#53: Californian suspended adolescence.

For Silicon Valley's most insecure, life is a perpetual dress rehearsal.

In Silicon Valley, everything is a work-in-progress. There’s always code that can be improved upon, features made more user-friendly. You can keep optimizing ad infinitum.

That works great in business.

But what happens when we reflect that mindset back onto ourselves?

If you’re a perpetual work-in-progress, you never have to admit you’ve failed.

I recently had a relationship-ending falling out with a friend.

My core issue with him was that he would jolt me in and out of his life with little warning, and then explain it away with self-help mumbo jumbo.

Thanks for being patient with me, I’m still figuring myself out.

The pattern had been the same since the beginning of our friendship.

Three to four months of stable, if sometimes intense, communication. And then, one day, usually out of nowhere, I would stop hearing from him. Sometimes it would be a formal ending, other times it would be closer to ghosting.

I’d back off, give him space, wonder what happened, move on.

A few months would pass. Maybe a birthday or a holiday would happen, and he’d pop up again with, “Sorry for disappearing, I’m working on myself and…”

I’d forgive him, we’d start talking again, rinse and repeat.

This friend, let’s call him A., is perpetually working on himself. Everything with A. is in flux. Emotionally, he’s stuck in that period of time right when you’ve graduated college, but before you’ve gotten your first real job. He doesn’t know who he is or where he’s going, and I don’t think he ever will.

All behavior, from his professional ups and downs to simply being a bad friend, is explained away by “I’m working on myself right now.”

At first, I thought it was because he was in a transition period in his life. Until very recently, I was too. I was compassionate. After all, this was part of what made us such good friends in the first place, this shared experience of restarting your life when you’re already an adult. But as months gave to years of knowing one another, I realized that he had self-help brain and there was never going to be real forward momentum.

He was always going to be “figuring himself out.”

The minute he stopped being a work-in-progress, forever half-way through a Brenée Brown or Tara Brach book, he would have to take accountability for his life. He would have to accept that this is who he is.

For A., part of that accountability would be admitting that some of his potential had been lost to the sands of time, that the world was no longer his oyster, and that he was closer to 40 than 20.

The different ways his life could shake out were no longer unlimited.

In California in particular, I don’t think he’s alone.

Optimization culture.

Optimization culture is baked into everything we do in the Valley, and that’s because the businesses we’ve created or helped create are baked into everything we do, too.

Optimization culture helps businesses thrive; why not people’s individual lives?

From the obvious (wearables, fad diets, all manners of apps that promise to cut out the middle man) to the less immediately recognizable (psychedelia and polyamory on one side of the spectrum) we are always striving to become better versions of ourselves.

The link between how we view our work and how we view ourselves is clear.

Not only to me, but to everyone on the outside looking in. People criticize the lack of boundary between one’s work and one’s personal life in tech. But the truth is, there’s no boundary in tech in the same way there’s no boundary in the arts. Art imitates life imitates art, tech imitates life imitates tech.

You might not want this to be true, but technologists and artists are cut from the same cloth. (Having been funded by Old Money New Yorkers to create art, I’d even go as far as to say that I don’t think artist patrons and VCs are that different, either.)

If you think about how personal art is to the artist, and really own that this similarity is real, why this optimization trap is so easy to fall into becomes a lot more sympathetic.

But it’s easy to get stuck on the “optimizing” part, without ever applying those learnings to concrete actions. You’re working on it.

It’s time to build, but not everyone is building.

In some circles, it’s not only that everyone dreams of being an entrepreneur, it’s that this dream is virtuous. For some (not all), it is something like a moral failure not to have this ambition.

You don’t dream of working for your hero. You must become your hero, and perhaps one day surpass them. The jackpot is if your network is composed of people with this same dream, and you’re all able to achieve it.

Delian Asparouhov sums this mindset up well in a single tweet:

And if you must work for someone? Work with the intention of transcending your status as an employee, and quickly.

It goes without saying that there are few founders without employees, just as there are few businesses without customers. At some point in everyone’s career, they have to work for somebody else. But a nontrivial number of people in start-up jobs have ambitions of their own: one day I will be a founder myself.

Eventually, you reach an age where it’s clear whether or not you’ll accomplish this, though. Whether you’ll be working for someone forever, or if it’ll be the other way around. If the culture you’re immersed in puts special emphasis on being a leader, though, this can be a tough pill to swallow.

You’re left with three options: accept it, deny it, or try and change it.

Some people accept it. At best, they’re happy to support projects and companies they believe in. They’re employees and that’s fine, not everyone wants to lead. At worst, they become status-hungry sycophants.

However, people often choose to deny it. They’re a work-in-progress. There’s still time to become Elon when they “grow up,” even if they’re already flirting with 40.

A while back, I read a wonderful article that posited planning—bullet journals, productivity apps, note-taking—is useful on the surface, but often is a form of procrastination. It gives the illusion of productivity without ever forcing you to start your project.

The plan can always be optimized, drilled down to more and more granular levels. If I recall correctly, the author made the analogy, “It’s like constantly refilling your gas tank without ever driving.”* 

Said another way? If you let the curtain rise, the show will eventually end. It’s easier to keep things in a perpetual dress rehearsal.


*I have no idea what this article was or where I even saw it, but I’ve referenced it a couple of times. If anyone recognizes that analogy, please send me the article! I want to link out to it.

Have a question? Drop me a line at defaultefriend@gmail.com, DM me on Twitter at @default_friend, or send me a question on CuriousCat.

For more writing on all things tech, check out my friend Trevor’s newsletter, How It Actually Works. And if I may, I recommend staring with Why You Should Ignore Every Founder's Story About How They Started Their Company.