An Antidote to Overthinking: Embracing the Freedom of Uncertainty

A prototypical case of overthinking: reopening a link to a comparison blog post that you’ve already read four times, wasting an evening on a decision that could have taken five minutes, three days ago, and yet feeling strangely accomplished afterwards. This false sense of moving forward - where the mind is working hard but merely just thinking - is what gets in the way of action. Ultimately, the decision itself doesn’t matter as much as the actions it will unlock.

Over the years I have spent countless hours in indecision masqueraded as “research” in a neverending quest of finding the “best”. Note-taking apps, digital audio workstations, furniture, shoes… The list of decisions that have spiraled down into the dark abyss of indecision is virtually endless. The curse of a perfectionist, you might say.

And while it does feel rewarding delving into the pros and cons of which tool or thing that may best serve your needs, especially for someone who loves learning, in the end it’s empty calories - satisfying in the moment, gone an hour later.

The issue, of course, is that, unless you are a reviewer, none of the feature comparisons, video reviews, blog posts, actually bring you any closer to a meaningful output. Endless thinking will never outperform just doing.

Doing Brings Clarity

There’s a hidden assumption in every overthinking spiral: the idea that if you think long enough you’ll eliminate risk. But uncertainty isn’t a problem you can easily think your way out of. At some point you have to make the jump knowing the ground might not be where you expect it. Kierkegaard called this the leap of faith, and he meant it literally; you act despite the doubt, not after it disappears.

I was long plagued by the idea that I needed the full picture before I could start. The right architecture. The right framework. The best plan. But over the years every meaningful project I’ve finished taught me the same lesson: the best information and insight came after I got started. Turns out, doing is really a superior form of information gathering. In the end, experience teaches what analysis can’t.

One way to break the overthinking loop is to lower the cost of failure. And reframing failure as learning.

Few decisions are lifelong commitments and the remaining majority should be made easily reversible. By making the decisions easily reversible you can more easily pivot without an emotional attachment. You are effectively giving yourself permission to be wrong and revise as needed. Doing this will lower the stakes of the decision which in turn breaks the decision paralysis. You decide, and move on.

Seneca said that we suffer more in imagination than in reality, and every overthinking loop proves him right. Your nervous system can’t tell the difference between a real crisis and a hypothetical one. With overthinking you end up exhausted from scenarios that never happened before you even start the real work. Your primary focus should be on what the next action is.

The Freedom of Uncertainty

Overthinkers tend to think in systems and see patterns others miss. They notice subtle inconsistencies, anticipate second and third-order effects, and connect distant dots. The struggle arises when there’s this depth of thinking without direction. It ends up pointing a high-resolution mind inwards instead of outwards.

Overthinking is a form of hiding from uncertainty. But uncertainty doesn’t have to be the enemy, it can be the canvas of opportunity for converting mental noise into meaningful output. Instead of “researching” the best writing software for the novel you want to write, just start writing what you have. Instead of countless video reviews of best desert hiking shoes, just go hike in the ones you have. It’s those actions that will bring clarity for what’s needed next.

The absurdist say it’s futile to search for meaning before acting. Life itself is a non-deterministic system, and you can’t optimize it by chasing perfect abstractions. It only responds with more ambiguity. The key is to participate despite the ambiguity.

Because the version of you on the other side of the action knows something the version still thinking about it never will.