The risk/reward asymmetry of difficult things

There is a huge (beneficial) risk/reward asymmetry in doing very difficult things.

One of the roles I played at my last company was pinch hitter. I got tagged into difficult customer accounts with the mandate: fix this. In those situations, failure is expected. If you can't solve the impossible problem, no big deal—you're in the same situation as everyone else that tried and failed to remedy the issue. Success is unexpected.

But by that same token, if you manage to solve the problem, save the customer, to win, it's a huge deal—you turned the tide and delivered an outcome that nobody thought possible. Your failure is low risk; your success is high reward.

With that realisation I threw myself into every ugly situation that came my way: rewriting rejected articles, trying to save customers that wanted to churn, pivoting failed strategies.

I struggled and failed a bunch of times—but people only remembered the wins.