discipline & freedom

on the duality of optimization

Paris on film, July 2022

Qualifier: I am not an expert on what I write about and mostly speak from personal experience. I know this is somewhat implied, but I want to make it especially clear! I don’t have answers—I only have questions & reflections :) 

---

Like nearly every teenage girl with a body, I went through my own set of woes when it came to food, body image, and eating. As a response (or a means of self-preservation), once I shook off that phase, I swore off ever tracking my food again or measuring anything really—I only wanted to go by feel. All things considered, this has worked pretty well. I have a healthy relationship with food and my body and generally like myself on most days (the small wins, right?). But lately I’ve been craving utter mental clarity, which often stems from a refined, structured physical and mental routine that creates the space for a clear, crisp mind. In service of becoming crystal clear mentally, I have felt a part of me wanting to reach back for those comfortable, structured ways of being: to track my food, my sleep, my steps, my screen time. To see tangible process. To bring measurement back into my life. To define success with some set of numbers going up or down. But then I feel my internal alarm systems ringing, cautioning me against doing that—asking: will this untangle all of the mental progress i’ve made to not hate myself?

This dilemma lead me to unpack the duality between discipline & freedom in this essay.

Note: this is the first in a series of posts I’ll be writing on duality. In the works are reality & delusion, femininity & masculinity, creativity & execution, authenticity & performance, and convergence & divergence. You can sign up to get the next ones here:

I saw this tweet once that made a lot of sense to me. There’s this widely accepted notion, popularized by Peter Drucker, that “what gets measured gets managed”, which I believe is true. But the tweet pointed out that there’s an important corollary to the statement missing—and that corollary is: what gets measured gets focused on. This made a lasting impression on me, because of how true it felt. Anything I’ve ever measured demanded my focus in enormous ways that I wasn’t even aware of at the time. 

My grades in school felt like the only thing worth my attention when I was going through the education system. In hindsight, they probably weren’t worth nearly the mental weight I gave them at the time. But the reality of facing something you’re being measured by so frequently is that you begin to attribute your worth and self image to the way that measurement reads. And that can become pretty fucking oppressive (and confusing) over time, especially when the world suddenly de-values something you spent so much time measuring (and hence focusing on). 

Grades are a low hanging fruit example because once you get far enough from school, you realize how trivial they are as a predictor of success/efficacy in the real world. And if you’ve ever obsessed over your body or your weight, you probably already know (on some level at least) how trivial that aspect of your life is. And yet, if you are in the throes of measuring it, you simply can’t stop giving it the attention it demands from you. 

There’s another common idea that (I think) was made mainstream by Jocko Willink—the notion that “discipline equals freedom.” I think generally, it’s a pretty good idea. The more disciplined and regulated your life is, the more hypothetical freedom you will get in both the short term and the long term. 

• In the short term, you get freedom by reducing decision fatigue and avoiding exhausting your own mental processes

• In the long term, you get freedom by having a regulated, structured life that is likely to track you towards whatever aim you’re optimizing for

BUT (yes, a big but) it leaves out a huge amount of nuance by ignoring the fact that for some people, discipline is just a coping mechanism to avoid facing what they would do with freedom if they had it sooner.

Meaning: you can create systems, processes, and structures to optimize every part of your life (how much you sleep, how much you eat, when you eat, how many minutes you’re on your phone, how many times a day you check your email, etc.) but the missing corollary is that discipline for the sake of pure optimization can be a means of avoiding the important problems.

Applying brute force discipline goes something like: if I can just become an anti-hedonistic modern day pseudo-monk, I don’t need to think about what I’m working towards, because I can figure that out when I get there. Once I get the freedom, I’ll know what to do with it. Once I get the freedom, I’ll relax. And I can’t get that freedom until I’ve disciplined my life to the thousandth of a decimal point in all of the areas I’m measuring.

This lost corollary is not the fault of the quote, but simply the consequence of nuance getting obliterated when a 3-word-principle gains traction at scale so quickly (the same phenomenon happened with “what gets measured gets managed”).

Tim Ferriss pointed out this phenomenon in a recent interview when an audience member asked him about his relationship with money—specifically how he dealt with “getting rich”, and whether it brought him happiness. He basically said: you don’t change when you get rich. While many of the people he knows who have accumulated wealth began with the aim of reaching “financial freedom”, when they got there, nothing about them changed, and in fact, the emotional issues and trauma they had not yet dealt with were exacerbated by the accumulation of wealth (i.e. if they were frugal when they didn’t have money, they just became more frugal when they got rich.. the same went for generosity and positive qualities, too). I thought this was interesting, because of how many people aim at freedom—specifically financial freedom—without a plan of what they will do when they get there, nor with a precise definition of what “freedom” means to them, or if it’s something they actually need to do the things they want to do. For example, most people aren’t exactly sure what will change when they’re thinner, richer, or more successful, but that doesn’t deter them from aiming at these things.

And listen: I am not anti-discipline. I grew up doing gymnastics competitively and doing well in school, both of which I was able to maintain due to being incredibly disciplined (I was always good at excelling at what I was being measured by!). But as I matured, I realized that while I was excelling at what the world was measuring me by, these might have been the wrong things to focus on. While it sounds simple, this was a pretty hard realization to come to during my teenage years, when every ounce of praise and reward I was getting came almost exclusively from the things I was measuring (and thus focusing on). 

As I’ve gotten older, I’ve realized that shifting my attention away from things the world tells me to measure myself by (grades, salary, weight, wealth), helps me clarify what freedom means to me, and how I want to achieve it. But this process of deriving my own version of freedom would not have been possible (at least for me) without an intentional diversion of focus away from the measurements the world was gluing my focus to. And it still requires daily active effort to do so.

Freedom to me means:

• In the short term—routines that can persist independent of my environment (i.e. a structure that I can depend on wherever I am), mental clarity, the time and space to explore my ideas and focus on what I’m interested in

• In the long term—complete autonomy over my time without financial stress

As I’ve shifted my attention away from generic external measurements and towards this internal definition of freedom, I’ve begun to notice how many people treat discipline like a religion, even though they don’t exactly know what freedom they are disciplining themselves for. This is not true of everyone, of course. But in some cases, discipline can be a way to avoid facing the hard problems that cannot be fixed by an earlier alarm clock or a pack of athletic greens in the morning. Discipline (when used to generically optimize for any metric you can tangibly measure) can divert your focus away from the things you actually need to devote attention to. Like: What is your definition of success? What is your definition of freedom? If you had freedom today (whatever that means for you), what would you do with it? Is there any way for you to do that now? Every day? Without waiting for some pot of freedom at the end of the discipline rainbow?

I think that discipline is an ultra useful tool that helps us optimize for an efficient, lower mental effort path to get where we want to go—and it’s a tool we should all use once we have defined where we want to go and why (not before).

So, yes, discipline equals freedom, as long as you have defined what freedom means to you and what you want to do with it when you get it. But without intentionally self-defining freedom, discipline can just be another distraction we use to feel good about ourselves—enlightened hedonism, so to speak.

The world doesn’t implore us to ask ourselves the really hard questions, because it’s better for everyone else if we don’t. If we just buy into the idea that if we keep working hard and disciplining ourselves towards capital F “Freedom”, then everyone gets what they want out of us: a good soldier who stays in line and does what they’re told, because they’re getting “Freedom” at the end of it all. But ultimately, if you’re using a one-size-fits-all version of discipline, you’re probably tracking towards a one-size fits-all version of freedom. And that’s a tricky destination to aim towards, because you won’t know if it fits you until you get there. 

So while I initially felt hesitant to implement more discipline and measuring back into my life, it also felt quite natural once I started to. Because this time, it wasn’t me blindly measuring trivial metrics that the world told me to care about, but specific metrics that will help me get to my personal definition of freedom, both in the short term and the long term. And it’s quite helpful to have this well-defined directional arrow to walk along, because I know it’s leading me to what I want (or at least what I want right now), so the discipline I implement feels liberating, instead of oppressive.

By creating my own personal vector of freedom, I also realized how much I love (and miss) discipline. But to use it properly, I needed to customize my aim, and curate a set of disciplined behaviours that specifically mapped there. 

So, with my newly minted definition of freedom in tow, I’m genuinely excited to bring discipline back into my life and reunite with the younger, hyper-focused version of me that thrived off of the tangible nature of measured success. It feels good to fuse the intense work ethic I had when I wasn’t worried about where I was aiming with the self-awareness that has brought me conviction in who I am and where I want to go. Or in other words—combining the part of me that revelled in measurable success with the part of me that knows what to measure. I think we are going to make a great team, because as Alan Watts said, “duality is always secretly unity.”