Annotations (15)
“When you have trouble choosing between following your interests and making money, it's never because you have complete knowledge of yourself and of the types of work you're choosing between, and the options are perfectly balanced. When you can't decide which path to take, it's almost always due to ignorance.”
Philosophy & Reasoning · Psychology & Behavior · Strategy & Decision Making
DUR_ENDURING
Indecision signals missing data
“The less sure you are about what to do, the more important it is to choose options that give you more options in the future. I call this 'staying upwind.' If you're unsure whether to major in math or economics, for example, choose math; math is upwind of economics in the sense that it will be easier to switch later from math to economics than from economics to math.”
Strategy & Decision Making · Philosophy & Reasoning
DUR_ENDURING
Choose reversible paths
“Many if not most of the biggest startups began as projects the founders were doing for fun. Apple, Google, and Facebook all began that way. Why is this pattern so common? Because the best ideas tend to be such outliers that you'd overlook them if you were consciously looking for ways to make money. Whereas if you're young and good at technology, your unconscious instincts about what would be interesting to work on are very well aligned with what needs to be built.”
Creativity & Innovation · Business & Entrepreneurship · Psychology & Behavior
DUR_CONTEXTUAL
Unconscious instincts find outliers
“So there's something like a midwit peak for making money. If you don't need to make much, you can work on whatever you're most interested in; if you want to become moderately rich, you can't usually afford to; but if you want to become super rich, and you're young and good at technology, working on what you're most interested in becomes a good idea again.”
Strategy & Decision Making · Business & Entrepreneurship · Economics & Markets
DUR_ENDURING
U-curve: passion works at extremes
“If you choose a kind of work mainly for how well it pays, you'll be surrounded by other people who chose it for the same reason, and that will make it even more soul-sucking than it seems from the outside. Whereas if you choose work you're genuinely interested in, you'll be surrounded mostly by other people who are genuinely interested in it, and that will make it extra inspiring.”
Psychology & Behavior · Culture & Society
DUR_ENDURING
Peer selection amplifies choice
“The odds are better when you have strange tastes: when you like something that pays well and that few other people like. For example, it's clear that Bill Gates truly loved running a software company. He didn't just love programming, which a lot of people do. He loved writing software for customers. That is a very strange taste indeed, but if you have it, you can make a lot by indulging it.”
Strategy & Decision Making · Business & Entrepreneurship · Psychology & Behavior
DUR_ENDURING
Strange tastes reduce competition
“If you want to make a really huge amount of money, hundreds of millions or even billions of dollars, it turns out to be very useful to work on what interests you the most. The reason is not the extra motivation you get from doing this, but that the way to make a really large amount of money is to start a startup, and working on what interests you is an excellent way to discover startup ideas.”
Business & Entrepreneurship · Creativity & Innovation · Strategy & Decision Making
DUR_ENDURING
Passion unlocks outlier ideas
“What do you do in the face of uncertainty? Get more certainty. And probably the best way to do that is to try working on things you're interested in. That will get you more information about how interested you are in them, how good you are at them, and how much scope they offer for ambition.”
Strategy & Decision Making · Philosophy & Reasoning
DUR_ENDURING
Reduce uncertainty through action
“When people talk about this question, there's always an implicit 'instead of.' All other things being equal, why wouldn't you work on what interests you the most? So even raising the question implies that all other things aren't equal, and that you have to choose between working on what interests you the most and something else, like what pays the best.”
Philosophy & Reasoning · Strategy & Decision Making
DUR_ENDURING
Question itself reveals the constraint
“There's one case, though, where it's easy to say whether you should work on what interests you the most: if you want to do great work. This is not a sufficient condition for doing great work, but it is a necessary one.”
Philosophy & Reasoning · Creativity & Innovation
DUR_ENDURING
Passion necessary not sufficient
“One useful trick for judging different kinds of work is to look at who your colleagues will be. You'll become like whoever you work with. Do you want to become like these people?”
Psychology & Behavior · Strategy & Decision Making
DUR_ENDURING
Judge work by future self
“There are even some people who have a genuine intellectual interest in making money. This is distinct from mere greed. They just can't help noticing when something is mispriced, and can't help doing something about it. It's like a puzzle for them.”
Psychology & Behavior · Economics & Markets
DUR_ENDURING
Money as puzzle not greed
“It's obvious that different people have different interests, and that some interests yield far more money than others, so how can it not be obvious that some people will end up much richer than others? In a world where some people like to write enterprise software and others like to make studio pottery, economic inequality is the natural outcome.”
Economics & Markets · Culture & Society · Philosophy & Reasoning
DUR_ENDURING
Inequality follows interest
“Don't wait. Don't wait till the end of college to figure out what to work on. Don't even wait for internships during college. You don't necessarily need a job doing x in order to work on x; often you can just start doing it in some form yourself. And since figuring out what to work on is a problem that could take years to solve, the sooner you start, the better.”
Strategy & Decision Making · Leadership & Management
DUR_ENDURING
Early exploration compounds
“The root of great work is a sort of ambitious curiosity, and you can't manufacture that.”
Psychology & Behavior · Creativity & Innovation
DUR_ENDURING
Curiosity cannot be faked
Frameworks (3)
Passion-Driven Idea Discovery
Why Working on Interests Unlocks Outlier Startup Ideas
Following genuine interests creates conditions for discovering non-obvious startup opportunities because: (1) the best ideas are outliers that conscious money-seeking would miss, (2) unconscious instincts about interesting problems align with what needs building, and (3) most breakthrough companies started as side projects done for fun. This framework explains why massive wealth creation paradoxically requires not optimizing for money in the early stages.
Components
- Recognize the Outlier Problem
- Trust Unconscious Alignment
- Start as Side Projects
Prerequisites
- Technical or domain competence
- Financial runway to explore without immediate monetization
- Ability to work on projects without external validation
Success Indicators
- Working on projects without needing to justify ROI
- Discovering problems that genuinely bother you
- Others asking to use what you built for yourself
Failure Modes
- Forcing every interest into a business model prematurely
- Abandoning projects when they don't show quick traction
- Choosing interests based on what seems fundable rather than genuine curiosity
The Wealth-Passion U-Curve
When Following Your Interests Makes Economic Sense
The relationship between wealth ambition and following passion is U-shaped, not linear. At low wealth targets, work on whatever interests you. At moderate wealth targets, passion becomes unaffordable; you must optimize for pay. But at extreme wealth targets (hundreds of millions or billions), following passion becomes optimal again because it enables startup idea discovery. This non-monotonic relationship explains why career advice depends critically on wealth ambition.
Components
- Assess Your Wealth Ambition
- Apply the Appropriate Strategy
- Recognize the Reversal Mechanism
Prerequisites
- Honest self-assessment of wealth goals
- Understanding of wealth creation mechanisms
- Willingness to make hard tradeoffs
Success Indicators
- Strategy aligns with stated ambition
- Not experiencing cognitive dissonance about choices
- Career trajectory matches wealth goal
Failure Modes
- Claiming extreme ambition but pursuing moderate strategy
- Following passion with moderate goals and being disappointed
- Not updating strategy when ambition changes
Uncertainty Reduction Through Action
How to Make Career Decisions When You Don't Know What You Want
Career indecision stems from three simultaneous ignorances: not knowing what makes you happy, what different types of work are really like, or how well you'd perform them. The solution is to reduce uncertainty through experimentation rather than analysis. Start working on things you find interesting immediately to gather information. Choose options that preserve future optionality (stay upwind). Recognize that apparent ties between paths signal missing data, not balanced options.
Components
- Diagnose the Ignorance
- Experiment Early and Often
- Stay Upwind
Prerequisites
- Intellectual honesty about what you don't know
- Willingness to try things without guaranteed outcomes
- Time and resources to experiment
Success Indicators
- Regularly trying new types of work
- Building evidence about preferences and aptitudes
- Preserving ability to change directions
Failure Modes
- Analysis paralysis without experimentation
- Closing off options prematurely
- Confusing lack of information with lack of passion
Mental Models (11)
Implicit Constraints
Decision MakingQuestions themselves reveal the constraints and tradeoffs being faced.
In Practice: Graham deconstructs the follow your passion question
Demonstrated by Leg-pg-001
Non-Consensus Positioning
Strategic ThinkingCompetitive advantage comes from genuinely unusual preferences: liking things that pay well but few
In Practice: Graham identifies strange tastes as a source of competitive advantage through reduced competition
Demonstrated by Leg-pg-001
Intellectual vs. Emotional Motivation
PsychologyDistinguishing between intellectual interest and emotional motivation changes behavior quality.
In Practice: Graham distinguishes intellectual interest in money-making from greed
Demonstrated by Leg-pg-001
Motivation vs. Mechanism
Decision MakingDistinguish between motivational explanations and mechanical explanations.
In Practice: Graham explains passion's value is mechanical not motivational
Demonstrated by Leg-pg-001
Unconscious Calibration
PsychologyUnder certain conditions, unconscious instincts about what is interesting prove more reliable than conscious analysis.
In Practice: Graham explains why unconscious interest-following finds outlier ideas
Demonstrated by Leg-pg-001
Three-Dimensional Ignorance
Decision MakingCareer indecision typically stems from simultaneous ignorance on three axes.
In Practice: Graham taxonomizes the types of ignorance
Demonstrated by Leg-pg-001
Experimentation Over Analysis
Decision MakingDirect experimentation generates better information than additional analysis.
In Practice: Graham advocates for action-based uncertainty reduction
Demonstrated by Leg-pg-001
Compounding Exploration
TimeCareer exploration has compounding returns because each piece of self-knowledge
In Practice: Graham emphasizes starting career exploration early to capture compounding retur
Demonstrated by Leg-pg-001
Peer Group as Mirror
PsychologyUse future peer groups as a heuristic for evaluating career paths: you will become like the people you work with.
In Practice: Graham suggests judging work by examining who you would become through peer influence
Demonstrated by Leg-pg-001
Selection Amplification
Systems ThinkingWhen people select into categories based on a shared attribute, that attribute b
In Practice: Graham explains how selection effects amplify the characteristics that drove sel
Demonstrated by Leg-pg-001
Directional Asymmetry
Decision MakingBetween two options, one may be upwind of the other.
In Practice: Graham introduces staying upwind as a heuristic
Demonstrated by Leg-pg-001
Connective Tissue (3)
Midwit peak
The essay describes the relationship between wealth ambition and passion-following as having a 'midwit peak': following passion works at low ambition (you don't need much money) and at extreme ambition (passion unlocks outlier ideas), but fails at moderate ambition (must optimize for pay). This invokes the mathematical concept of a bimodal distribution or U-shaped curve, where the optimal strategy differs at the extremes versus the middle. The term 'midwit' itself comes from internet culture referring to those of average intelligence who overthink simple problems; here it's applied to wealth-seekers who are ambitious enough to sacrifice passion but not ambitious enough to benefit from passion's idea-discovery advantages.
Graham uses 'midwit peak' to describe the counterintuitive non-monotonic relationship between wealth ambition and optimal career strategy
Staying upwind
Graham introduces the metaphor of 'staying upwind' to describe choosing options that preserve future flexibility. The term comes from sailing and aviation: being upwind means the wind is at your back, giving you the ability to easily move in multiple directions. A boat or plane that is downwind has limited options because fighting into the wind is difficult. In career terms, choosing math over economics keeps you upwind because transitioning from math to economics is easier than the reverse. The metaphor elegantly captures the idea of maintaining positional advantage and optionality by understanding the directionality of difficulty in switching between paths.
Graham uses sailing/aviation metaphor to explain how to choose options that maximize future flexibility under uncertainty
Selection bias in passion advice
Graham identifies that advice to 'follow your passion' comes disproportionately from famously successful people, creating selection bias. Those who succeeded by following passion survived the filter and became visible; those who failed following passion or succeeded through other means are invisible or silent. This is an application of survivorship bias, a cognitive error identified by Abraham Wald during WWII when studying bombers. The military wanted to add armor where returning planes showed bullet holes; Wald correctly argued they should armor where surviving planes did NOT show damage, because planes hit there didn't return. Similarly, passion-followers who failed don't give TED talks, creating a biased sample of success stories.
Graham explains why 'follow your passion' advice is misleading by applying survivorship bias to career guidance
Glossary (2)
midwit
ARCHAICInternet slang: person of average intelligence who overthinks
“So there's something like a midwit peak for making money.”
upwind
DOMAIN_JARGONPositioned where wind provides advantage; maritime term for favorable position
“I call this 'staying upwind.'”
Key People (1)
Bill Gates
(1955–)Microsoft founder; loved writing software for customers
Concepts (1)
Selection effect
CL_PSYCHOLOGYWhen groups form based on shared attribute, that attribute amplifies within group
Synthesis
Synthesis
Migrated from Scholia