Repetition Economics

In Repetition Economics: The Story of the Hunter, the Mammoth, and The Wolves, Matt Hollerbach writes:

Human decision-making is quite a complicated problem. One of the leading frameworks for how people make decisions is called Prospect Theory. It was was developed by Daniel Kahneman and Amos Tversky (K&T) in the 1970’s and 80’s. Kahneman and Tversky were not economists, but psychologists. They developed their theories by giving test subjects “games” and evaluating their answers for consistency. Through these games, they determined people value losses and gains differently.  Losses “hurt” more than gains, and therefore, when people view situations involving risk, they are likely to make decisions that don’t conform with the expectations. 

Kahneman and Tversky state this behavior is because people are risk averse in terms of negative outcomes. They then take that idea and expand it to identify that people misjudge probabilities, especially at the extremes. Essentially they treat a 2% chance more like a 10% chance, and they treat a 98% chance like a 90% chance (example only).

But where K&T conclude that people are irrationally biased, Hollerbach finds that the subjects’ choices seem to maximize the geometric return instead of the arithmetic return. Yet, how are they landing on such a strategy if they aren’t doing an explicit computation? What if people’s intuition for such gambles is more rational than the cognitive bias literature suggests?

The post shows how relatively recent findings in “ergodicity economics” challenge the notion of loss aversion presented in behavioral science literature. Instead, in ergodicity, or as Hollerbach prefers “repetition economics”:

Humans evolved a “gut reaction” to match probabilities based on the geometric average, not the arithmetic average because life is about repetition.  This is why the test subjects often got these problems “wrong”, and why economists believe we have behavioral biases.

Humans understand that decisions are not “one-offs”.

We are careful about things we do repeatedly.

  1. How much can you win and how often?
  2. How much can you lose and how often?
  3. How many times will the game repeat?

We might explicitly consider 1 and 2…but we have a native sense for #3.

If you play “Russian Roulette” with 1/100 odds once, you will probably win. Play the game every day, you have almost no chance of surviving the year. Estimate your chances of getting into a wreck when running a yellow light. They are really low. You might get through the light before it changes to red. There is a slight delay before the perpendicular red light turns green. And nobody is able to start accelerating right away when the light turns green. The “expected downside” is really low versus a benefit of getting to your destination sooner. So why don’t we do it more often?

It’s because we know we are going to be faced with these types of decisions 1000’s of times in our life. Each time you try and push a yellow light, you’re very likely going to be just fine. But try and run it 10,000 times, and you’re guaranteed to get into a very nasty accident.

It’s the future repetition that keeps us from risking the yellow light.

I’m a fan of the ergodicity argument and Hollerbach’s suspicion that what economists are labeling irrational, is quite rational if the subjects are defaulting to a system 1 mode of sensing that the choices they are confronted with are repeated games.

But humans are notorious for discounting the future. We prefer clear immediate benefits, like a juicy steak today, over speculative benefits tomorrow, such as “no heart disease” or “no gout”. We struggle to save money. We procrastinate. We permit lifestyle creep in insidious ways:

  • Amazon Prime lures you in with free shipping but you end up buying more
  • You tell yourself you’ll take an Uber this “one time” instead of the subway
  • You start Doordashing. And forget how to cook.

Repetition and habits are powerful. You shouldn’t let your impulses initiate them. You should be deliberate about what you allow to recur. The people you spend the most time with will shape your thoughts. Don’t leave this to chance.

If you start taking vitamins, do you have a plan for determining if they are “working”? Or have you signed up for a perpetual liability with an unclear benefit? You can’t solve that Sunday crossword without the ginko biloba. Right? You are now gripped by a health version of Pascal’s wager.

Subscription business models are the darlings of the investment world. Recurring cash flow that forgets to opt-out. Your neglect is their LTV.

If we thought about our decisions as repeated games, then “no” should be a stronger default.

I’ll close with a section from Gary Basin’s Action Echoes:

Rather than seeing this temptation as a one-off event, view it as repeating over and over into the future. Imagine the decision you make this next time also deciding how you act in similar future situations. Your actions echo into the future. Every “bad” move has consequences later in the game. Sure, you can sometimes find ways to dig yourself out of a hole. But it’s helpful to realize that every move you make contributes to your eventual position

Reframing a decision as a bundle of future repeated actions gives a more accurate view. The goal is not to entirely avoid urges but to reframe them in a way that best accounts for their consequences. Any single temptation is not unique! The actions you take now will establish patterns that determine your future.

A Drawer Of Curiosities

One of my deepest held beliefs is that our need for coherence is a profound source of misery. We agitate for universal theories to tie everything together. Our obsessions with gurus, religion, ideology, macro, or even astrology are symptoms. We search for meaning as if it is something that’s “out there” to be discovered. I’m not holding my breath. And I believe the quest is actively destructive when taken too seriously. When people become overly invested in any of these expeditions, they will protect their egos at any cost. It’s actually more insidious than this. They dehumanize opposition so they don’t even have to consider their plight a cost.

I just picked up Simone de Beauvoir’s book The Ethics Of Ambiguity because its description vibrates with my own feelings. I’ll report back after reading it.  (See How The Need For Coherence Drives Us Mad to see if you’d be interested in reading it.)

In the meantime, I’ll share a technique that I use to resist the seduction of coherence.

A Drawer Of Curiosities

In my notes, I keep an ever-growing list of “tensions” and “paradoxes” that I encounter from reading or experience. It is a constant reminder that every bit of advice you’ve ever heard is not universal. My buddy Jake likes to say that seat belts are the only free lunch. To which I respond, “unless the presumption of safety encourages drivers to speed or drive more recklessly”. Let’s be blunt. My response is utter ankle-biting tediousness (if you have this kind of thought, don’t make it a personality). The larger takeaway is there are paradoxes running loose everywhere and if we run around trying to corral them with some ill-conceived notion that it makes us “more right” or there are truths we can somehow own and wield, then we’ve done nothing but build intellectual totems to hubris.

Instead of trying to resolve the paradoxes, maybe just accept them. Name it to tame it, put it in a drawer, and move on. You don’t need the world to bend around your own brain to protect your ego. You can just have a big list that reminds you that the task is futile. That’s the antidote.


Just some excerpts of obvious relevance:

Why the ‘paradox mindset’ is the key to success (BBC)

  • Over a series of studies, psychologists and organizational scientists have found that people who learn to embrace, rather than reject, opposing demands show greater creativity, flexibility and productivity. The dual constraints actually enhance their performance. The researchers call this a “paradox mindset” – and there never be a better time to start cultivating it.

  • Contemplation of apparent contradictions can break down our assumptions, offering us wholly new ways of looking at the problem…study of how revolutionary thinkers had spent considerable time “actively conceiving multiple opposites or antitheses simultaneously”.

  • “Paradoxical cognition” can also help more average thinkers to solve everyday problems, and organizations to enhance their performance. In one of the early studies, Ella Miron-Spektor, associate professor of organizational behavior at INSEAD, and her research collaborators asked participants to write down three paradoxical statements. This, the participants were told, could be as banal as the idea that “sitting can be more tiring that walking”; they simply had to list any thoughts that were “seemingly contradictory but nonetheless possibly true”. She then gave them two of psychology’s standard tests of creativity. The first was the “remote association test”, which requires participants to find a common word that links three different alternatives. What links “sore, shoulder, sweat”, for example? The answer is cold – and if you get it right, you’ve been able to spot the hidden connections between diverse ideas, which is considered essential for many forms of creative thinking. [Me: Reminds me of Codenames!]

  • Although the participants’ paradoxical statements were not directly related to the task itself, their contemplation of the contradictory ideas seemed to have freed their thinking from its usual constraints, meaning that they were better able to think “outside the box” (or, in this case, inside it).

  • Questionnaire to measure the “paradox mindset”. The participants were first asked to rate statements about their willingness to embrace contradictions, such as:
    • When I consider conflicting perspectives
    • I gain a better understanding of an issue I am comfortable working on tasks that contradict each other
    • I feel uplifted when I realize that two opposites can be true

  • The participants were also asked to describe how often they experienced “resource scarcity” at work (the need to perform highly under limited time or financial resources). Their supervisors, meanwhile, had to rate their performance and innovation within the role. Sure enough, the study found that the employee’s paradox mindset had a large influence on their ability to cope with the demands. For the people who scored highly, the challenge of dealing with limited resources was energizing and inspiring, and their performance actually increased under the tension, so they came up with new and better solutions to the problems within their role. Those without the paradox mindset, in contrast, tended to crumble and struggled to maintain their performance when resources were scarce.
  • The prospect of deliberately embracing competing demands may sound arduous, but Chinese researchers have recently shown that people with this mindset also get greater satisfaction from their role. There is enjoyment, apparently, in reconciling two opposing goals – provided you have the right mindset

  • Simply note down any paradoxes you encounter – and to make a point of contemplating them before you set about solving problems. If you are stuck for ideas, you could look further into the paradoxes that inspired scientists like Einstein and Bohr. Greek philosophy is also full of paradoxical ideas that might get your creative juices flowing. Your own job may already contain many contradictory goals that could inspire paradoxical cognition. In the past, you might have assumed that you need to sacrifice one for the other – but if you want to cultivate the paradox mindset, you might spend a bit more time considering the ways you can pursue them both, simultaneously. Rather than seeing the potential conflicts as something to avoid, you can begin to view the competing demands as an opportunity for growth and a source of motivation. (And if there aren’t any external pressures, you could create your own – asking, for instance, how you could increase the efficiency and accuracy of your performance on a particular task, if only for an exercise in paradoxical thinking.)

Neural correlates of maintaining one’s political beliefs in the face of counterevidence (Nature)

  • People often discount evidence that contradicts their firmly held beliefs. However, little is known about the neural mechanisms that govern this behavior.

  • Data on any topic—from climate science to epidemiology—must first be successfully communicated and believed before it can inform personal behavior or public policy. Viewed in this light, the inability to change another person’s mind through evidence and argument, or to have one’s own mind changed in turn, stands out as a problem of great societal importance. Both human knowledge and human cooperation depend upon such feats of cognitive and emotional flexibility.

  • It is well known that people often resist changing their beliefs when directly challenged, especially when these beliefs are central to their identity. In some cases, exposure to counterevidence may even increase a person’s confidence that his or her cherished beliefs are true. Although neuroscientists have begun to study some of the social aspects of persuasion and motivated reasoning, little research is aimed directly at understanding the neural systems involved in protecting our most strongly held beliefs against counterevidence.

  • One model of belief maintenance holds that when confronted with counterevidence, people experience negative emotions borne of conflict between the perceived importance of their existing beliefs and the uncertainty created by the new information. In an effort to reduce these negative emotions, people may begin to think in ways that minimize the impact of the challenging evidence: discounting its source, forming counterarguments, socially validating their original attitude, or selectively avoiding the new information. The degree to which such rationalization occurs depends upon several factors, but the personal significance of the challenged belief appears to be crucial. Specifically, beliefs that relate to one’s social identity are likely to be more difficult to change.

  • Our results show that when people are confronted with challenges to their deeply held beliefs, they preferentially engage brain structures known to support stimulus-independent, internally directed cognition. Our data also support the role of emotion in belief persistence. Individual differences in persuasion were related to differences in activity within the insular cortex and the amygdala—structures crucial to emotion and feeling. The brain’s systems for emotion, which are purposed toward maintaining homeostatic integrity of the organism, appear also to be engaged when protecting the aspects of our mental lives with which we strongly identify, including our closely held beliefs.

Design Your Own Engine

Engine: a machine for converting any of various forms of energy into mechanical force and motion 

Merriam-Webster’s definition can be a model for your life. This is a post about how an engine metaphor snapped into consciousness as a way of gathering the things that interest me and using them to propel me to where I want to go. The post itself is an example of its underlying premise. You are about to inhale exhaust. But if I do my job right it will help, not harm.

A Philosophical Basis For Integration

Before we get into the model, we need to establish a shared understanding. I believe the model is generic enough that anyone can benefit from it. I use personal illustrations, but with reflection, you can map your own circumstances to my example. We aren’t doing this because it’s easy, but because it’s worth it. Even if it returns an affirmation of your current path, this exercise is a win-win because either way it relieves existential dread and lets you pour the associated anxiety into forward energy.  

I’ll start with by walking you through the thoughts that brought me to the model. The model’s ultimate goal is what I unimaginatively call integration

We have kindling to gather first. 

Catching Up

Long-time readers know I left a full-time trading career after 21 years. The specifics are unremarkable. 21 years is just a long time to do something. If you believe, as I do, that most of us are multitudes it’s not surprising that people would like to change it up. The inability to do so has more to do with expense than will. We’ll get to that. 

If you keep growing vertically in a profession, it can get stale. Every incremental bit of learning feels like pulling blood from a stone. The plateaus are thicker and longer. I never went to graduate school but I imagine the narrow focus of getting a PhD might feel similar. Still, even a grad student believes they will emerge from a cocoon to eventually find a new habitat and pattern of living. 

It’s sometimes possible to grow laterally within a profession without incurring heavy costs. You rediscover the vigor of a beginner’s mind where the strides are long enough to feel momentum. The wind in your hair.  You feel rejuvenated. You are actually getting more life out of the same number of minutes because novelty :dilates time

Unfortunately, many lateral moves are not enough. You are still in the same orbit of what you are doing before. If you design Nikes instead of selling Nikes you just replaced the “function” category in the Sneaker Industry pivot table. If you want to sell bicycles instead, you will need to convince a new orbit of contacts that your function can translate.

And still, there’s one more glaring issue we haven’t addressed. What if you don’t feel like doing any of the jobs your experience has sharpened you for? There’s no reason to think this is uncommon. We often get tracked in a career by our early 20s. How many of you feel like the same person you were 10 years ago? 20 years ago? Careers can stretch upwards of 50 years. I don’t have to speculate. In the many conversations I’ve had with people after leaving trading, I’m certain that many people feel mismatched and trapped. 


I want to be careful about how I continue. Effective communication rests on a shared understanding of the words we choose. Look around and you will find words that have become  too “big”. For example, the word “victim” can refer to a wide range of injustice. A child who was abused to a person who is passed over for a promotion. In the child’s case, the degree of injustice satisfies a floor that will have little variance regardless of who hears the word “victim”. The degree of injustice to the employee depends critically on the specific circumstances and even then a trial might be required to adjudicate. 

When I say trapped or mismatched, I’m not referring to people in jobs that few would aspire to. There are people working in minimum wage jobs at advanced ages for which the strong-form version of “trapped” is apt and regrettable. I would applaud them for duty, I respect their grit.  We all know people like this, but they are not the audience for this piece. When I use “trapped” I’m referring to a much less dire range of that word.

With that arduous caveat behind us, let’s proceed (“write in your own voice” they said, not knowing how seriously I’d take that advice). 

You feel you’re on the wrong path. Trapped. Out of sync with yourself in some way. You’re doing your job and maybe it’s going well, maybe it’s not. There’s lots of noise in careers, especially “knowledge” work. You can be in a good industry and you attribute success to things when it might be more accurate to say you’re succeeding in spite of those same things or even yourself! Nobody is bigger than the market they are in, so your individual strokes can get lost in the current. Epistemic purgatory. That means looking at results instead of paying attention to your internal barometer can easily mislead you. This goes both ways. You’re doing a great job in a shrinking industry, and you are blaming yourself. So the first important point is that your feelings about how you are doing matter even if they don’t show up in the stats. 

You accept this and trust your feelings.

What is this feeling?

True North Is Your Potential Calling

You feel the attraction. “I’d like to see what I’m capable of if I care. I’d like to see what happens if I was proud of my effort.”

Let’s turn to Lawrence Yeo:

If you hate what you do for work, then you will either (1) find a sense of purpose elsewhere, or (2) use your job to fund other activities that are meaningful. If you don’t do either option for a long time, then each day will feel like a pointless slog, and nihilism will be there to greet you each morning.

Sit with that for 1 second.

Lawrence continues: 

When you’re on a path that feels empowering, you don’t have to wonder whether or not you should keep going. It just feels right, and you know it. And herein lies the paradox:

The less you have to ask about your purpose, the more you embody it.

Through it all, remember that there’s nothing more real than your potential. Oftentimes, the awareness of that is enough to keep you going.

The name of the post says it all…There’s Nothing More Real Than Your Potential

The feeling of being mismatched exists because there’s a sense that you are capable of something more. Your highest power, your best chance for discovering your meaning1 is to move closer to integration if being compartmentalized tears at you. Your compass is pointing to its true North — integration. 

Now what?

A premature recap of course!

Let’s gather ourselves:

  1. We can get trapped in career paths. Sometimes we are prematurely tracked, sometimes they just get stale. Either way, the costs to switch can feel prohibitive.

  2. You are not a machine. You are a person with a sense of your own potential. You are also cursed. Condemned to find meaning in your life. How you deal with this is the very subject of philosophy. In other words, we ain’t solving that here. But there is a small facet we can address. 

  3.  Compartmentalization. We all compartmentalize to some degree. But since sustenance requires work (this is a normative statement — how much work this should require is another matter…again, beyond the scope of this post), we spend much of our waking hours doing “work”. If you are skilled at compartmentalizing or rationalizing, then a wide range of jobs will be suitable provided they meet your practical criteria. But what if you can’t make the connection between how you spend large chunks of your time to some nagging sense of purpose?

  4. North. You feel too divided. Nobody is a perfect arrow with a zero drag coefficient, devoting full resources towards their true North. We don’t even know what that is. But you can sense when you are heading in the wrong direction.

This is the audience I’m speaking to. Because I lived it. I’m living it. I’m trying to right my direction. I’m not trying to be grandiose. I didn’t find Jesus at the bottom of a bottle. I’m speaking to the people going about their regular lives, mostly feeling fine, but as my friend Khe says “have a pebble in their shoe”. If you are full-steam ahead on your current path, feel free to abort this post. People are envious of you. Me and my bank account would have loved to just blissfully keep printing trades.

(Yes, I’m a special snowflake. And so is everyone else. Because we are conscious. We are also insignificant dust in the shadow of galaxies, an inaudible murmur in the hallway of geologic time. The way you resolve such paradoxes is the alibi that defends your insecurities. Probably just better to accept the ambiguity as irreconcilable in the same way that you accept that you’ll never see a real dinosaur. It’ll help you shed the fictions that invisibly chain you.

Sorry that was weird. But you’re the one who climbed up the Moontower voluntarily.) 

I left my job nearly 18 months ago and only now do I feel that I have a checkpoint from which I can write about this path. 


A Change In Direction

Your compass points in the direction of your potential. 

Now what?

Lawrence offers a small step in a new direction:

Use your curiosity to explore a path that feels foreign, and play there for a while. If the questioning of purpose grows stronger, then turn back. It’s not the right one. But if that question begins to fade, keep walking. You’re getting closer.

Pause for a moment. What is the most important word in that passage?


“Explore” is the most important word in Lawrence’s quote. 

“Explore” is an active verb. It is hard to understate the importance of this. We often think inspiration precedes action but this is mostly backwards. You need to try things to earn the clues that allow you to break inertia. 

My Own Story 

I’m a risk-averse person. My story is gradual. Like watching car travel from an airplane window. It’s skippable if you want to jump ahead without context to the general model I’m building towards. 

Otherwise, let’s back up a bit. 

The First Step Was Unlearning

Rewind to 2018. My wife, Yinh, took a year off from work. I was working so this was doable. Again, be practical. Your personal cash burn, willingness to cut expenses, savings and goals are all factors. I hope this is obvious, but just covering bases. Enough disclaimer, let’s continue.

During my Yinh’s break 2 important things happened.

  1. She had the space to explore a passion — her love of people’s stories.

    Yinh loves to be inspired by others, but rather than focusing on wins, she wanted to learn how people overcame failure. Her show Growth From Failure was born. The joy of meeting these people didn’t let her down. She incurs great expense in time and money to produce these shows but it was more than worth it because it was so fulfilling. She had a clue that she’d like it, did the experiment, and now it’s a big part of who she is. It helps with her own sense of meaning. It allows her to channel something she loves into something useful. It satisfies her generative spirit in ways that her day job doesn’t. 

  2. Her year off provoked a lot of questions.

    Why were we both grinding so hard when the day-to-day slack of having only one parent working was so additive to our sense of well-being? We were really happy that year and while the opportunity cost was financially expensive, the benefits were plainly visible even if they didn’t show up in Excel. Leaving her job was not something she took lightly but as expected we got information about ourselves. A new set of questions loomed over our entrenched script. And these questions carried more weight because they were in the context of living the experiment not just imagining it. This was a formative experience that informed my view that you can’t simply introspect your way toward better outcomes. This might be obvious to many of you already but for a shoe-gazer like myself, it was profound. 

Honestly, the revelation from that 1-year experiment makes sense in hindsight. I saw how much energy the podcast gave my wife and it made me feel not only too closeted to possibilities but that I locked myself in that closet. Deep inside I was always aware of a thirst, but I was afraid to admit it aloud. I was afraid to give it power. It felt too dangerous. We were content so the risk/reward of questioning seemed like pure downside. Yinh’s year screamed, “you’re ignoring the upside!” Not financially of course. While a podcast incinerates cash (the equipment is cheap but the ongoing hosting, website, and editing costs are either time or money), her lost income was the real line-item. 

In that year we earned less money and you know what? It was fine. Obviously from a survival point of view, but that wasn’t the concern. It turned out to not be a concern from a mental point of view. I stopped checking in on the “net worth” cell because when you stop racing you don’t care about your lap time. It was liberating. It was the first time I had considered the cost of scarcity mindset 2. Spring had arrived and the risk-aversion thermostat was still set to blast heat.

Suddenly there was a lot to unlearn. But unlearning isn’t just whittling away. That just leaves you naked. You need to replace. 

Then Came Learning: My Own Experiment

My wife took her break in 2018. At this point, I was already devouring tons of blogs and podcasts because I wanted to learn about investing and crypto. I also had an extensive note-taking habit (I used an Evernote+Trello stack). All this information was building up. It was loosely organized into an index so when I would come across something interesting I would have to think about how it fit. Ideas would often compete with each other. Who’s right? Everyone sounds so damn smart (especially on podcasts…then I learned that all the “umms” and “likes” are edited out and it made me feel way better about myself). 

I started bombarding my friends with links along with snippets of my notes. Yinh, feeling the warmth that comes from creation and connection, made a simple suggestion. “Instead of blowing up everyone’s Whatsapp all day, why don’t you gather all your links and associated thoughts and send an email once a week?”

My first reaction was that it seemed both arrogant and scary, but it made sense. And I remembered that I was putting myself in that narrow closet. I made a list of about 100 friends and family and asked if they’d be willing to accept such an email. 45 agreed. 

As Matthew McConaughey said in his book. “Green light.”

Moontower was born. For months it was links and some commentary. Looking back at the start, I can appreciate what was happening. I was arbitraging the information gap between offline and online people. For example, people find “mental models” novel and fascinating.  But offline people are less aware of them. On Twitter such topics are commonplace. In fact, they are so overplayed because threadbois use trite ideas to audience-build. (The ideas are sound but become trite because they are a victim of their own success as they are condensed into bite-size, viral delivery units). Now, I wasn’t thinking about audience growth. I was a lamb naive to the online game. I was just talking about things I found interesting because I wasn’t overexposed to them (or I’m just a saccharine-loving caveman. I mean I do love 80s hair bands). 

The letter grew slowly but steadily. I had no expectations going into it, so I was just happy. As far as I was concerned, I was doing a little experiment, with my only constraint being that I had to be committed. No giving up. There was zero sense of entitlement to an audience.  I was taking notes anyway, might as well go the extra step and polish them just a bit, right?

Well, you can’t do something like this without having your personality leak through. I enjoyed the challenge of stringing a few words together in a catchy way. It seems inevitable now, but I didn’t foresee it when I started — the seeds of original posts. I’d explore contradictions in the advice that I’d read with what my trading career had taught me. I was reading about investing which is surprisingly different from trading which is more of a business (trading is not investing, it’s a thing you could invest in). By reconciling the concepts in my head, I was building bridges.

The lens resonated.

I’d start reply-guying on Twitter. I’d share ideas I’d put work into. Eventually, a large account takes notice that you are additive to the conversation (thanks @Econompic). Social proof. Green light. 


Having more readers and new followers was nice but it was never a goal. I still don’t know anything about growth hacking or marketing. This was probably for the better. Instead of video-gaming this new experience to level up, I just continued along my merry way. No pressure, no thoughts of “what’s the next step?”. It was a generative outlet for my note-taking and curation hobbies which until then were private habits. It was a chance to be creative on a different dimension than my day job allowed. 

It started as an experiment. And then it rewired my brain. 

I was changing. 

The joy of strides in this new area put the lack of stimulation in my professional life in sharp relief.  The sense that I was at a plateau was becoming more apparent. Just like an experienced lifter needs to resort to new techniques to maintain momentum, I was reaching the “blood from a stone” phase of my career. And I’m not talking about money. That was moving up and to the right. It was the pressure to scale up. The fund was growing. I had the go-ahead to build. My employers were confident and supportive. 

I felt torn. I didn’t find any meaning or fun in it. Either might have been enough. I was there for the money. It was getting harder to see why I should devote 40 or more hours a week to the gig. Trading is competitive. There’s no part-time version. And if I “quiet-quit” just for the income, I would’ve felt I was wasting everyone’s time. 

Covid forced my hand as it has many others. It was a chance to take inventory of the pros and cons of making a drastic change. 

On the cons side:

  1. Not working with the talented and amazing friends I’ve worked my whole career with. This remains the hardest part of leaving the job. And that might surprise you when you consider #2. 

  2. Umm, the lost income. The opportunity cost of going from my job to no job was embarrassingly large. My anti-preference for the job would need to equate it to waterboarding to even begin to make mathematical sense. 

To balance this, the pro column would either need to be substantial and/or the cons would need to be understated to have this decision make any sense.

Let’s work through it. 

Are the cons understated?

The anti-preference for the job was quite strong. I didn’t want to spend my time thinking about squeezing out more pennies from option prices. I didn’t want to haggle with brokers all day. Still, none of this is waterboarding. If these were the only issues, I could have tolerated it. So this con is real but not understated. 

Not working with my friends is actually an overstated con. For 2 reasons. As we grow, we can find new ways to collaborate. We can show each other deals and lean on each other’s expertise in novel ways because our knowledge becomes more complementary. As I spread my wings in other directions, they can have access to my newfound knowledge or even fund what I’m doing. On the flip side, every day I spend away from the arena, my job-level experience decays. If you last traded 10 years ago, you can’t compete today. I’m becoming more obsolete every minute I’m gone. But I’ll be able to invest in them and have trusted insiders to call on for diligence if needed. I can already see compelling ways to collaborate now that I’m gone. 

So if I’m not understating the cons, the pros need to be enormous. 

How about the pros of leaving?

  1. A head start on the next chapter. 

    I was in a race to retirement but I asked myself, “What would I do then?” I’d want to build things I was interested in. But I was partially doing that now by writing. If I waited 10 more years, I would have more money but I’d have less potential. I’d have less energy. I’d face more ageism.

    Put yourself in this comparison. It’s not as stark as it might appear qualitatively:
    1. You earn 10 more years of W2 money assuming you don’t flame out in a competitive business that you’re reluctant to be in


    2. You log 10 years of accumulated effort (with possibly an asset to show for it) on something you actually want to do so presumably you get good at it

Some notes on the comparison:

    • It is the most conservative comparison because it’s in units of dollars not utility. If you already have substantial savings relative to your expected liabilities, then the mental well-being aspects are understated relative to the financial considerations. 

    • Look at each leg of the comparison. Will you survive at something you don’t want to do as you get older? In some occupations you might be able to coast, but if you do you will have not had any growth after the 10 years is over. If you didn’t make enough money to have securely stamped out any concerns about future liabilities, you find yourself needing to re-invent yourself from zero. If you commit to learning and growth instead of a “rest and vest” approach, there’s a much better chance that your human capital will be higher in 10 years. With that comes confidence and a positive outlook to carry into years when many people just try to slow the perimeter from closing in on them. The duration of your financial capital depends on real rates of return. Skills, on the other hand, are inflation-protected and amortized into present value at a lower discount rate. To understand consider an extreme example where a hyperinflation destroys financial capital but you retain the ability to work, code, build, etc. It’s a fixed-for-floating swap when you want it most.

    • The lost income today is partially made up on the backend if you succeed at something that you enjoy. That makes it sustainable, meaning you can do it for longer. If you expand the time horizon of your earning life. It’s one less year of drawing down on your savings plus one more year of savings. That’s a double-whammy of benefits for every extra year you can work.

      With a longer earning horizon, the pressure is relieved. You can take a break for a year or work 4 days a week, or from wherever you want. The idea that you can work until you are 75  is freeing IF you can do it on your terms. 

2. Another benefit of leaving the daily grind today — my kids

Kids are young once. Yinh, the loving wife that she is, believes the kids are better off having lots of exposure to me for these special years. Let’s go ahead and be conservative. Mark it zero, dude. The extra exposure is a gift to me not them

Nobody else needs to feel this way. Many people recognize that in the balance of their own lives, they’d prefer less exposure to their kids than I have. Yinh needs to work for her sanity. This is nothing to feel bad about. But personally, this is my favorite way to spend the opportunity cost of my lost income. The last 2 summers alone have been epic memories for me. I hope they one day feel the same. But I’m willing to claim all the selfish benefits of this choice without needing to rationalize on their behalf. 

So is there any benefit to my kids?


Seeing me engaged. Seeing me stoked to work. I want them to see that integration is possible. When you work on things you care about, you feel alive. Flow, in the zone, whatever. If you have felt it, you need no explanation. If you haven’t, I’m sorry. 

Growing up, my mom was already sad by Sunday morning. The lesson: work and much of your life is something to be tolerated. Look we need to build tolerance muscles, but tolerance of your job is a short-term booster shot. If you find yourself tolerating 5/7 of your life, you have a problem. That’s not normal but people will act like it is.

That’s a failure of imagination. And before you protest that imagination is a luxury, we should remember that every immigrant that escaped home had imagination. Having imagination today means fleeing a stifling script, not an oppressive dictator. If anything, it is easier to be a refugee from corporate life than a war-torn country. 

The pro column considered in its entirety felt strong enough to make the decision to leave justifiable but certainly not a lay-up. What pushed me over the edge?


Thus far, it’s been a straightforward pro/con decision exercise. Clinical at best, garbage-in/garbage-out self-deception at worst. But I pulled the trigger and quit without looking back for a bigger reason. 


I had seen enough to bet on myself. Yes, I made sure my bases were covered so I had runway. But there was enough grainy data, that when combined with the pro/con list made the decision shockingly easy even without a concrete idea of what I would do. In fact, having a concrete plan wasn’t even a priority. 

To understand why confidence carried more weight than the foggy ideas on the pro/con list we should decompose the role of confidence into downside and upside. 

The Confidence Put Option

When I started writing, I said I was educating others or clarifying my thinking. There’s truth in all that. But it pales compared to what really happened…I started to “find the others”. The nature of the inbound told me that I could make money. This was a mentally important hurdle. 

It might sound surprising, but if you are a trader who doesn’t want to trade, your biggest fear is that the next bid for your services is…zero. You walk off the trading floor and straight to your real estate license exam to start at the bottom of your local Coldwell Banker office. Even they would look at me like an alien. Imagine the hiring manager as she looks up from my CV: “So you spent more than half your adult life…yelling in a circular arena that has since been replaced by an iPad?”

Seemed like a good idea at the time. I guess?

(Btw, when is she getting replaced by an iPad? I’m sorry, I’m sorry. If you’re a realtor reading this you gotta be self-aware that there is no profession people love to hate more than yours. It’s not personal.)

The confidence that I was employable was all I needed to de-risk the downside. Of course, my fears were overblown in the first place, but it’s hard to see that in an insular world where everyone is focused on the same inputs and outputs. Financially, my highest and best use is probably in a trading seat. If I define myself narrowly. 

In Why I Share Online And The Decision To Leave Trading, I wrote:

Twitter is a tool for relationships and to spread proof of work. I did one thing for 21 years. When I try to do something else I’m a major underdog. I’m not going back to school. I don’t enjoy school. My online presence is like a proof of work, so when I try to convince someone to take a chance on me in a new field I can show something that looks like a resume to someone that’s open-minded. If you wonder about my incentives on Twitter, I’m being open about it: relationships, proof of work, & optionality in distribution.

Writing led to online status.

Online status gets you inbound conversations.

Inbound conversations are informal interviews.

Such informal interviews are a way to demonstrate that you can repurpose your knowledge for a broader purpose. (As an exercise in existential self-soothing, I once spent a weekend re-writing my CV to be a “pivot” CV where I forced myself to re-imagine my experience as something with more universal appeal. I never tested it out, so I have no idea if it would have helped me land interviews in other fields). 

The value of Twitter is in the DMs. Ask people with high-quality Twitter followings how much they’d need to be paid to never use Twitter again, and the results will trigger offline people who don’t understand it. 

The Confidence Call Option

The internet is a network where high-value nodes are discovered, reinforced, and accumulate advantages. Like any compounding-type dynamic, it takes time to get to large numbers, but if you keep at it, the math is inevitable. In 6 months, I’ve picked up as many subs as I had in 3 years. We talk about options in this blog. 

See Portfolio Theory And The Invisible Option On Hobbies for the bull case to sharing your niche expertise in an increasingly networked world. Hint: it is an option that is increasing in value.


Reviewing The Starting Point: A Hobby

Let’s back up to remember how natural this process can be. 

One of the most popular categories of hobbies is collecting. Stamps, coins, vintage candy, guitars, cat JPEGs. For me, it is ideas. I like discovering concepts and taking notes on them. I used to think it was useful, but realistically it’s leisure. It’s how I entertain myself. Whitewashing it as productivity was mostly rationalization. But as you’ll see, that is great news because it’s a hint that the thing you’re into that’s “not productive” can be more!

I enjoy collecting ideas and taking notes. That’s a hobby. Checkmark. 

What else? 

I have problems. We all have problems. When you try to solve your problems, you generate information. 

Two problems that I feel compelled to work on (as opposed to fully outsource):

  1. Investing our assets
  2. Helping my kids learn

Between the notes, knowledge from working on my main problems, and the willingness to write  I’ve turned invisible potential energy into progress. Writing (and tweeting) allows you to learn in public. This leads to more inbound info that then gets processed through the same filters. There’s a ton of exhaust that ends up sitting in my notes. For a long time, I planned to publish about anything I took notes on.

Years ago I made this diagram:

The fact that I put the diagram in this post demonstrates why the idea that I would publish all my notes eventually was stupid (not to mention impossible — the backlog builds faster than I can output.) Because the plan to publish everything ignored path dependence. As you grow, your problems and priorities change. That diagram was supposed to make it into Part 2 of my Idea Triage Series. That series stopped at one post.

Over time I realized that embracing the hobby view of what I was doing was critical. Not everything needed to be part of an output. The hustle in me was worried about wasting time but of course, the unmotivated explorations serve a purpose. They give you space. They refine your taste. So that when you do commit to an output, it will be better. 

More personal examples:

  1. Coming from the options world it was natural to take my notes and turn them into posts but I also saw that I could be a capable curator for the Moontower Volatility Wiki. It doesn’t take much extra effort to bridge my collecting hobby into a public resource. 

  2. In learning about investing, I took my notes and started building the Moontower Money Wiki. again, solving my own problems, but taking the extra step to make it helpful to others. That’s a work-in-progress.

  3. I have notes on decision-making and career guidance. They sit in a private wiki I call the Human Capital Wiki. It’s divided into 3 sections: Motivation, Strategy, and Productivity. A few months ago I realized it was never going to see the light of day in the way I imagined. But the reason is illuminating. I started mentoring a HS student. I realized that the topics in that wiki would make a great resource for him. But not in the form it was in. So one of my current projects is to refactor that wiki and re-label it with a more concrete purpose: The Guidance Wiki (still unreleased). 

  4. I have tons of notes about learning and education that have survived the tournament of ideas on these topics in my reading. They are en route to being turned into another guide:  Principles of Learning (unreleased)

  5. The inbound from my efforts led to many conversations. In the same spirit of abundance I approach my writing with, I found it useful to be organized about people I meet. Just as some notes will turn into posts, something beautiful about these people made you want to meet them in the first place. What are people looking for? What are people offering? With just a bit of extra effort, you can have a CRM which keeps track so that you can facilitate intros. Who’s raising money, who’s looking to back others? Who can design, who can code? Who knows how to hire freelancers? Who’s on a later stage of the path you’re on?

    Besides helping others, you don’t know where your own interests might wind up. Your future collaborators are in that CRM, you just don’t know it yet. This isn’t “networking” like you did in an ill-fitting suit in college. This is bringing value to find value. If you are in a “having coffees with lots of people” phase, don’t discard the info. Be someone who looks to recycle exhaust and introduce people selflessly.


Business analysts use the term “flywheel” to describe this sense of flow where there’s a constant recycling of exhaust (unused information) that can be processed when the right time arrives. 


As I’ve been experimenting and exploring, the picture is becoming less foggy.

My primary domains of interest are:

  1. education
  2. investing
  3. writing

The more I do and learn about these topics, the more I want to do. This is what’s fun. 

Writing is the most meta of these categories because while it’s a stand-alone endeavor it makes the flywheel work. Acknowledging this has helped me narrow my focus. (At the beginning of exploration mode, you do not want to narrow. In fact, premature narrowing might be why you are 10 years into a career that doesn’t fit). 

What does it mean to focus? 

The projects that I entertain need to be interesting but also fall into one of those buckets or in the seams between them. My project page in Notion presents this visually:

This is what works for me. 

Bringing This Back To You, The Reader

All of this personal talk of my path and decision-making process is an informal case study of a few broader principles. The principles are universal but abstract. You need to assign your own concrete actions to the general recipe. Let’s review the algo:

  1. Calling: You are unsatisfied with what you are doing for whatever reason. 

  2. Experiment: You need to take deliberate actions in a domain that interests you. 

  3. Feedback: The actions return information. 
    1. Perhaps a new outlet enables you to compartmentalize better. That’s a win. We all compartmentalize to some extent. You may find yourself in a happier spot.
    2. The feedback is a clue to your own potential. Iterate and loop (2) and (3). 

  4.  Ejection [Optional]: You may find you want to make a drastic change. Consciously or not, many people, including myself, followed this recipe. It revealed and invited them to a higher degree of integration. If you can spot a line to a sustainable and integrated life you are lucky. Beware. This is where a lot of the real work begins. But…you are switched on now. Mondays are exciting. 

We will generalize this model so you can fill it in with your own projects.


The General Model: An Engine

A 4-stroke gas-powered engine is an elegant model for integration. For illustration:

The 4-strokes as described by BAP:

  1. Intake Stroke: The intake stroke is where the intake valves are open and the air is drawn into the cylinder. The fuel injector sprays the fuel into the cylinder to achieve the perfect air-fuel ratio. The downward movement of the piston causes the air and fuel to be sucked into the cylinder.

  2. Compression Stroke: The next is the compression cycle where both the intake and exhaust valves are closed. The upward movement of the piston causes the air-fuel mixture to be compressed upwards towards the spark plug. The compression makes the air-fuel combination volatile for easier ignition.

  3. Combustion/Power Stroke: During the power/combustion stroke, both the intake and exhaust valves are still closed. The spark plug produces a spark to ignite the compressed air-fuel mixture. The resulting energy of the combustion forcefully pushes the piston downward.

  4. Exhaust Stroke: The last cycle is the exhaust stroke where the exhaust valves open and the exhaust gases are forced up by the returning piston.

If you consider the work of your life as an engine you can think of each vertical of interest as a piston. For me, it’s investing and education. 

Each piston has its own strokes mapping to the engine metaphor:

  1. Intake: Information from content, conversations, and life experience. Mind your information diet and who you surround yourself with. High octane fuel = healthy, smart inputs. 
  2. Compression: Filtering, summarizing, and reducing the information so it is useful
  3. Combustion: Insight and ignition
  4. Exhaust: There’s always unused information or advice. Often it doesn’t apply or doesn’t fit in this precise moment. 

The Role of A Turbocharger: Efficiency

The engine metaphor is missing a magic component: the turbocharger.

A turbocharger recycles the power of exhaust to force pressurized air back into the engine’s intake. If you can strengthen the abstractions that link your domains, the exhaust for one project can feed into the others. If you improve your writing, communication, design, or people coordination (ie you get good at hiring freelancers or finding collaborators) you can recycle the exhaust from your projects faster. For me, writing is both a turbocharger and its own piston. 

[In The Why And How Of Taking “Discoverable Notes”, I unabashedly recommend a personal knowledge management system. Nerds refer to these as “PKMs”. I use Notion but this guide can help you choose one if interested. A system is a must-have not a nice-to-have for my own process.]

Integration is the feeling that your interests and work are aligned and fluid. A well-oiled engine, that wastes less exhaust will take you further for a fixed set of inputs. 

In other words, integration = efficiency


Once you begin thinking of your work as an engine, as self-integration, and not a single bilateral transaction with one employer (or overlord if you are especially cranky about your choices) you have replaced an existential problem, namely the rejection of over-compartmentalization, with a technical problem. The technical problem is “how do I sustain such a life?”

This is new to me and I’m learning on the fly so I’m not the best guide here. But I can offer my philosophical perspective, knowing that it will likely evolve with experience. I still think it’s important to lay out principles as a tether to your values as you head out into the unknown. 

  1. Extract less value than you create

    This is obvious. Strip-mining is not a renewable strategy. I’d rather underpromise and overdeliver. This isn’t altruism, it’s good business. If you leave the high-pressure race, you have chosen to focus on the long-term. The advantage is you can use a different playbook that relies more on compounding which pays off with time, instead of quick, but hard-to-repeat scores. 

    From Working For Free

    In business, I always enjoy the Costco example. Charlie Munger has written:

    “When other companies find ways to save money, they turn it into profit. [Costco] passes it on to customers. It’s almost a religious duty. [They] sacrifice short-term profits for long-term success”.

    It’s not as hokey as it sounds. Think of it this way. They are hiding profits in the customer’s own pockets. They will be return customers. That profit is hidden from competitors’ wandering eyes and the IRS. The strategy commits Costco to keeping the customers happy because the profit is realized over the long-term. It’s simple but requires rare discipline.

    The profit that “sits in your client’s pockets” has a bookkeeping entry called “trust”. The fact that it doesn’t capitalize as an asset on your personal balance sheet is a shortcoming of accounting. You can’t let it fool you from the reality that you have stored your future income with your clients and in their word of mouth. 

  2. Price your attention carefully

    When you consider a project, you must decide how much to charge. If the project requires diesel fuel and you are a sports car, it might not run or it might be inefficient. This feels like a one-off transaction. You should probably quote a “go-away” price. At some price, you’ll suck it up. But this should be rare.

    You want projects that have recyclable exhaust. If you suspect the exhaust is especially powerful, maybe you charge less. The point is to price your time or effort holistically. What is the first and second-order cost/benefit of taking on a particular project? 

    An example of holistic thinking: I don’t paywall my letter because the loss of subs would cut off a valuable inbound fuel source. The cash would not be worth it. Instead, I reframe the forgone income as “marketing cap-ex”.

I don’t know much about monetizing an integrated body of work. I’m not especially commercial-minded. But I have friends that are further ahead on this path that I can lean on. In thinking about creating your engine, realize you are not alone.

Identify your own principles. It’s a way to stay “green” as you experiment with sustainable business models that empower you to stay on the path. 

Getting Started: Identify Your Tools and Compass

You can start now.


Dump your interests and strengths on a page. Start drawing circles around things and lines between them. Don’t edit your thoughts. You are identifying your tools and capabilities. 


When potential is your true North, you are playing the longest game. And more importantly — it has an endpoint that nobody else including you can imagine. The goal isn’t a finish line, but a new trail that unfolds with every step you take. The uncertainty is something to be embraced not feared. 

Final Tips

  • You don’t need to blow up your life. You can’t just tear down or destroy leaving a vacuum. Instead, erect scaffolding, create a replacement, build towards beauty. You won’t need to tear down the old. It will crumble on its own as its relevance fades. Don’t waste energy on useless fighting. You can simply decide to use that precious energy to give, create, and share. You don’t need permission. These activities have a yield. They are investments even if the dividend dates and amounts are unannounced.

    [To break inertia, see Get Unstuck And Move. Do not miss the list of links at :the end of the post.]

  • Mind your inputs ruthlessly. Avoid complainers.

It has never been more convenient or possible to make a change. A permissionless, networked world is enabling you. If you create value, you will attract value. You will find others. Don’t horde the lessons. They are exhaust you can recycle to strengthen a community of millions who found themselves agitated. These are the others who want to unlearn the devices that Oujia-d them into their current stations. They are future partners that will remember you. 

It’s not easy to re-imagine. But it’s also never been easier. Higher levels of integration are out there to find. Right now you are adjusting your compass. Then through actions, you will design your own engine. 

Enjoy the ride. 







A Quick Hop From Note-Taking To Writing Online

I started writing online 3 years ago. I wish I started even earlier but as the sign that used to hang in our boys’ preschool used to read:

The best time to plant a tree is yesterday. The second best time is today.

I won’t rehash the benefits of writing online (I have a list of clipped articles on that if you’re interested) but I’ll share a thought on the topic.

I was recently chatting with an internet friend (or what your meatspace spouse might refer to as an “imaginary friend”) who has an established quant finance career. She’s at a juncture in her career but is finding that the most compelling options are coming from inbound opportunities based on her writing. While she has options coming from her direct experience and CV, they aren’t the most interesting. They are well-trodden, established paths. But writing has inadvertently cast a much wider net than her resume ever could have.

I see my writing the same way. I don’t know what my next endeavor is, but I’m making the bet that having a public body of work might allow future partners/collaborators/employers to take a chance on me even though my official career (“option trader”) has been narrow. Writing is a way to demonstrate range. Perhaps I’d be better off getting an MBA or other degree if I’m trying to pivot, but that’s why I call this a bet. It’s also a real-life example of the post I shared last week Portfolio Theory And The Invisible Option On Hobbies.

It’s never been easier to get started. A few thoughts about getting started from personal experience.

  • I did have one head-start. I am a note-taker.

    I’ve explained my system here.

    Just as storing a guitar in a convenient location (without a case) makes you more likely to pick it up and practice, your note-taking habits reduce the drag coefficient of traveling from “idle thoughts” to “words on a page”. The structures I built in Notion lent themselves to connecting ideas better than my old Evernote + Trello PKM stack. (PKM stands for personal knowledge management amongst the “productivity” cult).

    There’s lots of great software to host your PKM. Ann-Laure’s guide can help you choose.

  • For Notion users

    You are 95% of the way to publishing online. I use WordPress as a CMS (content management system) but I just subscribed to which allows you to point your Notion pages to a custom domain that you own. If I were starting over today, I would simply buy a domain and connect it to a service like or for a small monthly fee. If you want a free solution, with a little extra effort you can use Fruition.

    These solutions eliminate the need to learn a new CMS. So you can turn a key and have the Notion environment you are comfortable with be an elegant and flexible CMS. For evergreen content, like much of my writing, the chronology of blogs makes little sense. While you can use “categories” and “tags” the end result isn’t quite right for material that looks more wiki-like.

    Here’s a link to all my Notion pages that are now public. Note how Potion allowed me to use my MoontowerMeta domain be the host.

    This lets you:

If you were on the fence about starting to write online, I hope this was helpful.

The Most Important Solutions Are Simple Just Not Easy

Here’s an exercise.
Watch this 4 minute vid which shows how people solve their problems AND how corps study you to serve you solutions.  It’s also amusing. The late HBS prof Clayton Christensen reveals some surprising facts about the habits of people who buy McD’s milkshakes.

The Job Of A Milkshake (YouTube)


This post shows why you don’t need a manufactured solution. You don’t need a “milkshake”.

Decomplication (Link)
Nat Eliason

My takeaways:

We all know the concept of simple but not easy. It’s the truth to everything worth having. Good relationships, good health, good output. You can’t fool yourself and there’s no shortcuts to these things.

It’s easy to forget that because we want to forget that. It’s inconvenient. So we tie ourselves in confusing webs of apps, CBD and expensive mattresses to figure out how to do something babies just do: sleep. And that’s just one example.

We succumb to:

The Law of Artificial Complexity: As the number of people experiencing a problem increases, so will the artificial complexity of the solution.

We need to remember: 

The Law of Decomplication: The more people that are experiencing a problem, the simpler the solution should be.

So strip the problems back down to their essence.

      • Losing weight: People without access to food get very skinny. If I eat less, I will lose weight.
      • Networking: Famous people tend to hang out with other famous people, or people as accomplished in tangential fields. If I want to get to know someone I respect, then I should do something that puts me on a level where I could be friends with them.
      • Productivity: The goal of productivity is to get more done, and the biggest reason you don’t get things done is that you’re doing other things. If I remove the ability to do other things, I’ll do the thing I’m trying to be productive on.
      • Sleep: Removed from modern society, sleep is not a problem. If I can create a sleep environment as if I wasn’t in modernity, I should sleep fine

The Why And How Of Taking “Discoverable Notes”

I have been an active note-taker for years and a fan of how meta Tiago Forte gets about the process of taking notes. Tiago’s Building A Second Brain course is very popular in productivity circles. While I have never take it, I recently came across his essay Progressive Summarization: A Practical Technique for Designing Discoverable Notes. (Link)

It’s an outstanding framework for understanding the whys and hows of taking notes. I, by accident, have arrived at a very similar system so it was interesting to see someone explain it thoroughly as only Tiago can.

This is a summary of what resonated with me.

The Why Of Taking Notes

The Right Info At The Wrong Time

What you read is good and useful and very important, you’re just reading it at the wrong time.

The challenge is knowing which knowledge is worth acquiring. And then building a system to forward bits of it through time, to the future situation or problem or challenge where it is most applicable, and most needed.

Bridging The Acquisition And Use Of Knowledge

It’s too mentally expensive, if not impossible, to internalize all or most of the information we consume. A good system is intended to bridge the time between when you discovered the information to when you use it.

At that future point, when you’re applying that knowledge directly to a real-world challenge…By the time you’re done solving a real problem with it, book knowledge has become experiential knowledge [which you carry forever].

The How Of Taking Notes

Defining The “Second Brain”

An external, integrated digital repository for the things you learn and the resources from which they come. It is a storage and retrieval system, packaging bits of knowledge into discrete packets that can be forwarded to various points in time to be reviewed, utilized, or deleted.

Designing The “Second Brain”

Goal: You are trying to triage information in an organized way. You read something you know is interesting and you want to be able to reference later.

Challenge: You need to file it quickly, make it discoverable, and emphasize why it’s important so “future you” can make sense of the notes efficiently.

Tiago says:

A note-first approach to knowledge management means we have to think about design. You are, in a very real sense, designing a product for a demanding customer — Future You. Future You doesn’t necessarily trust that everything Past You put into your notes is valuable. Future You is impatient and skeptical, demanding proof upfront that the time they spend reviewing notes will be worthwhile.

Balancing Tradeoffs

  • Discoverable: Digestible notes. So needs to be compressed
  • Understandable: Context including sources, examples, details

Getting the balance between compression and context right is not a trivial matter. When the time comes for Future You to decide whether or not to review this note, seconds count.

When you fail, you successfully sent a packet of information forward through time, but not in a state where it could survive the journey… You have to summarize the note without knowing what it will be used for.

The Progressive Summarization System

  • Layer 0 is the original, full-length source text.
  • Layer 1 is the content that I initially bring into my note-taking program. I just capture anything that feels insightful, interesting, or useful.
  • Layer 2 is the first round of true summarization, in which I bold only the best parts of the passages I’ve imported. Keywords, phrases, sentences
  • Layer 3, I switch to highlighting, so I can make out the smaller number of highlighted passages among all the bolded ones. This time, I’m looking for the “best of the best”
  • Layer 4, I’m still summarizing, but going beyond highlighting the words of others, to recording my own…restating the key points in my own words
  • Layer 5 (as needed): Remix. for a tiny minority of sources, the ones that are so powerful and exciting I want them to become part of how I think and work immediately, I remix them. After pulling them apart and dissecting them from every angle in layers 1–4, I add my own personality and creativity and turn them into something else.

My Own Accidental Version of Progressive Summarization

  • Layer 0 is usually just the link without the text which is risky since the link can break. (With Slatestarcodex site being taken down I’m experiencing this firsthand)
  • Layer 1 same as Tiago
  • Layers 2 and 3 are combined. Mix of bold and italics.
  • Layer 4 is paraphrasing often drawing connections to other ideas. While time-consuming because it requires thinking I am rewarded by an easier retrieval stage. More selective about what notes I do this with.
  • Layer 5 usually means pasting the note in other notebooks when the content has multiple contexts

Mind Sprites

Inspired by Becoming a Magician by Autotransluscence

​By investing in ourselves whether our intentions are selfish or altruistic the world creates a result which looks the same on paper. The future you has more resources to share. In the massive multiplayer game of life you are leveling up:
  1. The ability to entertain or inspire
  2. Knowledge to make or heal
  3. The means to build or give
  4. A wildcard: physical or mental strength and energy to recursively feedback into the engine. Exhaust as fuel. Mechanically that’s the way a turbocharged engine actually works.
Aiming to complete a marathon is not about joy or the experience. It’s the story you tell yourself about the kind of person you can become. You want to become the kind of person that can finish a marathon. Imagine what else that person can do. Just imagine.

The quest is underway

Look at the mechanism that kicks off once you set out to train. There’s an unsaid fantasy:  I am going to be Me 2.0. The finish line will be a signal that the new you has arrived. The goal ain’t the thing, it’s a proxy for the thing. As urgently as you want to be the better thing, you will fixate on the proxy.

In your desperate pursuit, the unsaid vision of future you propels you forward. It builds an invisible audience in your mind. It cheers when you make good time on your practice run. It boos when you skip a session because you were out late the nite before. That audience is like lane assistance on your car, correcting your path when you veer.

That subconscious audience exerts a lot of influence for a bunch of nameless mind sprites. Their whispers are your self-talk. Their shouts are your self-doubt. You’re chasing a proxy and that’s ok. But beware to inspect your vision and don’t let its sprites into the game without a ticket.

Adjust your mirrors

Who does your fantasy future self serve?

What are the values of that future self?

Are you sure you want to conjure an audience for it?

The people you surround yourself in real life will also act as lane assistance. We commonly hear how we are the average of the 5 people you spend the most time with. They are your real-life audience. Their mindsets are contagious. Their optimism, pessimism, energy, and honesty are subconscious benchmarks. Think carefully about this. Are they nudging you towards the right course?

If I’m wrong about this it’s because I’m underestimating their influence.

Setting milestones

The small challenges en route should feel just slightly out of reach. The final destination should be uncomfortably ambitious. This compensates for the fact that we overestimate what we can do in the near term and underestimate what we can do in the long term.

A small change in initial conditions can result in a wide error in the point of arrival. The course correction tweaks along the way cannot overcome an angle of incidence that was wildly off the mark. Just ask a sailor.

How I Use Twitter

Stay connected on your terms

With the ashes of the information explosion layered miles high, modernity rewards people who know the effective ways to search the soot for the surviving insights. Knowing a lot about something in demand secures you place in the machine (for now), there may be more leverage today in knowing how to know things. Supply and demand is the force of gravity in the non-physical world. If the supply of information is abundant the bottleneck is in the questions. Give thought to abstracting how you learn things. The direct questions are frontal attacks. Learn to flank.

Crowdsourcing is the peace dividend of interconnectedness. Curation via tokenized reputations and customer reviews. Google’s Pagerank algorithm crowdsources search by ranking links by how likely it matches what people were looking for. Nextdoor brings you into word-of-mouth conversations that you may have been missing out on before.

Hands-on example: Twitter

  • Twitter is a fantastic platform to explore niches if you learn to use it effectively. I have learned so much from “Fintwit” (financial twitter) despite being a finance professional. Start following people that you like and as you read conversations you discover who else you like and before long you can, without their permission, find a tribe to teach and challenge you.
  • I have helped several people to discover and benefit from a thoughtful approach to Twitter. My 2 main techniques:
    • Use curated lists related to topics. You can subscribe to any of my lists and think of them as customized feeds. Make your own or find the lists of other “Tweeps” you may like.
    • On desktop use Tweetdeck. It uses your Twitter credentials and allows you to see column-based feeds filtered by a list, a hashtag, a user, or other dimensions. Here’s a snapshot of my Tweetdeck.
  • Twitter is a very entertaining and clever ecosystem. If you want a field guide to the Twitter prairie, check out Alex Danco’s playful analysis. Learn what it means to “get ratio-ed”.
  • Danco on Twitter’s disrupting influence in academia:

“Twitter is genuinely revolutionizing graduate research, in a way that’s eye-opening for graduate students and quite threatening to their supervisors. Twitter gives students a path to establishing their own brands, both for the work they’re doing but also for their critical thought, their participation in the scientific community, and their individual strengths and personalities.

This is really exciting for grad students who know how to use Twitter and the rest of the internet as a tool to build their academic careers. But it’s really dangerous for the model, which is leveraged on the fact that students do not have access to such tools, and can only acquire a brand and access through their supervisors.”

Danco dives deeper into how Twitter can relieve positional scarcity which has worn down the workhorses of scientific research — the postdocs. (Link)

  • If you are able to generate a following, one of the greatest tools afforded to you is the ability to crowdsource the answer to questions from a sharp community. Remember, you can follow anyone, unlike LinkedIn. You can always @ someone’s handle but to DM somebody they must follow you. I have seen people expertly crowdsource insightful business questions. I recommend following people who exploit this power so you can “draft in their lanes”.
  • Benchmark co-founder Bill Gurley:

“Twitter is the most amazing networking and learning network ever built.

For someone whose pursuing their dream job, or chasing a group of mentors or peers, it’s remarkable. In any given field, 50-80% of the top experts in that field are on Twitter and they’re sharing ideas, and you can connect to them or follow them in your personal feed.

If you get lucky enough and say something they find interesting, they might follow you, and the reason this becomes super interesting is that unlocks direct message, and now all of a sudden you can communicate directly or electronically with that individual. Very, very powerful.

If you’re not using Twitter, you’re missing out.”

  • If you don’t have a following (I do not), remember that crowdsourcing skill can be best rewarded on Reddit. Why is Reddit better than most internet forums? The top entries on the page are not the most recent but the most “upvoted”. Unlike Twitter, you may not “know” the respondents so it can be difficult to calibrate the value of the replies. The trade-off is you don’t need a following, instead, you must ask the right question in the right way to get responses and upvotes. A game in itself.

The Best Guides on How To Use Twitter

  • The Holloway Guide To Using Twitter (Link)
  • Nikhil Krishnan’s slide deck (Link)
  • Alexey Guzey’s Twitter guide How to Make Friends on the Internet (Link)

Twitter Doesn’t Kill People.

Last week, we talked about valuing your attention. It should be self-evident that reading nothing but US Weekly (“lowbrow brilliant”) or airport self-help nonfiction (“highbrow despicable”) is mostly a recipe for discardable knowledge. Of course, if you read nothing but academic journals and SSRN you are going to have some troubles relating to fellow humans. There must be a local maxima in-between these extremes. It’s unlikely you are sitting at that peak. Take a moment. Self-diagnose from which extreme you are approaching it. I realize that Dunning-Krueger might have something to say about whether folks who exclusively read supermarket rags can effectively self diagnose. Don’t worry, if you have gotten even this far, you aren’t in that camp.

From school days until now, you managed your info intake across the spectrum. Then social media showed up. You dipped your toe in. Maybe got in up to your knees. After some cautious steps, you made a choice. Go back to shore or dive in. You may even have jumped in only to find the waters too cold. You may be swimming where you can still touch the bottom if you stand on your tippies. What is undeniable is you are either in the water or have an oceanfront view.

The downsides of social media are touted everywhere including, non-ironically, on social media. It’s probably irresponsible to not be conflicted about its impact. People share hiatus stories like they used to describe diets — Don’t ‘Gram before bed. Unplugged retreats. Lock the donuts (cough) I mean phone, in a drawer. Personally, I don’t read Twitter on Fridays during work. Baby steps. So how do we use social media to parallel shift our info intake functions up to a higher Y-intercept?

The piece that best incorporated and extended my own take is Venkat Rao’s Against Waldenponding.


  • Waldenponding (after Thoreau’s Walden Pond experiment on which Walden is based). The crude caricature is “smash your smart phone and go live in a log cabin to reclaim your attention and your life from being hacked by evil social media platforms.” As a one-time interesting experience or occasional mental-health retreat, both Soft and Hard Waldenponding are a great idea. But as an attitudinal foundation for relating to society and technology, Waldenponding is, I am convinced, a terrible philosophy at both a personal and collective level.
  • It’s a world-and-life negation…a terrible yielding of agency. you are part of a Giant Social Computer in the Cloud (GSCITC) computing the future. The level and latency at which you consume information and act on it determines your “job” in the social computer. If you don’t manage your information economy career, you will default to the lowest-level job in the social computer: processing very low-latency information with small-minded cognition (bottom left) for small bets. It’s the equivalent of low-level bug reporting/testing.
  • The way to manage your attention is to be sensitive to your current mind size (small to great) and consciously target the zone you want to be in. There are THREE ways to fail at this: a) Thinking you can be Great Minded all the time. b) Trying to be Great Minded purely on a low-latency information diet c) Trying to consume a high-latency information diet without aspiring to more than small-minded thoughts
  • The goal is “being able to translate the information consumption/production choices you’re making into winning bets.”
  • The GSCITC is not a homogenizer of effort or imagination, but it IS a homogenizer of egos and identities. What you do counts. Who you are doesn’t. You are an ordinary part of an extraordinary process.
  • Waldenponding, I strongly suspect, is driven more by FOBO (fear of being ordinary) and ego-attachment than by any real fear of having your mind, productive potential, and rewards destroyed by “hacked attention.”
  • More excerpted highlights
  • His recent follow-up essay

My favorite ideas from it:

  • Waldenponding is about FOBO (fear of being ordinary). While our individual contributions to the great computational machine may matter our egos dissolve since the individual does not matter just his output (people try to get recognized, trademark turn of phrase, etc) which is a recognition that it’s difficult to claim credit for specific ideas and feed our egos. He goes on to discuss waldenponding as a remnant of religious meditation and unplugging. A useful distraction from which intermediary derives influence (also by having you be less productive). I think you can substitute intellectualism just as easily as religion here.
  • Segmenting info by latency and being aware that consuming info from all latencies has value because it dictates your place in the machine. The higher latency info being what some call “dead authors”. Classics as well as foundational math and science. Timeless concepts that withstand the weathering of time. Taleb categorizes such ideas as Lindy
  • Being too low minded or high minded may be counterproductive to you inhabiting your desired position in the great computation machine. Your desired position is personal (the machine needs people in all places so every position is worthy) but you must match your information diet with your goals.
  • Instead of waldenponding, he uses weightlifting analogy for training your attention. Just be aware that social media is just one type of load and should not constitute your whole workout if you want to achieve a higher place in the machine.

Stay connected on your terms

With the ashes of the information explosion layered miles high, modernity rewards people who know the effective ways to search the soot for the surviving insights. Knowing a lot about something in demand secures you place in the machine (for now), there may be more leverage today in knowing how to know things. Supply and demand is the force of gravity in the non-physical world. If the supply of information is abundant the bottleneck is in the questions. Give thought to abstracting how you learn things. The direct questions are frontal attacks. Learn to flank.

Crowdsourcing is the peace dividend of interconnectedness. Curation via tokenized reputations and customer reviews. Google’s Pagerank algorithm crowdsources search by ranking links by how likely it matches what people were looking for. Nextdoor brings you into word-of-mouth conversations that you may have been missing out on before.

Hands-on example: Twitter

  • Twitter is a fantastic platform to explore niches if you learn to use it effectively. I have learned so much from “Fintwit” (financial twitter) despite being a finance professional. Start following people that you like and as you read conversations you discover who else you like and before long you can, without their permission, find a tribe to teach and challenge you.
  • I have helped several people to discover and benefit from a thoughtful approach to Twitter. My 2 main techniques:
    • Use curated lists related to topics. You can subscribe to any of my lists and think of them as customized feeds. Make your own or find the lists of other “Tweeps” you may like.
    • On desktop use Tweetdeck. It uses your Twitter credentials and allows you to see column-based feeds filtered by a list, a hashtag, a user, or other dimensions. Here’s a snapshot of my Tweetdeck.
  • I don’t post much but I do engage conversations sometimes. Twitter is a very entertaining and clever ecosystem. If you want a field guide to the Twitter prairie, check out Alex Danco’s playful analysis. Learn what it means to “get ratio-ed”.
  • If you are able to generate a following, one of the greatest tools afforded to you is the ability to crowdsource the answer to questions from a sharp community. Remember, you can follow anyone, unlike LinkedIn. You can always @ someone’s handle but to DM somebody they must follow you. I have seen people expertly crowdsource insightful business questions. I recommend following people who exploit this power so you can “draft in their lanes”.
  • If you don’t have a following (I do not), remember that crowdsourcing skill can be best rewarded on Reddit. Why is Reddit better than most internet forums? The top entries on the page are not the most recent but the most “upvoted”. Unlike Twitter, you may not “know” the respondents so it can be difficult to calibrate the value of the replies. The trade-off is you don’t need a following, instead, you must ask the right question in the right way to get responses and upvotes. A game in itself.

Idea Triage Model, Part I: Objectives


A friend of mine who knows I am pretty OCD organized asked me if I have a system for centralizing the content I consume. He was mostly focused on blogs and videos but it prompted me to think about how I conceptualize my entire information stack. If you are an infovore you hopefully have a system that outperforms a bouquet of 50 open browser tabs and colored Post-It notes taped to your monitor. But what does it even mean to say your system “outperforms”?

It depends on your objectives. Let’s start there.

Objectives of a personal info management system

I’ve been thinking about how I organize info since my days of using an iGoogle homepage. I used to take notes in Gmail and used Google Keep to hold to-do lists. Since then my system has evolved to serve 3 key needs.

1. Automatically filter sources

A connected world with essentially zero marginal transmission costs means information is free. Like a fat dividend from electricity. The tax on this dividend is of course FOMO. It’s a battle for your attention and the beeps and notifications on your phone are its weapons. Your defense is curation. Who to follow on social media, what blog feeds to subscribe to, Spotify and Netflix profiles that invite desired recs.

2. File selected content for future reference

Your Chrome bookmarks are probably a dumpster fire. Go ahead, take a few hours — organize and prune it, agonize over folder names and what should nest under what. You still won’t reference it in the future. You’ll probably just google the thing you are interested in only to discover that you bookmarked it long ago. Bookmarks are not a system. At best, if you scan through them they remind you of something you might still care about.

Instead, bisect filing into short term and long term notes.

  • Short term filing: A low friction way to cache content or to-do lists. You will want to queue in a handy place so you can revisit it when you have time.
  • Long term filing: If it’s worthy of coming back to in the future to either use it, recommend it, or simply refresh yourself then it can be promoted to long term storage. To facilitate later retrieval you might take notes, highlight it, or tag it. How you promote it may be related to how you intend to use it in the future.

3. Retrieve content

It may seem obvious that you want to retrieve your notes or filed sources. But in thinking about the design of the file management system, it’s worth spelling out reasons you retrieve:

  • Teaching others
  • Writing for work or pleasure
  • Recommending a restaurant, attraction, or book. How many times have you drawn a blank when asked for a rec?
  • Surfacing research relevant to an argument at hand
  • Remembering pointers for how to perform your workout or presentation
  • Maintaining to-do lists
  • Researching a trip, a recipe, home project, financial plan
  • Affirmations or habits you are practicing to reinforce

Facilitating rapid and effective retrieval demands a proper mix of conceptual and technical features depending on the ultimate action you are retrieving for.

Conceptual Features

Ability to search or scan

Storage needs to be both searchable and browsable. You will often remember a keyword that will help you find the note you created. Just as you search your email. But it’s equally important that your notes are browsable so you can scan your notes to jog your memory or resurface content that your past self thought was interesting. Browsability implies that the note hierarchy is collapsible. By nesting notes, the entire data structure is compact and more navigable. The number of layers is debatable and a matter of preference. As an example, I find Evernote to be a bit restricted (stacks, notebooks, notes) but serviceable.

Technical Features

Cloud-based yet exportable

You will need to store and retrieve anytime, anywhere. Fortunately most tools these days will be cloud-based. However, apps come and go so the ability to export is non-negotiable. Turnover at Evernote’s parent company in 2018 prompted a rash of articles about how to back up and export your notes in the event they went under. You don’t want to be at the complete mercy of your cloud-based app. You may also want the ability to access your notes when offline. Airplanes come to mind here. Device/desktop sync should be mostly seamless. I’ve seen some glitchy behavior in modern apps (for example notes being duplicated or briefly invisible during an unusually long refresh) but these should be relatively rare exceptions or the app will be to frustrating to stick with.

Fast, clean design

These apps will be some of your most heavily used so the experience should be inviting. It should be consistently fast. Even brief moments of lag will become major annoyances once multiplied by your frequent use. There is some leeway here. Google Drive is probably too slow to keep to-do lists but its greater flexibility for handling more complex docs makes it a reasonable home for content notes or financial models. Your app’s maximum acceptable latency will be dictated by the fastest twitch activity it’s required to handle.


If you got this far, it is likely that you are considering your own objectives. It’s ok if they feel abstract at this point. In Part II of this series we will look at the conceptual design of my own system and what principles guide my objectives which can give you some clay to work with.

Go to Part II: Conceptual Design (pending)