You will never have an answer for how hard to push yourself

This is the fourth post in my series of daily posts for the month of April. To get the best of my writing in your inbox, subscribe to my Substack.

I wrote a few days ago that to write well, I’ll have to be brutally honest with you. So here’s some honesty: I spent two hours writing two different drafts for today’s piece, and then I decided that today’s not the day for either of them. The first one was gonna be titled “be careful when taking advice on the internet” and the second one was gonna be titled “what I talk about when I talk about reading”. I think they will both be good pieces, but they need more time.

A few cool things happened today: I had a call about my research with someone that I’ve been very excited to talk to (more on that soon 👀), and I also attended a fascinating talk about the state of psychedelic therapy. All of which is to say, it was already quite late by the time I got started with writing.

Which brings me to what I’m actually gonna talk about today: the question of how hard to push yourself. In this moment I’m pretty tired and sleep-deprived, so part of me wants to just go to sleep, but another part of me really does want to publish a piece today.

I remember when I pulled all-nighters in high school, I’d drink a lot of Nestea through the night to keep me going. It wasn’t about the caffeine, it was just about the nice sugary taste of the lemon tea that helped me grit my teeth and get through whatever problem sets and lab reports I had to write. But the memory that sticks out to me most around that time is not any particular all-nighter: it’s the memory of, years later, drinking Nestea in my childhood home, and suddenly being brought back to that horrible feeling of “I wish I could sleep but I have to force myself to stay awake and finish”. The tea literally tasted like exhaustion.

Which brings us to today. Having had experiences of “pushing myself too hard” in the past, I’m always a little scared of taking things too far again. For a long while I actually gave up on the idea of “pushing” altogether. I went into my “critical rationalist, fun criterion” phase, in which you convince yourself that it’s possible to live life in such a way that you never push yourself to do anything:

It’s the view that you should only do something if it’s fun. Or, put another way, you should never coerce yourself into doing anything. It should never be true that part of you is forcing other parts of you into submission to accomplish some task.

I concede that it might be possible to inhabit a state where there’s never any kind of “coercion” or “internal pushing”. But if it is possible (big “if”¹), it requires a level of enlightenment that almost nobody has. (Maybe Shinzen Young or Yongey Mingyur Rinpoche have it, for example, but I’m not even sure about that.)

So if the “never coerce yourself ever” stance is not possible, and “always coerce yourself all the time” is also bad given personal experience, where do we land? The conclusion that I’ve come to is that there is no specific answer you can rest your laurels on. That the question of how hard to push yourself is something you will always be figuring out—going a little too far in one direction and then a little too far in the other.

In other words, I don’t think this is a problem you can just resolve once and for all. Imagine you have a fear of dogs because of a frightening encounter with a German shepherd as a kid. With the right resources it’s possible to resolve this psychological problem completely (e.g. exposure therapy or memory reconsolidation). You solve it once and you never have to deal with it again. But the problem of how hard to push yourself is not like this. I like to call it an “existential problem”.

A few days ago I started making a list of such problems:

• How hard to push yourself.
• How much to attend to the needs and expectations of others versus your own needs and desires. In other words, how much to care for others.
• The problem of choice: there appear to be many possible paths in front of us, but we can only ever take one of them.

These are problems that never go away. I was especially vindicated in my belief that “how hard to push yourself” is such a problem because I read Dan Shipper’s essay on how hard to push yourself, which begins like this:

How hard should I push myself?

It’s a question I ask myself a lot, and I bet you do too. On the one hand I really want to push myself. I’m ambitious, I want to leave it all out on the field—some of my peak work moments have come from times when I’ve pushed myself to a place where I didn’t think I could go. We all have more ability to adapt to stress and pressure than we think we do.

On the other hand, I want to be kind to myself. I wonder how much the drive to push myself is really just a drive to make up for something that I feel is missing or inadequate—and whether pushing myself will actually fill the hole. I also sometimes wonder whether letting myself off the hook is just laziness masquerading as self-care. It’s hard to tell.

This is an excellent framing of the question. Unfortunately the rest of the essay doesn’t actually give us an answer to it. To be clear, it’s still a helpful essay because he shares some great tips on how to manage stress, but there’s no prescription on how to figure out the exact point at which you could be deemed an “overpusher”.

And that is probably a good thing, because maybe there isn’t a prescription. (Obviously there isn’t a universal prescription that works for everyone, but my claim is stronger than that: maybe, even for a specific person, it’s not possible to find a prescription.) The reason I made the list of “existential problems” was so that I could keep reminding myself that there is no point in trying to find a “final answer” to them. Whenever I catch myself trying to identify a formula for optimal self-discipline, I can stop wasting my time and just try my best to balance it as I go, and learn from my mistakes.

As I come to the end of this piece, I feel genuinely happy that I pushed myself a bit to get it done. I know I want to get over some of my struggles with writing, and even in the past few days I’ve started to enjoy it more, so I decided that today I was gonna prioritize keeping my commitment to myself over going to sleep a little earlier. Maybe tomorrow I’ll decide differently.²

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