The Working On Hard Problems Principle
Choose work by its difficulty and interestingness, not its payoff
The Working On Hard Problems Principle is Graham's insight that the single most important factor in a successful intellectual or creative career is not talent, effort, or luck — it is choosing which problems to work on. Graham observed throughout his career that the people who achieved the most were not necessarily the smartest or hardest working, but the ones who had the best taste in problems. A hard problem that matters, once solved, creates disproportionate value and opens up new hard problems. An easy problem, no matter how efficiently solved, produces incremental value at best. The framework involves developing taste in problems — the ability to sense which challenges are simultaneously hard enough to be meaningful, tractable enough to be solvable, and important enough to matter if solved. Graham demonstrated this principle when he chose to work on web applications in 1995 (a hard and important problem that few people took seriously) rather than continuing with more conventional programming work. The key is that hard problems are generative: solving one reveals several more worth working on, creating a compounding career trajectory.
- Problem selection matters more than effort or talent in determining career impact
- Hard problems that matter create disproportionate value when solved
- Solving one hard problem reveals several more worth solving, creating compounding returns
- The best problems sit at the intersection of hard, tractable, and important
- Working on easy problems efficiently is still less valuable than working on hard problems inefficiently
- Audit Your Current Problem PortfolioList every problem or project you are currently working on. For each one, rate it on three dimensions: difficulty (1-10), importance (1-10), and tractability (1-10). Identify which problems are too easy to be meaningful and which are important but you are avoiding because they are hard. Most people discover that the majority of their time goes to medium-difficulty, low-importance problems.Pro tipThe problems you are most tempted to avoid are often the ones most worth working on. Resistance is a signal of importance.
- Identify the Hardest Problem You Could Plausibly SolveLook for the problem that sits at the edge of your capabilities — hard enough that success is not guaranteed, but tractable enough that you can make meaningful progress with sustained effort. This is the zone where the most growth and the most impact happen simultaneously. Consider what tools, knowledge, or collaborators you would need to make the problem tractable.Pro tipAsk yourself: If I solved this in the next year, would it be the most important thing I have ever done? If not, look for a harder problem.WarningDo not confuse hard problems with complicated busywork. A genuinely hard problem has an elegant core that is difficult to solve, not a bureaucratic process that is tedious to navigate.
- Protect Time for Hard ProblemsRestructure your schedule to give your best hours to your hardest problem. Graham wrote his essays in the morning when his mind was freshest. Easy problems can be solved with leftover time and attention; hard problems require your cognitive prime time. Block your calendar, minimize meetings, and treat time spent on your hardest problem as non-negotiable.Pro tipStart each day with at least 90 minutes on your hardest problem before opening email or attending meetings.
In 1995, most serious programmers dismissed web applications as toys. Graham saw that running software on servers accessed through browsers was a genuinely hard and important problem. He chose to work on this when it was unfashionable, building Viaweb as one of the first web application companies. The problem was hard enough that few competitors emerged.
Graham noticed this pattern across all his career transitions. When writing short stories in high school, he was working on easy problems and producing mediocre results. When he switched to programming and tackled genuinely hard technical challenges, the quality of his work improved dramatically. The pattern repeated: his best essays emerged from tackling the hardest questions he could identify about startups, education, and society. Y Combinator itself was born from working on the hard problem of how to systematically help startups succeed. The essay What I Worked On is essentially a meditation on how problem selection shaped his entire career trajectory.