How to Fall Asleep When Lying Awake at 3AM

& Other Things I Learned This Week - 2/4/24

Can One Try Too Hard?

Monday night was eventful.

Going to bed with an overactive mind, I fell into of those mental zones where I was sleeping, definitionally, but in reality was getting no sleep at all. I woke up at 3am, unrested and groggy. Knowing I had an important day at work, I pulled out all the stops that I typically pull when unable to sleep in the middle of the night - 10 minutes of yin yoga, 10 minutes of meditation, some water - and got back into bed, focused on getting the best sleep possible for the rest of the 4ish hours of sleep I could.

I knew what I had to do. Focus on my breathing. Relax my body. Relax my mind. Count some sheep. Done it before, definitely could do it again. You got this, Nick - I told myself (Yes, I do more talking to myself than I'd care to admit).

10 minutes passed. Another 10 minutes. I was incredibly tired, yet couldn't fall asleep. I tried every "how to fall asleep" tip in the book I've heard about, but to no avail. Even an apparently foolproof method sanctioned by the US military.

Over an hour in (I remember seeing 4:30am on my Google Home device), I lay awake, incredibly frustrated. How can I get everything I wanted done later today if I'm poorly rested?

It was at this point I thought to myself - I give up. This is a lost cause. I resigned myself to staying awake for the rest of the night and struggling through work the next day.

But lo and behold, 5 minutes later, I was deep in slumber, and the next 3 hours of sleep ended up being restful enough to compensate for the first 5 hours.

As I went about the rest of my day, I couldn't help but reflect on the irony of it all - that it was the moment I had given up on trying to sleep that I actually fell asleep. Which got me to wondering, is trying hard overrated?

All of my life, I have had the impression that the keys to success were hard work, effort and intensity. That as long as I tried my very best, I can do anything that I want to. And for so long, that proved to be accurate - I studied hard and got good grades. I worked hard at work, and the hard work was recognized and rewarded. Time and effort were correlated with positive outcomes. Always has been in my head. And don’t get me wrong, it certainly is important - it's hard to argue that trying hard and working hard aren't correlated with positive outcomes.

But I recently read a pretty life changing book - The Inner Game Of Tennis by Timothy Gallwey, which changed the way I looked at hard work. I picked it up because I've played tennis most of my life and I'm always trying to get better, but I ended up learning so much more about life than I did about tennis.

One of the most insightful parts of the book for me was when the author, a tennis coach, talked through the mechanics of how to hit a serve well. A tennis serve involves a subtle but rapid wrist "snap" at the top of the serve, which generates a chunk of the speed and power needed to hit the serve powerfully and accurately. Gallwey realized that often, when students consciously attempt to introduce more power into their serves, they end up tightening all their muscles in their serving hand. Since muscles are what generate power, our thinking brain tells our muscles to tense up. But this tensing motion ends up reducing the flexibility of the muscles in our serving hand, preventing the wrist snap, and in the process, the serve tends to lose rather than gain power. They spend too much of their strength tensing their muscles that it reduces their ability to generate strength on their serves.

Conversely, it is when students stop the focus on serving hard, allowing their arm muscles to be more relaxed, that they actually serve harder and faster.

This triggered a lot of reflection for me, as it's a phenomenon I've witnessed across a lot of my life, both in my sporting endeavors (tennis, golf), but also my work life. In certain instances, the harder I focus on something and trying for something, the more limited my ability to perform at my peak.

A University of Virginia study once showed that participants who were told specifically to avoid moving in a pendulum a certain direction ended up moving the pendulum more than participants who were just told to hold the pendulum steady. The focusing, the trying hard, to get something done ended up working counterproductively for these participants.

I think this phenomenon might have something to do with flow. It's widely considered that we are at our peak when we are in flow, moments when we are "in the zone", fully immersed in an activity. When our bodies and mind perform with no qualms or concerns. We've all heard the athlete talk about "blacking out" on the field, or having an out of body experience, when referring to an extraordinary feat they accomplished - that's flow.

The state of flow, to me, involves being the most natural and simple versions of ourselves. It occurs when our mind and bodies are most intuitive, when self-doubt and self-criticism are absent. Research on flow has shown that moments of flow involve the deactivation of the part of the brain that controls self-monitoring, i.e. the "voice in our head" making judgments about our actions. While the voice in our head can be very valuable at other times, it seems that it can also be a hindrance to our ability to perform, as it results in unnecessary hesitation and self-doubt that weighs on our most intuitive selves, getting in our own way.

Perhaps trying too hard to sleep induced a determination that activated the self-judging parts of my brain, which in turn prevented me from accessing the muscle memory of how to sleep. Since sleep is a natural, intuitive, and effortless action involving the most unconscious parts of our brains, my attempts to "manufacture" sleep were misguided, since the attempts were unnatural and effortful and therefore antithetical to the true essence of sleep - natural and effortless. Similarly, trying too hard to serve in tennis, attempting to force something that should be natural and intuitive, is the path towards failure rather than success.

And so, perhaps, this is all a reminder I need a better relationship with hard work in my life - an understanding that while hard work is necessary, working too hard and trying too hard for something could end up negating a lot of the positive effects that hard work brings. That I should prioritize working smart over working hard, although that doesn’t mean working less hard for the sake of it, but rather having the wisdom to know when I've passed the threshold point when incremental work is tied to negative marginal utility. That I should, before trying to brute force my way through tasks and obstacles through hard work and determination - which I've always seen as differentiating traits of mine - pause and reflect on whether the tasks at hand are really intuition-oriented tasks for which determined effort is a poor strategy, and the impacts that the brute force and hard work could have on my ability to perform.

Helpful thoughts as I embark on the more entrepreneurial next phase of my career.

Quote of the Week: "Money is a Byproduct of Excellence, not a Goal" - Ray Dalio, Principles

We're getting a bunch of Dalio-adjacent quotes recently, as I work my way through his 500+ page behemoth of a book.

This quote particularly resonated with me, and made me think a lot about the relationship I'd like to have with money. I spent most of my initial part of my career surrounded by many money-oriented individuals - for whom self worth and success seemed to be defined by the continued acquisition of wealth. I often heard quotes like "I don't care one bit about title or accolades - the only thing that matters is how much I'm getting paid".

That has never sat well or right with me, as I’ve always felt that money, while important, couldn't be the end all and be all. Not just that there's so much more to life and our careers (influence, power, legacy, relationships, health, knowledge) than money, but also because it's so hard to ascertain how much money is "enough".

Perhaps it is possible to set ourselves an absolute target as the yardstick for "enough". But what, really, is "enough" money? $1 million? $10 million? $1 billion? "Enough", after all, is such a subjective and illusory term, one that can and does change over time, so how can I know that my absolute wealth target won't shift when I get there?

I find it hard to believe that this absolute target won't shift upwards, consistently, as we attain more wealth over time. I've seen it in my own life. As I have had more exposure to increasingly wealthy and privileged social circles, my baseline for what is "enough" has shifted over time. Nice things are called nice things for a reason - and as I get my taste of nice things, enabled by increasing income and wealth, I can't help but want more of it. Lifestyle creep, as some call it. As I move up the wealth ladder over time, why wouldn't my definition for what is "enough" keep shifting? Even if I set an absolute wealth target, when I hit it, how can I be sure that I’ll have the wisdom to know when the "enough" of the past is enough for the future?

The alternative, using relative comparisons of wealth, certainly doesn't work either. The wealthier one gets, the wealthier one's social (or at least professional) circles likely become. I've seen so many multi-millionaires who salivate at the wealth of billionaires. And I'm sure many money-driven billionaires thirst after the wealth of the richest in the world. Who we compare ourselves to, therefore, will consistently shift upwards as we shift upwards ourselves. And so, unless we are Bernard Arnault or Jeff Bezos, it feels inevitable that we will always feel behind, like we are less than, if we guide our lives on attaining money and wealth.

So, whether trying to look at it from an absolute or relative basis, using wealth as a guiding light in our life journeys feels to me like walking up the wrong side of an escalator. Futile.

Which is why this Dalio quote stood out to me. Because it recognizes that while money is valuable, it should never be the goal, but rather a byproduct of our goals and targets.

And while whether excellence should be the goal is very debatable (topic for another week, perhaps?), I think we can easily replace it in the quote with many other things that we aspire to in life - knowledge, power, influence, agency, the ability to make things happen, the desire to improve the world… and in the process build a better relationship with money than the soul-crushing and life-draining one so many of us have with it today.

And interestingly, in doing so, I wonder whether we will end up finding it easier to build wealth. In the same way that I fell asleep when I stopped focusing on falling asleep, perhaps focusing less on making money might free us up from the burdens of too much focus on making money and trying too hard to make money or not lose money - in the process unlocking our ability to act like the best, most intuitive versions of ourselves. And wouldn't those best, most intuitive versions of ourselves be best positioned to succeed, and therefore, maximize our earnings potential?

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That's it for this week! As always, so appreciative of anyone who read this top to bottom - if you have thoughts, please send them my way. You (should) know how to reach me!