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Motivating questions

  • How do we know when to push and when to rest, both at the micro level (e.g. in daily/weekly subproject level) and at the macro level (e.g. what projects to take on, when to quit a project)?
  • What is the relationship between striving and acceptance?
  • How do I personally make sense of these two opposing forces?
  • What is the point of striving? Does it actually make us better?
  • How do I reconcile the fact that I both want to make amazing things and chill the fuck out?

There was a time in my life when one could have referred to me as Buddhist and not been too far off the mark. I spent a lot of time meditating and studying the modern buddhist elders. I loved it and took it seriously. I had a daily practice, regularly attended the local dharma center’s events and went on a handful of silent retreats.

But I also didn’t like it sometimes. The advice and the dharma talks made me feel bad about myself as often as they lifted me up. It felt like I wasn’t doing it right or I wasn’t improving enough. I felt guilty when I bought beer or skipped my morning sit. sometimes I just wanted to forget about trying to be a better practitioner and have some beers.

This tension between wanting to be good and wanting to feel good is still with me. These days, I mostly feel it when listening to, or reading, or otherwise seeing the work of people that inspires me and also makes me feel a little bit inferior. The following is a great incapsulation of something that raises these two conflicting emotions. It comes from a David Perell interview with Tyler Cowen:

Why don’t knowledge workers as a class take improving their skills as seriously as we’re implying here and as you and I have discussed; like why don’t they have the same rigour as, say a LeBron James?

Cowen goes on to offer an explanation involving the historic lack of incentive for this type of improvement. Historically there has been little reward for this type of practice as there was nevee a good way to evaluate the skills required to excel in knowledge work. He and Perell speculate that the internet may be changing this by providing ambitious, motivated individuals a platform to display their abilities and motivations in a way that was previously not possible. The internet is a threshing machine, efficiently separating the wheat from the chaff.

Perhaps. But perhaps it’s more rudimentary than that. Maybe most of us (regardless of industry or field) simply don’t want to strive in such a way. After all, there are many people (Cowen included) who played ball in high school or like to shoot around every once in a while, but have no desire to play at the level of Lebron James. This is a hypothesis that I can personally relate to, given the tension I feel between pursuing lofty goals and eating a pint of ice cream while binging Schitt’s Creek.

There is an implicit value judgement in Cowen and Perell’s discussion: more knowledge, more doing, more training, more better. It is very much in line with the optimize-everything, achievement-oriented mindset that drives us to work more, work harder, do better. If I just push myself a little more, get a little better, then I will be the person I want to be.

I feel very ambivalent about this idea. On the one hand, I want to be better and move intentionally toward the things I want. On the other hand, when optimization and performance improvement are one’s north stars, it seems that something very fundamental about being human is lost. This view was expressed very directly by Anna Gat in a recent tweet:

I completely agree, but at the same time the economist in me wants to tell her she just needs to put beauty and pleasure in her utility function1. Utility Tyranny, however, is a phrase that quite delights the rebellious economist in me.

Another beautiful example of what may be lost in the optimize-everything paradigm comes from Ted Gioia’s book, Music: A Subversive History in a story from soundscape ecologist2 Bernie Krause about the origins of music in the natural world:

Krause describes a memorable encounter with an elder of the Nez Perce tribe named Angus Wilson, who chided him one day: “You white people know nothing about music. But I’ll teach you something about it if you want.” The next morning, Krause found himself led to the bank of a stream in northeastern Oregon, where he was motioned to sit quietly on the ground. After a chilly wait, a breeze picked up, and suddenly his surroundings were filled with the sound of a pipe organ chord—a remarkable occurrence, since no instrument was in sight. Wilson brought him over to the water’s edge and pointed to a group of reeds, broken at different lengths by wind and ice. “He took out his knife,” Krause later recalled, “and cut one at the base, whittled some holes, brought the instrument to his lips and began to play a melody. When he stopped, he said, ‘This is how we learned our music.’”

These two examples serve to illustrate that certain life pleasures, insights and experiences happen precisely when we step away from the drive to perfect every aspect of our lives. Beauty will always find a way to push up in the cracks. But if we don’t take a moment to allow ourselves to see it, was ever there in the first place?

The truth of the matter is that both striving and stopping have their place. Agnes Callard presents an idea about how these two forces exist within us and why it is easier to focus on the former and shun the latter:

I think we’re way too quick to identify ourselves with the long-term goals, especially when we’re not in the moment of being tempted. So we can say, look, I know how I should really live. And I know that I should really read those books, and I should not eat the cookies, and I should be less stressed about these things, and I should spend more time with my family. These are things I know.

And I think the truth is that I do not know any of them. I believe them, and then I also believe the opposite. And some of my beliefs are, in a way, more presentable to other people, right? So I am more presentable to you if I say, “Yeah, I know I should really spend more time with my kids,” than if I say, “I have a profound need to escape my kids.” But both of those things are true of me. And I think that the violence to the self occurs as long as they are both true of you.

I think — but this is me just agreeing with Socrates about something, which is that, if you had knowledge, you would not have that conflict. And a lot of people have the goal of mastering themselves — which is to say, of exerting enough violence over themselves to silence or to quiet that other voice, because they know — they say they know — the other thing, right?

But the truth is that the fact that the other voice is there means you don’t know it. And the violence over yourself is the trying to quiet it when it’s really there. And knowledge would mean that you unanimously and obviously, and in a very simple way, did the thing you thought you should

This is a more realistic vision of how the unstoppable force of striving for something better and the immovable object of consenting to our inadequate present are able to settle into equilibrium. She doesn’t tell us how to do this3, she just allows that the existence of both of these things at once is the natural order of things.

How do I think about these two desires (or beliefs as Callard calls them)? To be frank, much of the time I just want to do the one thing when I feel like it and do the other when I feel like doing that. Obviously, this is a highly imperfect plan and probably not something that most people would consider an effective way to achieve anything!

But the truth is I like a bit of chaos. I like noise. Maybe it’s the years of loud, immediate, tactile bakery work that shaped my brain or maybe it’s how I’m built. Whatever the case, there must be a way for me to commit that sweet sweet violence upon myself from exactly where I am. There must be a way to take the spirit of all of this self improvement, optimize everything approach and do it the way that makes sense to me. Maybe I’m already doing it. Maybe frantically scanning Hacker News and Marginal Revolution first thing in the morning, scrolling through twitter for five minutes every couple of hours, copy-pasting links and tapping ideas into my phone whenever they pop into my head is just the way I am going to make it work. Hell, probably 80% of the time I’ve put into this essay has been sitting on an exercise ball, bouncing my daughter to sleep, writing on my phone. Context switching and implementation intentions be damned, at least I’m doing the thing. To illustrate this tug of war I have been discussing here, I’ll end with a personal anecdote.

The other day I was standing in line to get into my local farmers market (since we are still in a global pandemic, entry is tightly regulated) and was thinking about focus. How do we create an environment in which we can concentrate on achieving those lofty, presentable goals that look so good on a LinkedIn bio or upwardly mobile Twitter thread? I made a quick list of sensible, boiler plate advice that any self respecting, extremely-online human has absorbed by merely existing in their every day (virtual) reality:

  1. Develop habits (if you get used to doing the same thing every day out will get easier to do the same thing every day)
  2. Organize your physical environment to minimize distraction and promote concentration
  3. Minimize your ambition set (i.e. Don’t have to many goals)
  4. Take care of your mental and physical needs (sleep, exercise, etc)

These things make sense! They are simple and logical and set you up for the perfect bucolic office-scape wherein you are sitting at your desk, steaming mug of tea in hand, white walls reflecting off a dustless desk with nothing but a blank page on the computer screen in front of you (for what it’s worth, in this image I also have a full head of hair, perfect posture and smell like I just walked out of a misty forest). The perfect launching pad to build your utopia or write your novel or found your startup.

The problem is that this just doesn’t work for many of us. It especially doesn’t work if, like me, you have a full time job and two kids under three years old (one of whom is sleeping on my chest as I write this). Not only is it not natural for me to work like this, it is very easy to waste a lot of time trying to prepare the right conditions for getting shit done instead of just getting shit done.

Because I am neither a LinkedIn influencer or a stratup founder, I instead tweeted this:

Obviously, this is a joke, but as they say, every joke carries a bit of truth. The joke attempts to both mock the efficiency influencer stereotype and poke fun at myself for doing the exact opposite of what this person would do in the same situation. To be clear, I don’t think that following the sincere list that I presented first is a bad or ineffective thing, just that if it doesn’t work for you then there’s no point in trying to force it. Just do what works. Doing the work is much greater than preparing for the work.


  1. Of course this doesn’t actually solve the problem if we are still maximizing the function, it just perverts the idea of doing something for its own sake, optimizing the very thing that is rebelling against the Utility Tyranny in the first place. ↩︎

  2. I can’t imagine a job title that more effectively incaapsulates whatever the opposite of the optimize-everything mindset is. ↩︎

  3. There is another great section in this podcast where she is speaking about how the natural devolution of podcasts is into tepid advice giving - idiosyncratic people giving their highly unusual recipe for greatness as if it is something that can be replicated and applied to your life too! She is none too impressed by this phenomenon. ↩︎