Annotations (6)
“Forcing yourself to commit to some specific string of words gives you a starting point, and if it's wrong, you'll see that when you reread it. At least half of essay writing is rereading what you've written and asking is this correct and complete? The prize for being strict with what you've written is not just refinement.”— Paul Graham
Philosophy & Reasoning · Creativity & Innovation · Operations & Execution
DUR_ENDURING
Precision forces false assumptions to surface and collapse
“Writing essays, at its best, is a way of discovering ideas. An essay should ordinarily start with what I'm going to call a question, though I mean this in a very general sense: it doesn't have to be a question grammatically, just something that acts like one in the sense that it spurs some response. You don't need to have a complete thesis; you just need some kind of gap you can explore.”— Paul Graham
Creativity & Innovation · Philosophy & Reasoning · Operations & Execution
DUR_ENDURING
Discovery starts with incomplete question, not complete thesis
“Professional traders won't even trade unless they have what they call an edge: a convincing story about why in some class of trades they'll win more than they lose. Similarly, you shouldn't attack a topic unless you have a way in, some new insight about it or way of approaching it. You don't need to have a complete thesis; you just need some kind of gap you can explore.”— Paul Graham
Strategy & Decision Making · Creativity & Innovation · Philosophy & Reasoning
DUR_ENDURING
Need edge to commit; gap to explore counts as edge
“Usually you should follow whichever branch offers the greatest combination of generality and novelty. I don't consciously rank branches this way; I just follow whichever seems most exciting; but generality and novelty are what make a branch exciting. If you're willing to do a lot of rewriting, you don't have to guess right. You can follow a branch and see how it turns out, and if it isn't good enough, cut it and backtrack.”— Paul Graham
Strategy & Decision Making · Creativity & Innovation · Operations & Execution
DUR_ENDURING
Follow excitement; rewriting makes wrong paths cheap
“The quality of the ideas that come out of your head depends on what goes in, and you can improve that in two dimensions, breadth and depth. You can't learn everything, so getting breadth implies learning about topics that are very different from one another. You can also get ideas by talking to people, by doing and building things, and by going places and seeing things. While breadth comes from reading and talking and seeing, depth comes from doing.”— Paul Graham
Creativity & Innovation · Philosophy & Reasoning · Operations & Execution
DUR_ENDURING
Breadth from diverse reading; depth from solving problems
“To be the evergreen kind of timeless, an essay has to be ineffective, in the sense that its discoveries aren't assimilated into our shared culture. Otherwise there will be nothing new in it for the second generation of readers. If you want to surprise readers not just now but in the future as well, you have to write essays that won't stick: essays that, no matter how good they are, won't become part of what people in the future learn before they read them.”— Paul Graham
Philosophy & Reasoning · Creativity & Innovation
DUR_ENDURING
Evergreen means ineffective: won't stick in culture
Frameworks (2)
Discovery Through Writing
Question-Response-Rewrite Cycle
A systematic method for discovering ideas by starting with an incomplete question, committing to a specific written response, then rigorously rereading to expose false assumptions. The framework treats writing as an iterative process where precision forces hidden premises to surface and collapse, revealing deeper truths.
Components
- Identify a Gap or Question
- Commit to Specific Words
- Reread with Extreme Strictness
- Discard False Assumptions
- Follow the Recursive Tree
Prerequisites
- Willingness to be wrong publicly (to yourself)
- Comfort with extensive rewriting
- Intellectual honesty
Success Indicators
- Discovering ideas you didn't have when you started
- Finding false assumptions you didn't know you held
- Written output becomes sharper and more surprising over iterations
Failure Modes
- Stopping at the first draft
- Being too kind to your own writing
- Keeping bad material because it was hard to produce
Greedy Algorithm with Backtracking
Branch Selection in Iterative Creative Work
A decision framework for navigating choices in creative or exploratory work. Follow the most exciting branch (where excitement signals generality plus novelty) without worrying about optimality, because low-cost iteration lets you backtrack and try alternatives. The framework converts what would be a paralyzing optimization problem into a manageable greedy search with error correction.
Components
- Identify Branch Points
- Follow Excitement
- Explore Fully
- Evaluate Results
Prerequisites
- Low cost of backtracking (e.g., rewriting in text, rapid prototyping in code)
- Willingness to discard work
- Comfort with uncertainty
Success Indicators
- Faster forward progress despite backtracking
- Reduced paralysis at decision points
- Higher quality final output through iteration
Failure Modes
- Keeping bad branches due to sunk cost
- Never backtracking (staying on first branch regardless of results)
- Backtracking too frequently without sufficient exploration
Mental Models (5)
Iterative Refinement
Decision MakingPrecision emerges from successive approximation.
In Practice: Graham describes the rewrite cycle as core to essay writing
Demonstrated by Leg-pg-001
False Consensus Bias
PsychologyThe tendency to assume others share your knowledge, beliefs, or mental models.
In Practice: Implicit in Graham's discussion of how rewriting reveals false assumptions
Demonstrated by Leg-pg-001
Explore-Exploit Tradeoff
Strategic ThinkingThe fundamental tension between trying new things (explore) to gather information and doubling down
In Practice: Graham's branch selection and backtracking strategy in essay writing
Demonstrated by Leg-pg-001
Breadth-Depth Complementarity
Systems ThinkingThe principle that different modes of learning serve different purposes. Breadth
In Practice: Graham's discussion of how to improve idea quality through inputs
Demonstrated by Leg-pg-001
Self-Defeating Success
EconomicsWhen success changes the conditions that enabled it, potentially undermining future success.
In Practice: Graham's paradox that evergreen essays must be ineffective at propagating their ideas
Demonstrated by Leg-pg-001
Connective Tissue (2)
Professional traders only trade when they have 'edge': a convincing story about why they'll win more than lose in some class of trades
The trading concept of 'edge' (an exploitable information asymmetry or structural advantage) applies directly to intellectual work. Just as traders won't commit capital without edge, writers and thinkers shouldn't commit effort to topics where they lack unique insight or angle. The parallel reveals that resource allocation principles in markets apply to attention markets: both require conviction of asymmetric advantage before deployment.
Graham uses trader edge as analogy for when to pursue a writing topic
Darwin's essay on natural selection (1844) was the best possible essay of its time, but would be boring now because everyone already knows it
The paradox of teaching: the most successful ideas become invisible through assimilation into shared knowledge. Natural selection as discovery was revolutionary; natural selection as known fact is mundane. This reveals a fundamental tension in knowledge work between impact (changing what people know) and timelessness (remaining fresh to future readers). The best teaching makes itself obsolete by succeeding completely. Applies beyond biology to any domain where ideas can be absorbed into culture.
Graham contrasts timelessness in art (Greek sculptures still beautiful) with timelessness in essays (Darwin's essay now obvious)
Key Figures (1)
Robert Morris
1 mentionsComputer scientist, co-founder Y Combinator
Graham cites Morris as an example of a specific person who generates more new ideas per conversation than talking to many new people. Used to illustrate that depth of relationship can be more valuable than breadth of network for idea generation.
- One afternoon with Morris generates more new ideas than talking to 20 new smart people
Key People (1)
Charles Darwin
(1809–1882)British naturalist who developed theory of evolution by natural selection
Concepts (1)
edge (trading)
CL_FINANCIALA trader's term for a systematic advantage: a convincing reason to expect profits exceeding losses in a class of trades
Synthesis
Synthesis
Migrated from Scholia