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. 







  1. Anytime you invoke “meaning” you are going to ruffle feathers. I don’t pretend to be objective. I don’t think there is a Meaning with a capital “M”. You create your own meaning. Sitting peacefully with all the requisite ambiguity and paradoxes that you feel in the fibers of existence is probably your best chance to discover your own meaning. If it matters, I don’t think the model we are building here relies in any way on you sharing my philosophy. If you were interested in some of the thinking that has influenced my view see How The Need For Coherence Drives Us Mad.
  2. In option terms, I’ve explained it this way:
    Scarcity mindset is adaptive when you are young and broke, because the scarcity can be quite real. The mindset is protection. Like a 40d put. But as you earn, that put becomes further OTM. You are going to be ok. No need to pay theta in the form of suboptimal decisions because you feel the need to service that put as if it’s 40d when it’s really 1 delta.

3 thoughts on “Design Your Own Engine

  1. Discovered your… what is this? A “blog”? A “Digital Garden”? A “website”… anyway, I discovered Moontower a few days ago and I’m addicted to it. Thanks Kris, I’ve been through a similar decision process a few times over the previous couple of years and I can’t empathize more with everything you’ve written.

    I’m going to steal, ahem “get inspired”, by your Engine Model and will share the word.

    Keep up with he exceptional work 😉


  2. Been a reader for about a year now, this post converted me to paid sub. Thanks for sharing your journey in such a digestible (and groovy) manner.

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