My brother Justin once took forty minutes to order a coffee in Saigon. Forty minutes. I watched him read the entire menu twice, ask the waitress about the beans, check his phone for reviews of the cafe, and then finally, exhausted, order the same thing he always orders anyway. A flat white.

I laughed at him, but honestly, I’ve done the same thing with bigger decisions. What to name the site. Whether to sell a property. How to word an email. Most overthinkers don’t realise it, but their brains are running a completely different operating system when it comes to decision-making.

And once you see it, you can’t unsee it.

There are two kinds of decision-makers.

The psychologist Barry Schwartz split decision-makers into two camps in his book The Paradox of Choice. On one side, you have “satisficers.” These are people who know roughly what they want, find something that meets their standard, and move on.

On the other side, you have “maximizers.” These are the overthinkers. The ones who can’t commit to a choice until they’ve examined every possible alternative, because the only acceptable outcome is the best one.

Gretchen Rubin wrote a great piece explaining the satisficer vs maximizer split, and it nails something important. Satisficers aren’t lazy or uninformed. They just have an internal “good enough” threshold. Once it’s met, they’re done. Maximizers don’t have that threshold, or they’ve set it so high it’s almost unreachable. Which means every decision, no matter how small, becomes a full-blown research project.

Ordering a coffee. Picking a hotel. Choosing a sentence to put in a text message. Each one gets treated like a PhD thesis.

It’s not that overthinkers are more careful. It’s different wiring.

Here’s the part most people get wrong. They assume overthinking equals being more thorough, more responsible, more intelligent. Like, “I think a lot, therefore I make better decisions.”

The research says otherwise.

Schwartz’s work, expanded on in a Psychologist World piece on maximizers versus satisficers, found that maximizers often do make slightly better objective decisions. But they’re significantly less happy with those decisions. They experience more regret. More buyer’s remorse. More rumination. More “what ifs.” They’re also more prone to depression, perfectionism, and anxiety.

So the overthinker wins on paper and loses in real life. They book the technically better hotel and then spend the whole trip wondering if the other one had a better view. They take the technically better job and spend six months checking LinkedIn to see what else is out there. Their brain is optimising for “best,” but the cost of the optimisation is higher than the value of the upgrade.

Most people would trade a little optimality for a lot of peace. Overthinkers can’t.

The decision doesn’t end when the decision ends.

This is the biggest difference I’ve noticed, both in myself and in people I love. For most people, once a decision is made, it’s closed. They picked the restaurant. They’re at the restaurant. End of thought.

For overthinkers, the decision is never really closed.

You pick the restaurant. Halfway through dinner you spot the place across the street that looks nicer. You start evaluating whether you made the right choice. You imagine the alternate version of the evening where you’d gone there instead. You can’t stop mentally comparing the meal you’re eating to the meal you theoretically could have had.

This is what psychologists call counterfactual thinking, and it’s the overthinker’s signature move. An article from Mind Health Group on the difference between rumination and overthinking explains it clearly. Rumination focuses on past events, while overthinking concentrates on current and future scenarios. Both create a loop where the brain keeps processing a decision long after the decision has been made.

Most people decide and move. Overthinkers decide and keep deciding.

Why the overthinker’s brain does this.

There’s a reason this happens, and it usually isn’t a character flaw. Many overthinkers grew up in environments where getting it wrong had consequences. Maybe parents who were volatile. Maybe teachers who shamed mistakes. Maybe just a temperament wired slightly more toward threat detection than reward seeking.

So the brain adapted. It said, “If I think through every angle, I’ll never get caught out.” That strategy actually works when you’re seven years old and trying not to get yelled at. The problem is, the brain keeps running the program long after you’ve moved out and started your own life.

I used to do this with every email I sent to clients. Draft. Rewrite. Re-read. Check tone. Imagine how they’d read it. Rewrite again. Send. Then lie awake at night wondering if that one sentence could be misinterpreted.

That wasn’t caution. That was a nervous system stuck in a protection loop.

How to loosen the grip.

The good news is, this is not a fixed personality trait. It’s a habit your mind has built, and habits can be re-trained.

The first thing I did, and still do, is ask myself one question before any decision. Is this reversible? If yes, I give myself a hard time limit, usually under two minutes. Reversible decisions are not worth the mental real estate of a three-day analysis. Most decisions are reversible. You can leave the restaurant. You can change the outfit. You can send a follow-up email.

The second thing I do, which has taken me years of daily meditation to actually implement, is notice when the decision-after-the-decision starts running. The moment my mind begins replaying options I didn’t choose, I gently bring attention back to where I actually am. It doesn’t stop the loop every time. But it weakens it.

I write about this in my book Hidden Secrets of Buddhism. The Pali word papañca roughly translates as mental proliferation, the endless spinning of thoughts on top of thoughts. The Buddha considered it one of the main sources of human suffering. Not because thinking is bad. But because thinking about thinking about thinking is how we lose entire afternoons to decisions that should have taken thirty seconds.

The third thing, and probably the most important, is learning to sit with the possibility that another option might have been slightly better. And choosing to be okay with that. Because here’s what most overthinkers eventually realise. The best decision isn’t always the one that was objectively optimal. It’s the one you can actually live inside without torture.

A slightly worse hotel you enjoyed beats a slightly better hotel you spent the whole trip questioning. A less perfect sentence you actually sent beats a flawless sentence still sitting in drafts.

Peace, at some point, has to start beating precision.

And for an overthinker, that shift, from chasing the best to respecting the good enough, is one of the quietest revolutions there is.