Does leaving mean all those years were wasted?

The story worth knowing here

Stewart Butterfield set out to build an online game. It failed. One feature was worth keeping, a way of sharing photographs, and that became Flickr, which sold to Yahoo for twenty-five million dollars.

Then he tried the same game idea again. More computing power, a better team, a track record, and seventeen and a half million dollars from Andreessen Horowitz behind him. It became Glitch. He killed that too, and the internal tool his team had built to talk to each other became Slack.

Two enormous companies, both of them salvage from quitting the thing he actually wanted to build.

Nobody describes those years as wasted, and the only reason is that he stopped. Had he kept going on either game, the same years would have produced nothing and the story would be about persistence.

What sunk cost actually is

The years are gone. That's the definition. They're gone if you stay and they're gone if you leave, which means they carry no information about what to do next.

This is obvious stated plainly and almost impossible to feel, because staying looks like honouring the investment and leaving looks like admitting it was wrong. Neither of those is a financial fact. They're both stories about identity.

And the cost of the story compounds. Every additional year spent protecting the previous ones makes the next decision harder, which is why the people most trapped by this are usually the ones furthest in.

The people nobody tells stories about

Annie Duke opens her book on quitting with Everest in 1996, which is the last place you'd expect an argument for stopping.

Three climbers on the Adventure Consultants expedition, Stuart Hutchison, John Taske and Lou Kasischke, turned back short of the summit.

You have not heard of them, and that is the entire point. Good quitting is invisible. It generates no story, no photograph and no admiration, while the people who pushed on became a book. We learn about persistence from survivors and about stopping from almost nobody, and then we wonder why quitting feels like failure.

The question that actually helps

Not whether the years were worth it. Ask what they produced that transfers.

Skills that move. What can you do now that you couldn't then, that somebody else would pay for.

People who'd take your call. Usually the most valuable thing anybody accumulates and the most consistently forgotten in this calculation.

Knowledge of what you don't want. That's real and it's expensive to acquire. Knowing precisely which parts of the work drained you is a specification for the next thing.

If the honest answer is that the years produced very little that transfers, that's painful and it's also the strongest possible argument for not adding more of them.

The regret you're actually weighing

Daniel Pink's work on regret found that the most common regrets involving boldness are about inaction rather than action. The things people carry tend to be the moves not made, the voice not used, the thing not tried.

So the question is rarely which choice is safe. It's which regret would hurt more: leaving and finding you had it good, or staying and reaching the same conclusion three years later with three more years attached to it.

Both roads have a version where it goes badly. Pick the one you could carry.

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