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42 admissions

One. So here's the deal: I didn't get to do a birthday post this year because it was the day after the attempted coup, and it just didn't feel right at the time. We're still in the aftermath - it's been a little bit over a month, and the impeachment trial is winding down - but I feel like there's been enough room now.

The thing is, "42 things I've learned" feels like a thinkpiece, and that's not really what this space is about. There's a gaping chasm between "here's what I'm thinking about" and "I! Am! A! Thought! Leader!", and I don't want to intentionally be in the second camp.

Instead, I like the idea of admissions: things I got wrong, or feel uncomfortable about, or that wouldn't ordinarily be something that most people would want to tell other people. It feels human. In the midst of the pandemic and all these other things, being human - creating community by dropping our masks and sharing more of ourselves - is all we've got.

Two. Lately I've started to tune out of long Zoom meetings, and I'm beginning to wonder if people mostly just want to have them because they're lonely.

Three. I sometimes wonder if I should be intentionally trying to build a personal brand. Some people are incredibly disciplined with how they show up online: their social media personalities entwine with their websites and mailing lists as a product; a version of themselves that they're putting out there as a way to get the right kind of jobs or to sell something later on.

That's not what I'm doing. I'm putting myself out there for connection: as one human looking for like-minded humans. That's what the promise of the internet and social media always was for me. It's not a way to sell; it's a way to build community. We have an incredible network that links the majority of people on the planet together so they can learn from each other. Using that to make a buck, while certainly possible, seems like squandering its potential. We all have to make a buck, or most of us do. But there's so much more.

The more of us we share, the more of us there is to connect to.

Four. Somehow I have all these monthly costs that I didn't have when I was younger. They just grow and grow; I feel like I'm Katamari-ing things I have to pay for. Each bill is like a tiny rope, tying me down. Everyone wants money.

Five. I took forensic medicine in my second year of university. My Director of Studies thought it was a terrible idea: I was a Computer Science student, and for reasons that I don't think stand up to sense of reason, the British system discourages breadth of knowledge. He was this fierce, Greek man who yelled at me on a number of occasions, once because I dared to arrange an appointment with him, which made me anything but more inclined to listen to his advice.

Anyway, despite his objections, I took forensic medicine for a semester. The truth was, I still wanted to be a writer more than I wanted to be a computer scientist, and I figured it would be useful knowledge for some future detective novel. (That's how I chose a lot of my formative experiences: is this something I can write about?) The class gathered several times a week in old, Victorian lecture halls, where the Edinburgh Seven had sat over a century before and learned about how to piece together the facts of a crime from the evidence found in its aftermath.

The most important thing I learned in forensic medicine was Locard's exchange principle: every contact leaves a trace. In the context of a crime, the criminal will bring something to the crime scene and leave it there; they will also take something away with them. However small, both scene and actor will be changed.

Years later I would read another version of this in Octavia Butler's Parable of the Sower, which starts with the epigraph: All that you touch you change / All that you change changes you. The root of the idea is the same. Nobody comes out of an interaction unchanged by the experience.

That's the promise of the internet for me: every contact leaves a trace. All that you touch, you change. The internet is people, the internet is community, the internet is change itself.

Six. I spent my adolescence online. I got my start on the internet on a usenet newsgroup, uk.people.teens, where you can still find my teenage posts if you search hard enough. We used to meet up all over the country, hopping on public transport to go sit in a park in Northampton, Manchester, or London.

I met my first long-term girlfriend, who is still one of my dearest friends, through this group. Even now, thousands of miles away, I talk to these people every single day. I'm lucky to know them, and it shaped me inexorably.

Virtually, I also met Terri DiSisto, the alter ego of a middle-aged assistant principal in Long Island who solicited minors for tickling videos who later became the subject of the documentary Tickled (which I still haven't seen). And decades later, I learned that there had been a pedophile stalker in the group. I guess, on balance, I was just lucky.

Seven. I sometimes lie in bed and think, "I have no idea how I got here." I mean, I have all the memories; I can recount my path; I intellectually can tell you exactly how I got here. Of course I can. But I don't always feel like I had autonomy. I feel like I've been subject to the ebbs and flows of currents. I'm just doing the best I can given the part of the vortex I find myself in today.

Eight. While I was at university, I accidentally started a satirical website that received over a million pageviews a day.

Online personality tests were beginning to spread around blogs and Livejournals. They ran the gamut from the kind of thing that might have run in Cosmopolitan (What kind of lover are you) to the purely asinine (Which Care Bear are You?). So one evening, before heading off to visit my girlfriend, I decided to write Which Horrible Affliction Are You?. It was like lobbing a Molotov cocktail into the internet and wandering away without waiting to see what happened next. By the end of the weekend, something like a quarter of a million people had taken it.

So I followed it up and roped in my friends. We slapped on some banner ads, with no real thought to how we might make money from it. MySpace approached me with a buy offer at one point, and I brushed it off as someone's practical joke.

The tests were fluff; a friend, quite fairly, accused me of being one of the people that was making the internet worse for everyone. The thing that was meaningful, though, was the forum. I slapped on a phpBB installation, and discovered that people were chatting by the end of the same evening. Once again, friendships flourished; we all met people who would stick with us for the rest of our lives. We all cut our teeth seriously debating politics - it was the post-9/11 Bush era - as well as more frivolous, studenty topics like food and dating.

There was a guy who claimed to be based out in Redding, California, who was really into Ayn Rand, presumably as a consequence of his own incredible selfishness. Another guy (who IP logs told me logged on from Arlington, Virginia) we constantly trying to turn people over to conservatism. While the former was just kind of a dick, I came to think the latter was there as part of a bigger purpose. Our little forum was on one of the 1,000 most popular sites on the internet, after all. I still quietly think some organization wanted to seed a particular ideology through internet communities, although I have no way to prove it.

All that you touch, you change. All that you change, changes you. Every contact leaves a trace.

What if someone intentionally designs the contact and the trace?

Nine. I feel like I'm constantly living in playlists of musicians I used to enjoy, without meaningfully adding to them. What's new? What will pull me in new directions? What should I care about but don't know about yet? I don't know how to look effectively. I do know that the curated playlists, the ones created by brands looking for engagement, are probably not the way to discover what people really like.

My sister is much better at this (and many things) than me: her radio show, The Pet Door Show on Shady Pines Radio is full of new music. In this and lots of ways, I wish I could be more like her.

Ten. Despite everything, I still hold onto this really utopian view of what the internet could be. Whenever people from different contexts interact, they learn from each other. The net effect of all this learning, all these interactions, could be a powerful force for peace.

It's quixotic, because it just hasn't played out that way. At least, not always. The internet empowered genocides and hateful movements; it memed a fascist President into power and convinced millions of people that Democrats are pedophiles. It made a set of people incredibly wealthy who aren't meaningfully different to the generations of wealthy people who came before them.

The thing is, even with all this in mind, I'm not willing to let go of its promise. I don't want to let go of open communities. I fundamentally want someone in the global south to be able to log on and chat with someone in Missouri. I fundamentally want someone who is homeless to be able to log on at their local library and keep a blog or jump on Twitter. I want those voices to be heard, and I think if equity is shared and those voices really are heard, the entire world is better off for it.

The alternative is to be exclusionary: wealthy Americans talking to other wealthy Americans, and so on. It's socially regressive, but more than that, it's completely boring. The same old, same old. I want to meet people who are nothing like me. We all should.

We need to embrace the openness of the internet, but we need to do it with platforms that are designed with community health and diversity in mind, not the sort of engagement that prioritizes outrage.

I'm not sure how we do that. It will be hard. But I'm also sure that it can be done.

Eleven. I know of at least two separate people who secretly lived at the accelerator while they were going through the program because they were homeless at the time. I don't know what that says about hope and possibilities, but it says something.

Twelve. The rhetoric about misinformation and disinformation - "fake news" - scares me more than it seems to scare most people. I'm worried, with some grounds, that people will try and use this to establish "approved sources" that are automatically trusted, and that by default other sources will not be. The end result is Orwellian.

That's not to say that some speech isn't harmful and that some lies can't be weaponized. Clearly that's true. But it would be a mistake to back ourselves into a situation where certain publications - which in the US are dominated by wealthy, white, coastal men - are allowed to represent truth. What would that have looked like in the civil rights era of the fifties and sixties? Or the McCarthy era? Or during the AIDS epidemic?

The envelope of truth is always being pushed. It needs to be. The world is constantly changing, and constantly changing us.

I think the solution is better critical skills, and it could be for the platforms to present more context. Links to Fox News and OANN and disinformation sites in Macedonia absolutely need to come with surrounding discussion. Just, please, let's not lock out anyone who doesn't happen to be in the mainstream.

Words are dangerous: they can change the world. There will always be people who want to change the world for the worse. And there will always be people who want to prevent us from hearing other peoples' words because they would change the world for the better.

Thirteen. When I was in high school, I had a crush on this one girl, Lisa, who was in my theater studies class. I thought she was amazing, and I really wanted to impress her. I imagined going out with her. In retrospect, I think she might have liked me too; she would often linger to talk to me, and find innocuous ways to touch me on the shoulder as we were saying goodbye. Maybe she didn't like me like that; I wouldn't like to say for sure.

But she was far cooler than I was, and when I spoke to her, I would clam up completely, in the same way that I'd clam up completely when I spoke to anyone I liked. I'd lose my cool and start trying to nervously make jokes. By the end of high school, the shine had clearly come off, and it was very obvious that Lisa didn't like me at all. There was nothing really wrong with me, but my anxiety made me into someone worse than I was.

I was so scared that she wouldn't like me that I became someone she wouldn't like. It wasn't a fear of rejection; it was an outright assumption that she wouldn't like me in that way, because why would someone? And that assumption became a self-fulfilling prophecy.

Throughout my life, anyone who liked me practically had to knock me over the head and drag me back to their cave. My history is of being completely oblivious, or scared, or both, and sometimes changing into something I'm not because I nervously think that this is something other people want.

Fourteen. This is true on its face, but it's also a parable.

Fifteen. Another girl I used to like, and knew it, explained to me that she wanted to date someone else because his house was nicer. Later, her dad told me, about where my family lived, "you'd have to be crazy to live there."

For a long time - decades - I wanted to be richer, better. I know those things are not the same. But I wanted so badly to be someone I wasn't.

Sixteen. Talking about the past is a vulnerable thing to do. Talking about people who I used to like is a particularly vulnerable thing to do. And I need to acknowledge the imbalance here, speaking as a man. In a patriarchal society, I have a power that, while I didn't ask for it, I nonetheless can't avoid, or shouldn't pretend doesn't exist.

All I can say is: I genuinely wish nothing but the best for both of them.

The reason I bring up these stories is this: I wish I hadn't spent all that time and energy wishing I was someone else. And we all have our motivations; the chips on our shoulders that drive us.

Seventeen. My utopian ideal for the internet - or rather, my utopian ideal for people, enabled by the internet - led to me founding two open source projects, which became two startups. The first, Elgg, was a community platform. The second, Idno (which became Known), was a way to self-host a feed of any kind of content authored by any number of authors.

I genuinely don't know if I did it right. Or, to put it another way, it's not a given that I got it wrong.

I'm not a born fundraiser. I didn't set out to make money, and it's pretty much my least favorite thing to try and do. What I love is learning about people and making things for them, and then watching them use those things to great effect. I want to keep doing that, and I want anything I make to keep existing, so I want to raise money. But it's hard and painful, and I don't really know if investors buy into what I'm saying or if they think I'm an idiot.

What you need to do, I've realized, is put as much of yourself out there as possible and hope that they see value in that. Trying to turn yourself into something people see value in backfires. Even when it works, you get trapped into being a version of yourself that isn't true.

Eighteen. I left Elgg because the relationship with my co-founder had become completely toxic.

"It's funny we're co-founders," he would tell people, "because we would never be friends." True enough.

Nineteen. When I left Elgg, I had a pretty ambitious idea for a way to create crowdsourced, geographic databases. You could create forms that would record geodata as well as anything else you wanted to capture, so you could send people out in the field with their smartphones to do species counts, or record light pollution, coffee shops with free WiFi, fox sightings, or anything else you wanted to do. The web had just added the JavaScript geolocation API, and iPhones had GPS for relatively accurate location recording, and overall it seemed like a pretty cool idea.

Elgg and its investors threatened to sue me for building "social software". I got a pretty nasty letter from their lawyers. So I stopped and made almost no money for over a year.

Twenty. On my very last day working for Known, I went to have a meeting with the British CEO of a well-known academia startup in San Francisco. At one point, I made a remark about our shared history with Oxford, my hometown. "Yes," he said, "but I went to the university."

Twenty-one. So you see, it's sometimes easy to wonder if you should be someone else. But it's a trap. It's always a trap.

Twenty-two. Every contact leaves a trace. I remember the interaction with that CEO like it was yesterday. I remember those conversations with my co-founder. I remember the investor who told me Known was a shit idea and I needed to stop doing it right now. I remember the guy at Medium who made fun of my code when he thought I was out of earshot.

I used to say: "I'm sorry I'm not good enough." And I used to mean it.

Twenty-three. I think I can pinpoint exactly when the switch flipped in my head. When I stopped caring so much.

For a little while, I thought I was probably going to die of a terminal disease. It wasn't hyperbole: my mother had it, my aunt died of it, and my cousin, just seven years older than me, had just died of it. We knew the genetic marker. And we knew that there was a 75% chance that either my sister or I would get it.

Of course, we both hoped that the other would be the one who wouldn't get it. When the genetic counselor told us that, against the odds, neither of us had the marker, we cried openly in her office.

I've still been spending most of my time helping to be a carer for my mother, who is dying. Maybe I broke my emotional starter motor; I might just be numb. But forgive me if I no longer give a shit about what you think of me.

Twenty-four. I don't begrudge anyone who wants to work on the internet to get rich, at least if they don't already come from money, but I don't think it's the way we make anything better for anyone.

If you want to get rich, go join Google or Facebook or one of those companies that will pay you half a million dollars a year in total compensation and feed you three times a day. But don't lie to yourself and say you're going to change the world.

Twenty-five. I've come to realize that none of the really major changes that the internet has brought about have come from startups. It's certainly true that startups have come along later and brought them to market, but the seismic changes have all either come from researchers at larger institutions (Tim Berners-Lee at CERN, for example), from individuals (Ward Cunningham and the wiki, Linus Torvalds and Linux, all the individuals who kicked off blogging and therefore social media), or from big tech companies with the resources to incubate something really new (Apple and the iPhone).

Twenty-six. That's not to say that startups don't have a place. Twitter was a startup. Facebook was a startup. So were Salesforce and Netflix and Apple and Microsoft. I've removed myself from anything Facebook owns, but I use the others just about every day. So maybe I'm being unfair, or more precisely, unfair because I'm jaded from some of my own experiences.

90% of startups fail. Some of it is luck; not all of it, however.

Twenty-seven. I wonder if changing the world is too narcissistic an ideal; part of the overstated importance that founders and technologists place in themselves. Being able to weave a virtual machine out of discrete logical notation and the right set of words can give you a false sense of importance.

Or worse, and most plausibly, it's just marketing.

Twenty-eight. Here are the things that I think will cause a startup to fail:

Culture. 65% of startups fail because of preventable human dynamics. A lot of it comes down to communication. Everything needs to be clear; nothing can linger; resentments can't fester. Because so much in a startup is ambiguous, communication internally needs to be unambiguous and out in the open. Everyone on a founding team needs to be a really strong communicator, and be able to face conflict head-on in the way that you would hope an adult should.

Hubris. Being so sure that you're going to succeed that you don't examine why you might fail - or don't even bother to find out if you're building something anyone might want.

Being the wrong people. It's not enough to want to build something. And so many people want to be entrepreneurs these days because they think it's cool. But everyone on a founding team has to bring real, hard skills to the table, and be strong on the "soft" people skills that make a community tick. You can't play at being a founder. And beware the people who want to be the boss.

Buying the bullshit. Hustle porn is everywhere, and it's wrong, in the sense that it's demonstrably factually incorrect. I guess this is a part of being the wrong people: the wrong people have excess hubris, don't communicate, and buy the bullshit.

Twenty-nine. If you're not the right person, that doesn't mean who you are isn't right. At all. But it might mean you should find something to do that fits you better. Don't bend yourself to fit the world.

Thirty. When my great grandfather arrived at Ellis Island after fleeing the White Army in Ukraine, which had torched his village and killed so many of his family, he shortened his last name to erase his Jewishness. He chose to raise a secular family.

When his son, my grandfather, was captured by the Nazis as a prisoner of war, he lied about his Jewishness to save his own life.

Sometimes wanting to be someone you're not is a small thing, like wishing someone would see value in you. Sometimes it's a big thing, like wishing someone would see value in your life.

Thirty-one. I actually really like being a part of startups. There's something beautiful about trying to create something from nothing. But in understanding myself better, I've had to create spaces that help nurture what I'm good at.

I work best when I have time to be introspective. I think better when I'm writing than when I'm on my feet in a meeting. That's not to say that I can't contribute well in meetings, but being able to sit down, write, and reflect is a force multiplier for me. I can organize my thoughts better when I have time to do that.

I also can't context switch rapidly. I secretly think that anyone who claims to do this must be lying, but I'm open to the possibility that some people are amazing context-switchers. What I know for certain is that I'm not one. I need time and space. If I don't have either, I'm not going to do my best work, and I'm not going to have a good time doing it.

Engineering ways to work well and be yourself at work is a good way to be kind to yourself, and to show up better for others. My suspicion is that burnout at work is, at least in part, an outcome of pretending to be someone else.

Thirty-two. If I start another company, I already know what it will do. I also know that it will intentionally be a small business, not a startup. Not for lack of ambition, but because always worrying about how you're going to get to exponential growth is exhausting, too.

Thirty-three. Although I intend to see the startup I'm currently at through to an exit, I also know it's not an "if". There will be another company, mostly because I'm addicted to making something new, and in need of a way to make a new way of working for myself.

Thirty-four. A company is a community and a movement. Software is one way a community can build a movement and connect with the world. It's a way of reaching out.

The counterculture is always more interesting than the mainstream. Always, by definition. Mainstream culture is not just the status quo, but the lowest common denominator of the status quo; the parts of the status quo that the majority of people with power can get behind without argument. Mainstream culture is Starbucks and American Idol. It's the norms of conformity. The counterculture offers an entirely new way to live, and beyond that, freedom from conformity.

Conformity is safe, if you happen to be someone who fits neatly into the pigeonhole templates of mainstream culture. If you don't, it can be a death sentence, whether literally or figuratively. Burnout is an outcome of pretending to be someone else.

The most interesting technology, companies, platforms, and movements are the ones that give power to people who have been disenfranchised by mainstream culture. That's how you change the world: distribute equity and amplification.

Every contact leaves a trace. Maximize contact; connect people.

Thirty-five. I've been teaching a Designing for Equity workshop with my friend Roxann Stafford for the last year. She's a vastly more experienced facilitator than me, and frankly is also vastly smarter. I've learned at least as much from her as our workshop participants have.

I've been talking about human-centered design since I left Elgg, and about design thinking since I left Matter. Roxann helped me understand how those ideas are rooted in a sort of colonialist worldview: the idea that a team of privileged people can enter someone else's context, do some cursory learning about their lived experiences, and build a better solution for their problems than they could build for themselves. The idea inherently diminishes their own agency and intelligence, but more than that, it strip mines the communities you're helping of value. It's the team that makes the money once the product is built - from the people they're trying to help, and based on the experiences they've shared.

Roxann has helped me learn that distributed equity is the thing. You've got to share ownership. You've got to share value. The people you're trying to help have to be a part of the process, and they need to have a share of the outcome.

Thirty-six. A lot of people are lonely. A lot of communities have been strip mined. I don't yet fully understand how to build a company that builds something together and does not do this. I wonder if capitalism always leads to this kind of transfer of value. How can it not?

Thirty-seven. This isn't a rhetorical question. How can it not?

If I want to sustain myself by doing work that I love that makes the world at least a little bit better, how can I do that?

What's the version of this that de-centers me? If I can make the world a little bit better, how can I do that?

Thirty-eight. A couple of years ago, Chelsea Manning came to a demo day at the accelerator I worked at. She was on the board of advisors for one of our startups - an anarchist collective that was developing a secure email service as a commercial endeavor to fund its activities. I was proud of having invested in them, and I was excited to speak with her.

As I expected, Chelsea was incredibly smart, and didn't mince words. She liked the project she was a part of, and a few others, but she thought I was naive about the impact of the market on some of the others. Patiently but bluntly, she took me through how each of them could be used for ill. Despite having had all the good intentions in the world, I felt like I had failed.

I would like to be a better activist and ally than I am.

Thirty-nine. I sometimes lie in bed and wonder how I got here. We all do, I think. But just because we're in a place, doesn't mean that place is the right one, or that the shape of the structures and processes we participate in are right. We have agency to change them. Particularly if we build movements and work together.

If the culture is oppressive - and for so many people, it is - the counterculture is imperative.

If we're pretending to be people we're not, finding ways to make space for us to be ourselves, and to help the people around us to do the same, is imperative. We all have to breathe.

Change is imperative. And change is collaborative.

Forty. I think, for now, that I am a cheerleader and an amplifier for people who make change. I think this is where I should be. I would rather de-center myself and support women and people of color who are doing the work. I want to be additive to their movements.

It's not obvious to me that I can be additive, beyond amplifying and supporting from the outside. It's not clear to me that I need to take up space or that I'd do anything but get in their way. I would like to be involved more deeply, but that doesn't mean I should be.

One of the most important things I can do is to learn and grow; not pretend to be someone I'm not, but listen to people who are leading these movements and understand what they need. Can I build those skills? Can I authentically become that person? I don't know, but I'd like to try.

Forty-one. I feel inadequate, but I need to lean into the discomfort. The cowardly thing to do would be to let inadequacy lead to paralysis.

Forty-two. In the startup realm, I'm particularly drawn to the Zebra movement. Jenn Brandel kindly asked me to read the first version of their manifesto when we were sharing space in the Matter garage; she, Mara Zepeda, Astrid Schultz, and Aniyia Williams have turned it into a movement since then.

It's a countercultural movement of a kind: in this case a community convened to manifest a new kind of collaborative entrepreneurship that bucks the trend for venture capital funding that demands exponential growth.

I'm inspired by thinkers like Ruha Benjamin and Joy Buolamwini, who are shining a light on how the tools and algorithms we use can be instruments of oppression, which in turn points to how we can build software that is not. I'm appalled by Google's treatment of Timnit Gebru and Margaret Mitchell, members of its ethical AI team who were fired after Google asked for a paper on the ethics of large language processing models to be retracted. And I'm dismayed by the exclusionary discourse on platforms like Clubhouse that are implicitly set up as safe spaces for the oppressive mainstream.

Giving people who are working for real change as much of a platform as possible is important. Building platforms that could be used for movement-building is important. Building ways for people to create and connect and find community that transcends the ways they are oppressed and the places where they are oppressed is important. Building ways to share equity is important.

And in all of this, building ways for all of us to connect and learn from each other, and particularly from voices who are not a part of the traditional mainstream, is important.

All that you touch, you change. All that you change, changes you. Every contact leaves a trace.

This is the promise of the internet: one of community, shared equity, and equality. Through those those things, I still hope we may better understand each other, and through that, find peace.

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