I’ve come to realize that, especially for writing with a single central claim, large language models are often better at elaboration and structure than I am on a first pass.

I plan to share more work in this form. It’s the most faithful way I’ve found to quickly turn rough thoughts into something coherent, and I don’t yet know of a better place for these notes to live. Going forward, I’ll always indicate whether a piece is AI-assisted or fully authored, so you can decide whether to skim or to read it as something written slowly and deliberately, as my past writing has been.

Abstract

Founder work is often described as a search for leverage: identifying the few actions that disproportionately determine outcomes. This description, while accurate in early and exploratory phases, fails to explain large classes of founder activity that are linear, exhaustive, and resistant to optimization.

In this paper, we propose a two-mode theory of founder work: Pareto Mode, which maximizes upside through power-law leverage, and Integrity Mode, which minimizes downside through comprehensive coverage. We argue that these modes are incompatible in simultaneous execution, must be temporally separated, and that a core founder responsibility is explicit mode arbitration. Failure to recognize and declare the active mode leads to miscoordination, execution slippage, and organizational stress. The framework provides a lens for understanding phase transitions in startups and for designing appropriate operating cadences.

1. Introduction

Founders are frequently advised to “focus on what matters most,” implicitly assuming that work admits a Pareto-optimal structure. While this advice is correct in many circumstances, it breaks down in later phases of organizational development, where success is constrained not by opportunity discovery but by system integrity.

Empirically, founders report periods in which no single action dominates outcomes, yet failure to execute on multiple parallel obligations leads to catastrophic loss (e.g., customer churn, regulatory disqualification, or loss of credibility). These periods are often experienced as unusually stressful, misaligned with founder identity, and difficult to manage.

This paper proposes a theory that explains these experiences as a consequence of switching between two distinct optimization regimes.

2. Two Modes of Founder Work

We define two primary modes of founder work.

2.1 Pareto Mode

Objective: Maximize outcome per unit effort.

Pareto Mode assumes a power-law distribution of impact. A small number of actions dominate outcomes, and the cost of neglecting lower-impact tasks is negligible relative to the upside gained from focusing on high-leverage work.

Characteristics

• Non-linear returns

• High ambiguity and exploration

• Tolerance for sloppiness elsewhere

• Strong reliance on intuition and synthesis

Examples

• Selecting an initial market wedge

• Securing a key design partner

• Crafting a compelling narrative or demo

• Identifying a single architectural abstraction that collapses complexity

In Pareto Mode, the guiding question is:

What single action, if done well, makes many other concerns irrelevant?

2.2 Integrity Mode

Objective: Minimize the probability of disqualifying failure.

Integrity Mode assumes that outcomes are constrained by weakest links rather than dominant actions. Here, failure is not gradual but discrete: missing any critical requirement invalidates success elsewhere.

Characteristics

• Linear, checklist-driven work

• Low creativity, high discipline

• High coordination cost

• Emotionally aversive to founders trained in leverage-seeking

Examples

• Compliance (e.g., SOC 2)

• Multi-tenant correctness

• Contractual and delivery obligations

• Documentation and operational hygiene during scaling

In Integrity Mode, the guiding question is:

What failure would cause us to be fired, sued, or lose trust?

3. Mutual Incompatibility of Modes

A central claim of this paper is that Pareto Mode and Integrity Mode are temporally incompatible. Attempting to operate both simultaneously leads to predictable dysfunction.

• Pareto behavior during Integrity Mode produces sloppiness and dropped obligations.

• Integrity behavior during Pareto Mode produces over-coordination and lost leverage.

The cognitive and organizational requirements of each mode differ sufficiently that partial execution of both yields suboptimal outcomes for each.

Put more simply:

Pareto Mode is about winning.
Integrity Mode is about not losing.

Optimization requires mode selection, not weighted averaging.

4. Mode Arbitration as Founder Responsibility

We argue that a core, under-articulated founder responsibility is mode arbitration: explicitly determining which optimization regime governs the organization at a given time.

This responsibility includes:

1. Declaring the current mode

2. Aligning team expectations to that mode

3. Suppressing behaviors appropriate to the opposite mode

Failure to arbitrate mode manifests as:

• repeated re-litigation of decisions,

• miscommunication and context loss,

• team anxiety and execution drift.

Importantly, mode arbitration itself is high-leverage work. A small amount of clarity prevents widespread inefficiency.

5. Phase Transitions in Startups

Startups naturally transition between modes as they mature.

Early-stage companies predominantly operate in Pareto Mode. As customers, regulators, and partners accumulate, Integrity Mode becomes periodically mandatory.

These transitions are often experienced as identity crises by founders, who may misinterpret the demands of Integrity Mode as a loss of effectiveness or creativity. In reality, they reflect increased system coupling and responsibility.

Integrity Mode is typically episodic. Successful execution restores the conditions under which Pareto Mode can resume at a higher level of abstraction.

6. Implications for Practice

This framework suggests several practical interventions:

• Explicitly time-box Integrity Mode phases

• Reduce exploratory discussions during Integrity Mode

• Design operating cadences appropriate to the active mode

• Normalize the emotional difficulty of Integrity Mode for founders

Most importantly, founders should resist the urge to justify all work in Pareto terms. Some work is valuable precisely because it prevents loss rather than creates upside.

7. Conclusion

Founder work is not a single optimization problem but a sequence of regime shifts between incompatible objectives. Pareto Mode enables growth. Integrity Mode enables survival. Both are necessary. Confusing them is costly.

A caveat: the lessons and commentary are only really applicable to venture-backed startups, not so much traditional SMBs.

The story

Stage 1: Vision and lies

One day, you come up with an idea. You think it’s a great idea. An excellent idea, perhaps. You read some quotes from Reid Hoffman and Paul Graham and find yourself nodding along, so you decide to start a company. You plow through a “how to build a company” checklist you got from Google/ChatGPT, feeling more and more empowered as you go: you set up a domain, start a Notion workspace, incorporate a Delaware C-Corp. And then you buckle down and get to work, spending your evenings building a prototype on your [non-work] machine. And it’s fun — you’re in flow until midnight every day. Progress is addictive, and after a few weeks you’ve built a respectable prototype. It feels good to build something with your own hands, owned entirely by you. The world opens itself to you, rich and wild and full of possibility.

You decide one day that your product is good enough to show people, so you begin looking for customers. You start with your friends (“design partners”) and they claim they “love” it, but really they value your friendship far too much (but not enough) to risk it with truly honest feedback. And validation is what you secretly want to hear anyway. You’re looking for the dream to keep floating along, unchecked, buoyed by a healthy dose of confirmation bias. Propped up by their optimism, you launch, and some people even buy your product. Perhaps it’s not confirmation bias after all, and your last shred of honest skepticism is buried beneath layers of ego and artifice.

And you figure if you can believe it’ll work, so will the rest of the world. So, filled to the brim with gaslight, you puff up your chest and begin to spread the gospel. You launch, repeatedly. You build up hype. You take irreverent stances on Twitter. You get quite a few eyeballs, some of which are excited potential investors, so you take the opportunity to raise capital.

From your first few investor calls, you find out that there are products that already exist to solve this problem, that your vision is not particularly compelling, that they don’t think this is going to work because they don’t understand what you’re doing, as much as they like you, etc. etc. But you tell yourself “they just don’t get it” and double down on your esoteric value proposition. You come up with more elegant arguments, you improve your ability to speak concisely and extemporaneously respond to increasingly predictable investor questions.

And with enough hits at bat, some investors latch on — you manage to raise some pre-seed/F&F/seed funds. They run due-diligence, talking to your design partner friends, who have nothing but wonderful things to say about you and your product. Money comes in, and as soon as you see the cold, hard cash hit your bank account, you take it as validation that all your ideas are correct. Confirmation bias thickens the white matter of your brain, so you forge ahead, bolstered by dopamine-rich validation. Your competitors are doing great, after all, and you have a better product.

Stage 2: Going Through the Startup Motions

You read a tweet somewhere that execution is all that matters, so you don’t stop for a second to think whether any of what you want to be true — what you’ve convinced yourself to be true — is actually true. You take the advice as sanction to silence your brain and feed your flow addiction. Still, you struggle to find customers that love you, so you pile feature on feature, hoping that the next one will bring your product to take off like wildfire. To sustain that iteration process, you desperately follow the “build fast, break things” mantra circa 2015, tripping over yourself to ship. Naturally, you take on heavy amounts of tech debt, but “tech debt is a strategy”, after all. It’s a little painful to build such garbage, but fortunately, you’ve heard it said that “if you’re not embarrassed of your product, you shipped too late”, so you know by that metric you’re shipping right on time, every time.

You do all the standard startup things: you hire a team, write OKRs, hold lavish off-sites in the name of “brand”, and otherwise perform a watered-down reenactment of HBO’s Silicon Valley. Unfortunately, you still have no customers, and your first cohort has churned entirely — you’ve exhausted the patience of {your close friends, investor intros, other startups in your incubator}, and you realize you have to get a proper lead generation process working. You try cold calling, emails, social media marketing, blog post writing. You hire advisors, marketing experts, hoping you can outsource your problem.

And sometimes, at this point, your death is written, for sometimes there is no path through. And in all likelihood, you’re missing the mental fortitude to untangle the web of fallacies you’ve constructed, to take ownership and responsibility for the decisions you’ve made — whether explicit or not — to accept that you not only can but are failing and need to pivot, in some shape or form. You’ll instead push harder and harder with Sisyphean futility until you’re ultimately forced to face defeat. But still, in all likelihood, your ever-resilient narcissism will spin the loss to protect your ego — “you learned so much”, “the market was just not ready”.

Stage 3: Getting to PMF

But for some of you, either as a result of gut-wrenching pivot(s), sheer luck, or some combination thereof, something eventually sticks, and you establish a steady trickle of customers in. Hallelujah! You’ve validated that you might deserve to exist. But unfortunately, that’s all. For still, through this process, you eventually come to the realization that you have not reached PMF, in spite of the 5 happy customers you have. Because something’s still not quite right. Because hundreds of failed sales calls later, you realize no one really knows what you’re selling — not even you.

You iterate on positioning, on marketing, on your go-to-market engine. And if you have not come to value intellectual honesty at this point, you better figure it out fast, for the iteration cycles need to come rapidly and with a healthy dose of brutal, honest scrutiny. You try dozens of different GTM motions and tweaks, sourced from hours of Lenny Rachitsky interviews. Your copy varies wildly from the onerously specific (“SALES DATABASE WITH SOCIAL MEDIA INTEGRATION”) to buzzword bingo (“ALL-IN-ONE SALES PLATFORM FOR KNOWLEDGE WORKERS”). But as the creativity faucet finally purges itself of crud, you unearth a laser-focused value proposition: “Modern CRM”. And the sales calls go substantially better. And suddenly, some (even many!) of your GTM systems start to work. You have leads, and they are converting.

Stage 4: Rebuild

If you’ve been following the advice of late 2010 startup content until this point, this is usually when you’ll realize that your shitty architecture is coming to bite you in the ass. Your product is compelling, but it’s unstable. Your engineering strategy was built on faulty platitudes. And by direct consequence, while you can sell the product, few will tolerate it long enough to use it. You spend months (or years, or forever) trying to crawl out of that hole. You set up a p0 Slack channel that is so constantly full of alerts that your team — you — burn out. Why is your team so bad? How did we get in this situation? Well, the answer is clear: you fucked up. “But we had to!” you say, but you’re just avoiding the truth that all of your knowledge of company-building came from Twitter, and most of it was profoundly wrong for {this point in time, this product, this industry}.

For the truly honest few, you own up to your mistakes, think from first principles about how to solve the problems you’re facing, and have enough capital less your launch parties or domain name expenses that you can rebuild the product and team correctly. And it all finally works. It’s stable and loved. You have a repeatable lead gen motion, a steady conversion rate, net negative churn. You rejoice! You know you have a business because your first 100 customers love your app, and if 100 customers exist, surely thousands — nay, millions — exist.

And so you forge ahead. You raise a Series A, even a Series B, with a deck full of optimistic projections based on your current growth. With fresh funding, you’re off to the races. Everything works, you can relax — you just need to 10x, 100x everything you’ve been doing. You go to conferences, you hire social media influencers, you start a Slack community, you host webinars, you buy absurd swag. The world seems primed for a takeover — you, inc., the next unicorn, decacorn, even.

Stage 5: Face what your lies have wrought

For the lucky few, scale happens. But for many, here is where your first deception comes to call: you’d convinced yourself and your investors that the market was huge, but is it, really? Can you really unlock $60B of “knowledge worker” value? No one can blame you for believing it was when you started the company — everyone else did, after all. But the growth seems suspiciously slower than you’d like. It feels as if all your best efforts are just barely enough to reach parity with the initial burst of revenue that fell into your laps when tailwinds were favorable. The hockey stick was certainly a hockey stick, but by your projections, the slope of the handle is enough to reach unicorn status in about 30 years. You could’ve invested your fundraise into the S&P500 with about the same outcome.

So you make asymmetric changes, hire tried-and-true tech executives, crank up the revenue machine, all the while cautiously watching new bright-eyed seed founders slice up your market further. And while you know that you can hold your ground for now, you know it’s only a matter of time until that changes. The ever-growing open source world will spawn new, more cost-effective starting points every year. The underlying infrastructural options will only get faster. And the sheer number of founders will abound to a point that it becomes a statistical inevitability that one will subvert you, take your place as zombie king, and force you to exit to private equity.

For that is what you are now: a zombie company. So you have a tough choice to make — sell your business, perform an unprecedentedly dizzying pivot, try to SPAC, or rebuild as a “lifestyle business”, dragging investors along on your zombie company leash.

The lessons

Lesson 1: Some things matter more than others.

The most harrowing thing about this story, in my opinion, is the brutal inevitability of the outcome. Your grit, your ingenuity, the good fortune that you happened upon, your hard-won personal growth — none of it mattered in the end. Because the zombie company outcome was a consequence of a single decision made early-on: choosing the wrong space. No matter what transpired between inception and exit, the bounds of your fate were largely sealed by that one choice you made around what to build, decided when you were the stupidest.

Ergo, the single-most important thing to take away from all this is that not all decisions are made equal. Existential decisions — like your choice of market, your choice of team, and later, your choice of architecture — can make or break you. But others — like where to have your offsite or how you should structure your meetings — will generally make no difference whatsoever, but are still easy time sinks. Fortunately, the remedy is simple: just focus on getting the right people working on the right problem, and remember that focus is about saying no.

“It doesn't matter how amazing your product is, or how fast you ship features. The market you're in will determine most of your growth. For better or worse, Gumroad grew at roughly the same rate almost every month because that's how quickly the market determined we would grow.”

- Sahil Lavingia, “Reflecting on My Failure to Build a Billion-Dollar Company”

Lesson 2: Intellectual honesty is the only thing that will save you.

Of course, even with that knowledge, you’re going to make the wrong decisions, even when it comes to the most important ones. Even the best of us can only see so far in the fog. And the only thing that will save you from those mistakes is brutal honesty. Did you really hire the right people? And did you really choose the right space? These two in particular are the two most difficult questions to ask, particularly because addressing errors against those decisions is so painful: you’re either going to have to fire someone or pivot.

But it must be done. To counteract the immense amount of pain this might cause you, you need a commensurate commitment to intellectual honesty. And if you’re able to maintain that commitment, you’ll be fine. For as fatalistic as I sound, bad decisions are rarely catastrophically bad — they only become truly catastrophic when you gaslight yourself into believing that they were actually good decisions, allowing their consequences to unfold and ramify, unchecked.

Final points

I hope some of this was helpful, particularly if you’ve ever thought of starting a company. Before founding my first company, I held only this vague notion that it’d involve primarily bracing myself for the folklore of entrepreneurship: sleepless nights, 18-hour days, mental exhaustion, constant uncertainty. And certainly, those things would come. But those are only common patterns of behavior, not to be confused with any sort of methodology. I believe this misconception (and many of the failings listed above) stems from a perspective common in the startup world that building a startup is all about execution, but this advice is often warped into sanction to act (“hustle”) without thought.

But here’s the thing: companies aren’t MMOs. You can’t mindlessly grind your way to the finish line. The game is one where you must think about what you should do, then do it. There’s an element of expediency involved, but that expediency cannot be undirected. Sometimes the best thing to do is live in the factory for 3 years, but only if you’ve determined that the best thing to do is to live in the factory for 3 years. You can’t just live in a factory for 3 years and expect to conjure Tesla. Doing painful things that do not drive the needle is pointless, toxic self-flagellation optimized for virtue signaling, not success. As heroic as these stories might sound when recounted by successful founders, they’re byproducts of dedication, not a recipe for success.

Startups are about honesty. Pre-PMF, your job is primarily to repeatedly form hypotheses then gather data to test them. Rinse and repeat, rinse and repeat. Action is sometimes the rate-limiting step, but in my experience, most people who want to start a company know how to work hard. So more often, you’ll find that you’re rate-limited by your capacity to confront and think about the truth. Of course, sometimes it’s hard to, psychologically traumatizing, even, but if you’re not willing to do it, you should seriously reconsider whether you should be building a company, or your story may ultimately look not so unlike the one I just laid out for you.

1. Read the problem statement.

2. Read other things (textbooks, e.g.).

3. Repeat 1-2 until understanding materializes.

It’s the grade-school formula for approaching problems, and it’s deeply reinforced in us because it works in school. Tests are often filled with questions that require only direct regurgitation of content. If you don’t something, the best thing you can do is look it up — the answers are all in the textbook, after all. And so the patterning becomes reinforced until calcification. Reading becomes the only way your brain learns to unblock itself.

Even in more quantitative fields (often heralded as natural catalysts for exceptional thought), problems often simply become composites of the lower-level fundamentals. You can still find the answer in a textbook, you just need to have seen the concept before in the textbook. And so the solution is ultimately still can be approached as a matter of building up the fundamentals, then recombining them to find a solution. At least, one can hobble through graduate-level physics and mathematics like this (I, for one, did).

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This fails because most important answers aren’t simply found

The reason why this is so painfully ineffective in the real world is because many of the most important problems in the real world are not solvable by this method. Of course, you can still happily get through life Googling everything, you’re restricting yourself to solving only the most shallow of problems: those that have precisely been solved before. And there are a few canonical problems that cannot be solved in this way:

1. Important problems. The problems that no one has solved.

2. Malformed problems. Problems that are stated poorly, obscuring the main problem you’re trying to solve.

3. Internal problems. The problems that heterogeneously plague you and your specific internal state.

For these problems, the reason why you can’t solve a problem is often not because you simply haven’t stumbled upon the answer. It’s usually because you don’t understand something, either about the way the problem fits into a unifying objective, something specific about a particular concept, or something about the way your mind is getting caught in some sort of discouraging feedback loop.

Unfortunately, we are poorly equipped to handle these roadblocks. Instead, we are raised with a single brute force method at our disposal — read more, read more, read more. And so we get trapped in a loop where, as we try to read, we fail to diagnose our misunderstanding, we fail to see the forest from the trees, and we get battered by our own internal loop of frustration and insecurity — “I must not be smart enough”, “this is so hard”, “I’m so tired” — with our only method of recourse being to grind it out.

The solution: the three eigenvectors of unblocking

Everything that happens in your head when you can’t solve a problem can be untangled by asking three questions:

1. What’s the point?

   Not always necessary, but important to start here first, in case you have the objective implicitly wrong. E.g. “to get good grades” vs. “to understand physics” — generally try to focus on the latter, though that’s a topic for another post I suppose.

2. What’s happening inside of me as I struggle through this?

   Recognize the feeling tone — feeling discouraged, feeling pressured, feeling bored — so you can deal with them in light of your established objective.

3. What don’t I understand, and what’s the best way to solve that?
   Finally, you can try to dissect your failure into the highly specific sub-points that you don’t understand, then figure out a step to take that gives you the best chance at solving that more clearly defined problem.
   (LLMs are exceptional for pushing you to do this, btw)

Every single blocker to solving a problem can be categorized as insufficient scrutiny against one of these three questions. And, while, I’ve written about the first two before, I’d like to talk a bit more about the last — while it might sound obvious, this is the core unblocking method that stands in opposition to the method of simply reading and regurgitating.

Reading is quite difficult to beat as a method of answer-finding, because it’s pretty painless. It’s completely straightforward — anyone can read one more sentence. And, as a result, it can be almost entirely passive, particularly when leveraging it to solve a problem. Just keep going until you get to an answer. Unfortunately, the problem is that this also reinforces you to read the wrong way — skimming towards the particular aim of unblocking yourself.

Of course, this is not to say that reading isn’t valuable — deeply reading something, I would argue, is one of the best ways to truly know a subject. But the habit of dissecting your misunderstanding has to exist beneath. Without answering the question “what don’t I understand” repeatedly, the best you’ll achieve from any problem set or coursework is a patchwork set of facts and formulae, not a deep intuition that can form a foundation for flexible problem-solving.

Final comments

There are a couple unfortunate things about this whole unblocking yourself thing. The first is that it’s kind of hard to realize you need it until you really need it. In general, it doesn’t help that, if you read enough, you can still be extremely successful. Almost all questions that are asked of a person have been solved before, so you can race along in life regurgitating the solutions of others. But here are a couple examples of where this methodology can confer unfair advantage:

• This is what makes incredible employees, because:

  • When everyone is regurgitating existing solutions, establishing an objective, dissecting a problems into basic components, then reasoning through the solution space from first principles will find you constructing something asymmetrically better. You’ll have the capacity to jump from one local maxima to another, which few employees have.

  • Nothing will be out of reach of your understanding, so your slope will often exceed that of your colleagues.

• This is a necessary (though not sufficient) condition to start a successful company, because your situation will be so heterogeneous and pace of iteration so rapid that you need a way to rapidly traverse the maze comprised of the parameters of your business and your own internal state.

The second unfortunate thing is that, while this is a sufficient system to unblock yourself, it’s not sufficient to spell success. That, in my experience, is usually about building systems and habits that point to where you want to go, not about instantaneous skill. But that’s also another post.

So I went in far too fast and overshot the landing by about 20 feet. And as soon as I popped off the lip, I started to panic:

oh my god the ground is too far away
oh my god the ground is too far away
oh my god the ground—

I tried to fly like a chicken for 3 seconds, then woke up in the ski clinic with a stranger asking me to repeat “trains planes and daffodils”. I complied, reassuring my wife with a quick “see I’m fine!”, to which she replied, “that was the 5th time he asked, Robert!”

I’m digressing. My objective is not to talk about the trauma imposed on myself or my friends and family in doing stupidly dangerous things2, but to point out how crippling fear can be, and how ski jump fear can prove to be an apt pedagogical metaphor for understanding fear and, more generally, anxiety. Let’s dissect what happened.

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The panic arc

There’s some clarity we can get by just dissecting what happens when you’re afraid. Here’s a diagram of my emotional arc mapped onto my botched jump — it was just a direct line from fear into panic:

And I think there are two primary ways of mitigating that fear — you can either:

1. Reduce the difficulty of establishing resolve by starting with a plan, or

2. Strengthen the muscle of establishing resolve itself

You won’t think clearly if the fear is too large, and in that regard preparation can mitigate the magnitude of the fear. This was clearly the mistake I made.

But in the moment, there’s also a level of training that can bring you through the fear. A self-awareness that fear is happening, that the fear can wash over but not consume you, that you can still find yourself underneath it. And to boot, you find yourself with a greater resolve propelled by a heightened awareness you siphon from that fear state. This is a thing you can learn to even love practicing, and was largely why I loved snowboarding so much — you get to repeatedly pass through your body’s adrenal response and learn to leverage it. Adrenaline, coursing through your veins, can induce deep panic states, but when you let it course over you without consuming you, it can be empowering.

Fear is everywhere

Snowboard jumps, of course, are an extreme example, but the response pattern is general. Adrenaline response is a distillation and condensation of pure fear into a few seconds, and as a result, bears an intensity that makes it feel different from the kinds of fear we encounter day-to-day. But fear’s nominal, low-grade but persistent counterpart — anxiety — bears a striking resemblance, and this is something that I think most of us encounter more regularly.

And, on the one hand, I’ve found that the strategies for dealing with anxiety are quite similar to those for dealing with fear. As with fear, having a plan can summon resolve in the moment, making it less likely for anxiety to devolve into a deep panic state. And, if the anxiety is still overwhelming, summoning some self-awareness to see yourself under the anxiety, under the fear, can give you clarity of thought when your body is just screaming to move. Learning to let the feeling wash over you without carrying you away can be almost pleasant, eventually. Where adrenaline can manifest as either panic or thrill, so too can anxiety manifest as either stress or excitement.

That said, I think we undervalue the utility of anxiety, and in that sense, “dealing with it” — the most common framing of anxiety narratives — is perhaps not quite right3. I’ve been watching lately when my brain falls into anxiety, and I’ve noticed it’s a strong propellant. It pulls you to do things. You find yourself in a situation that needs to change, you intuit that you can indeed exert some agency over it, and anxiety arises as the physiological mechanism that compels you to take action to resolve it. I think in the same way that you can find greater resolve beyond fear, it’s possible to find a similarly motivating determination beyond anxiety.

This might sound impossible to internalize for those of you routinely consumed by your anxiety, but I think this is because we’re so used to mapping judgment to anxiety — we value it as a negative trait, something to escape from. But in reality, it’s simply a physiological response that doesn’t inherently mean anything. And as such, once you strip it of the thoughts you have about it, it can exist as a state, like any other state — and in this way, you can either choose to let it pass away or engage with it. And if you engage with it, sans judgment, you can find yourself with greater energy to push through and get something done than those without it.

This has been so valuable to learn for me because fear and anxiety are everywhere, and for the bulk of my adult life, I considered it a bug, not a feature. I’ve white-knuckled my way through all kinds of anxiety about almost everything in my life, from the more obvious macro-arc things, like fear of failure, to even the smallest of circumstances — social anxiety, relationship anxiety, fear of public speaking, financial anxiety. But there’s a power to naming that anxiety, and acting in recognition of what it’s compelling you to do — to work harder, to prepare more deeply, to do what it takes to win.

And in that sense, while anxiety might feel overwhelming, it can also make it a lot easier to get shit done — there's a deep, coursing energy to it that’s hard to match. Without understanding what your anxiety is, there’s little you can do but haphazardly flail against it. But once you see it, you can choose how you want to engage. Let it pass, or ride it somewhere.

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The state of the art is to simply try to catch oneself before exiting mindful state and falling into default state. And this, of course, is already quite helpful. My greatest advances in personal practice have been recognizing different default states when they happen, slowly pulling back the curtain on what brought me there, and learning to preemptively catch that signature before it manifests. But I’ve started trying to characterize this state as of late, and I suspect there’s some great value here for, not only is everyone’s default state different, but we also all have different default states depending on context. And failing to recognize that variability can make progress more difficult for some than others.

In particular, I’ve found that a useful framework for me is to identify three aspects of default state: context, mood, compulsion. I.e. what context am I in, what is my mood and the physiological signatures of it, and what is my desired default behavior? The following, for instance, summarizes my difficulty in staying present with my daughter.

Another example: in the evenings, I feel particularly prone to scrolling endlessly on my phone. And in this situation, I don’t [usually] get a proper, building, all-consuming, endocrine-dipped craving. Rather, the pull just seems to manifest as deep mental patterning — vices just flit across my consciousness as options. I can watch Netflix. I can scroll Youtube. I can open a dumb mobile game. And sometimes it doesn’t even manifest as an idea, but there’s a short circuit that directly goes to muscle memory. I’m on my phone, and — while my mind wanders — I’ve somehow already opened Instagram.

I’ve found this to be a useful instrument for reflection — a diagnostic when simply pulling myself back to mindfulness isn’t enough. In preparation for a particular context, this allows me to predict what my mood is going to be, why, and what I will be driven to do, which has helped me establish a level of proprioception against the standard sequence of events that I otherwise have historically not been able to observe. I think the reason this works is as follows:

1. Context is important. Some situations are simply harder to be mindful within. Recognizing this variability makes it easier to steel yourself against it when it comes. By analogy, trying to be mindful without recognition of this variance is like climbing a hill in the dark — you can’t anticipate where you’re going, so each step risks a fall.

2. Mood is a critically important undercurrent to recognize. It may sound obvious from a practical perspective, as common knowledge carries this wisdom: it’s harder to resist binge-eating when stressed. But from a mindfulness perspective, disentangling this from the hunger itself is clarifying, particularly when trying to execute some self-control.

All in all, I hope there’s some utility here for you. A final comment: breaking your default state down in this way must be quite an important part of the human experience, no? To learn to recognize what it is that our default state is pulling us toward, then to try to execute some agency against that? If free will exists, it must only be possible within this nexus of reasoning. Our consciousnesses have taken host in these arbitrary bodies with highly variable design. You can live a life where you are carried by the arbitrary patterns that it creates, or you can recognize what those are, and design around the constraints.

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But of course that’s not quite true, is it? I can’t lose 10 pounds once, then only eat donuts for the rest of my life.1 I can’t study for a few years, then never again — knowledge is steadily winnowed by time. And I can’t achieve mindful enlightenment, allow my brain revert to its old muttering patterns2, and expect my enlightened state to persist. Yet I’ve somehow convinced myself that I'm working through a finite checklist of goals, when, in reality, I'm cultivating habits that must either continue until death or be consigned to inevitable decay. It’s quite Sisyphean, from that vantage.

I suppose my mistake is that I still implicitly subscribe to a skill tree view of life — that progression is permanent, that time and mind are infinite, that my career as a professional musician can resume once I’ve reached everlasting checkpoints on my other skills. But of course, internal equity decays, and for the things you love and want to sustain, you can't stop. But I think that’s the idea — you can only sustain effort forever if you love the act itself, anyway. The goals need to vanish behind the joy of the process itself, or over-focus on goals will make it harder to continue after each milestone (or even harder: after setbacks).

I was recently talking with a pro golf instructor about how golf has this process-not-goals philosophy baked in3. There certainly are natural goals to pursue: hitting a certain distance, achieving a certain score. But golf is a sport where mess-ups are both so inevitable and obvious (it’s you against you), that it often matters more that you establish a strong love of the iteration process when you mess up than to just keep swinging. “Golf is a game of seeking perfection but never achieving it,” my friend explained. And so one must love the pursuit of perfection — not the signals of perfection — to succeed.

But this is how we tend to approach the things we love anyway, isn’t it? You don’t do things you love doing to hit arbitrary milestones, but because the act itself brings you delight. We don’t watch TV to simply watch all the TV4. Of course, this isn’t to say that we can’t enjoy rewards that come with effort. But love of the act itself can be a much more powerful sustaining force, particularly when your goals have been reached (or, more importantly, when you fail at reaching them).

I need to remind myself of this regularly, but luckily, for the things I do regularly, some love is usually there anyway, underneath the goals. I weightlift because I love the purity of the mental effort required when pushing myself to failure. I love to study, not simply as a means of attaining expertise on a subject matter, but because I love the way ideas turn over in my head, spawning new ideas, evolving my beliefs. I love meditating because the awareness that I am able to cultivate makes every present moment more alive.

And while those “hard things” perhaps aren’t so canonically hard, I give them as examples because they are predictably recurring, and so I’ve found them to be be strong instruments for practicing this mindset shift. But I’ve found that the benefits in making this shift can extend to truly hard things — playing games you can’t win, choosing a least bad outcome from a set of truly terrible options. The desire to engage just has to run deeper. and I have been repeating this Nietzsche quote to each other as of late, which neatly captures the nature of such depth:

In short, this is all a rehash of the old “journey, not destination” bit, but I hope this has given you a different dimension for internalization. I, for one, often take “journey not destination” as a mantra to repeat as I white knuckle through process, but I hope you can see the wisdom beyond the utilitarian. It offers a different system for life — one where life is loved, not merely tolerated.

Other comments

This is quite a different perspective than one of my last posts, where I advocate doing absolutely nothing. But I think the more general theme is that there is value in understanding where your biological compulsions are trying to bring you — whether that means chasing achievements or chasing productivity.

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Technical discussion: happiness v. money

Literature review

Discussions around the relationship between money and happiness generally cite one of two seminal works:

1. Daniel Kahneman & Angus Deaton’s work, which suggests that “experienced well-being” stops increasing at about ~$75,000 in annual income.

2. Matthew Killingsworth’s work, which purportedly refutes the above, finding that “experienced well-being” is not so bounded, increasing steadily with household income, without limit. He concludes that “There was no evidence for an experienced well-being plateau above $75,000/y, contrary to some influential past research.”

These are reconcilable

However, the two had different measurement tactics: Kahneman et al. used a binary measurement of well-being, while Killingsworth used a multiple choice one. What’s missing in the discourse, it seems, is that this difference in measurement method makes these two results completely reconcilable, as follows:

• More money increases your experienced well-being.

• But whether or not your experience of well-being is positive or negative does not change beyond a certain level of income.

And the mechanism that could lead to this is not so hard to see. You can imagine that the question of “how do you feel right now” can be broken down into two questions:

1. Are you happy?

2. How happy?

First you choose whether you are happy or not. One might surmise that, above a certain level of comfort, this is more a measure of your subjective inclination towards happiness. I.e. above your needs being met, you do not factor in money when evaluating whether you are happy or unhappy. And so we obtain a harsh cutoff beyond a critical income threshold in answering “are you happy” (which is precisely how Kahneman’s survey phrased the question).

However, with regards to the second question of "how happy are you", one might surmise that you naturally point to how comfortable you feel, how well your needs are met, etc., all of which seem that they would be dependent on the amount of money you make. And so, we obtain a measure of happiness that increases with income without limit (which, again, is how Killingsworth’s survey worked).

A simulated example: “are you saving money?”

To make this a bit more concrete, one can artificially create these two plots by using a trivial example. Imagine if you asked the question “how much money are you saving?” This could be divided into two related questions:

1. Are you saving money?

2. How much are you saving?

(And, one can imagine, these two perhaps directly relate to the questions “are you happy” and “how happy are you”, respectively)

We can very simply simulate this out — create a distribution of incomes, a distribution of expenses, and plot the resulting data in these two ways, and put them side by side with the Kahneman / Killingsworth plots.

The Kahneman-style plot still exhibits an asymptote, because the proportion of people saving money doesn’t increase after a certain point.

And, of course, the Killingsworth-style plot continues to increase, because a person’s savings certainly does continue to increase as income increases.

From this, a plausible conclusion we can draw — if both these studies are to be trusted — is that being happy or not is more likely to depend on the existence of disposable income or not. At the same time, the degree of one’s happiness will scale with the magnitude of that surplus. [Colloquially, of course. This is a blog post, not a paper]

The final conclusion

From these studies, one might reasonably conclude that, beyond a certain amount, money is salt. It adds flavor, but not sustenance. Money is great, but it alone is not sufficient. That said, I think the framing of all money vs. happiness discussions are off. In particular, I have two qualms with these studies and their conclusions:

1. The questions given in the study don’t seem to definitively reflect anything real.

2. Even if money increases happiness, it’s not clear how important it is.

I’ll briefly touch on these points in this final section.

Are people really happier, or do they just feel like they shouldn’t be unhappy?

For one, “happiness” in these studies is measured with respect to the questions “How do you feel right now?” and “Overall, how satisfied are you with your life?” And it’s not clear whether these questions get to anything meaningful. What do answers to such questions represent?

The value of money seems, of course, blatantly obvious when money is tight—if you are drowning, of course a life jacket changes your answer to the question “how do you feel right now”. But beyond a certain point, the relationship seems tenuous at best. I can buy more things? I feel good about my life in a self-congratulatory way? Or perhaps I just feel more compelled to answer these questions positively, as I have everything I could ever want and more and saying “I am not satisfied” seems childishly unaware.

Money produces happiness, but how much, even?

Moreover, something I find painful about these kinds of articles that highlight some [arguably] causal effect is that it doesn’t really signify how practically important that effect is. I agree that money can make a person feel happier and more satisfied with life. But how important is it relative to other effects? For instance, wisdom seems to far exceed income in predicting one’s life satisfaction, and financial situation seems to be quite inadequate alone.

Academics are careful here, of course, adorning their articles with measured titles. “Experienced well-being rises with income” (Killingsworth). But the insinuations of such a title, even when stated in a measured way, seem obvious, do they not? Experienced well-being rises with income, so we should care about it.

Money as introspection utility; money as optionality

Rather than seeking definitive scientific evidence here one way or another, I find a more useful exercise here is introspection: answer these questions for yourself, then think about why your answers are the way they are. “How do you feel right now?” and “how satisfied with your life?” If you can’t answer positively to either, why not? And if money is a factor, why? Does the ensuing argument hold water, or are you just so used to white knuckling your way to the ends of rainbows that you can’t imagine what any other happiness might look like?

For me, I’ve found that it’s far too easy to pursue money for the wrong reasons. I remember when I was in graduate school, I planned for a career where I’d have a $50,000 post-doctoral salary for, well, almost forever. And I counted myself lucky, knowing that I’d be able to do something I loved and be able to support my family with that income. Of course, I went into tech and my salary ballooned, but the strangest thing happened — I went from having a low salary, which was enough, to having successively higher salaries, which were never enough. I realized that I had a strong tendency to chase money in and of itself, and while the studies I’ve mentioned seem to legitimize this chase, it’s a trap.

While implicit, the framing of these studies therein reinforces a view on life that doesn’t just view money as an augmentation, but as an end in and of itself, supplanting those things that might offer greater meaning. In my opinion, beyond a certain level of base security, money should never be an end in and of itself, but a mechanism by which one can purchase more optionality. That is, with sufficient money, you can choose the next adventure you play.1 And that’s what life is, no? A series of wonderfully unpredictable adventures. And rarely is the end of an adventure the best part of it.

Then it occurred to me that I could just sit. So I sat there, doing nothing at all.

And in my sitting, it became readily apparent to me that my mind was being completely directed by this persistent low grade buzz. What’s next? What’s next? What’s next? On the one hand, the crude pull to do more traditionally addictive things has always been quite clear — scroll endlessly on Youtube shorts! It’ll be fun! But for once, I noticed that those pulls were actually not so different from the compulsion to do more “productive” things.

It felt like I was just a brain teetering at the top of a hill. And on all sides, there are different slopes that lead us down all-consuming feedback loops. Down one side is dopamine and cheap addiction. But down the other, purportedly "better" side is still just exercise and endorphins or work and work-induced dopamine. And for the first time, it all felt, in a way, like everything was addiction. There were all these different hormones tugging at my brain. Some flavors just happened to be more culturally sanctioned.

But when did I lose the capacity to just sit at the top of the hill?

I used to play a lot of video games, and one of my favorites was a game called Skyrim. And I remember my first minutes of the game distinctly — it was so graphically innovative compared to any other game out there, that all I wanted to do was walk around. So I walked around for hours, ignoring all quests and NPCs beseeching me. And I just looked at things. I climbed up a mountain. I climbed down the mountain. It was probably hours until I did my first quest. I talked to some NPCs, listened to what they had to say, and continued on my way.

Many games are like this — they're so visually stunning that you’re left with a deep sense of awe when you first start playing. But then, of course, the dopamine drip turns on, and you rush from quest to quest, skipping cutscenes, chasing the end, though you know that there's nothing at the end but no more game.

Isn't this what we do in life? We optimize for chasing goals. And then, at the end of it, there's of course nothing, really. Just a bunch of steadily decaying hormones and a dwindling sense of accomplishment.

The trite aphorism, of course, is obvious: "it's the journey, not the reward". But fundamentally, we are constructed to chase the reward, so to internalize this is not so trivial as to have knowledge of it — we need to recognize that our default mode is to chase the reward, in all things. We move from one thing to the next unthinkingly, because we are programmed to seek out the next hit. Even having practiced mindfulness for some time now, I'll find that, at best, I punctuate this endless chain of tasks with moments of clarity, only to proceed to bury my nose in the next thing as soon as it appears.

And this is the great irony of being human. On the one hand, everything wonderful comes from the journey, because the only meaning that can possibly exist comes from the fact of our consciousness. It’s impossible to find meaning in one’s life without being there to live it. Yet we are programmed to chase the reward instead, making it quite difficult to focus on the journey without some serious introspection.

So I tried just sitting. Being mindful, sure, but not in the way I usually do my practice. Where I typically set some clear intent, this time, I just noticed how amazing it is that I can even exist, Skyrim-style.

I managed to sit for like 5 minutes. But in that time, I just stewed in the idea that I didn't really have to do anything at all. And it was really nice. I think I'll do it again. Maybe you should try it too.

Sometimes I love picking my 4-year-old daughter up from school in the middle of the day. Sometimes I keenly feel the respite that it provides. The forced pull back to what I know is important.

But other times I hate it, and I feel so bad about it. I’ll be in the middle of a conversation or in the middle of some all-consuming work thought or in the middle of nothing at all but consumed by the anxiety that comes with doing nothing at all. And she suddenly becomes an inconvenience, keeping me from the things that purportedly matter more.

Of course, I can recognize the twistiness of my internal state: the ever-present anxiety of not doing what I purportedly should be doing. And I see the runaway endocrine loop in my head, keeping me anxious. I see the mixed bag of motivations — the addiction to work, the desire for success, the need to validate my self-importance — all mixing in that space. I can look at it and try to create distance from it, but I can’t stop it. It’s still there, coloring my mood, seeping into the tone of my words, chipping away at the imagination-augmented world she’s walking around in — Totoro characters running alongside here, Paw Patrol characters flying there. “Eleanor, we have to go home, no more running. Listen to Daddy.”

We were watching My Neighbor Totoro the other day (her new favorite movie), and I had already set aside time to watch her. And I knew the most important thing I could do was to immerse myself in the experience and watch the movie with her. I watched for an excruciating 45 minutes before I pulled out my laptop and started doing something “productive”. And, 10 minutes later: “Daddy can you stop typing on your keyboard?”1 Ouch, my heart.

Well, here’s where I’m at. I’ve at least found some things that help, and other things to ruminate on:

• Mindfulness has been difficult here, but I’m starting to think that’s because I’d been focusing too much on the anxiety itself2. I’ve noticed instead that trying to anchor on the present moment seems to be better… which sounds kind of trivial, doesn’t it? — if you want to be more present, be more present. But it looks like this: I engage with the present, pushing away the anxiety3 temporarily, then recognizing its pull as it inevitably returns, seconds later. There’s something in the recognition that anxiety is trying to pull you out of the present (which, almost definitionally is true — what else is anxiety but a compulsion to not do what you’re doing now?). Then I notice it pull, and let the pull pass over me, and repeat. The slight difference in posturing helps me sit by the river, rather than float along in it.

• It’s also been helpful to recognize that the pulls happen far more frequently, and so resets have to happen quite often. Expecting one quick nod to mindfulness to solve my compulsion is like hoping that sopping up a spill with a paper towel will solve the problem of water gushing out of a broken pipe.

• On a more practical level:

  • I suspect this pattern in large part comes from the oozing-over of the persistent low-grade level of anxiety and stress that compels me to do my work, in general, all day. On days where I’m not working, the feeling isn’t nearly so all-consuming. And it makes sense — the half-life of cortisol is about an hour, and I’m not leaving nearly enough time to let this dissipate (but there’s no way that’s even possible!). While it’s not always possible, loading up less high-stress activities just before pickup also seems to be helpful.

  • I think the way I default handle time is also not so appropriate for dealing with a 4-year-old. Usually, I just try to do as much as I can all the time, including making progress toward some time-boxed goal, like going home. It sounds obvious, but because of that inclination, setting timers helps me relax, at least for the time during which I know the timer is holding that urgency for me.

All that said, I’ve also come to accept that, to some extent, a low-grade level of excitement and anxiety is just the way my brain interfaces with the world in general. I spend a lot of time flushing the creativity faucet, and the flow just tends to be quite difficult to ignore when I’m trying to focus on something else. I recall this quote describing Socrates quite often in this regard:

And perhaps that’s just the nature of creative work in general (barring the ugly nose). I certainly find myself catatonically consumed by my thoughts sometimes. Maybe the difficulty of turning that off is just one of the tradeoffs that I have to accept in being fortunate enough to be able to turn it on and be in a line of work that values that in the first place, and maybe I just to accept that I need to drop some ideas without rumination. Drinking from that faucet was one of the most important things in my life for a long time, so to try to supplant it with my daughter will certainly create some cognitive dissonance against decades of conditioning.

No silver bullet solutions here, only a mixed bag of thoughts. But if you have anything else for me, let me know, because this one’s been hard.

"Look for your head. Where your head is supposed to be, there's just the world."

Harding, Douglas. On Having No Head.

There’s this practice in mindfulness where you try to look for yourself, only to discover that no such sense of self exists. It’s a revelation called nondualism, and Douglas Harding has this wonderful little book where he explores the concept by scrutinizing the headlessness of his existence — that where his head should be, instead he finds only his window into conscious experience. That is: of the ways one can dispel the illusion of self, one such way is to notice that even one’s physical conception of self (a full-bodied human with a head) is a construct that differs quite greatly from the reality of one’s experience as that physical self (in which one can not directly see one’s head, except by extrapolation)…

Hilarity of this description aside, it represents an experience in mindfulness meditation that I’ve always found a bit arcane, but as I’ve recently come to understand it a bit better, I want to spend some time talking about it.

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Progress in nondualism: looking for my hands

Certainly, cerebrally (haha), it’s easy to see that there is no trace of your head in your visual field when looking out from it, but it’s quite unclear what the significance of such a revelation is. At best, in trying to practice this, I’d often glimpse a brief impression that there is nothing there where my head (and so, my sense of self) should be. That my self is just a construct that I have assigned to this signature of feelings that are arising in consciousness: the edge of my nose, the thoughts that arise, the illusory feeling that those thoughts originate and exist within me. But quickly, the glimpse would dissipate and I would no longer be able to disentangle myself from the dual nature of reality — there’s me, and then there’s the world.

Of course, this is quite difficult to internalize, but I recently came to an exercise that helped make this stick longer for me. I started by noticing the same headlessness exercise could be applied to my hands.1 And then I subsequently listed out the things that I felt described my hands. The pinkness of my flesh, the visual boundary between the hands and everything else, the sensations that I felt within them, the quickness and automaticity of their actions. And, while this is certainly more visceral for the head, I realized that a large part of myself was embodied in these hands, but they were not me. They are an abstraction that sits over all the things that I perceived them to be, alongside decades of conditioning and muscle memory that has blurred the line between their individual signatures within my consciousness and the higher-order sense of them that my mind interacts with, almost unthinkingly.

It’s all concepts, even your sense of self

This may sound as abstract as the whole headlessness ordeal, but it was a breakthrough for me simply because I had another pattern by which to see my headlessness — headlessness is, too, a sense of concepts and muscle memory tied to them, just far more strongly engrained. So, too, is one’s internal impression of self (what I tend to call my “soul”): there’s all the conditioning I have around how my thoughts invoke action; then there’s this extremely strong illusion that my thoughts are me — a deep, deep concept layered on top of the thoughts themselves.

And this observation extends beyond one’s sense of selflessness — we tend to layer everything as humans. All of our knowledge and understanding is just layers on layers on layers. Concepts on concepts on concepts. We hide the inherently intractable nature of raw experience under the lossy story that we are telling ourselves about it. We layer definitions over the physical world, burying the ineffability of those concepts beneath an intricate network of facts and abstractions. We humans are somehow experts at dealing with these abstractions, cataloguing definitions alongside intuition paintings in our minds, hardening this connection until you can believe in the illusion strongly enough that you can reason around it. And our muscle memory — our conditioned habits and thoughts in response to these concepts layered over stimuli — is culpable in perpetuating this illusion. Recognizing all this has been a fun way to see almost everything with fresh eyes, from aspects of my consciousness to my relationship with words. We are so well-acquainted with our lives that we forget that almost all things are almost inherently unknowable.

As an example exercise: go pick up a book you want to read later today. On the one hand, your mind has deep-etched pathways for figuring out what book to read, and your body knows how to contort itself to find that book. But you’re also unknowingly dealing with a whole host of concepts all at once — your sense of self, in that you are doing the thinking and the searching, of course. But also what a “book” is. What it is to “want”. What it is to “read”. And deep in this cavern I find there are three things: (1) my open conscious awareness, being buffeted by (2) a slew of conditioned behaviors, interacting with (3) layers of useful concepts.

This has had two points of particular utility for me as of late:

• On the one hand, the meditative exercise is quite nice on its own. The formerly stochastic, serendipitous process of evoking nondualism is becoming steadily more repeatable to me: halt the muscle memory, break down the concept, observe its constituents. We’ve layered two things over ourselves: concepts and conditioning. But on trying to identify the things in our heads that are and are not those things, I find myself face-to-face with the totality that is my consciousness.

• I’ve always had a really hard time catching my thoughts before they happen. But even just having the label “conditioning” in my vocabulary to describe what’s happening in my brain has helped me finally feel the tether before I’m pulled along (though I admit, the timing may be entirely coincidental). In particular, I’ve been able to notice lately what happens when my mind is being creative, which often pulls me quite quickly out of meditation practice. I’ve noticed lately that there’s a physiological signature first, where I’ll feel a building muttering in the back of my head or a rising excitement in my chest or, for lack of a better description, this widening feeling in my brain. And then there’s this conditioned response to that feeling — a narrowing of my focus (the entire world falls away). It usually starts with a few seeder words, then it’s almost as if my eyes don’t see anymore — the words act as a sort of sorcery, quickly invoking images of a rich world that those words paint in my head.

I think it’s quite easy to forget that this whole thing — the miracle of just being here in this moment, let alone reasoning with higher order layers on top — is absolutely wild, and this has all been this very arduous exercise in re-internalizing that absurdity. Still, I’d highly recommend it.

This week

• One final note: If the above was confusing but you want to get started, I really love ’s meditations on this topic from his Waking Up app — here’s a recent one I found particularly compelling.

• I really love this post from . I know my post above might seem a bit esoteric to some of you, but he very nicely describes some of the states that mindfulness practice bring you to, and they are quite compelling.

• I also recently have been reading some of ‘s work. He seems to embody a wonderfully similar worldview to my own, so give him a read if you have a minute. He touches on topics like the above every so often.

It’s a life philosophy wherein being human is about running from our animal instincts, establishing and adhering to an objective, rational value system. (And it’s a worldview that drips from my newsletter, if you haven’t noticed.) But I recently shared this perspective with an old college friend, and he asked me, quite poignantly:

“So your goal for life is efficiency?”

I struggled to respond. I tried to pontificate about adhering to a higher set of values, about pursuing the human ideal, but it was all glaringly shallow. It is just efficiency from a certain vantage, isn’t it? And while efficiency is certainly an interesting skill tree to pursue, it can’t possibly be everything. Efficiency, by definition, can only gain value through something else. It’s tempting to view my life as a striving toward the Randian hero, but I don’t think there’s really much there once you untie your knots (if that’s even ever possible).

So I’ve recently started to revisit my view on meaning, and I’m going to drop some of my thoughts here. While I find it a bit overwhelming to think about something so grand and nebulous as meaning, I think we can actually get quite far by applying to it some very reasonable constraints — e.g., in particular, that such a sense of meaning exists, that such meaning should then be fair and so, that such meaning ought to be possible for everyone, regardless of the circumstances of one’s birth.

So excuse me while I pontificate for a bit and try to reason through this. But in short, my conclusion is pretty self-apparent: meaning must be what you make it to be.

Welcome to my midlife crisis, in newsletter form.

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Some very reasonable assumptions

If meaning exists, there’s a principle that measures it.

The first constraint one can apply to one’s understanding of meaning is simply that such meaning exists. And if you believe that some universal sense of meaning exists, then there must be some principle that defines it (which I ultimately contend should be that you define it for yourself). But, on the other hand, if you believe that such a universal sense of meaning does not exist, then you can still define it for yourself.

If meaning is rational, that principle must be universal, and it must be about consciousness & choice.

The second constraint to apply is that meaning must be rational — one that reflects human values. If this is not true, then of course, again, we can define that meaning for ourselves because have no hope of inferring what it actually is.

But if meaning is rational, we can infer that such a meaning would be fair (well, barring solipsism). And given you did not choose the body in which your consciousness inhabits, meaning should be something attainable for all humans and under all conditions of life1.

The only two byproducts of human life that could hold under these constraints are choice and consciousness. Moreover, given that meaning must follow some principle, that principle must also be universally acceptable to all humans as well. Therefore, meaning must follow a universally accessible principle, and that principle will pertain to consciousness and choice.

The punchline

That principle must be what you want it to be.

So the final question to answer is this: how do I decide on which principle should govern my choices? Again, for any principle to be the principle, it must be sufficiently self-apparent, otherwise it cannot universally apply to any existence one can dream up. And in that situation, the only principle I can imagine fits this constraint is whatever principle you choose for yourself.2

That said, I don’t think this means you should devolve into pure hedonism and moral bankruptcy. At the risk of sounding quasi-spiritual, I think there is some deep intrinsic sense of judgment that’s present in all of us. There’s a sense of what is correct for you to do. Something that is in line with a deep-seated congruence to who you are. It’s implanted in us, without any real necessity for instruction. My current thinking is that this is what you should be following.

If you’re reductive about it, sure — it’s perhaps simply some biological/social brainwashing, but I’ve nonetheless found that it’s deeply rewarding when I listen to this internal barometer. It’s the only voice that has the capacity to surpass my most regretful biological inclinations — my anger, my pettiness, my ego, my lust, my addiction. It’s knowledge of good and evil, perhaps. I think we just tend to attribute it less significance because its effects are so intangible.

By comparison, for example, reason may too be of somewhat dubious origins, but as it’s the basis of all logic and science and knowledge, it’s quite easy to trust. But judgment is an internal state — there are external manifestations, certainly, but it’s quite difficult to recognize fidelity to this system in anyone else. Principles can be faked, and routinely are. Still, our evolution gave rise to our reason (and that’s awesome), so perhaps it’s not too far of a stretch to believe that judgment too is something as universally fundamental.

And I’m realizing that this is a common thread through philosophy.

• Nietzsche:

  While the Übermensch often gives off this sense in pop culture of the Randian hero, the idea is actually quite different — it’s precisely the idea that one must define for oneself what values to live by:

  • "I teach you the Übermensch. Man is something that shall be overcome. What have you done to overcome him?"

• Emerson:
  This is the theme behind all of his seminal work, “Self-Reliance”.

  • “Trust thyself: every heart vibrates to that iron string. Accept the place the divine providence has found for you, the society of your contemporaries, the connection of events. Great men have always done so, and confided themselves childlike to the genius of their age, betraying their perception that the absolutely trustworthy was seated at their heart, working through their hands, predominating in all their being.”

• Thoreau:

  • "If a man does not keep pace with his companions, perhaps it is because he hears a different drummer. Let him step to the music which he hears, however measured or far away."

• Viktor Frankl:

  • “Ultimately, man should not ask what the meaning of his life is, but rather must recognize that it is he who is asked. In a word, each man is questioned by life; and he can only answer to life by answering for his own life; to life he can only respond by being responsible.”

End

Perhaps this is all a bit obvious. But it’s taken me more an embarrassingly long time to strip myself of enough of my deep-seated biological compulsions + external moral barometers fed to me so that I can think [somewhat] clearly about what meaning is outside of that, and my conclusion is almost astonishingly plain: the fact that you are experiencing your life is what gives life meaning, and you ought to define what that meaning is for yourself. We are not hyper-optimized robots being undermined by our human wrappings. We’re consciousnesses with little else anchoring us in this dark universe.

This week

• I’ve been reading Nietzsche (lol, if you couldn’t tell), and he’s so wonderful to read slowly. I’ve come to appreciate that he was very careful in his framing of the Übermensch: he called life a “bridge”, recognizing that it wasn’t about being Übermensch, but the “over-going” towards it. And I think this was quite intentional. Life is not the Übermensch or animalism, but the bridge.

Here’s my attempt to formalize this process — for myself, mostly, but hopefully it helps you too.

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Thinking from first principles is about finding the right governing principles.

In an article by James Clear on the subject, Clear talks about how Elon Musk used first principles thinking to reduce the cost of launching a rocket by 10x by going down to first principles — i.e. by considering the cost of raw materials used to build rockets.

But my great complaint about this account is that (while I greatly respect Clear’s work) it doesn’t really help me understand how to think from first principles. The first principle Elon gets to is only really obvious in hindsight. Yes, Elon was able to get to a very fundamental concept — the price of raw materials for rocket production. But he could’ve just as easily arrived at a different fundamental concept — the necessity of those raw materials in satisfying the physical constraints imposed by rocket design. Or, gaining ownership over raw material sources to cut a deal with rocket creators. There are a number of “first principle” solutions, so while the first principle seems obvious in hindsight, it’s not nearly so obvious in the process of trying to find it.

And this is what I’ve found to be the biggest misunderstanding around first principles thinking: to do it well is not about your deductive capacity. It’s more often about defining what the relevant first principles are from which to begin your deductive reasoning. It’s certainly not always the correct solution to go down to physics1, for example, if you’re talking about something decidedly more abstract, like product or engineering or relationship problems. So there must be some means of finding the correct level of abstraction at which the salient properties of the system can be explained. Identifying the proper principles for the system you are attempting to understand is key.

… and objective-seeking is next.

In reality, problems that I’m trying to solve from first principle usually have a very dubious objective. While it’s important to identify the principles that govern your system around that objective, it’s equally important to refine that objective as needed.

If we revisit the Elon example, for example, one can easily imagine how an initial objective would have to evolve. Imagine if his objective started as “negotiate cheaper rocket prices”. Regardless of what principles you use to describe the rocket-price system, reasoning in the realm of this objective would never amount to the solution Elon got to — building rockets himself. The objective adds a constraint to the principles you can reason around. The key, then, is to iterate on the objective: “launch a rocket as cheaply as possible” is the correct improvement, widening the aperture to include the prospect of building one from scratch.

Here’s another example: I want my daughter to learn piano. That was my objective, to start. The core, first parameter to consider at that point was the quality of the teacher — I believed in the principle that the quality of teaching vector largely defined the experience that she would have. I then, of course, found her a teacher and started to bring her to lessons.

But on practicing with her, I quickly discovered that, while I was impressed with the progress she was making, she was getting frustrated while practicing. I revised my set of initial principles, now believing that the quality of her experience came from multiple parameters, including:

• The quality of the teacher.

• The quality of her experience during practice.

  • The quality of her practice.

  • Her level of enjoyment.

I revised my objective accordingly: I want my daughter to gain enough piano skill to be able to experiment with and love music. The action to take toward that objective and in light of the fundamental governing principles was clear: practice with her only enough so that she isn’t frustrated, and then let her play around thereafter. Maximize piano skill against the constraint that her love for music cannot decrease.

It was an iterative process. My objective changed, and as it did, so too did the first principles that mediated that objective. The way to reason from first principles, then, isn’t to choose some a priori principles that seem to be fundamental and comprehensive, but to continually scrutinize your objective and what you believe to be the governing principles behind that objective until both, in conjunction, effectively describe the core problem you’re trying to solve.

Some other things that have helped me: sacred cows

One final comment here: one of the biggest things that gets in my way when trying to think from first principles are sacred cows — the things I want to be true, for reasons orthogonal to my principal objective. The insidious, destabilizing bias trying to creep in.

This is something that the startup world is rife with. When building a new product, for instance, it’s quite natural to start to love the product you’re building. This, of course, imparts a bias which can undermine your initial choice of objective.

Here’s a view of how first-principles problem solving unfolded when we first pivoted our company:

I like this particular because it has two clear messages:

1. It’s clear that sacred cows are abound at every step.

   The sacred cow in the above example was that I wanted the existing business to work, so I’d already started the framing of the problem under the assumption that choice of business was not a parameter that I could play with.

2. It makes clear the utility of revising one’s objective.

   Without revision, we would never have executed the pivot.

Final comments

One of my advisors frequently reminds me that, though I am naturally inclined to think of everything from first principles, first principles thinking is not always the most optimal solution. Oftentimes copy-pasting an existing solution can lead you to a more optimal solution, particularly if you lack the data to arrive at the correct conclusion from first principles yourself. Moreover, this sort of reasoning by analogy is often much faster. (Of note: pattern recognition and wisdom are the mirror skill sets, which is articulated well in the quote below:)

“Frequently, when I am faced with what would appear from the outside to be a challenging problem, the grinding mental computation is somehow circumvented, rendered, as if by magic, unnecessary. The solution comes effortlessly, seamlessly, and seemingly by itself. I seem to have gained in my capacity for instantaneous, almost unfairly easy insight. Is it perchance that coveted attribute … wisdom?”

- Elkhonon Goldberg, The Wisdom Paradox

But I’ve found that, in instances where you are indeed doing something entirely novel — operating at the forefront of scientific understanding (research), for instance; or building a product that has never been seen before — first principles thinking, while it should never be your default means of operation, is the only way to do something truly novel. But of course, apply sparingly.

Playgrounds are wildly different. You do you. You build castles, you dig holes, you bury leaves and make messes. Most of what you do is terrible, but sometimes wonderful. Your curiosity is driving, not your hubris, so of course, you find things you can’t find on a stage. Most people wouldn’t want to watch you play in a playground, so value proposition remains intrinsic, by and large. Again, not incorruptible, of course, but the incentive structure is certainly preferable.

I think all of us tend to view the world as a stage to some extent. It’s deep-seated within us to care about what other people think. This isn’t necessarily a bad thing — it can be noble, even, particularly when your work is in service of others. But there is this curious tendency for this incentive pattern to warp (and ruin) the best of us.

In general, I believe life is better approached as a playground.

We all start on a stage

I think everybody starts on a stage. We need to establish base value assignments to things in the world, and as children, I suspect we do this largely through mimesis — we internalize the value attributed to things by observing those around us. And inevitably, we look to these people for their validation. Our core values become this mix of the values of the people around us.

In fact, we can extend this concept to everything in your life, up to a point. Everything is given to you in the beginning. You are plopped into a life that you neither designed nor [in all likelihood] desired. Initial conditions are set without your consideration, and the mimesis ramifies and elaborates until you mix your arbitrary upbringing with the present cultural ethos. We commonly think of opportunities and circumstances provided by our parents as falling within this scope, but without your own internal value system, so too do all of your actions.

And so, you establish a hornet’s nest of mimicry instead of a deep, internal understand of what you want. And often, this can become quite distorted. Your innate, legitimate (but quiet) need for friendship and understanding turns into a need for external validation met by Instagram follower count. The wonderful, beautiful capacity of your mind to compose rational thoughts turns into some warped need to be perceived as smarter than others. There are some things that we all instinctively know are of inherent value and we, as humans, find deeply rewarding, but above them we stack layers on layers of want and need incepted in us by our circumstances, our genetics, our parents.

And so, inevitably, we all start on the stage, addicted to the drip.

Tearing down the stage

So here’s what happens next: unfortunately, most of us attain some modicum of worldly success — we graduate from school, we receive some recognition, etc. etc. And so we kick the self-awareness can down the road. We continue to maintain the dopamine drip by reinforcing the circumstances that led us there — the circumstances that have been, unfortunately, shaped by others.

I think, generally speaking, there are two paths to reaching escape velocity and refactoring against an internal value system: through failure, or directly through careful self-reflection. With failure or trauma there’s a chance of mustering enough self-awareness to establish your own internal value system. But only a chance. Inadequacy will always creates one of three things: change, acceptance, or lies. And lies are dangerous here — oftentimes, we’ll internalize plausible lies (it was this other person’s fault; I'm brilliant enough I just don't work hard). And so you end up with a string of half-truths and motivational quotes papier-mâchéd over your reality.

But of course, direct reflection can also directly get you there — it’s just that most people aren’t motivated to reflect except through suffering. The key is to dissociate yourself from the arbitrary stimuli that are guiding your actions (including the default external value system that your brain has latched onto). At the end of the day, it all comes down to mindfully living. Being directed by your own value system vs. an external one is the difference between summoning clear intent and, effectively, being lived.

The playground mentality: you don’t need to do a thing

I recently read a wonderful piece by . She talks about finding new “mundane” hobbies after her father became ill:

“I wish I’d spent more time with my family. I wish I’d lived a life that was true to myself, not what others expected of me. … In a world that wants us to be permanently cool, glamorous, wealthy and good-looking, it can feel revolutionary to prioritise slowness, learning, human connection and the natural world.”

I think there’s something profound in realizing that you don’t have to do anything. There’s this beautiful Mary Oliver poem that a good friend shared with me years ago:

You do not have to be good.
You do not have to walk on your knees
for a hundred miles through the desert repenting.
You only have to let the soft animal of your body
love what it loves.
Tell me about despair, yours, and I will tell you mine.
Meanwhile the world goes on.
Meanwhile the sun and the clear pebbles of the rain
are moving across the landscapes,
over the prairies and the deep trees,
the mountains and the rivers.
Meanwhile the wild geese, high in the clean blue air,
are heading home again.
Whoever you are, no matter how lonely,
the world offers itself to your imagination,
calls to you like the wild geese, harsh and exciting
over and over announcing your place
in the family of things.
- Mary Oliver, Wild Geese

I remember when I first read it, I thought it a call to inaction — a proposal to drift dreamily through life, to accept your place as a goose. But I now understand it as quite the opposite: it’s an articulation of why we strive. It’s a means of toppling the narcissistic inclination that comes with any sort of effort/success and replacing it with something genuine. Start with nothing — you are a wild goose, after all. Only then can you relish the way the world offers itself to your imagination. We shouldn’t create to win, we should create because it’s wonderful that we can.

Our culture compels us to read quickly. Rationale is easy to find: reading is good for us; reading more, faster must therefore be better for us. It’s plausible, and the convenient virtue signals deter introspection.1 Granted, reading quickly does achieve certain objectives well: reading more exposes you to more concepts, which can yield a wider corpus to draw on while thinking. If you are trying to solve a specific problem, reading more increases the probability that you will encounter something pertinent.

That said, I don’t think we spend enough time reading slowly: reading, then rereading, then thinking. A kind of reading where you play with the words. A kind of reading where the words don’t simply settle thinly over your short-term memory for future use, but take residence in your core. And it’s taken me embarrassingly long to figure out the value of reading slowly, though it should’ve been obvious early on — it’s where my best ideas come from, I retain more of what I read over longer time scales (years), and while it might not be the best way to ingest volume, it’s certainly been the most effective way for me to change myself. While reading fast maximizes exposure, reading slow maximizes internalization. The ideas you consume slowly have room (time) to grow and elaborate, giving them the opportunity to integrate into your deep brain and ramify.

Of course, it’s not one or the other. To read everything slowly could mean effectively reading nothing at all. But I think we generally err on the side of speed too often. The prospect of speed just has too much momentum, so a correction is warranted. When deep thought is my objective, I try to read something like this:

• Read fast until I find something. I like to read as fast as I want until I come to an idea that I either (a) find interesting or (b) don’t understand. Too many books are filled with fluff and garbage so to waste your time reading them slowly can be a huge waste of time (don’t read something deliberately if it clearly wasn’t written deliberately).

• Read that thing slowly. Upon finding a compelling idea, though, I read it slowly and savor it, as I’d savor a good meal. To rush is equivalent to scarfing down a Michelin star meal. Let it swim around in your brain. Write it down, write about it. See how it fits into your worldview. Turn it over in your head until you are satisfied with the shape, the taste. Fit it with metaphors and your life circumstances and thought experiments until it carries its brilliance through the long tendrils of your brain.

• Switch books. In the past, I’d often then just toil on, but more recently, I’ve started to embrace taking breaks — once I’m satisfied with my ingestion of an idea, I’ll switch books or do something else entirely. Ideas need time to grow in your brain.2 I have this odd compulsion to want to read one book at a time and slog my way through it without distraction. But I’ve come to realize that this is a far worse way to read books — yes, the dopamine feels more predictable, but by reading many books at once, you organically create stop points where your brain can have time to let the ingested ideas evolve internally.

Of course, if you have your own system for reading, please share — I’d love to optimize this further.

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This week

Going to try something new and just share some other notes / things I’ve found interesting but don’t quite fit into the post. Let me know if you find this interesting or superfluous 🙂

• Writing about what you read is a great way to force yourself to read more slowly. Or, when a computer / notebook isn’t available, sometimes I’ll just record myself talking about it, which has been a reasonable replacement.

• I’m re-reading Ray Dalio’s Principles, and it hits way differently now than from when I was in my 20s. It’s an easy book to skim, but really finds its value through deep thought. His first principle — “Embrace Reality and Deal with It” really is everything.

• I’ve been listening to Billie Eilish’s Birds of a Feather. This song is incredible. It’s been a long time since I’ve heard a pop song where the arc of the vocals and the arc of the production so synchronously hold, release, and play with tension.

But eventually, I dropped the practice in favor of exercise, socialization, writing — behaviors that felt equally effective but more rewarding. The value just wasn’t enough to warrant the time spent, particularly when I felt the benefits could be achieved through more productive means. And I count myself one of the lucky ones — a lot of folks have more infuriating experiences. I recently read “What the Bones Know”, and in it, Stephanie Foo1 articulates a sentiment that a lot of folks end up having:

“Meditation does not bring me peace. I’ve tried it maybe a dozen times before, and it always goes the same way: I try to clear my head. I close my eyes and try to think about nothing. I want to make my brain a blank slate, but images keep popping up: an idea for a story I should follow up on, the laundry I haven’t done, the shoes I should take to a cobbler.”

And so I filed meditation away in my mind under “natural low-grade Prozac that works for some people” and promptly moved on with my life.

Years later, though, I discovered mindfulness meditation2. And while this flavor of meditation kind of feels the same — you sit calmly, relax the eyes, notice the breath — I came to realize that it was fundamentally different, in a way. The initial objective felt orthogonal to the wellness path3: rather than trying to directly achieve calm through dissociation, the goal of mindfulness meditation was… well, just that — to simply to be mindful. To notice what’s happening, whether that’s the calm cadence of your breath or the intrusive thoughts that are getting in the way.

And this subtle shift in the objective is powerful. While being calm is an effect, being mindful is a state of mind. With mindfulness practice, you aren’t simply trying to force an outcome (though such outcomes will inevitably happen). Rather, you’re altering your relationship with reality. Mindfulness is a means of become aware of what your brain is doing, rather than a means of simply mediating its outputs. And, as a consequence, the effects are far more profound than its physiological benefits.

I’ve written about this before, so I won’t expound the virtues of mindfulness meditation. But in short, you become more aware of everything, and in doing so, you incidentally become aware of the precise flavor of things that are motivating you or stressing you out — their precursors, their signatures. And so you develop this space away from your feelings and thoughts that not only helps you react more conscientiously, but more than that, provides comprehension of those things that would otherwise be impossible.

That said, one of the chief problems in getting started with mindfulness is that it’s not trivial to get started, particularly when every meditation app claims to be a mindfulness app. It’s easy to spend hours going down the mindfulness path when, in reality, you weren’t practicing mindfulness at all — you were just repeatedly getting overwhelmed by all the chatter in your brain.

So, that’s what this post is about. This’ll be my quick attempt at providing an explanation on the core principles of mindfulness that, once internalized, I hope can help you start mindfully meditating yourself.

How to meditate

The overarching goal of mindfulness meditation is to notice what you notice, NOT to achieve a state of perfect calm4. The practice is this:

1. Notice something.

   Usually the breath, but sounds, sensations, feelings also work well. Notice this as long as you can.

2. Notice the thing that distracts you from that first thing.

3. Go back to #1.

And that’s it. The process is one of focusing on a thing, then noticing distractions. Unlike wellness meditation, in mindfulness meditation, your initial point of focus is not necessarily the end goal but more of a zero-ing mechanism — a means of going back to a blank slate so you can more clearly observe what’s trying to come distract you.

For me, these distractions typically come from one of three sources: thoughts, feelings, or songs that I get stuck in my head (really specific, I know). Sometimes you’ll start reflexively planning the rest of your day (thinking). Other times, you’ll feel heavy, exhausted, and it’ll compel you to scroll on Youtube (feeling). Sometimes you might even get frustrated by the fact that you’re not able to focus on your breath (thinking). The catch is this: these are all the things to notice, and so are part of the practice. And by noticing them, you not only rob them of a lot of their power, but you give yourself a laboratory to observe and study them.

I'm focusing here more heavily on distractions because I’ve found that distractions tend to be commonly misunderstood. Distractions don’t distract you from practice — noticing distraction is the practice. Almost everything that will happen during your meditation practice falls into the realm of distractions. And once you realize this, you’ll realize there’s no sense of doing it right — it’s just about noticing all those things, from your random thoughts to your anxiety to the feeling that the presence of these distractions must mean you’re doing terribly. Nothing escapes scrutiny.

Adyashanti has a great quote that I believe captures this distinction well:

"Being in the moment, it's not like you have to find a special place to show up. The problem isn't that people can't find the moment -- I think the problem that most people have is that they can't get out of the moment. I think if most people were honest, they would say 'well, I'm actually trying to get out of the moment, but I'm hoping that when I get into the moment, the moment will be different than this'."

Why this is better

Perhaps “better” is a strong word. I’ll share a bit on why this manner of meditation is preferable to me. I talk a lot about thinking. That’s the principal subject matter of this newsletter, after all. And if you’ve been reading, mindfulness is often the solution to most of the cognitive traps that I try to untangle in my posts.

And this is not a coincidence. Most of the chaotic things that your brain does are a result of not noticing what your brain is doing. When we let our ego run amok, when we perform mental gymnastics to bend the truth, when we succumb to addiction — it’s usually not a result of intentionally sabotaging yourself, but of failing to notice how your default brain is invisibly guiding your actions. And mindfulness, as defined above, is tautologically the exercise of noticing those discursions. And it’s a lot easier to direct your brain once you know where your brain is trying to take you in the first place.

Moreover, once you increase the aperture on meditation to include everything, it can start to function as a laboratory of studying the experience of consciousness. And while this might sound somewhat abstract, I think this is something we all deeply long to understand better — what are we? What is life? While I can’t promise meditation can answer those questions, it can certainly provide perspective on what you are in relation to them.

Final comment, if you’re starting out

One final comment I want to make: you can (and should) do this all the time, not just during a circumscribed meditation time. The goal is to be able to be mindful all the time (and particularly in instances where it’s very difficult to be mindful) — to extend the pristine, clean-room awareness that you cultivate during practice to the rest of your life.

To that end, one of the biggest unlocks for me in my mindfulness practice has been trying to actively bring my mindfulness practice to moments where I’m stuck in an all-consuming default mode. Sometimes that’s when I’m feeling particularly emotional: when someone cuts me off while driving, when I’m locked in a heated argument. Other times, it’s when I’m in a state of bliss — when I’m on vacation, when I’m having a great conversation with a friend or my wife, when I’m snowboarding or exercising.

In reactive situations, mindfulness gives me some distance from the feeling itself, allowing me more room to process it well. And in more positive situations, it allows me to be present in the moment to a far greater extent than I would otherwise. And what value is there in life if you’re not present in it?

I think the way to think about this isn’t so complicated: actions are about getting more data. Thinking is pathfinding.

Thinkers vs. doers

I’ve noticed recently that the world tends to divide itself into two camps: thinkers and doers. The doers extoll Silicon Valley hustle culture.

I don’t think either camp is wrong, but in a way, both are wrong. This might sound obvious, but sometimes you have to do things, sometimes you have to think about things. But, unfortunately, this is a sort of naturally polarizing endeavor. You have two options — only one thing will be principally important at any given moment. So you’ll likely learn a lesson at some point that thinking is all that matters (if you don’t think enough) or doing is all that matters (if you don’t do enough).

While this might make sense for you, certainly both are important.

The doing trap

This, especially to you readers of this substack, is probably most familiar to you — I made this substack because I think, in general, people don’t spend enough time thinking, and if you’ve read this far, I suppose you’d agree. In general, I think most important decisions suffer from too much execution, too little thinking. For instance, if your decision will have any scale of impact at all (e.g. if you’re working in a company where your decision will impact the work of many others), the best thing you can do is make certain it’s the right decision. Spending just a few hours thinking about a problem can save you from:

• Losing collective time: Wasting months or years developing a product or running a test that didn’t need to be run.

• Wasting individual time: Everyone below you wasting their time running in the wrong direction.

Good decisions come from good thinking.

The thinking trap

I’ve found that there are two instances where continued thinking ceases to provide additional value:

• When you reach the limit of your existing data

  There’s a point where incremental thinking is no longer useful, in that you’re extrapolating on thin data. If doing something will get you more data, and if that data would benefit your thinking better than incrementally bashing your head against the wall, it’s a better idea to go get some data.
  
  That said, I think most people tend to underestimate where this point is. As a rule of thumb, for the most consequential decisions, I generally do the following:

  • Spend a couple hours thinking about the problem by myself.

  • Spend a couple hours talking to someone else to get their take.

  • Give myself at least a full day break to let the ideas sit in my head.

  • Spend another couple hours thinking about the problem by myself.

  • Spend another couple hours getting to consensus with the other person.

  
  Usually this means each decision takes at least 2 days to make. There are simply far too many pitfalls in thinking about a decision and making a decision in the same moment — the novelty effect, the validity effect, confirmation bias, etc.

• When the decision is easy to reverse

  I’ll concede that the pattern above is a reflection of my own bias — I’m a founder, so generally the decisions (and the level of decisions I make) are existential. Do we pivot? Do we fundraise? Do we shut down the company entirely? Do we take on debt?
  
  But, of course, many, many decisions are easy to reverse and are not so ambiguous. You’ve likely heard Jeff Bezos’ advice on the matter, which sums this sentiment up quite nicely: when the decision is a one-way door, you need to think methodically, as you’ll have to live with the consequences for some time. When it’s a “two-way door” — an easily reversible decision — the decision should be make quickly.
  
  Methodical decision-making is, of course, slow, and that’s the problem. Setting this as the default for an organization can be crippling — slow experimentation kills the invention flywheel, and this can just as easily kill a company.

In short, better data begets better decisions, and better data usually comes from action.

Final comments

So a final caveat: this is all dependent on so many things — your role, your scope. If you’re an IC and mostly just executing, there’s little need to agonize over your decisions. Usually, the scope is small enough that you ought to just experiment, then move on (well, barring hugely consequential architectural decisions, of course).

But I think this is something folks tend to misunderstand about moving up — you need to make decisions differently. The more senior you get, the more consequential and irreversible your decisions tend to become, meaning the more the tradeoff should tip in the direction of spending more time on the decision.

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“I fact checked the book and found the exercise claims solid, but when I gave the book to 6 people none of them exercised more.”

Of course! Of course reading a book that extolls the virtues of exercise does not make you more likely to exercise. We all already know exercise is good for us. That’s not the blocker. The blocker is entirely one of motivation.

And there are so many books in other categories just like this — I think this is why people roll their eyes so often at the self-help book category. Yes, I do want to be healthier. Yes, I do want to think better1. Yes, I do want to adopt the 7 habits of highly effective people. But of course, knowing what to do is a very different thing from actually doing the thing you know is what you want to do.

I think you can divide problems into two categories:

1. Problems where you don’t know what to do.

2. Problems where you do know what to do, but don’t want to do it.

Let’s talk about type 2 problems.

The anatomy of not wanting to do a thing

So why don’t I listen to my own advice? I think it’s tempting to oversimplify the underlying mechanism as something like this:

A few years ago, I went through the futile exercise of trying to map these two curves out in excruciating detail — to identify triggers of ebbs and flows so that I might appropriately titrate my caffeine intake and energy-giving activities, solving the problem of procrastination altogether. Of course, that was a complete and utter failure.

I think the issue is that reality is a bit more complicated than that. And to smush all the complexity of human emotion (and consequently, inhibitors of motivation) onto a single “stress” axis is too lossy. At any given moment, you of course don’t just feel something as simple as stress or exhaustion. It’s this assorted mix of feelings. Looming tiredness. Lack of motivation, felt as a heaviness in the chest. Stress, manifesting as a buzzing in the head. A broken thought loop where you obsess over the person that didn’t fully stop at the stop sign and almost hit you. Rage at your coworker’s mistake, but mostly hanger building as an all-consuming emptiness deep in your core. It’s a mess.

Looking at it gives you space

If you’re like me, you’re probably tempted to try to understand how this soup of emotions boils down to a binary signal — motivated or not. When am I angry? When am I happy? What seems correlated to better performance? Can I hack this in any way? But I’ve started to think this is the wrong approach. You can map out your life all you want, but the possible mixtures of feelings and stimuli that can bombard you on any given day are too infinite to fall neatly into some universal theory of motivation.

However, something that has helped me is using my periods of low motivation / high procrastination as moments to practice mindfulness — and in doing so, notice the physiological signature of that lack of motivation. Not the cause, mind you, which often just leaves me spiraling down this deep rabbit hole of revisionist history. But that tension in your head. The heaviness in your arms. The slight buzzing around your temples.

I’m not certain why it works, but I suspect by simply becoming aware of any cognitive blockers that keep you from taking your own advice, you learn to stop identifying with them (they are not you), and you thereby gain some modicum of power over them — it’s easier to fight a thing if you can see what you’re fighting, after all. And it seems like this is a legitimate effect, not just my anecdata: mindfulness can improve one’s intrinsic motivation, and I’d wager that the mechanism comes down to creating this sort of mental space to gather some willpower.

Brain rest

All that said, that often isn’t enough for me. Sometimes I feel like not doing a thing, and I see the feeling that’s getting in the way of me doing the thing, then I don’t do it anyway. For a month or two earlier in this year, I managed to combat all of it, but ended up feeling utterly drained and foggy, and I generally felt that my mental performance against critical problems was going down, even if I was “productive” all day.

Lately, my daughter has been learning piano, and sometimes during a lesson, I’ll see her think deeply about a question her teacher gives her. “What note is this?” After a 10 second, mind-grinding pause, she’ll say the right answer: “G”. And then promptly after the lesson, she’ll complain about everything. Her personality will 180 — she goes from sweet little girl to tear-down-everything-tyrant. And I’ve seen this story before. When I overwork my brain, there’s this level of cognitive exhaustion that follows.

I think to some extent, your brain needs rest. And metaphorically this makes sense — when you exercise, growth happens during rest, so rest is as important as the actual act of exercising itself. The same must be true of your brain. And certainly, the scientific literature supports this, at least within somewhat contrived environments: adding a mid-task break to a task, for instance, significantly improves subsequent performance on that task.

Of course, it’s a fine line to walk between letting your brain do what it wants to do and binge-watching Netflix all weekend. So one of the most difficult things to figure out is: what counts as a break and what doesn’t? What are the [action, break] activity pairs that work optimally together? In the end, I think we all have this tendency to view our brains as these infinite reservoirs of intelligent thought, but I think this is often more harmful than helpful. This kind of stance compels us to exert ourselves in ways that are tantamount to trying (and inevitably, failing) to exercise all day.

Final comments

In general, all I want to say is:

1. It’s hard to follow your own advice.

2. Mindfulness can help in the moment.

3. Breaks can help recharge you.

But my main point is this: I don’t think we collectively spend enough time understanding why we’re not doing what we want to do. We tend to chalk up poor motivation or procrastination to our own intrinsic deficiencies, but even if that is, to some extent, the case, I think you can go a long way by just scrutinizing it and seeing what you can find.

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The relationship between certainty and competence is fascinating. I’ve noticed that certainty tends to increase with both competence and incompetence. And this gives rise to a dangerous form of Batesian mimicry: certainty posturing.

On the one hand, certainty often does come from intelligence, knowledge, competence — it’s justified assuredness from having the truth on your side. But sometimes, less competent individuals (especially those who have some level of undeserved external validation) will wear a cloak of certainty to fool others (whether consciously or not) into thinking they are competent.

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This is a huge problem, because the actual intentions and actions of these people will never align transparently with the objectives of any project, and nearly everything they do will be, at best, pointless, and at worst, actively against the primary objective. Their goal is to win discussions, not to get to the truth.

Ego is at fault

I’ve been trying to figure out where this all comes from. I’ve historically been quite confused as to how people can be so certain, in general, and I imagine there’s some level of cultural and genetic variability that begets over-leveraged certainty. But I’ve also noticed there are other predictable mechanisms that trap you in a world where unjustified certainty becomes your only path of recourse.

I suspect the most common of these is one where your ego outpaces competence.

When ego is low, you are motivated. You need to be better, so there’s a deep-seated intrinsic motivation to improve yourself. And if you can keep your ego low forever, you can learn forever.

Conversely, when your ego is high, you run the risk of entering a limit cycle in the ego-competence dynamical system. I.e. you get stuck on the wrong side of the diagonal forever. When your ego outpaces your competence, you have two options:

1. Gaslight yourself even more, letting your ego run even more wild (and making it harder to correct next time).

2. Accepting that you’re incompetent, thus decreasing your ego and propelling you into a stance of learning.

But once you take path 1 once, you are more likely to perpetuate the lie forever — you’re in too deep, and honesty only gets harder with more lies. So, with statistical inevitability, let your ego go unchecked, forever. You may learn some random things to try to catch up, but your fundamental misalignment is incorrigible.

And eventually you learn that learning is not what feeds the value system you’ve created for yourself — it’s your own self-delusion. And so you only ever learn just enough to sustain that delusion. The depths of your incompetency become nested deeper and deeper in your psyche, until you’re forever unable to pass a certain level of competency — I call this the narcissism asymptote.

So there you go — it’s pathological narcissism, and it’s just looming over the horizon for us all.12

A solution?

Individually, I think the remedy comes down to mindfulness. With just a little meta-cognition, it’s easy to see that you’re lying to yourself about a thing, and that’s often enough negative feedback to break the pattern.

But then there’s the perhaps more practical question: how do you inoculate yourself against other people doing this? (Especially important if you’re trying to hire people into your organization/team) On this end, I’m growing more and more convinced this is an important auxiliary benefit of why a person’s intellectual honesty is critical to gauge — if someone is intellectually honest (or just generally, honest), the competence-certainty relationship is linear, and so you can just rely on certainty as a gauge.

Following that thread, the following statement shouldn’t be so controversial: if your primary objective is to be exceptional at something, you shouldn’t choose a game that you’re not good at.

(We ran through an analogy to video games that I thought was particularly poignant: if you’re born as a warrior, you don’t run around trying to cast spells. You’ll have a much better time if you learn to swing a sword. It’s all about person-game fit.)

So I’m going to talk about how I’ve been thinking about how to find/construct a game you could be world-class at. It’s nothing profound, and the punchline is simple, so I’ll just say it now: statistically-speaking, you can become a much rarer commodity if you find a domain that requires an intersection of multiple superpowers that you have.

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The standard approach: find a thing you’re good at

Let’s talk about how we’re usually inclined to find excellence in ourselves: the standard approach is to generally just find something you’re good at. If you’re good at something, after all, you’ll have a stable career, stable job, and can anticipate some steady level of progression. If you’re exceptional, you might even find yourself rising to some level of seniority. If you’re world class, you’ll get to the very top, but it’s a very binary outcome — you either have some genetic predisposition to that level of excellence or you don’t. If that’s your goal, there’s no amount of hard work that’ll close that natural talent gap.

This is a very reasonable way to live, of course. Find what you’re good at, and live a rewarding, fiscally-stable life. If you’re lucky, you’ll be one of the few people that can be truly exceptional in your domain. But I want to offer a different way of thinking about this whole endeavor so that you might find something you are truly world class at.

The rigorous approach: fundamental skills and intersections

I think we tend to view exceptionalism as tied to particular professions, but these are just composites of more fundamental latent factors — skills, propensities. What makes you a 1% PM, for instance, could be broken down into a multitude of things you are good at or bad at: your raw intelligence and superhuman empathy, perhaps. One of the most useful things you could do, then, is to figure out which of those latent skills are your superpowers. What makes you excellent at a particular endeavor?

The goal, then, is to find a domain where your particular set of skills and liabilities are optimal. If you’re 90th percentile at 3 things and those three things are critical for success in a particular profession, you’re suddenly 99.9th percentile1.

Of course, this is not to suggest some sweeping career shift (though, of course, that’s possible). I think a lot of folks would benefit from reflecting on this sort of thing when making even more seemingly inconsequential career decisions — should I be in industry X or Y? Should I go the IC or manager route? Should I be more technical or more high-level? If you know what makes people in these roles exceptional, and if you know your own superpowers, you’ll have a much easier time making these sorts of decisions.

Final comments

A few final points:

• It’s hard to give things up, particularly when you’ve spent a lot of time on an endeavor. But this is why thinking about the latent skills has been so helpful — you can quantify what you’ve gotten out of the experience.

• This is all later-stage career advice, not early-stage career advice. You can’t know what you’re good at without trying something, so some level of error early on is necessary.

  • Having a variety of different skills can be quite helpful in forming strong analogies in other disciplines, so it’s generally not so productive to worry about hitting the mark on your first try.

• This is all about finding something you can be world-class at, but says nothing about finding something you enjoy. But that’s a discussion for another time.

1. “move fast, break things”

2. “do things that don’t scale”

3. “if you’re not embarrassed by the first version of your product, you’ve launched too late”

Within the appropriate scope, these are, of course, great pieces of advice. From my own experience, for example:

1. By moving fast and breaking things, I’ve found I can quickly learn how to build the thing I need to build, which is a substantially better means to learn the limitations of my understanding than to try to shoot the arrow in the right direction from the get-go. The best way to see 5 feet further in fog is to walk forward 5 feet, or so they say.

2. By doing things that don’t scale, you can optimize for what really matters, e.g. manually giving customers untenable, manual spikes of delight, rather than agonizing over building system to accomplish this worse at scale.

3. By shipping something “embarrassing”, you are effectively prioritizing better, forcing clear thought on which product features are essential to test the hypotheses you are going after.

And that’s because these pieces of advice align very tightly with very specific objectives. And when those objectives are your objectives, of course you should follow this advice. But that said, there’s no free lunch — with each one of these objectives, there’s something else being sacrificed.

And as these aphorisms have become meme-ified, they’ve also been blindly applied without properly navigating these tradeoffs. For instance:

1. Build fast, break things is great when you don’t know what to build and need to optimize for learning how to build. But it’s a terrible philosophy for actually building a scalable product. It means “learn fast”, but it’s often taken to mean “ship garbage”.

2. “Do things that don’t scale” is a great mantra for GTM and product teams, particularly when trying to garner customer love — the essential thing about love is that it comes from relationships, so focusing on that main component rather than scalability will always keep the main thing. This does NOT mean you should “do things that don’t scale” when trying to build a scalable engineering backend, for instance.

3. Finally, shipping something “embarrassing” is too often taken to mean “ship something that’s a pile of worthless shit.” If you already know what’s wrong with your product, this is going to generally just get you feedback that you know already and churn your leads. It’s one thing to build an appropriately scaled-down product, but another to build a product with such jarring deficiencies that no one will be able to use it any meaningful way and so won’t be able to give you any reasonable feedback (at least, nothing more than Figma mockups alone could do).

In engineering work, in particular, misapplication of these tropes can be very destructive. Adopting these patterns carelessly can lead to an immense amount of tech debt that you can never crawl out of, which inevitably reduces stability and usability of the product. Your employees burn out trying to resolve issues from within a mountain of garbage code. All of your early design partners churn — losing those who would be your fiercest advocates and ruining your brand perception to boot.

All this is to say: you should generally try to think about things before you do things, however obvious that sounds. As with most bits of meme-ified advice, these tropes are not inherently bad. But just remember that they can go completely awry when misapplied. You’d be wise to think before you blindly apply them.