Optimism as Strategy

There's a version of optimism that's naive—the belief that things will work out regardless of what you do. That's not useful. It's magical thinking dressed up as positivity.

But there's another version that's deeply practical: the belief that your actions can influence outcomes, that problems are solvable, that effort compounds.

The Asymmetry of Belief

Here's the thing about pessimism: it's self-fulfilling. If you believe a problem is unsolvable, you won't try to solve it. Your belief becomes true, but only because you made it true.

Optimism has the opposite asymmetry. If you believe something might work and you're wrong, you lose time. If you're right, you gain whatever value the solution provides. The expected value calculation favors trying.

The pessimist is often right, but the optimist changes the world.

I don't know who said that first, but it captures something important. Being right about why things won't work is easy. Making things work despite the reasons they shouldn't—that requires a different disposition.

Calibrated Optimism

The trick is holding optimism about outcomes while maintaining pessimism about plans. Expect things to go wrong in ways you didn't anticipate. Build in buffers. Have fallback positions.

But underneath all that contingency planning, maintain the core belief: this is worth attempting. We can figure it out. The solution exists even if we can't see it yet.

That's not naive. That's strategic.

The Social Dimension

Optimism is also contagious—for better or worse. Teams take on the disposition of their leaders. If you're working on something hard, the people around you need to believe it's possible. Your optimism isn't just for you; it's infrastructure for everyone else's effort.

This doesn't mean performing false confidence. People see through that. It means genuinely believing in the work while being honest about the challenges. "This is hard and we might fail" can coexist with "I think we can do this."

The best leaders I've worked with held both truths simultaneously.