Help! I'm stuck at a local maximum

I’m at a local maximum. It was not obvious at the start. But once I realised that’s what it was, it has plagued my thoughts.

This is the first time in my life I’ve noticed it happen. That doesn’t mean it’s the first time I’ve been at one. I’d say it’s actually very likely it has happened before. Previously, though, if I felt frustrations in my work, relationships, or even simply my thoughts, I probably just thought something oversimplifying like “Work sucks” — rather than stepping back and trying to understand the bigger picture.¹1 Additionally, I think local maximums get harder to overcome as you get older. Maybe — that’s a hypothesis. In part because, if your life has gone well, you should be closer to the global maximum. There’s less room to move. But I think the global maximum is essentially infinite — which is why I consider this a lesser factor. More importantly, I think, is the pressure to stay as you are due to the chains of habit and peer-reinforced identity. Arguing for the inverse might highlight the greater knowledge and capital at your disposal when you’re older — which I think has merit.

For that reason, I really admire people who can detect something is wrong, in the moment, get their bearings, and re-orient their trajectory — mid-flight.

I’m trying to be one of those people I admire.

Symptoms

It began as a feeling of being contained; even slightly trapped. That feeling, which was initially pre-verbal, was background noise for weeks but really announced itself for around 1-2 days — alongside some additional agitation. After that period of greater salience, I was able to articulate what the feeling meant. It said “You can’t reach what you want from where you are.” ²2 For more on extracting information from feelings, check out the brilliant little book Focusing by Eugene T. Gendlin. My terminology and process has been heavily influenced by him — as well as meditation and the occasional psilocybin-induced psyche-wrestling match.

It was as if I couldn’t expect to get something out of my fridge if I continued to stay seated on my couch. Or, more specifically, even if I moved the couch closer to the fridge, I still wouldn’t be able to. They were in different rooms, on different levels. The two were incompatible.

And that’s exactly the case, figuratively speaking. There’s little room left for improving my life, without changing the structure of it.

I did this to myself. And I can undo it, too. Although change brings unknowns, which brings trepidation, I’m actually way more scared of this life trajectory crystallising as is. Waking up in two decades’ time with more what-ifs and if-onlys than a content mind can carry.

To be clear, I have a great life. I’m not (super) stressed (too often); I derive meaning from my work; I get to partake in hobbies I enjoy; I see my friends and family a decent amount; I live in a desirable area; I’m (decently) successful comparative to my peer group. Life is busy, but — in most ways — not challenging. It’s comfortable. Too comfortable.

A comfortable life — at least for the moment — is not what I want. If the book of my life were to be published now, I would be proud, genuinely, but I would not be entertained. Not as much as I would like. My character yearns for a more substantial plot.

I could give you a million reasons why things have turned out the way they have (so far). But I won’t. You can’t cling to a reason for why you don’t have something and obtain the thing. The two are logically exclusive.³3 We often think of excuses as self-serving reasons to not do something. I find it more useful to think of them as a forcing function — a phenomenon of physics acting on what would-be parallel universes. The excuse ensures you exist in the universe where you don’t have the thing. Because if you did have the thing, you would not have the excuse. No billionaire has a valid excuse for why they aren’t rich. It just doesn’t hold. Sure, they might not be as wealthy as they like, but that’s a matter of degrees. And to the extent that they have an excuse for that, the same can be said again.

So, let it be said (if only for myself to hear): I want adventure. The strength that comes from challenges. The wisdom from uncertainty. And, for better or worse, Gandalf doesn’t knock on your door and just offer one to you. Most of the time, you have to go find it yourself.

Diagnosis

Before we can consider a remedy, let’s first nail down the malady.

I’m time-poor

There is very little slack in my week. Monday to Friday especially, which I have filled with income generating tasks.⁴4 There’s my career, which I put quite a lot of energy and time into. Outside of that, I coach kids MMA/Muay Thai 4 evenings a week for an hour. On two of those nights I then take an additional private session. Once you factor in some exercise and the biological chores of acquiring, preparing, and consuming food, there’s just enough time left to sleep. Prima facie this might not seem so bad — but time is the ultimate resource, and I can do nothing to change my trajectory if I have no time to use for enacting.

The right people don’t know, or care, that I exist

The self-made person is a myth. However, a certain type of ambitious, conscientious person can easily over-index on doing everything themselves. And while those are amazing traits, that is still a trap. Every disposition has its failure modes.

If you want to go fast, go alone. If you want to go far, go together.

There’s a time for both. It’s not cut and dry. But I still think we are — on average — too bullish on speed and too bearish on distance. More on that in the next mistake.

The final thing I’ll say here, is that in my experience some parts of your life are easier — or can only be — changed from the inside. If you want to quit an addiction, or lose 30kgs, then those require you to make an adjustment to your own internal configuration. How you think, how you act, how you see yourself. No one can do that for you.

By the same token, I think — unfortunately, for the high internal-locus of control people — some parts of your life are best changed from the outside, by someone else. You still need to show up and kick the door down when it is presented to you, though. Which makes one of the tasks required of me — and you, if you relate to this — doing things to draw the attention of the right people, and demonstrating that I have value to offer when the moment arises.

(I’ve written more about networking, and how I think you can do it well here.)

Too much focus on efficiency

Efficiency has merit. A lot of it. But the more experience I’ve acquired, the more I’ve realised that no matter how much merit efficiency has, it’s still Robin. Effectiveness is Batman.

The world is full of power-laws, and when it comes to the top 50 problems you have, you’re often better served by solving your single biggest problem than problems #2 through #50 combined.

Too much focus on efficiency, though, can tend to push us towards solving more of the easier problems — even optimising them to the point of staggeringly diminishing returns. All at the cost of not spending time on our biggest, baddest, but highest pay-off problems.

I’ve been guilty of this. Many times over. That’s why I’m putting it here.

Up until my late 20s, I spent more time worrying about saving than earning. I focused too much on getting good at things quickly, and too little on what I should be getting good at. Even more recently, within the last year or two I’ve thought too much about optimising my career success for my current company.

I’m not even suggesting that I want to leave. What I am saying is that time is the ultimate resource. Efficiency is a good way to ensure you’re not using too much of it on any one thing. But the right amount of time to spend on some things is never too much. Sometimes it’s a little. Other times it is none.

Not enough skin in the game

Without skin in the game, you are protected — to an extent — from negative outcomes. But you are, unequivocally, “protected” from experiencing the asymmetric upside. Fixing this, and having more skin in the game can substantially increase the potential utility you gain from any of your activities.

Of equal — if not greater — importance, is the not being shielded from risks.

This was something that Muay Thai sparring taught me at a deep, physical level. When you start, people tend to be more afraid of hurting someone than of being hurt themselves. And this results in a situation where most beginners are pulling their shots; scared of making too much contact with someone in case they hurt them.

But the reality is Muay Thai is a combat sport. Regardless of whether someone is training to compete, or for self-defence, you are not helping them by continually stopping your punch 95% of the way through its trajectory. Your fear about over exerting power leads to a perception of safety on their behalf that is unfounded. They think “I cannot be touched from here” — and it is that miscalibration which poses far more risk than the punch you accidentally landed a little firm in training.

Surviving risk, and not having experienced it to begin with, may look the same on the surface — but one builds your capacity and the other atrophies it. The goal is to tolerate, withstand, and grow from as much risk and stress as you can reasonably tolerate. Not insulate yourself from it.

Thus, too little skin in the game both caps your upside in a predictable way, yet also prevents the accumulation of desirable qualities in a much more insidious manner.

Diagnosis summary

There’s not much upside optionality in my current life.

Financially, there’s still some room to improve the money-for-time ratio — more money for the same number of hours; condense the coaching work into fewer evenings, cutting down on travel time. But these are going to be incremental, not categorical, improvements.

Or, I might meet someone completely unexpected that influences my life positively. But the likelihood of this is low. I work fully remotely. While I’m coaching I’m busy trying to herd children — who already recognise they’re within an environment that provisionally condones hitting each other.

All of us, in moments of day-dreaming, fantasise about being plucked out in life’s lottery — getting some amazing surprise that opens the door to everything we’ve ever wanted.

But how are you supposed to get a surprise — positive or otherwise — if all of your life (or mine, in this case) has been optimised to avoid them. A local maximum means you’ve reached the top of this hill. There’s no journey left. No unknowns. Nothing to discover.

Unless you’re willing to back down and scale a more daunting hill.

Treatment

Here’s my plan to fix that. Well, fix might be a strong word — but get things moving in the right direction by shifting the structure of my life. Getting me closer to a global maximum, where the hill I climb requires more of me than reaching the summit of my current one did.

Of course, no plan survives contact with the enemy (reality). But this is my first iteration. The art is in the updating.

Treatment philosophy

Before I get into the tactics, let me quickly make the underlying philosophy/strategy explicit.

1. The world doesn’t reward you for wanting

It will give you results based on actions. Smarter actions give you better results.

2. What got you here won’t get you there

Nothing changes if nothing changes. The pull to do the same things is the temptation that keeps you stuck.

3. I need to increase upside optionality

This one is more personal and context specific. But the way my life has played out I’ve played a game of security, rather than large rewards. With this foundation in place, though, I need to be more willing to suffer some small costs for the potential of asymmetrically large wins. Positive black swans.

Treatment tactics

I know this defies “good habit-building” (focus on one thing at a time until it’s sustainable) and “good science” (control one variable and monitor the results) — but I think this is one of those gaps between theory and practice.

It’s also about clusters of books. In that when I think about programming, for example, it would be hard for me to answer this question and not cite any programming books. Programming has been so influential in my mind and in my life, but I can’t really point to any single programming book. I can name 10 that I think in aggregate work together.

• Patrick Collison (The Knowledge Project #32)

This sentiment resonates strongly.

I’ve found the most useful approach in my own life is to try clusters of activities that all push in the same general, but not identical, direction. If for no other reason than some things can not be changed independently.

1. Starting this blog

These words that you’re reading right now, probably mean more to me than they do to you. They’re small, initial symbols of me putting myself out there — increasing my surface area.

This will help demonstrate what I think — or, more importantly, how. Posting online will also increase my chances of connecting with people who I can help, find interesting, and/or learn from. Beyond that, it will help me improve my writing to a greater extent than if I kept it all hidden. Finally, it comes with some risk — as any increase in exposure does.

All good things.

2. Create some slack in my life

To make any change, you need time to undertake the new behaviours within. If you have spare time, you can use that. If you don’t, you’ll need to cut a few things. That’s what I will need to do.

An important part of this reality, is that I’ll probably have to find more time than I expect. Especially as I’ll be moving from domains of relative competence to ones of relative incompetence.

Practically, this means I’m going to have to cut down my coaching hours. Freeing up at least two more weeknights would be a good start.

3. Write, study, think new thoughts

With the time I liberate, I will spend it doing several things:

• Writing. Writing is like exercise. It’s not always pleasant, but you (often) feel good afterwards and you get better the more you do it. It’s cliche, but nothing has refined my thoughts like writing has.
• Studying material that intimidates me. I have a whole list of things I know I want to learn, and acquired the books to learn them from, but have convinced myself I don’t have the time or mental-bandwidth. In part, this is true — which is why I need to free up more of those resources. But equally true is that there is a level of fear. (Have you ever opened a textbook on probability theory? I can’t be the only one who finds that a little scary.)
• Giving my brain the space to make new connections and think new thoughts. Our brains seem to follow non-linear dynamics, at least experientially. Giving myself 1 hour of uninterrupted time to ponder yields qualitatively different results to the same time split across 2 (or more) bouts.

4. Connect with more people within domains I’m interested in

There’s plenty of communities that interest me, but I’ve only ever been a passive observer of them. Never really got involved.

As a start, I noticed there was a reader of LessWrong/Astral Codex Ten that lives near me. I sent them a message and said let’s catch up for a coffee.

I also am going to make a habit of telling people I enjoy their work. There’s several blogs I enjoy — a list that includes but is not limited to Making Connections by Jax, Escaping Flatland, Alexey Guzey and Nabeel Qureshi.⁵5 If you’ve somehow found this piece of writing then I can only assume you’ve encountered them before. If you haven’t check them out. There’s no agenda with this. It’s more intrinsic than extrinsic. Building the muscle of communicating with people outside my established network.

As a manager, I’m actually perfectly fine with delivering feedback — positive or negative — including to those above me in the hierarchy. But that same attitude has not carried over to my life outside of work.⁶6 Along the path to discovering who we are, we often find that we are many things. A bunch of different modules, watered, ignored, and spat on by the environment around us. Integration can only come after first discovering this. The voice inside my head says “Don’t bother them, they don’t care what you have to say. You can’t help them.” And, far too often, I listen to it.

5. Stop unnecessarily delaying myself

There’s a few things that I would say I am actively interested in, but have also thought that I have no right to be thinking about doing that thing.

I think most of this fear comes from social reasons — I’d be laughed at for trying to put myself in rooms I don’t deserve to be in. But it equally may be I have a fear that I’d fail or not be good at it. I’m conscious that our brains often trick us into blaming other people for our own lacks or fears.

To type words that still feel foreign and embarrassing: I’d like to do angel investing one day.

But, ignoring these transient feelings — which is all they are — I applied for a course in it.

I’m fascinated by epistemology. Programming (my career), science (my first love), and investing, are all domains where you can have a model of reality — but then there’s this thing that comes along and tells you whether you were right or wrong. I love disciplines like that. You have to be bold and creative enough to propose a hypothesis; then receptive and resilient to listen to the (often uncomfortable) feedback you get.

Getting a chance to get up close to investing — and investors — is less about the money and more about the opportunity to interact with probability, scale, and leverage in the real-world.

Another is writing. I’ve spoken about writing already, so I won’t belabour the point here. I only highlight that I also put in an expression of interest for the Inkhaven fellowship. Making blogging — thinking in public — more of what I do would be an amazingly fun way to get more skin in the game.

6. Build more things of my own

Again, this blog is one. It is something I can control, learn from, and can compound.

Another is a startup I started working on a few months ago with two of my friends. All of us met 10 years ago working in the fitness industry. One stayed (and upskilled), the other moved into operations and management, I took the plunge into tech. We believe strongly that our combined skillsets and experience will result in coaching software that smokes both the legacy products and the new competitors. There is nothing out there that clearly looks and feels as if it has been built by anyone with coaching experience.

Regardless of what happens, though, the journey will be rewarding.

So that’s two things ticking that box.

Treatment summary

Hopefully, you didn’t expect me to reveal the secrets of the universe to you here.⁷7 42 This is as far as my understanding goes about how to navigate life.

I don’t have a better way to upgrade your circumstances than learn more, do more, and connect with the right people. The first two are 100% in your control. So take ownership of them. You can only do so much on the last one, but you should certainly try stack the deck in your favour.

Spit in one hand and wish in the other. See which one gets full first.

• My father

Extra credit / Still considering: Moving

Changing your location is a sure fire way to shake things up. I’m not certain about this one yet. If I were to move, it would either need to be for a promising opportunity, or because I had decided on a particular thing I want to do — and then go to the place for that thing.

Destinations that may be relevant:

• Sydney. The epicentre of Australian startups and investing.
• Silicon Valley. Still the best place on Earth to be amongst it when it comes to tech.

Any other recommendations welcome. I’m sure there’s places I haven’t even thought of.

Desired outcomes

Honestly, I’m not sure.

I don’t like highly concrete plans — I think they are fragile and disproportionately end in disappointment. I find general direction and then some navigation methods to be more effective.

If I were to be as transparent as I can, though, the things that I think about regularly are:

• Improving as an individual
• Making the world a better place
• Meeting a great partner
• Creating a level of wealth I didn’t imagine possible so I can care for my family (and hopefully start one of my own)⁸8 I want to retire my mother — and show her a white Christmas; something we’ve spoken about since I was young. I was hesitant to include this, as it feels like virtue signalling. But I understand a curious reader may actually want to know more about my motivations. A footnote seemed the appropriate compromise.

If one of those things occurs then the project was a success.

And with that, I’ll leave you with two closing thoughts:

• Failure is not a teaching tool. It is risk (wilfully undertaken), results, and reflection that actually generate wisdom — mistakes are just a by-product of that process. But mistakes and failure are not the same thing. Failure requires stopping — and, as such, failure cannot exist where iteration lives.

• The path illuminates as you walk it.