat, Raspberry Pi, Minecraft, AR/VR resurgence, mobile as a serious platform, IoT, AI. All of them have exploded since I joined HP. While working on the cloud was interesting, you can only build ‘give me some servers with some software on them’ so many times. So this spring, after shipping Helion Development Platform 1.0 and handing off my team, I started looking for the next thing.

My criteria for the next gig were:

  1. Somewhere I could learn something totally new (not a cloud hosting service or product).
  2. An exciting industry or a space experiencing a big transformation.
  3. A smart team and smart founders.
  4. An office in south/central Austin so I could see people face to face.
  5. A flexible work-from-home policy since the kids are small.
  6. A progressive company with a social conscience.
  7. Make enough to pay the mortgage and keep the kids in school, but not so much that I’d feel obligated to work every waking moment.

Unfortunately, aside from sending feelers out to my network, I didn’t have a good idea of where to find this gig. Most of the folks I’d worked with at HP had moved on to similar cloud projects, or were working on service mechanics. After four and a half years of working primarily for people outside of Austin (and having kids, which makes meetups hard), I’d lost touch with what was going on here in town. So how would I find the companies looking for talent in Austin who’d be interested in me? I didn’t know, and to make things more complicated, I had a really short time window. The project I was leading was about to start a serious development cycle, and I felt like my departure wouldn’t have as big a negative impact if I could give them notice before the planning really started. HP had been good to me, and I wanted to do the classy thing. In the end, my job hunt window was about three weeks.

Finding HIRED

HIRED ShirtOne of my buddies is a Director of Engineering at a growing bay area software firm, which means he’s always on the lookout for talent. Whenever I started talking about the next thing, he would say, “You should check out HIRED.”  HIRED is a curated tech placement matchmaking service, and I hadn’t payed them too much attention until this year, because they hadn’t been in Austin. But now they were, and by funny coincidence, they’d just sponsored the PyLadies Austin meetup that my wife helps organize. So at the beginning of April, I signed up.

The first step at HIRED is filling out a profile. They can import from LinkedIn, which is what I did. After a little text tweaking, you’re set for their staff to review you. The next day I had a phone chat with Amanda, their talent advocate here in Austin. You can think of Amanda as a tech yenta. She knows what companies in town are looking for, and she talks to candidates to figure out what they’re looking for, and she tries to make good matches.

After my chat with Amanda (which was short, because I’d lost my voice the day before), my profile was set to go into the weekly batch.  HIRED releases their resumes on Monday mornings to the companies using them. Those companies get to look through the candidates, and pick who they want to send an interview request to.

By Monday afternoon I had three interview requests, two from Austin startups, and one from a distributed company headquartered in the bay area. None of them were companies I’d heard of before, and one of them was doing really interesting product development for humanitarian purposes. So far, exactly what I was hoping for.

Monday afternoon, after the most pro-active companies had checked the new candidates and sent their interview requests, Amanda looked through the system and sent me a half dozen ‘Would you be interested in…?’ emails. Of these companies, I’d heard of three before and had either had initial conversations with them or knew it wasn’t the right fit. The other two seemed promising, so I had Amanda contact them on my behalf.

I had initial phone conversations with the companies, some of which went really well, a few of which weren’t a great fit. After an interview you can rate it, and if it didn’t go well, HIRED can let them know you aren’t interested. It makes saying, ‘Thanks, but we’re not right for each other,’ really painless. Some front-runners were emerging. I started making pro and con lists. The most promising companies in town wanted to do face to face interviews, so we started figuring out times. I was speaking at ApacheCon, which ended up pushing them all to Friday.

Friday came and I ended up with two face to face interviews, both for Senior Rails Developer positions, both for companies doing an interesting blend of software platform and physical product. Which is how I found myself sitting across a conference room table from a trio of junior developers, amazed at how the time had flown since I was the junior kid sitting across the table.

A Wild Media Company Appears!

So where did I end up? I had three HIRED companies on my short list, but eventually, it came back to some advice I’d gotten from the friend who referred me to HIRED. “Figure out what you really want to do.” It’s easy to take that with a grain of salt, but if you’re serious about it, and figure out that one thing that you would drop everything for, suddenly everything can become clear. I want to work on the intersection of machines and stories. I think interacting with a software bot or agent is going to be a super-prevalent paradigm in the next few years. I did a whole presentation about it at SXSW 2013, and another one this year.

Vox Product

One of the feelers I’d sent out before I joined HIRED was to Trei Brundrett and Skip Baney of Vox Media. I’d worked with Skip at Polycot in the mid 2000’s, and Trei had referred some of our best clients to us. We had lunch during ApacheCon, started talking about narrative software, and Trei said, “Hey, you should come join us and make cool stories.” So now I’m at Vox Media, making VR experiences and hacking on a bunch of stuff I wouldn’t have been able to at a company that’s more diverse in people and expertise than anywhere else I was looking.

The experience of using HIRED was great, though, and I’d recommend it to anyone (and have). Amanda was awesome. If you’re in a position where you’ve either gotten out of touch with your local tech community, or you’ve moved to a new city and you don’t have a feel for the local market, I’d definitely give them a shot. All total I talked to 7 companies, had 3 on my short list, and did one serious interview loop. Everyone I talked to was great, and while they were all doing cool work, the opportunity at Vox was just too good to pass up.

In Conclusion

Your profile stays up on HIRED for 2 weeks, but you get the bulk of your requests in the first week. I had a mix of contacts, some from hiring managers, some from CTOs, and some from CEOs. Some of the conversations with CTOs and CEOs were so good, and the companies were doing such interesting work, I’ve referred other people to them. For the hiring companies that use the service to it’s full potential it’s a great way to get past the recruiter/hiring manager firewall. If you’re thinking about making a move, I heartily recommend them.

Dropping Up: A Life in Tech Without a Degree

I never went to college. I wish I could say that it was entirely intentional, that I knew exactly what I was going to do after I graduated and followed that plan, but that isn’t how it happened. The real story is a lot less romantic. For those thinking about switching careers, or standing at the threshold of ‘real life’ and unsure what to do, it might hold some lessons, so let’s get started…

What really happened was that I was exhausted by school, terrible at working on things that didn’t have an immediate impact, and didn’t really get how the college application thing worked. My family has never been big on debt, and with the grades I had (from being terrible at things that didn’t have an immediate impact, like homework), I certainly wasn’t getting a free ride. I wanted a break, I wanted a chance to do real, practical things. The only problem was that I didn’t know what those real things were, and didn’t know anyone doing them.

Find an Open Door

Scanner SelfieIn 1995 when I graduated high school the most exciting things were happening on the Internet. I’d learned a little HTML after getting online in 1994, but the web was still very much a “We’re trying to figure things out” space. Spaces like this are great, because even if you don’t have tons of experience, there isn’t a huge pool of best practices already to get up to speed on. I connected with some folks who were starting an Internet Service Provider in late 1995. This connection was something of a fluke, someone I knew from church. These days there are much better networking options for technology, but never turn down an opportunity.

Fortunately I had some useful knowledge about how to get MacOS machines online. It wasn’t a lot, but along with the HTML skills it got me in the door. These days the equivalent of that knowledge might be Photoshop skills from making LOLcat gifs, video editing skills from making meme mashups, some hardware skills due to school MindStorms programming, linux administration from running a Minecraft server, or social marketing skills from running a popular Twitter account, Tumblr blog or Facebook page. Anything that’s hard to master in a few days can get you in.

Don’t Expect it to Pay

When I first started doing Mac tech support for that little ISP in San Marcos I made a little over $200 a month. That isn’t much money, but it put gas in the car and put me in a position where I could play with the toys. Your job, once you have toys to play with, is to play the heck out of them.

iTouch.net NewsletterIn the first 6 months after I got my ‘job’ at the ISP, I built them a web site (you can still see it here) setup San Marcos’s first quake server, created Austin’s first streaming radio station (I registered mix947.com in February of 1996, and got the streaming working with a demo license of Real Media Server for BSDI and an old shop boombox), created a weekly user newsletter, started weekly user meetups at the shop, and even got involved with the local Internet Users Group at the library (which I ended up running).

You only do those kind of things if you’re in a space where there are no conventions or expectations. When there aren’t any streaming audio stations, setting one up with a 5 stream limit isn’t a deal-breaker. When all your users are early adopters you don’t need a marketing expert to write a user group email. You just do it. Luckily the ISP was run by Chad Neff, a great artist and stalwart defender of the user. He encouraged me to try things, and was my first great mentor in technology.

Hold on Passionately, but Loosely

I Fight for the UsersAn early, hard lesson to learn is when to let go. I didn’t let go of that job well, and though there were extenuating circumstances, and more people than just me were caught up in it, it made my life really messy for a few years. When you’re in the middle of the job, fight for the users as hard and as passionately as you can. If you aren’t creating things for someone, it’s a waste. Whether you’re knitting hats or writing tweets, you’re doing it for someone. Strive to make them as happy as possible.

Conversely, you have to know when it’s time to go. All things come to an end, and being able to sense that end and depart gracefully is a skill. Learn it. If you’re going into tech, read founder stories, especially the stories from founders who get kicked out. There’s a shift at each phase of a project or company life-cycle, from startup to growth and growth to long-term maturity. Finding out which phase you fit into best is important, as is being able to sense when that shift is coming.

Aside: Do you like to experiment, throw things together and see what sticks, with little heed for long term consequences? You’re probably startup minded. Do you like some stability, but enjoy seeing success build, working long nights to land the next client? Maybe growth is your bag. Are you risk-averse? Do you like long-term stability, dependable processes and maybe even enjoy corporate politics and intrigue? Then maybe you want a project in its mature phase.

Also, strive to recognize when things are heading for the toilet. There’s some honor in being the last one to turn off the lights and lock the door, and I’ve done it more than once, but it’s rarely the best thing for a career. Try and step back once in a while and assess things from the outside. Get some opinions from people you trust. Do right by your users, but recognize that not every situation is salvageable.

It’ll Be Embarrassing

Not a German design school
Not a German Design School

For a long time I had a vision for starting a web design firm like Vivid Studios, a bay area web design shop that had the mid-90’s Wired techno-punk aesthetic nailed. It was a techno rebellious company producing amazingly creative, cutting edge work for great clients, and I wanted to be just like that. Unfortunately I was in San Marcos, Texas, not San Francisco, California, and I didn’t know anything about running a business, much less a hip design business. I didn’t know Bauhaus from an outhouse, if you know what I mean.

I carried that dream around for a lot of years, wanting to belong in a group of smart, forward thinking creatives. The dream took a lot of different shapes, and matured as I did. The first attempts were… laughable. In 1997 I started doing business as 57th Street Productions (yes, we apparently offered ‘innovative thinking’ as a service), which in 1999 became 57th Street, Inc. 57th Street lasted a year and a half before ceasing to be.

Aside: A while ago I’d read something that said you can find a lot out about a person by how they view their youthful mistakes. People who think ‘look at me, I was so stupid’ versus people who think ‘look at me, I was so cute’. People who realize that youth and inexperience is a perfectly valid excuse for shortcomings are more likely to grow and be happy than people who judge themselves harshly. Don’t be down on your past. Everyone has been the fool. Don’t settle for that being the whole story, though.

When you read stories about Bill Gates or other tech luminaries starting companies in their 20’s and being wildly successful, what you don’t read is about the support networks they had that made it possible. You don’t hear about the people they knew who had business experience, the years they’d had access to computers in their teens, the contracts they’d gotten due to flukes. When you don’t know how to get from point A to point B in business, don’t assume you can just muddle through. Go out and read some business books. Realize that if you don’t know people who need your services/product/etc, you can’t make money. Realize that if you only have one of these clients and don’t have any way to find a second, your business isn’t really a business, it’s just a relationship. Go find people who run real businesses, and get them to teach you the ropes. Ask them how they find clients, especially if they’re in a business similar to yours (say, physical engineering services to technology consulting). If you can’t sell your product for more than it costs to make, again, no business. You don’t need an MBA, but you need to know how to balance a checkbook, forecast earnings, pitch a client, close a deal, and make a profit.

I ended up doing some things I’m not really proud of at 57th Street in the hope of forcing that Vivid Studios dream into reality. I made some bad decisions (hiring people for personal reasons, not diversifying the client base, not making enough connections), and the only reason we made it as long as we did was that it was hard not to make money in technology in the late 90’s. If you’d like to get a taste for my embarrassing phase, you can check out these two tours, one from my ISP days at itouch.net, and one from my days as 57th Street, Inc.

You’ll Get a Break

Cory and JonWhat seems to happen is that eventually, if you keep plugging along, you’ll get a break. It will almost always be a result of some risk you’ve taken, or avenue you’ve explored. If you’re well connected, I guess it could be a connection your parents or buddies have, but that wasn’t my experience. In 1997, after joining The WELL, I met Jon Lebkowsky. We got into an online discussion about FreeNets, something I was interested in from my connection with the San Marcos Internet Users Group, and ended up having lunch at the Waterloo Ice House. We ate at the Ice House because it was next door to Jon’s gig at the time, Internet Guy at Whole Foods Market.

Nearly everything that has happened since, I can trace back to meeting Jon. Jon was having some trouble with Whole Foods in-store kiosk system. They were Windows NT Workstation based PCs with touch screens that browsed an internal web site in a locked-down browser. They were always breaking, stores shipped them back to WFM Central, and they had to be fixed. Jon needed someone to do the fixing, and I took the job. Your break may not be glorious. For me it was a windowless room fixing and re-imaging Windows NT machines, but it was a foot in the door at a company that had real enterprise-level problems, and even better, I got in at a very unique time.

Don’t Be Afraid to Go Up

My time at Whole Foods, in retrospect, was very strange. I’m sure some people have had similar experiences in other places, but now that I look back on it, it was kind of crazy. I think, though my memory is a little foggy, when I started working contract for Jon on the kiosk project I was making about $15/hour doing run-of-the-mill PC maintenance. Over the next 3 years my rate ended up peaking at something like $150/hour, and I was on a 40 hour a week retainer. Somewhere near the end the CIO of Whole Foods Market asked me into her office and offered me the chance to rebuild their programming team, hiring whoever I wanted. I was… 22. So, it’s a weird story.

Whole Foods SelfieI think my experience at Whole Foods comes down to two things. One, the luck to be in the right place at the right time, and two, never saying no to a problem. When I started on the kiosk project I was just re-imaging systems, fixing ones that were broken, and shipping out the replacements. That’s $15/hour work. Eventually the vendor that was supplying our keyblock software (so you couldn’t get out of the browser and break the machine) disappeared, so I offered to write a new one. I’d never written Windows NT device drivers before (or really any C code), but you don’t know you can’t till you try. Once you’re maintaining source code you’ve suddenly become more than an IT tech, and I think my rate bumped to $35/hour.

Now comes the right place/right time side of the story. This was in 1998. The Internet was hot, E-Commerce was boiling hot, and all the sharp programmers who’d toiled away for years on awk scripts and maintenance software wanted to go do the hot new thing. Whole Foods Market started WholeFoods.com, and nearly all the programmers from inside of Whole Foods left to join it. This left a gaping hole in the company that was being filled by one person.

Simultaneous to this exodus I, too, was exploring the job opportunities at WholeFoods.com. They made me an offer for $35k a year, and after verbally accepting it, I drove over to Whole Foods to get some dinner. In the parking lot I ran into Mark Mills, that one guy holding closed the gaping hole in internal development. While swinging around a pole in the parking lot, Mark gave me my next big break. Come to work for me, he said, and I’ll pay you $85/hour contract full time. You don’t have to be great at math to know that’s a lot better than $35k/year, so I declined WholeFoods.com’s offer, and went to work for Mark. Sometimes the opportunities are obvious.

You Have Potential in Others Eyes

When I joined Mark on the programming team, I was not a great programmer. I wasn’t even an ok programmer, but Mark, like Jon and Chad, must have seen potential, so he gave me problems to solve, and let me solve them. He gave me advice, showed me some tricks, and let me do things how I needed to do them. Mentors like this are great, seek them out, cleave to them, and strive to be like that when you’re in a position of authority.

After a few months of building data exports, Mark left Whole Foods as well. And then there was one.

Again, this is a right place, right time story. I had web skills, sys-admin skills, network skills and programming skills, and was in a large company with no internal programmers. Over the next few years I was able to build a suite of web applications (job posting, CMS, inventory management, document management, etc), working directly with the teams who would be using them, without any real technical oversight. I like to think that I did a good job, but I suppose that isn’t for me to judge. I just know that they were still using some of those applications years later, and the people I worked with always seemed happy to see me.

WFM TMNOnce you get an opportunity to work on projects, it’s a chance to prove yourself and get experience shipping real product. During this phase I never had a project cancelled, I always delivered them on time, and I supported them myself. Strive to be the best, work professionally, and treat your users and customers how you’d want to be treated. You’ll make mistakes (always compress uploaded documents in a document storage system, your network storage admins will thank you later), but you learn from them.

Surprisingly, during this phase I even got called back in to WholeFoods.com (and later WholePeople.com) by Jon to build some integration software with Yahoo! Store, and managed to deliver in a few weeks what another consulting firm said wasn’t possible. This is your ‘don’t know it isn’t possible’ phase, enjoy it. Work your butt off, learn as much as you can, try new things. Responsibility comes next, and it’s a bear.

Out of the Garden

Eventually the gravy train ends. Whole Foods Market’s CIO offered me the job as lead developer, and the opportunity to hire anyone I wanted to rebuild the programming team. My life would have been completely different if I’d accepted, but I couldn’t in good conscience. I was 22. I didn’t really know what I was doing, but I knew I didn’t know what I was doing. I didn’t really want an employee gig. I turned her down.

The next few years heralded the popping of the dot-com bubble. I drifted away from Whole Foods Market as they hired programmers internally, though I kept maintaining the systems that ran the WholeFoodsMarket.com web site until they replaced the entire thing in the late 2008. From the time we launched it (on time) in 2000 to 2008, it was powered by the same Apache Server-Side Include based architecture, running on a single Sun machine.

Polycot PieAfter WholePeople.com imploded with the dot-com bubble, Jon Lebkowsky and I started talking about starting a web consulting company. Visions of Vivid Studios started dancing in my head. I even managed to rope my buddy Matt Sanders into joining us. Together we founded Polycot Consulting, and started learning all those business lessons the hard way.

Remember how I said that a business with only one customer and no way to find more isn’t a business? That was us at Polycot. We spent a lot of time in the wilderness, trying to find work in the post-dot-com rubble. It wasn’t easy. We learned a lot of lessons the hard way. A few of them:

  • You can’t pay your rent with leads, you can only pay your rent with paid invoices.
  • There’s a difference between the things you want to get the job done and the things you need to get the job done.
  • Doing cheap jobs for ‘exposure’ is a trap. You will end up just doing cheap jobs, and your customers will expect the world.  Our CPA once told us that Pro Bono work was a great way to get other work, but the other work will always be Pro Bono.
  • Corporations view the world differently than non-profits and mom-and-pops. Don’t ask a Fortune 500 if they want to pay $100 extra for a life-time license of some software you’re using, that isn’t real money to them.
  • You need someone who knows how to sell. You can evangelize a product, but you have to sell consulting.
  • Make a product, and make sure that everyone’s willing to put the time into it. Better yet, make a bunch of products. When you’re scraping by on hourly work it’s easy to say ‘this doesn’t pay, I’m not going to do it’, but look at it this way: Each of those products is a learning opportunity, and in consulting, if you don’t learn you die. One might even make some money.
  • Evangelize your successes. Write up each project that you do. Publicize the heck out of it. If you did something awesome and no one knows, it doesn’t matter.
  • Recurring income is what keeps consulting businesses afloat. Just because you, as a scrappy developer, think that support contracts are a ripoff doesn’t mean they are, and if they didn’t exist, most of the things you like wouldn’t, either.
  • Running a business is crazy hard, most of them fail, if yours doesn’t, good for you, but be open to the possibility that it should have.
  • Realize that you could very well be doing work in technology for the rest of your life. Take every opportunity to learn a new thing. The more you know, the more valuable you are, and in the end…
  • You are your product.

The Soft, Cozy Womb of Corporate Life

One upside to doing a bunch of projects for a bunch of people is that we met a bunch of other technology people. I did a few projects for Mitch Kapor (of Lotus fame), we had Matt Mullenweg in our office before WordPress got huge, I worked with the guy who designed Google+ on a project, and some guys we worked with are behind SB Nation, The Verge and Polygon. Once you meet smart people and show them you’re a decent sort of person, other doors start to open. These doors are sometimes soft, inviting, and open onto worlds of bureaucracy and 401k plans.

TechConOne of the last projects we did at Polycot before the founders went their separate ways was MindBites. MindBites is a video commerce platform, and after we built the prototype, we migrated the customer to a company called Squeejee for ongoing development work. A few years later, some folks from Squeejee would end up at Hewlett-Packard, brought in to spearhead HP’s push into the public cloud space. They would bring on Matt Sanders, and thanks to the good impression I apparently made, me.

I’ve been at HP for two and a half years, and I’m finding that a lot of the lessons I learned earlier still stand. Namely:

  • Look for a space where people believe in forgiveness over permission. Then do what you feel needs to be done.
  • Look for smart people and learn from them. Communicate. Converse. Network, even if it’s hard.
  • The people above you want solutions, so when you’re presented with a problem, come up with one, and do it.
  • People in the corporate world are used to passing the buck and bureaucracy They are impressed by responsibility and rapidly delivered solutions.
  • Take credit when it’s due, share it when it should be, make sure contributions aren’t overlooked.
  • Don’t let yourself get stuck. Corporate life can be a trap. A slow moving, slow progressing trap. Always be on the lookout for the next spot, the way to gracefully exit, the new problem. This counts double if you’re a startup phase person.
  • Many (most?) corporate projects get the axe eventually, some before they even ship. Don’t take it personally. Try to lead the inevitable downturn. Play from a position of innovation. If they want to kill it, be the person proposing the exciting new possibility.
  • Take every opportunity the company offers to learn, present, meet, train, etc. Just because you got a job doesn’t mean you get to stop hustling. Again, the cardinal rule is…
  • You are still your product.

Fill in the Gaps

One thing I’ve come to realize, the longer I’ve worked in tech, is that the knowledge space is huge. Enormous. There’s no way to know everything. There are entire fields you haven’t heard of, entire ecosystems that have existed for years that you know nothing about. Your job in improving your product (yourself) is to fill in those gaps as much as you can. It’s better to be a generalist than a specialist. It’s better to know two programming languages than one, and better to know three than two, especially ones that compliment each other, like Python, Javascript and Go or Ruby, Javascript and Node.

If you’ve focused on the frontend, do some backend tutorials. If you’ve done HTML and CSS, try Drupal or Django or Rails. If you’ve done databases and integration projects, do some front end stuff. Look at jQuery. If you’ve done just web stuff try loading up a server, setting up backups, and installing software. If you’ve done server stuff, try creating some HTML5 Twitter mashups. If you’ve only done sites for a small set of users, go big, pull down some giant Twitter datasets and start playing with R and Hadoop. If you’ve used imperative scripting languages, try functional ones. If you’ve mainly done P-languages or Ruby, try Lua or Go or TCL or LISP. Write a compiler. Do some computer vision projects. Hack on Arduino or the Raspberry Pi. Write an Android app. Go outside your comfort zone.

As to how deep you get with these things, here’s an arbitrary rule of thumb I just made up: Learn enough that you could give a 45 minute talk about it. If you’re single, learn a major new thing every quarter. If you’re married, every 6 months. If you have kids, especially little ones, every year. Adjust as you see fit.

Above all, don’t beat yourself up if you find yourself behind some imaginary curve. If you’re 35 and only know Java, that’s fine. That’s great! There’s tons to learn, and it’s going to be crazy and exciting and you’re going to look at technology in an entirely different way. If you’re 50 and think you’d really enjoy this, there’s never been a better time to learn, and it’s never been easier to get from nothing to a working product. Try one thing. Pick one of these things that interests you, and spend a weekend on it, if you can. Commit to just getting one thing working. If you can relate it to your job and do it on company time, all the better. If you enjoy it, keep going.

Life Without College

So, I may have strayed from my original point about college. There’s a maxim I’ve heard that goes like this: Your degree gets you your first job, and after that it’s all about the work you’ve done. For people who don’t go to college, the trick is getting that first job, and filling in anything you may have missed by not going to school.

Look for under-saturated specialties. It isn’t a great time to get into small business web design. That ship has sailed to custom WordPress themes.  If the web really floats your boat, get into Drupal, but don’t stay there forever.  Technology moves, albeit sometimes slowly.  Mobile development was ripe a few years ago, but making a profit in it is really hard.  It’s a good skill to have, but a hard market to compete in.  Look at things like RubyMotion, to get your feet wet.  There are opportunities in DevOps (a fancy word for programmers who deploy their own code into production), big data, personal and business clouds, personal analytics, and integrated Internet enabled devices.  There are always jobs to be had in enterprise software.  Tech companies introduce software to solve new problems, so look at the announcements that are getting a lot of buzz.  CloudFoundry had a lot of buzz, and now Docker is really hot.

Getting your first job:

  • Find something you feel excited about (programming, networks, server administration, HTML, design) and do a bunch of it. If you’re a lecture-learner, watch videos. If you need practical applications, ask people for ideas of projects. If you have collaboration skills, pair program.
  • Meet people. Go to Meetups. Join online groups. Listen a lot. Don’t be afraid to ask questions. Follow the rabbit hole down. Don’t be afraid of not understanding. The pieces will fit with time. You have to practice, though. You have to actually write code, create graphics, code web pages.
  • Share what you’ve learned. If you can teach it, maybe you’ve learned it.
  • If you’re programming, share your code on GitHub. If you’re creating videos, post them to YouTube and Vimeo (I partied with those guys once, they’re cool, but New York-trendy).
  • Ask for feedback, don’t expect it to be glowing. Don’t try and change everything, but internalize what you get. You’ve created something, don’t doubt yourself. The goal is to get better, not to be perfect.
  • Talk at meetups with people from companies you respect. Look for open doors, even if they aren’t exactly what you want. Expect to do a lot of hard work that isn’t glamorous and isn’t fun. It’s better to do less fun work at a company you love than cutting edge work at a place you hate.
  • Get some experience doing contract jobs, say, on oDesk. It will suck. You will hate it, but it will teach you about shipping code, supporting code, and dealing with clients.
  • Technology managers rarely care about the jobs you’ve had, and almost never care about what school you went to. They care about the work you’ve done. When I’m hiring now, education is nearly irrelevant. How you spent 4 years as an immature post-20-something is nothing compared to how you spent the next 5 or 10. Google seems to agree. Google has teams where 14 percent of the folks never went to college… Google!
  • Hierarchical academic environments still exist (HP Labs is really oriented that way, I’ve heard), and are probably places you want to avoid. Most places like this have a reputation for being so. If you ask around, you can probably get the skinny.
  • If the opportunity appears, jump on it.

Once You’re In:

  • Never turn down an opportunity to do something that excites you.
  • Find a mentor, someone who shares your interests and has experience. Don’t go crazy with their time, but don’t underutilize them. People who’ve been around for a while want to share what they’ve learned, but they want you to show initiative.
  • Find excited, cool people. If you’re in a corporate environment it can be easy to get depressed. Don’t be an antagonist. Be the person you want to hang out with. The future is wide-open and unknown. The present is temporary. Always be dreaming.
  • Take advantage of learning resources and your newfound credibility.
  • Watch for the phase changes. Be sure you’re where you’re most productive. Seek out managers who understand that personality fit, and strive to keep you there.
  • If you get hired with no prior tech experience, you probably aren’t going to make much money. Work on your skill set, network, and realize that you may need to join a different company to work your way up the salary ladder quickly. Learn to negotiate salary. Google it. It’s important.

Once You’re an Old Hand:

  • Share your knowledge.
  • Protect those below you.  You’re experienced and have tough skin, sometimes they don’t.  They need to know the realities, but they may not need to know how the sausage gets made.
  • Look for people who need mentors. Encourage them. Connect them with things you think will help them.
  • Take the time to learn about the people you work with. Everyone has a story. Maybe they didn’t get a CS degree. Maybe they’ve had similar challenges. Maybe they have an amazing background or skill you knew nothing about.
  • People come into technology with different skill sets There is no such thing as the complete programmer. Look for your own gaps and those in others, and figure out ways to fill them.
  • Lead by example. Do good work, don’t be a jerk, and treat everyone with respect.

A Few Last Notes

Getting Started EarlyIf I’ve learned anything in the last 15 years of being in technology, it’s that patterns repeat. I’m sure there will be changes in the future. Once you have kids, your desire to really jump on those transitions may start to slow down, but in the end they’re what a career is about. I’ve been fortunate to meet some very smart people inside HP who’ve been there for 30 years or more. They started out on calculators and are now in cloud. Maybe I’ll start in the web and end up in synaptic AI. Maybe that’ll be at HP, maybe it’ll be somewhere else. There’s always something new to learn, and there’s always that product of ‘you’ to work on.

If anyone reading this is looking for specific advice, needs a mentor, or would like some feedback, let me know. A lot of very gracious people have given me a lot over the years, and I want to pay it forward.

Dwarf Fortress, Facebook, Big Data and the Search for Story

Last night after driving home from the Austin PyLadies meetup, my wife sat in our driveway for 20 minutes listening to the end of an episode of WNYC’s Radiolab.  Later, after we’d headed to bed, she spent another 20 minutes retelling the story to me, minus Radiolab’s flourish and production.  The story was still interesting second hand, and comes down to this (I’ll wait if you’d like to go listen to the episode of Radiolab, I’m sure it’s excellent):

Two people discover hundreds of letters from WWII on the side of Route 101.  They’re from soldiers replying to a woman on the homefront.  The soldiers call her mom, but she isn’t their mother.  The two ask around, no one knows anything about them.  One of them, a creative writing professor, ends up using the letters as projects for his students.  He gives them a letter, and their task is to create a story around it.  A soldier, a woman stateside, an unlikely connection.  The other discoverer wants to track down relatives, she wants to uncover the truth.  She ends up discovering it, but he’d rather not know.  He wants the possibilities.

Even told second hand, the story stuck with me on a meta-level.  There aren’t a lot of things that would make my wife sit in the car in the driveway for 20 minutes listening to the radio, but a good story is one.  We love stories, we love it when they’re well crafted and well told.  But we also love the possibilities of them.  Sometimes we don’t want the truth, we want magic, we want to dream the dream of what could be.  Sometimes the truth can’t exist, and the closest we can get is a dim outline of it.  Sometimes the dream is better.

The Promise: Stories that Tell Themselves

A few days ago I ran across a blog post by Tynan Sylvester, a designer on the game Bioshock Infinite.  It’s all about the dream of simulations for game designers, how we think that by creating more and more complex systems, we might eventually build a system that is complex enough to manifest stories.  Austin Grossman’s latest novel, YOU, is about that, in a way.  The protagonist is a game designer and the antagonist is just a manifestation of some long-running game rules.  As game designers, we want to design games that surprise us.  That’s the ultimate payoff, to build a game that entertains you, and not just a twitch game that is enjoyable for its mechanics, but a game with stories compelling enough to sit in the car in the driveway for 20 minutes at 9 o’clock at night.

Lots of game designers have tried to do this. Tynan talks specifically about systems in early versions of Bioshock where the player would have to play autonomous bots (splicers, gatherers and protectors) off each other to progress.  They hoped that amazing, emergent gameplay would be the result.  In the end it didn’t work, and the game moments that they’d hoped would happen spontaneously ended up being heavily scripted.  Players crave story, but that story can’t be left up to their persistence and chance, especially when creating a commercial title.  In that environment, a great story has to be guaranteed.

Dwarf Fortress: Madness in Text Mode

There are a few notable exceptions to this principle, and they’re mainly smaller games driven by singular minded creators.  The best example of this is Dwarf Fortress, a massive and inscrutable simulation game where the the player takes on the role of an overseer, and the titular dwarves are simulated autonomous entities inhabiting the world.  Dwarves have names and hair colors, what Tynan calls Hair Complexity, things that add perceived simulation depth without effecting anything else.  (When was the last time you played an RPG where a plot point hinged on your hair style?)  They also have more integrated systems like hunger and social needs.  They have personalities, they get sad, and sometimes they go crazy.  The dwarves live in a randomly generated world, so your game isn’t like my game, and even my second game won’t be like my first.

Dwarf FortressDwarf Fortress has a very dedicated core following, and one of the reasons is that it really lives at the edge of apophneia, the experience of seeing meaningful patterns emerge from random data.  At the core of Dwarf Fortress is a collection of rules governing behavior.  A dwarf without food will eventually starve.  A dwarf without personal interaction may eventually go crazy.  Dwarves are scared of wolves.  Dwarves exist in a world generated fractally, a world that feels real because it mirrors patterns in nature.  Therefor, as more and more rules get layered on, and more and more people play more and more games and get better and better at creating experimental mazes for these digital rats to play in, stories begin to appear, or so we perceive.

Two of the most famous stories to come out of Dwarf Fortress games are Boatmurdered, the tale of an epic game played out by members of the Something Awful forums in 2007, and Bronzemurder, a beautiful infographic-style tale of a dwarf fortress and a terrible monster.  Go read it, it’s great.

Dwarf Fortress didn’t generate these stories, though.  People played the game, sometimes hundreds or thousands of times, and while gazing into the mandala of the game, they nudged and pulled the threads of the world and created stories based on the events that occurred there.  Dwarf Fortress isn’t a windup toy, it’s a god-game, and the players impact on the game world is more than negligible.  The stories generated there are as much created by the players as by the game.

I Fight For the Users

While my wife was out at PyLadies last night, I coincidentally watched TRON: Legacy.  It occurred to me as I was thinking about writing this post, that it’s a movie about this possibility: The dream of a world inside a computer, a world created by a brilliant programmer, a world that once set in motion can create stories, unexpected events and enthralling narrative.  The creator steps aside, and no longer controls the game from the top-down.  The creator becomes a god among men, watching things unfold from their level.

Tron: Legacy - Quorra

In TRON: Legacy, the magic of digital life comes in the form of Quorra, the last of the ISOs, Isometric entities that appear spontaneously from the wasteland of the computer.  Digital DNA, digital life.  Enough rules, enough circuitry, enough care and magic happens.  That premise is exciting, and to programmers it’s intoxicating.  For those of us in the digital generation, that’s the dream we live with.  That’s what we keep trying to make happen wherever we go and whatever project we work on, be it big data or software bots.

But the lone programmer, no matter how brilliant, and working for no matter how long, can only produce so much code.  Stories from one person only grow so far, only change so much, and rarely surprise and enthrall.  Dwarf Fortress as a dwarf isn’t a game most people would play.  It’s hard to see the overall story, and the game isn’t good at presenting it.  But if there were more players…

EVE Online: More Interesting to Read About Than to Play

If it’s possible (albeit insanely difficult) to have stories appear in a single player game, it must be easier for stories to manifest in a multi-player game, right?  Games like World of Warcraft have largely fixed, planned out stories.  It comes back to the challenge that Bioshock had, complex systems are exciting to designers, but players want immediate story gratification.  Complex systems take dedication to understand, dedication most players don’t have.  When new multiplayer games are announced they sometimes hint at players making a real impact on the world, but those systems usually fail to live up to the hype.  The latest game to promise this is The Elder Scrolls Online.  We’ll see if they can do it.

One game that does this and thrives is EVE Online.  EVE is a massively multiplayer online space combat simulation, one that spans an entire universe.  It’s possible to play EVE as a loner, but it’s also possible to align yourself with a faction, and have your small efforts merge with hundreds or even thousands of others to build armadas and giant dreadnaught ships, to control entire solar systems and even galaxies.  The designers and administrators of EVE take a largely hands-off approach.  They don’t want to kill the golden goose, so they design the game for balanced conflict, and let the players sort it out.

EVE-Online-Battle-of-Asakai-3Every once in a while something epic happens in EVE, either a massive fraud, an invasion a faction planned for months, or a random accident that led to a game-rebalancing war.  There are battlefield reports, and once the space dust settles, people start to put together a history, and an accessible storyline appears.  Here are a few great EVE stories.  More people probably enjoy the reports of epic battles in EVE through these stories than actually play the game.  To quote a MetaFilter comment thread: “This game sounds stressing as hell if you really play it and not just dither around. Fascinating to read about, however, almost like news from a parallel universe.

You could say that EVE is a computer program for generating stories, and in fact the’ve even made a deal to do a TV show based on player stories from the EVE universe.  Except again we find that that EVE isn’t the thing generating the stories, EVE is just a place where the stories happen.  To a player only experiencing the events inside the game it may seem mysterious and amazing, and it certainly is to those of us who read about the events afterwards, but it’s really just a sandbox.  People play pretend with enforceable rules, but you can’t separate a story that happens inside of EVE with the real life stories that happen outside of it: The scheming that happens on IRC or in forums, the personal vendettas, the flexible allegiances  and the real-world money that flows through the system.  There’s no way to watch something occur inside of EVE, and even if you had perfect clarity on everything that happened inside, have any way of knowing for sure what really caused it.  If you take away the players, the legions of dedicated fans scheming and plotting, you just have an empty universe.

Facebook and the Timeline of Truth

I think a lot of web developers secretly wanted to be game designers.  Becoming a game designer is difficult, there aren’t as many jobs and the hours are terrible.  Instead we build web sites, but we’re building systems too, and we want to tell stories.

I joined Facebook back in April of 2006.  I had a @swt.edu address from Southwest Texas State (now Texas State University) from an extremely brief stint (sub 1 day) as an IT staff-member, so I got in a few months before they opened it for everyone.  Getting into a new, exclusive social network is a bit like finding a new simulation.  We hope the software can tell us new stories, that it can make some sense of the data it has.  With Facebook the promise was that if it collected enough information about us, it could tell us that magical story.  That’s what Timeline was supposed to do.  Give Facebook enough photos, enough checkins, enough friend connections, enough tagged posts and it would be able to tell the story of our lives.

Facebook Timeline

In the end, though, Timeline doesn’t tell you a real story.  It reminds you of stories you’ve heard and experienced, but Facebook is only a dumb algorithm working with imperfect data.  It’s smart enough to target ads, but it can’t understand the meaning, and it can’t remix the data in really compelling ways.  It can’t be Radiolab.  Most of the time the prioritization it comes up with I just want to turn off.  Its attempts at story are so bad I’d rather use my own organic cognitive story filters.

With every new Facebook feature announcement, with Google+ or the next thing that processes all your activity, the promise is that the system can get better at telling those stories.  We want to believe it will happen.  We want to believe that a couple thousand web developers and a couple billion dollars could create a story machine, but I’m not sure it can.  I was reading an article about HP’s R&D budget the other day that said Facebook invests 27.5% of revenue in R&D, a larger percentage than any other company they tracked.  You can bet a good chunk of that is going towards the search for story, in some form or another.

Weaving a Web

I’d be remiss if I didn’t mention Weavrs at this point, since they are essentially digital actors that derive stories from the mess of social media.  Weavrs are designed specifically for apophneia, they produce content one step up from random, and rely on our desire for patterns to throw away the things that don’t fit.  We project stories on to them, and for a project with the limited resources that it had, it’s exceedingly good at it.

My weavr twin is posting about HP Moonshot servers.  That’s almost eerie, but it’s also posting about hockey tickets.  The story makes sense if I’m picky about the things I include, but it isn’t an internally consistent narrative.  The narrative is impressed on it by the people who see it, like reading digital tea leaves.  Your story of my weavr is different than mine.

With enough resources and time, weavrs might become a real story machine.  That’s a moonshot program, though, and I don’t know who’s going to step forward and make that happen.  Investment follows money, and right now the money is racing towards big data.

Autonomy: Billions and Billions

The lure of story, the promise of meaning from the chaos of data isn’t limited to games or the social web.  It’s the romantic beating heart of big data.  It’s the stories about Target knowing you’re pregnant before you do.  It’s what lured HP to spend $8.8 billion dollars more than it was worth to acquire Autonomy.

Autonomy’s main product is called the Intelligent Data Operating Layer, or IDOL (symbology, ahoy!).  They call the processing of information with it Meaning-Based Computing.  From what I’ve heard it’s certainly good at what it does, but while it promises Meaning from Data, and that promise separated HP from 9 Instagrams or 2,500 Flickrs, there has to be some apophenia at work here.  Just like watching solar system battles inside of EVE gives you a piece of the story and playing hundreds of games of Dwarf Fortress will result in games worth telling stories about, the system data is never the entire picture.

Screenshot_6_13_13_11_52_PMI really like Stephen Wolfram.  Stephen believes in the fundamental computability of everything.  While I love reading his blog posts, and I am interested in and admire his idea, I have to wonder how far the hyperbole is from actual execution.  Given enough computable facts and enough understanding about the structure of narrative, a perfect Wolfram|Alpha should be able to tell me stories about the real world.  But it can’t.  They aren’t even trying to approach that.  Wolfram|Alpha isn’t creating Radiolab.  They want answers, not stories.  You know what tells stories? Dirty, messy, all-too-human Wikipedia.

A Different Kind of Magic

My friend Matt Sanders works for a bay area company called Librato.  Librato is a big data startup, having pivoted from some other work to running a service that collects vast amounts of metrics and provides dashboards on top of it.  With Librato Metrics you can feed data points, set alert triggers, create graphs, and watch activity.  It’s big data without the prediction.  It promises no magic, but relies on our own.  It optimizes data for processing by human eyeballs.

The 3 pounds of grey matter between your ears is still the best computer we have, running the best software for deriving stories and making sense of data.  Librato works because it doesn’t try to be what it can’t.  Google Analytics tries to offer Intelligence Events, but more often than not, it can’t offer anything more helpful than that visits are up from Germany 34%.  You would think that by combining traffic source analysis with content changes and deep data understanding Google would be able to tell you why visits are up from Germany, but most of the time that basic percentage is the best it can offer.  It still takes that 3 pounds of meat to pull together the data and interpret it into a story.  While computers may be generating articles on company reports or sports games, they’re not creating Radiolab.

Wrapping Up

I think there’s still a lot of room for innovation here.  The Archive Project I dreamed of long ago is essentially a system for telling stories and discovering meta-stories.  Maybe someone will finally build it.  Maybe the next Dwarf Fortress will be a world that runs persistently in the cloud, a world where our games interact with other people’s games, where crowdsourced Hair Complexity snowballs until you can get lost in the story if you want to. A game where if you want to turn off a random path and follow it down to the river you’ll find a fisherman who will tell you a tale interesting enough to make you sit in your car for 20 minutes, enthralled by a narrative.

Maybe the framing of a story is what big data needs to become personally relevant.  Maybe that’s its magic trick.  Maybe narrative is the next great big data frontier.

Future Past


I sometimes wonder about the generation of kids growing up today, in this big data, analytic-driven, always-on world.  I wonder how they will embrace it, like we embraced computers and connectivity.  I wonder if they’ll have the ability to hear the prognostications of the computer, to listen to the story from the machine, and consider it a kind of truth.  To internalize it, but also keep it separate.  To know the machine knows a truth, but not necessarily the absolute truth.  Maybe that will be their power, the thing they can do that those of us from the generation before can’t. Maybe that is where the dream finally comes true.

The Personal Cloud: Innovation Happens at the Edges

Personal CloudA couple of days ago I was cleaning up my recently migrated server, and ran across a directory filled with a couple thousand text files and some perl scripts.  The directory wasn’t obviously named, but after some poking around I realized I was looking at the remains of a small consulting gig from 4 years ago.  It was a pretty straightforward data mining job: There was a bunch of information on a public web site that an organization needed.  Filings or grants applications or something like that.  I needed to download it and remix it into a spreadsheet.  What should have been a really easy spider and collate job ended up being complicated by the fact that said web host had a rate limiting module setup, so no IP address could grab more than 10-20 pages every hour.  There were thousands of them.

If this problem sounds familiar, it’s similar to what Aaron Swartz was doing, and the problem that he was trying to overcome when he snuck that laptop into an MIT closet.  In my case there was no login or private, privileged access, and I was running all this stuff in the middle of the night as to not inconvenience anyone else, but the problem remained: If I’d followed the rate limiters desires, it would have taken weeks or months to grab the data.

I ended up getting around the rate limiter by using something called Tor, The Onion Router.  Tor works by sending your traffic through a distributed network of hundreds of other participants computers, anonymizing your physical and digital location in the process.  For me, that meant that I could download all the files in 15 minutes or so in the middle of the night.  For other people it means posting to Twitter or accessing dissident web sites from Syria or China or where-ever.

Running across these files reminded me of something I’ve been thinking about for a while: That what the Personal Cloud really needs to take off is an immediate problem-solving use case, and to find useful examples, we might want to look in the grayer areas of the internet.  We can talk about companies bidding for our orders VRM style or Internet of Things devices dumping metrics into our personal data warehouses, but both of those things are going to require a lot of supporting infrastructure before they’re really viable.  If you want to get a lot of people excited about something today, you solve a problem they have today, today.  And that brings me to the edges…

The Edge: Where Innovation Happens

One common aphorism shared by those in technology or innovation is that new things develop at the boundaries.  Change and chaos happens at the edges, it happens at the borders, where things mix and intermingle.  Here’s the MIT Media Lab’s Joi Ito talking about it, for instance.  MIT is a large, stable organization.  Businesses are large, stable organizations.  The Media Lab is where they meet, where they cross-populate and where the friction in developing new ideas is reduced as much as possible.  The same can be said about border towns.  New York City is an American border town.  It’s the edge between our country and a whole bunch of immigrants, both old and new.  The mix of ideas and talents and experiences creates new things.

Joi Ito: Innovate on the Edges and Embrace… by FORAtv

A lot of the innovation that happens on the edge happens in the gray area outside the strictly legal, or deep in the illegal.  Across our southern border we have very advanced drug and gun smuggling tunnels, complete with ventilation and electricity.  Neal Stephenson’s last book REAMDE was largely about northern border smuggling.  Chocolate, toy filled Kinder Eggs are illegal in this country, so people smuggle those in.  I brought some back the last time I went to Mexico, and some friends brought back a whole carton when they went to Germany recently.  In Gaza they even have KFC delivered by tunnel:

Given that innovation happens at the edges, that people solve their problems at the edges using interesting methods, and that the Personal Cloud needs some need-driven use cases in order to flourish, I think it’s useful to look at some of the ways people are using things like the Personal Cloud already for dubiously legal purposes (though the legality they’re avoiding isn’t always our own).  Perhaps by digging into what makes them compelling, and how their developers have solved those problems, we can learn something about developing Personal Clouds for everybody.

Some Personal Cloud Definitions

When looking for products that fit the Personal Cloud mold, I’m specifically looking for interesting uses of on-demand computing and networking.  Especially things that don’t inherently scale beyond the individual, either due to privacy concerns, the need to be distributed, or some other unique aspect of the approach.

A job that only takes 10% more time to run for another person isn’t a good candidate for a personal cloud, because the economy of scale is going to keep it expensive.  Running your own mail server is a bad idea these days, because your data and address can be portable (with IMAP and a personal domain) and running the spam filtering and staying on whitelists is hard.  It’s a lot better to register your own domain and let a trustworthy third party do it.  I should mention that Phil Windley has a good post about IMAP being a proto-Personal Cloud protocol, if you haven’t read it.

So, with that said, let’s look at some examples…

Tor: Anonymize All the Things

Tor OnionSo back to Tor.  Tor is built as a distributed, self-organizing network.  There are Tor nodes that you connect to, the address for which you get either by getting passed an IP address on the side, or by looking one up publicly where that won’t get you thrown in prison.  Once connected to the Tor network your public internet traffic is bounced through the network of Tor nodes in a randomized, encrypted way, and eventually finds its way onto the public internet through Tor Bridges.

The people who run Tor Bridges are paying for your traffic twice, because your connections come into their machine and then out again.  Running Tor Bridge is a labor of love, done by people who believe in anonymity and freedom of speech.  It doesn’t pay, but knowing that a political dissident somewhere can speak freely about an oppressive regime has a karmic payoff.

A few years ago Amazon’s EC2 cloud computing service started offering a free micro level of service.  You could sign up and run a really small cloud server for development or testing without paying.  It didn’t cost Amazon much to run them, performance wasn’t really great, but it got people onto their platform.  Usually people start up Amazon provided server instances to install software and play around on, but the folks behind Tor realized that they could create a pre-configured server image with the Tor Bridge on it, and let people spin those up in Amazon’s free usage tier.  They call it the Tor cloud.  You still pay for bandwidth, but if you bridge 15 Gig of bandwidth a month, your bill will only be around $3.  It’s less than the price of a latte, and you do something good for internet freedom.   You don’t have to know a lot about the cloud to set it up, you just register for Amazon Web Services, pick the image, and hit Start.  The images are pre-configured to download software updates and patches, so there’s virtually no maintenance work.  Just the kind of simplicity you need for a Personal Cloud feature.

Back It Up Or Lose It: The Archive Team

Archive TimeI’ve harped on our tendency to not take care of the things we create before.  Web sites get acquired and shutter within months.  Promises are made that users will be able to export their data, but promises are made to be broken.  Fortunately for us, there’s a group of archivists led by Jason Scott called Archive Team.  Archive Team scrapes sites that are destined for the Internet trash heap, and uploads the data to the Internet Archive.  So far they’ve archived sites like Apple’s MobileMe homepages, Yahoo Groups, and are currently trying to grab as much of Posterous as they can before Twitter drops the axe.  This may sound pointless till a few years after a company acquires and then shutters the site your mom or sister blogs at or posts family photos to, and you realize there’s no way for you to get that stuff back.

Archive Team runs into a lot of the same issues I had around rate limiters.  Yahoo! and Twitter don’t want them slurping down the whole site, they want to take the engineering resources off those projects and let them die a quiet, cost-cutting death.  To get around this, Archive Team offers a virtual machine, the Archive Team Warrior.

The Archive Team Warrior is a distributed but centrally managed web spider.  The Archive Team central server slices the archiving work up into little chunks, and the Warrior on your computer asks the server for some work to do.  The central server gives it a small to-do list of URLs to fetch, and the Warrior starts downloading those until it hits the sites rate limit.  Any data it can download, it sends back to the Archive Team server for bundling and uploading into the Internet Archive.  Then it waits and retries until the site will let it back in.

Warrior ScreenshotThe Archive Team manages the projects, and the Warrior presents a simple web interface where you can tweak a few settings and track how you’re doing.  Most importantly, it’s hands-off.  You can set it up once, and let it run in the background forever.  It manages its own software updates, and you can tell it to work on whatever the Archive Teams priorities are, and ignore it from then on.  If you have a PC sitting around that you don’t use a lot, running the Warrior is a nice way to give back to the Internet that’s given us so much.  It’s good karma, and it’s easy.

Pirate All the Things: Seedboxes

So far we’ve talked primarily about projects which give good karma, now let’s talk about a project that is often used for… not so good karma.  In 2001 the BitTorrent protocol was introduced, allowing for a (then) secure way to share lots of files in a bandwidth-optimized fashion.  Users get pieces of a file, trackers know who’s downloading the file at any one time, and clients cooperate to distribute the pieces as widely as possible.  When you’re downloading a file from BitTorrent it’s entirely likely you’ll be downloading chunks of it from people who don’t have the entire file yet, and likewise you’ll be sharing parts of the files you’ve downloaded with other people who don’t have those pieces yet.  By working this way everyone gets it faster.

Not Sure if Network Is Busy Or If They're On To MeWhile BitTorrent might have been secure once, it’s now entirely likely that your ISP knows what you’re downloading, who you’re downloading it from, and what you’re sharing back.  They can look at payload sizes, the trackers you’re talking to, traffic bursts, and pretty reasonably reconstruct your activity.  If they’re the MPAA or other pirate-hunting groups they can even run their own clients and integrate themselves into the network.  Running a BitTorrent client from your home computer and downloading anything remotely illegal is like asking the bagger at the grocery store to help you out with your shoplifted goodies.

So let’s say you’re sharing something that you think should be legal but isn’t, or you’re trying to use BitTorrent for a legal end, like sharing a bundle of book materials or distributing an Operating System or a big chunk of GeoCities and don’t have the bandwidth at home to support it.  (Or, sure, you could be downloading Iron Man 3.)  This is where something called Seedboxes come into play.  A Seedbox is a server at an ISP somewhere that just runs a BitTorrent client.  You can use them to get your torrents out to a bunch of people really fast, or you can use them to download files that you wouldn’t be comfortable with downloading to your home IP.  You can even buy them in another country, increasing the difficulty of tracing the traffic back to you.

Seedboxes are managed servers, you don’t install software updates on them, the provider does that, but they likely won’t give you much in the way of customer support.  Lots of them use a Web UI called ruTorrent, an open source frontend for the rTorrent BitTorrent client.  You don’t SSH into these machines, you probably don’t even have a server login, but you can use the web UI, and conduct your business in the cloud.

In this way ruTorrent Seedboxes are a perfect prototype for our Personal Cloud.  The providers don’t watch the servers or monitor their quality.  Privacy is implicit when you’re doing something at the edge of legality.  What they don’t know won’t hurt them as much when Interpol comes calling.  The web UIs are built for self-service.  You have a login, but the web UI is your entire management plane.  rTorrent has an Android front-end, but most people likely manage them through the web.  There isn’t any software on your home computer, just a username and password to a web site somewhere.  The data’s yours, and if you wanted to shove it sideways into a cloud storage provider, you probably could.

Points of Presence: The Personal VPN

SpoilersAs an addendum to these offerings, a sort of post-script on the idea of exploiting technologies at the edges for personal gain, I’d be remiss if I didn’t mention personal VPNs.  Tor’s good for anonymity, but what if you just want to appear like you’re somewhere else.  Say, for instance, somewhere the new season of Sherlock, Doctor Who or Downton Abbey is available for streaming 6 months or a year before it comes to your country.  (Or vice versa, where we get new episodes of Mad Men a year before they do.)  What do you do then?

The same technology that your company uses to securely connect you to your corporate network can be used to make you appear to be in the UK, or the US Midwest, or Japan, or wherever else the content is region-limited.  You run the software (likely built-in to your Operating System), and connect somewhat securely to a computer in some other country or even continent, and all your internet traffic appears to come from there.

A few years ago I was in Mexico over Christmas, and there were some really good deals on Steam’s Holiday Sale.  I have a US account, with a US billing address and a US credit card, but I couldn’t buy anything because my computer was with me in Mexico.  I ended up installing a bunch of software on one of my servers and setting up a VPN to it, just to buy some cheap games.  These days I could just plunk down a few bucks and be good to go, and a lot of people do.

A Few Learnings Lessons Learned

Users have problems, and will go to considerable lengths to solve them.  None of these services are as easy as they could be, either because they’re niche offerings (Tor and Archive Team) or because of their dubious legality (Seedboxes).  ruTorrent is a lot easier to use than it probably was, but it still isn’t as easy as using the Netflix or iPlayer iPad apps.  The Warrior is a 174 meg download that requires installing Virtualbox on your computer.  The Tor Cloud Bridge requires signing up for Amazon Web Services, and navigating their UI.  To get a VPN provider or Seedbox requires research, dealing with a company that might not be entirely legit, and really falls in the class of early adopter technologies.

Even though all this stuff is hard to use, people do it.  Seedboxes and private VPNs give people things they want.  You may not have known that you wanted to watch the new season of Dr. Who before it comes out in the US, but once you know you can, you’ll go to some pretty extreme lengths to make that happen.  Motivation can be powerful, and people will overcome serious technical hurdles if they’re properly motivated.

So looking at these examples, we can see that a Personal Cloud app really needs to offer 3 things:

1. Motivation: It needs to solve a real, immediate problem.

2. Self-Service: It needs to be super-easy to start using and offer a familiar, understandable interface.

3. Hands-Off: It needs to have software updates and easy maintenance built-in.

Any Personal Cloud offerings that don’t check these boxes may get some niche use, and may excite developers, but they aren’t going to start climbing up the adoption curve.  As you build your Personal Cloud app, keep these things in mind.  Users have needs we can solve, and we can empower them, but our solutions need to be compelling, simple to use, and simple to maintain.

Security Through Isolation

Yellow SubmarineThey say no good deed goes unpunished.  In internet hosting, that’s almost always the case.  For the last fifteen years I’ve had servers that I’ve given friends accounts on.  At first they were co-located machines I built by hand, then leased servers, and now cloud VMs.  I hosted friends and family’s blogs, sites for activism causes that I or friends believed in.  I’ve even had a web site of a well known Silicon Valley venture capitalist on there.

Unfortunately whenever you do that, especially whenever you hand out accounts or host web applications that people were once enthusiastic about but then moved on from, security is going to become a problem.  A few months ago while doing maintenance on the machine I noticed that an account for someone had been logging in, except it shouldn’t have been, since I created the account while trying to troubleshoot a problem that we solved another way.  But there it was, in the last login log.  Digging into that directory I realized that the password had been simple (in the heat of troubleshooting you don’t always make the best decisions for security), and someone had brute forced the SSH login.  The machine had been compromised and used as an IRC bot host.  How very 1997.

Today I decided to migrate between cloud providers.  While I could host all this stuff for free at HP Cloud, but I do some dangerous stuff in the context of my account, and it’s nice to have a stable VM elsewhere.  It’s also nice to see what the competition are up to.  I’d been hosting this VM at Rackspace ever since they bought my preferred VM provider, Slicehost, but while poking around pricing I realized I could cut my monthly bill in half if I migrated to Linode.  I’ve admired Linode’s geek-friendly control panel, ever since I tried it while designing the beta versions of HP Cloud’s.  I was also on an ancient Ubuntu 9 version at Rackspace, and this would be a good opportunity to upgrade the OS and software.

After copying all the home directories and web sites over, I did a last pass to pick up any straggler processes.  These usually live in cron jobs, so that’s where I went looking.  Lo and behold, an account I’d setup for a friends mom to host her business web site had been compromised at some point.  Another bot.  Joy.

Fortunately her web sites had long since been migrated off the server, so I was able to disable her account (and remove the stashed authorized_keys file with a bot installer in them) and a bunch of others I knew wouldn’t be used, but it really goes to show how vulnerable these machines can be.  Who knows how they got her password.  It might have been an easily crackable password, it might have been a web script compromise, it might have been an email exploit.  More than a few of these usernames and passwords are sitting in mailboxes or in saved FTP connection files on easily crackable machines.

Two weeks ago I got an email from a former client.  We built a pretty complex web site for her in 2003, lots of bells and whistles.  It’s held up pretty well, but it hasn’t had any serious maintenance work in a lot of years.  She’d gotten a call from the FBI, saying that data from her web site was circulating in Russia.  Fortunately it was just an exported mailing list, not encrypted passwords or other secure data.  In her case I think one of her employees had either an easily guessable password, or a trojan was installed on her computer that logged her keystrokes.  How do you guard against the guardians?  Nobody was thinking of two-factor authentication for small business web sites in 2003, but the next time I build one, I sure will be.

Sharing accounts on a machine, or having admin accounts into a web based system is an inherently insecure thing.  The more keys there are to a lock, the more likely someone you don’t want to have one will get one.  I created user accounts on our shared server because that’s how you did it, back in the day.  Create a user account, setup a directory for the web site, add a database for them, and let them go.  Now we have linux kernel exploits that let anyone with user level privileges become superusers.  Adding random accounts to systems and handing out the passwords is an insane thing to do.

So the only hope we can have of having any kind of security is by shrinking the permissions scope down.  When everyone has user accounts on a machine, that entire machine is vulnerable.  When everybody has a small VM, only that VM is vulnerable (usually).  Even better, give them a single-process Linux Container, like those managed by docker.io, and suddenly they don’t even necessarily need to manage dependencies anymore.

I’m sure docker has its own set of security issues, but hopefully we’re more cognizant of them now.  Don’t create unnecessary user accounts.  Use password protected SSH keys.  Don’t re-use ssh keys.  Keep your dependencies up to date.  Watch the security mailing lists.  It really starts to sound like something the hosting provider should be doing…

So I think there’s a real opportunity here for a trusted IaaS operator to create a generic Linux Containers As A Service offering.  Push down one level from VM into Process.  Bring your own docker image, buy a set amount of RAM (say, 128 meg for a big PHP or Python process) and bill by the minute. Route them inside of the machine through some kind of nginx or go based proxy, like CloudFoundry does, but a little less specialized.  Something between CloudFoundry and an IaaS VM.  Upgrades in CloudFoundry are a pain.  If I could just shuffle a docker.io image around, that’d be way easier.  Oh, and don’t sign up for too many hosted services.  Each one of those you use is like another shared account, and the more you share your data with, the more likely it is it’ll be exposed.  Build small, build focused.

So back to security.  This is a plea to all those who have friends who’ve given them accounts on servers, or people who run servers and create accounts for friends.  I know the complex password requirements are a pain at work or on bank web sites, but they’re really even more important in less maintained environments.  Nobody’s watching that shared server, keeping it water tight is a shared responsibility.  If someone creates an account for you, change the password immediately.  They won’t remember to go delete it if you end up not using it, and if they set it to something simple, there’s a good chance someone will be able to brute force it.  Don’t store passwords in plain text anywhere.  Don’t email them to people, or have people email them to you.  You’ll be happier in the long run if you don’t.  Use best practices, and save us all some heartache.