Choosing the adventure is easier with a floor under it
Looking back from the end of a life is a useful way to weigh a risky choice. It works best for people whose downside is survivable.
When I’m old and dying, I plan to look back on my life and say “wow, that was an adventure,” not “wow, I sure felt safe.”
In 2008 Tom Preston-Werner had a job offer from Microsoft worth around three hundred thousand dollars a year in salary, bonus and stock. He also had a side project, a code-hosting site he had started with two friends, that was paying a little but not enough to live on. He turned down the offer, went full-time on the side project, and explained the decision in a blog post that ended with this sentence. The side project was GitHub, which by the end of 2010 had become the default home for a large share of open-source code.
The sentence is a version of a thinking tool that many people use without naming it. Faced with a risky choice, imagine looking back on it from very far away. From that distance the short-term discomfort of uncertainty shrinks, and the question becomes which story you would rather have lived. People who care for the dying often report that regrets about unlived lives come up far more than regrets about lost security. Preston-Werner simply decided to apply that view in advance.
The test is useful because the fear of a risky choice is usually loudest at the moment of choosing, and it is often out of proportion. A developer in 2008 with strong skills had little to lose by trying a start-up for a year. If it failed, Microsoft and companies like it would still be hiring. The real downside was a gap on a résumé and some lost income, and the deathbed view shows that clearly.
The line goes wrong when it is applied to people whose downside is not like that. Someone supporting children, paying off medical debt, or living on a visa tied to an employer can face a failure that does lasting harm to other people. For them, “I sure felt safe” is not a timid epitaph; it can be the description of a responsibility met. Safety has value, and the value is highest for those with the least cushion.
There is also a selection effect in who repeats the line. It is quoted by people whose adventure worked out. Those who took the same leap and spent the next five years paying for it rarely frame their story this way.
The honest version keeps both halves. Use the long view to quiet fear that is out of proportion. Then check the floor: how much can be lost, who else loses it, and whether there is a way back. An adventure with a known floor is a very good bet for most people with skills in demand. An adventure without one deserves more thought than a deathbed image can give it.