Iterating Through the Unknown: How To Make Decisions About an Uncertain Future

Mitchell Earl
The Playbook by Praxis
3 min readMar 20, 2024

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Photo by Héctor J. Rivas on Unsplash

I used to feel intense pressure when I made big decisions. The idea of making a wrong decision seemed high stakes. Even when it wasn’t.

This inevitably resulted in decision-fatigue. Not from making too many decisions. But from exhausting too many resources laboring over single decisions.

Eventually I developed a better system for making decisions.

I like to call it decisions through iteration.

There’s nothing revolutionary about it really. You just try a bunch of stuff you think might work until you find the path forward.

In the context of a single decision — even one that feels really big and important — iteration takes the shape of educated guessing. When I’m uncertain, I make the highest conviction bet. Then adapt if I’m wrong.

Most decisions are reversible. They’re not life-or-death. Even if they feel like it. You can change course later if you’re wrong. You can pivot.

Photo by benjamin lehman on Unsplash

James Clear’s Hats, Haircuts, and Tattoos

I really like what James Clear has to say about the reversibility of most decisions.

Screenshot below from one of James’ newsletters.

James Clear’s framework for decisions

Most decisions can be altered after-the-fact. That should give you confidence. It should reduce the pressure.

It’s empowering to know you can change your mind.

Of course, sometimes decisions are permanent. Those require a bit more self-study and due diligence.

Iteration & Permanent Decisions

You can’t always iterate your way through a permanent decision. But sometimes you can.

When I have an irreversible decision, I like to iterate through brainstorm. I imagine each scenario. Then I try to visualize the best and worst case scenarios. I attempt to catalog the range of possible reactions or outcomes, and familiarize myself with my own emotions for each of those.

It sounds silly. But it works for me. Especially for the big ones.

Often what happens, I discover the worst case scenarios aren’t that bad. They’re undesirable, but manageable. Just knowing helps ease the anxiety about the risk.

It also helps me visualize a roadmap for overcoming failure.

“I could survive that,” I’ve told myself many times before.

Sometimes it’s just the process of sitting down and iterating through imagination that lightens the burden of a big decision.

But for smaller decisions, the reversible ones, it’s almost always easier to just take action based on your best hunch. You can always change your mind later if you’re wrong.

I don’t feel the same pressure making decisions I used to. In fact, making decisions comes a lot easier now.

If you enjoyed this piece, you may also find value from my other work. Check it out and let me know what you think!

Mitchell Earl is the Chief Operating Officer at Praxis, a career mentorship program that’s helped thousands of entrepreneurial young adults start successful careers without college. He writes regularly about how young adults can take agency over their lives, careers, and money. His work has been read by millions across the globe. He is the host of The Career Bound Podcast, and author of Don’t Do Stuff You Hate.

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Mitchell Earl
The Playbook by Praxis

COO @DiscoverPraxis | I write education, career, and money advice for young adults who are just getting started.