Careers
Choosing the game
A salary pays for your time, while ownership pays for what your work keeps producing. Before choosing a career by its expected income, decide which of those games you want to play.
I have been thinking about these questions for a long time. They turned into six essays, meant to be read together.
- Choosing the game (you are here)
- The paradox of ambition
- What are the important problems in your field?
- How to know when to change course
- Rejection is data
- How to get luckier
- A high salary and a high-leverage career are not the same thing. The difference is how closely your earnings are tied to your own time.
- Ownership lets you capture value from something that scales beyond your own labor. But about three-quarters of venture-backed startups return nothing to their founders.
- People can rationally prefer different distributions of outcomes, and no salary comparison captures that.
- The self-employed report more satisfaction with their work at the same income, which suggests autonomy is part of the pay.
General pediatricians in the United States earned about $274,000 on average in 2025, according to Doximity’s 2026 Physician Compensation Report. It takes years of medical school and residency to get there, and the career that follows is far more predictable than a founder’s. By most measures, medicine is an excellent career.
Yet the size of a salary is the wrong thing to compare. A physician who mainly sees patients is limited by time, because there are only so many patients one person can see in a day. Physicians can also own their practice, and software founders can end up running service businesses that depend on their own hours. The line that matters runs between earning through your own hours and owning something that keeps producing value without them.
Income and wealth are not the same thing
Naval Ravikant’s How to Get Rich (without getting lucky) draws the clearest version of this line. He separates renting out your time from building wealth through ownership and leverage.
Imagine two people. The first earns $300,000 a year providing a professional service. The second owns a large stake in a software company used by thousands of organizations. In any given year the first may well earn more, and can build real wealth by saving and investing. But that income still depends on continuing to work. The second person’s company can serve thousands of customers without the founder serving each one.
Software is the clearest case, because serving one more user costs almost nothing. A book or a video works the same way.
Leverage lets output grow faster than effort. Ownership decides how much of that output comes back to you. Creating value and capturing value are two different problems.
How a career pays you matters as much as how much. The difference shows in whether your income stops when your hours stop, and whether anything you build keeps earning after you move on.
Uncapped upside is not a better bet
Many professions have a well-defined path. You finish the training, then climb a ladder that institutions built long before you arrived. Starting a company has no training program that tells you what to do next, and after years of work you may discover that nobody wants what you have built. In principle the upside is uncapped, but it is easy to confuse the size of a possible outcome with the likelihood of reaching it.
The economists Robert Hall and Susan Woodward studied venture-backed companies from 1987 onward, close to the full set. About three-quarters returned no cash at all to their founders. We mostly hear about the rest.
So the case for starting a company cannot be that it pays better. For most people, it does not.
The better argument is that people can rationally prefer different distributions of outcomes. Some want a stable career with a clear trajectory. Others will accept much more uncertainty for a chance at an extraordinary result. Neither preference is wrong, and knowing which one you hold matters more than any salary comparison.
Autonomy is part of the pay
Salary comparisons also leave out freedom. The economists Matthias Benz and Bruno Frey found that self-employed people get more satisfaction from their work than employees, regardless of income or hours worked. The study does not show that becoming self-employed makes people happier. It does suggest that people value having a say in their work for its own sake.
That does not make founders free. They answer to investors, and in the end to whether customers pay. A founder who cannot find customers is no freer of outside judgment than a researcher waiting on a grant review. What changes is who makes the call. You get more say in which constraints you take on, and you face the consequences yourself when the direction turns out to be wrong.
For people who value autonomy, it is part of the pay, and a lower expected income with more control over the work can be the better offer.
Choosing the game
No career is right for everyone. Starting a company, whatever its upside, is a bad choice for someone who values predictability. A high salary invested steadily over decades can buy real financial independence, and many professionals do enormous good without owning a company.
Two people can be equally successful by conventional measures and spend their days doing entirely different things. If a goal takes ten years, those ten years are part of what you are choosing.
- Which problems fill your days.
- How much uncertainty and responsibility you carry.
- How much say you have over your work.
- What outcome would make the effort worth it.
My own answers point toward ownership. Yours may point elsewhere, and that is just as reasonable. Whichever game you choose, choose it on purpose.
Further reading
- Naval Ravikant, How to Get Rich (without getting lucky), on why renting out your time won’t make you rich.
- Doximity, 2026 Physician Compensation Report, on pay across medical specialties.
- Hall and Woodward, The burden of the nondiversifiable risk of entrepreneurship (American Economic Review, 2010), on what founders actually receive.
- Benz and Frey, Being independent is a great thing (Economica, 2008), on autonomy and job satisfaction.