An essay in which my friend feels stuck and I suggest relaxing some constraints

This is an extended version of a note I published last week. It can, if you want more nuance, be read as a part of this series:

1. “Everything that turned out well in my life followed the same design process”

2. “Becoming perceptive”

3. “Rationality is an underrated way to be authentic”

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I’ve been talking with a friend who is an artist—and a talented one—but who has not had much success. A thing I notice is that he thinks about what he is doing in a slightly different way than I do. I can’t make him adopt my perspective, and I’m not sure that would help, but I suspect so. Maybe what I said to him can be of use to someone.

The short version is that my friend, in my opinion, thinks about what he wants in a too constrained way.

His main calling in life is writing songs. To this end, he has signed with a record label, put out EPs and albums, and slept in cars behind concert venues—the full package of what “being a musician” means to him. It hasn’t worked. As in, he spent his twenties stressed and doing things he didn’t enjoy (like negotiating contracts and writing social media updates) at the expense of making songs. Looking back, at thirty, he felt a bit like he’d sold out, except he got no money for it. Then the accumulated stress came back to collect its debt in the form of anxiety and heart palpitations, and he was physically unable to write music for several years. His strategy was, in other words, a failed solution to the problem he was trying to solve.

Despite this, when it comes to the problem of how he should carve out time for his music, I can’t get him to consider any solution that pushes beyond the constraints of his default narrative of how to be a musician.

Walking in the fog covered heather fields by the sea, I say things like, “Ok, but what if you think more concretely about what you want to do? Like, what are the precise day-to-day activities that make you feel alive and proud of yourself?”

Regarding music, the activities he actually likes are (1) coming up with new songs and (2) performing live.

“What would be the most effective way to design your life so that you get to do more of that—assuming nothing about the shape of the solution and reasoning up from first principles?”

Instead of thinking “I want to be a musician (and that means having a label and making albums, and so on),” I suggest that we think about it as a design problem. The first step when designing is to map the constraints on the solution space: what needs to be true for him to move through a week and feel good about it at the end?

Needing to express himself through song (preferably together with others) is one such constraint: without it, he doesn’t feel fully himself. Another constraint, obviously, is that he needs to pay his bills. There are a few more such fundamental constraints that can't be ignored for a life to turn out well (keeping up his health and relationships, for instance).

But, I say, there are far fewer constraints than you think.

You have to find the real ones.

As we talk on the phone, my friend is willing to entertain this thought experiment. I have walked into my neighbor’s pasture and go around patting the horses while he talks. When he concludes that being on a label and putting out albums is probably not the most effective solution to his precise problem—I notice that he gets uncomfortable. He backs off, saying, “. . . I don’t know.”¹

He is treating “doing the default thing” as a constraint, I think. This is a very broad and problematic constraint. It blocks nearly everything else he cares about.

For me, who does not operate with the same assumptions as my friend (though I surely have my own limiting beliefs!), listening to him sometimes feels like being in Lars von Trier’s Dogville. In Dogville, the walls are chalk lines on the floor. The viewer can see straight through the entire village. But the actors behave as if they can’t; they treat the lines as walls.

What my friend says sometimes bewilders me because he looks like a thirsty person standing right in front of a glass of water, yet when you suggest maybe he should drink it, he goes, “No, can’t drink that. There is a wall in the way.”

No, there isn’t!!

This makes me realize that what I said earlier in this essay is not enough. You can’t simply list what you want to do and figure out how to do more of that. You also need to surface the unarticulated constraints that you have floating around, and that are making what you were born to do needlessly hard or impossible. You must bring into light the hidden thoughts that bind you.

If you don’t relax some constraints, you might discover that there is no viable life in the Venn diagram of assumptions you have about yourself and the world.

Take a close look at what you assume the solution to your life must look like. Are there any of those assumptions that you could turn into variables instead? As in: “Sure, I’ll sign with a label if it helps me spend more time jamming and less time doing things that frustrate me. Otherwise—no.”

And if you think something has to be done in a certain way, ask yourself, “How do I know that is true?” Have you looked for people who have solved the problem before you, to map how they did it? Have you run an experiment to see if you can falsify your assumption?

Have you walked face-first into the wall to see if it is a chalk line?

(Some examples of constraints I had to unlearn to make my life tractable: I used to think my day job needed to feel meaningful, rather than act as a funding scheme for my projects; I used to think that I had to write in Swedish, that I needed to have a publisher, and that I couldn’t write essays because no one reads essays in Sweden. All of this made my life miserable.)

Once you have figured out which constraints are real (and matter), it gets much easier to find a life that fits you. You can now do the iterative design process that I described in “Everything that turned out well in my life followed the same design process.” Knowing what you like, you can iterate on the design of your life, run thousands of experiments, and gather skills and experience. Maybe you end up writing music for video games, or maybe you end up working part-time as a programmer while staying in the woods where rent is cheap and you can jam without thinking about making an income from it. Don’t overthink the destination—follow the design process where it wants to go. You probably can’t predict the shape of the life that feels best to you anyway.

But the point is: you have to loosen some constraints to give yourself a chance at solving the key problems: they are hard enough in themselves. If you impose as many constraints on yourself as the average person does, the likelihood that you will pull off what is most central to you approaches zero. So, seek clarity on which constraints are real and shape your life to fall within them.

It would be fun, Jacob, to see what you would grow into if you unblocked yourself.

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Thank you Esha for help with copy editing.

1. When I wrote about this on Substack Notes, someone suggested that the reason he acts like this is because he’s more invested in the identity of being a musician. In other words, he wants social status. But I don’t think that is the problem. It was probably partly true when he was in his early twenties; it does not fit my impression of where he is at today.

I suspect the reason he feels uncomfortable about pruning the constraints, keeping only those that affect his well-being day-to-day, is that it feels too trivial. The problem he is facing feels existential—it is literally his entire life that feels off, like it doesn’t fit him—and he wants a solution that matches the scale of the problem. And here I come, saying, “Maybe you should change your schedule slightly so you can jam two more hours every week?” My experience is that small improvements like this compound. But he doesn’t want to compound in an open-ended way; he wants to crack the problem. He wants to figure out, in one grand moment, what he should do to make the problem go away. Sometimes, he talks about maybe inventing something and then living off the income from that.