If you have a choice, choose difficult. If you don’t have a choice, make it difficult by overperforming.
Here is Paul Graham, talking about strategic choices for businesses.
Use difficulty as a guide not just in selecting the overall aim of your company, but also at decision points along the way. At Viaweb one of our rules of thumb was run upstairs. Suppose you are a little, nimble guy being chased by a big, fat, bully. You open a door and find yourself in a staircase. Do you go up or down? I say up. The bully can probably run downstairs as fast as you can. Going upstairs his bulk will be more of a disadvantage. Running upstairs is hard for you but even harder for him.
What this meant in practice was that we deliberately sought hard problems. If there were two features we could add to our software, both equally valuable in proportion to their difficulty, we’d always take the harder one. Not just because it was more valuable, but because it was harder. We delighted in forcing bigger, slower competitors to follow us over difficult ground. Like guerillas, startups prefer the difficult terrain of the mountains, where the troops of the central government can’t follow. I can remember times when we were just exhausted after wrestling all day with some horrible technical problem. And I’d be delighted, because something that was hard for us would be impossible for our competitors.
Deliberately choose the harder way. Everyone else follows the easier, softer way. You are different.
In exercise: if you’re doing 8 reps, add one more. In running: if you’re running 5 km, push on to 5.1 km. In business: seek the activities that others shun, the ones that take years of effort to master. In family and friendship: just give and shut up.
Your brain will start to believe in you. You will see yourself as the person who runs straight into his shitstorm. The person who deliberately and routinely goes the extra mile. The person who delivers a bit more value than promised.
Who doesn’t love a person like that?
And from that self-perception — hey, I am an admirable person — everything else will follow.