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How I let myself finally become an artist

Nearly 9 years ago, I got my first tech job at an e-commerce company that sold appliance parts. Since then, I’ve had eight different jobs in tech, hoping that the next one would feel more okay, or make me less depressed and despairing, or would just use my talents well enough that I wouldn’t be bored. And that mythically good, sustainable job in tech never showed up, never transpired, never emerged spontaneously from all my trying and resolving and trying again.

I worked at a total of three YCombinator-backed startups. I worked on every side of a software team – as a developer, a product manager, a designer, and as a product marketer. I worked for big companies and small ones; I worked for non-profits and for a startup that had a dozen employees and which sold for $70-something million shortly before I arrived. I worked as a startup founder for three years. I received many grants of stock options, none of which would have wiped out the debt I accrued as a founder. None of the permutations I explored of life in startups worked for me. Usually, I’d hit some sort of wall at 10 months, and be fired or have to quit to try to get un-depressed.

The truth was, it wasn’t about tech. The issue was that I was unable to accept something that felt dangerous about myself. I’m an artist. I always have been. And I was trying quite hard to survive by shovelling this reality into any other box that felt safe, which would let me feel creative and productive, but which could also never let me get in touch with who I was and what I wanted to say as an artist.

Everything I made with computers was just one step removed from the actual thing I wanted to do. The first thing I remember making with code was a website about an imaginary band I belonged to. The next thing I wanted to make was a game – though I never really got around to that until twenty years later. And then the third thing I made was a music startup.

I really have done the actual thing, too. I’ve been in bands and I’ve acted in plays and musicals and I’ve written fiction and non-fiction and poetry and songs. All along the way, I’ve kept some sort of creative practice going. But when the moment came to ask what I could allow myself to do as a job, as an adult, I could never let myself get closer than one step removed from the actual thing.

That carried through to my startup, Strings.fm. Here is an instructive email exchange between my then-new friend Matt and I, about a year after I took the leap and started Strings.

Matt​: Ok, so, now I have to ask. What are you in it for? I don’t really believe you’re in it for the “building”. Builders go to Myanmar and execute on rainwater systems that look amazing and save hundreds. Or build their own hydro systems in their backyard, including hand-wrapped transformers. I know guys like this, and you’re not one of ‘em. The easy line here, vis-a-vis that quora quote - “Woz was a builder, Jobs his sociopathic narcisist co-founder”. You’re not a Woz.

But you’re not a Jobs either. I’m not going to comment on your fighting ability, I don’t know you well enough, but your choice of industry, product, location, and lack of Woz under your thumb belie that that ain’t you.

Best I can come up with, knowing you very little, is lifestyle artiste/hacker.

He was right. Also look at the language we had, and how restrictive it was! And how terrifying: if I don’t fit in the Woz-Jobs binary of startup founder archetypes, what would I do? I had resolved to make shit work here. If I couldn’t do this kind of work successfully, then I’d have to let go of even having a single degree of remove from what I really wanted to do. I’d just have to give up the possibility of having any connection to being creative, to having a fulfilling career, to ever making myself whole.

Now, looking at my reply, I think I knew then what I know now – that I do have some necessary connection to being an artist, to expression:

Andrew​: Man, I don’t know what I’m in it for. I think I’m in it because I need to say something. Not just to express myself, but to so fully change how people express themselves that it validates my long-held and slightly narcissistic belief that I know something important about the human condition that other people have forgotten.

And actually maybe that means I’m pretty firmly on the artiste side of things. Because I’m pretty sure that’s the point of great art - to say something important that no one knew how to say until you said it, while also agreeing that they wanted to say that all along.

There! I said it! I’m an artist, and always have been one. Sure, neither my friend nor I could say the “artist” word without adding a cutesy “e” at the end. But there it was.

And right in there is also the reason I was unable to accept that I wanted to be an artist. I call it “narcissism,” but really, that was my way of shaming myself into shutting down my awareness of this need to express what I had to express. It was my way of stopping myself from asking: why am I so incapable of accepting that that’s what I want to do, and then doing it, unfiltered through the needs of a tech startup?

In the place of actual self-expression, I found myself deeply committed to the simulacra of expression. I made these apps that looked like they’d enable self-expression, but which were devoid of it – both for users, and for me creating it. If an app creates a playlist for you, it takes away the choices that you have to make for it to truly be expressive of yourself. If you create an app for self-expression, you lose the chance to have spent that time actually expressing yourself.

That conversation happened six years ago. I’ve been unpacking the reasons why I was unable to actually accept my calling as an artist ever since. What would I need so that I could not just say that I’m an artist, but actually allow myself to feel and believe that?

It was so much easier, then, to stomach that I was just a closet narcissist whose delusions of grandeur prompted him to believe he knew best some generic truth about “the human condition.” I could not stomach the idea that my own expression was worthy, and to pursue it regardless of what form it took. Hence: describing myself as “narcissistic,” rather than “artist.” Hence: expressing “the human condition,” rather than expressing myself.

I could not stomach the possibility of actually having something to say, and tolerating where that took me, so I’d resolved to make a business that would make my self-expression and that of so many other people possible. That at least felt better than working in someone else’s startup, which kept making me depressed. And it felt safer than pursuing self-expression as an artist, where it felt like I would just panic and drown. Talking or thinking about my “self” and what I myself wanted left me feeling like I was floating in a dark, bottomless pool, and I would constantly wonder what terrifying force would pull me under.

So, I needed a tool and a schema to make my expression possible, and if I succeeded on the terms of that schema, the good regard of the many people whose expression it enabled might make me finally feel deserving of my own forays into expression. Startups really fit the bill! They tell you what is success and what isn’t, and they are, for the most part, binary in outcome: it either really takes off and is successful, or it isn’t. I wanted to look at a term sheet that would finally tell me: wow, the real world thinks you are worthy of the opportunity to express yourself.

But even if I got that, it wouldn’t have been enough. It’s funny: making a startup that helps people make playlists is very cool and all, but it’s not enough if you’re the person who actually just wants to make music and can’t accept that about him or herself. Learning to code can’t make you whole.

The reasons I went into tech startups are deeply contingent. It could’ve been anything, but it had to be something big and challenging and hard, and tech startups were the first mountain I came to. Startups also have all sorts of ways of saying: oh, you feel trapped and struggling? That’s because you’re not being challenged enough by the job you’re in, so come do work in our world!

Startups encourage over-commitment. They love it. They want you to put in all your money and all your effort and for you to believe that that’ll turn out okay. They want you to do that at the beginning by going full-time well before it would make sense, and they want you to do it at the end by extending your money and energy as long as it’ll go just in case one last pivot will do it.

And because I was doing a startup to finally prove that the thing in me that has always been in me and probably always will be in me was something I was allowed to have, I committed completely. I only stopped when I had no money left, and had spent all the debt I could accrue.

I wanted something so simple. But I could not allow myself to hear it, because that was dangerous.

The thing is: honest self-expression needs you to believe to some degree that your self is worthy, interesting, good, whole. And maybe you can be persuaded by external regard that you’re okay for a while (e.g. by the enormous success of a startup you created), but that’s always pretty fleeting. You’re still out there, without a self to buoy you.

The story of me going neck deep into tech is the story of me wanting to do anything but be in touch with myself. If I listened to myself, and read the words I was even writing in emails to my friends, then I would have faced something very scary: me.

When I was growing up, I had a lot of moments where I’d do something that was important to me, that I felt was right, that I felt I wanted. And I’d face enormous consequences. I grew up in an environment where I didn’t really get the chance to have my own feelings; when I did, it often led to intractable conflict, which would escalate until I backed down.

I worried (and still do worry) about what would happen if I stop managing anyone and everyone else’s feelings about myself and what I do, and instead begin to listen to myself and what I want.

But now, I’ve learned that the terror I feel means opportunity. I was avoiding the terror for so long, because it mapped quite well onto the experience of being hurt until I let go of what I felt.

Still, it all was about ​me​ and my experience of something authentically me. The terror is about what will happen if I stay in myself, rather than in other people’s feelings. The shame was about believing that my self wasn’t actually worthy of expression, so I shouldn’t try, lest I feel overwhelmingly shameful when I fail. And then there was the trying: that’s what was left when I had to finally prove, through others, that I was good enough to be in myself. I could try endlessly, and overcome any failure, because the stakes were that fucking high: if I stopped trying, I would be admitting that I am failed.

There’s a plus side to all this. Terror, shame, and trying too hard are like fucking road flares leading right to ​me​. The brighter they get, the more likely I’m actually in myself. If I’m feeling any of those, it’s likely because I’m right on the other side of just being in me, and I just have to cross the dotted lines.

The other day, I was talking to a friend who also kinda stumbled into the startup path. He pointed out that a lot of the startup culture and venture capitalist discourse works as a substitute for thinking about what you want. They tell you how things should work, what success looks like, and how high to jump. That can free you up to just commit, and in turn discover how to make life within the confines of startupdom work. But for folks like me, it was a technique of self-avoidance – of getting up close to myself without ever really being in it.

I have always sought out ways to leave myself behind and transcend it, ideally through someone else’s convenient rubric, so the startup version of that wasn’t especially new to me. The distinctive thing with startups is that if you do a startup, you also believe you’re keenly independent, visionary, and risk-seeking. You might be! But imagine what you’d do with that energy if you didn’t just use it in exactly the ways that venture capitalists want you to.

I’m about three weeks out of my last job in tech, and every single day, I am terrified. I wake up and fight the knowledge of what I really have to do, just as I fought it all these years in tech.

But the difference is that now, I do it. I sit in the fear and hear what it is afraid of, and I do that. And I know that when I feel terror, it is because I am here. I am here, in myself, looking at the world from my own eyes, finding that my path was there all along. And I am finally ready to start walking.