Everything Is Figureoutable

People have accused me of being an eternal optimist my whole life. They say I always think everything is going to work out for me. I’ll admit there’s some self-confidence in that, and the people who know me best might call it arrogance.

But optimism isn’t really what I believe in. I believe that, given enough time, information, and resources, almost everything is figureoutable. That’s a different thing. An optimist hopes it works out. Someone who believes things are figureoutable goes and does the work to find out.

I learned it by negotiating my way through school

One of the best things my parents ever did for me was let me negotiate my way through school.

Going into my senior year of high school, I needed one more science credit to graduate, and the class I’d normally have had to take was one I didn’t want. So instead of accepting it, I pitched an alternative: an independent course built on the scientific method, where we’d design our own semester-long experiment and test it properly. We pitched it to the school leadership, and they said yes. I wrote my own curriculum, ran the experiment, finished it in about three weeks, and earned the credit. A handful of other students got credit through it too.

Nobody thought to stop me. That’s the lesson. Most of the walls we accept were never tested.

Get comfortable messing things up

I wasn’t great at many things as a kid. I tried sports at five foot three and about 100 pounds, and I got demolished. I kept playing anyway, and my parents supported it.

What I got really good at was being okay with messing things up. Failing never became a big deal for me. It just meant I’d found one way that didn’t work, so I’d go try again. Getting knocked down in practice by the biggest guy on the team made me fearless on the field, because nobody on the other team was going to hit me harder than that.

That’s the hidden gift of surviving failure. Once you’ve lived through it, it stops having power over you.

“This won’t work” is also an answer

When my co-host Daniel asked me what figuring things out looks like in the middle of a failure, my answer was this: sometimes the solution is “this won’t work.” That still counts. A solution is a solution, whether it’s a go-forward plan or a clear explanation of why something will never work.

And once you know why it won’t work, you have something to negotiate with. This won’t work because of X, Y, and Z. Fine. Can I change X, Y, and Z? If I can turn them into Q, R, and S, maybe now it works.

That’s what figuring it out actually looks like. You rarely end up with your first assumption. You negotiate the parameters, and the goal often gets reached in a way you didn’t expect. You keep going until you run out of letters, or out of energy.

Know the level of risk you can carry

Believing things are figureoutable doesn’t mean being reckless. There are things I’m not willing to risk. I have kids, and I won’t gamble with them.

But financially, professionally, and organizationally, there are very few things I couldn’t rebuild if they burned down. That knowledge changes how you play. If the worst case is that you have to start over, and you’re not near the end of your life, then the worst case is survivable.

I think the riskier path is the one a lot of us were taught: wait decades, work toward a pension, and plan to start living at 60. If the company folds a few years before you get there, everything you built your life around is gone. I’d rather live fully now and keep my ability to rebuild sharp.

You can’t win loud if you insist on losing quiet

Here’s the part people struggle with. You can’t want to win loud and lose quiet. Those two are connected.

If you’re always trying to lose quietly, protecting yourself so nobody sees you fall, you’ll never give enough to win big. Every time you hold back, you turn down the volume on your win. I want to win loud, so I have to be okay losing loud too.

Figure out the soft skills, too

One of the biggest roadblocks I hit was competition. When someone else wants the same opportunity, it isn’t enough to be good at the task. You also have to show the person holding the opportunity what sets you apart.

People get frustrated when someone else gets the job even though they think they’re better at the core task. What they miss is that the other person is often a stronger team player, communicates better, is willing to stay late, and has people vouching for them. Soft skills are part of the work. Figuring out an opportunity means figuring out how to position yourself for it, not only how to do the job.

Figuring it out is a skill you practice

None of this is a personality trait you either have or don’t. It’s a habit. Every time you test a wall, renegotiate a parameter, or survive a loss, you get better at it, and you get calmer the next time something looks impossible.

That’s why I’d encourage anyone, especially young people, to start practicing early and on small things. Push back on a rule that doesn’t make sense. Ask for the alternative. Try the thing you’ll probably be bad at. The stakes will never be lower than they are right now.

Practical takeaways

1. Test one wall. Pick a rule or process you’ve assumed can’t change. Ask whether anyone has actually tested it, and pitch an alternative.
2. Write the “why it won’t work” list. For a stuck problem, list the specific parameters blocking it. Then ask which of them you can change.
3. Define your non-negotiables. Write down what you won’t risk. Everything else is open to experiment.
4. Practice losing loud. Share one attempt publicly this month before you know how it will turn out.
5. Audit your soft skills. For the next opportunity you want, list how you’ll show what sets you apart, not just the task you can do.

Work with LeadFast

LeadFast Co helps entrepreneurs and leaders turn “I can’t” into a plan. Start at leadfastco.com.

Here’s my question for you: What’s one wall you’ve never actually tested?

This article is based on Episode 1 of the LeadFast Podcast, “Everything Is Figureoutable.” Listen to the full episode.