Overthinking Decisions? Why Smart People Get Stuck and How to Move

Have you ever spent longer choosing a notebook than some people spend choosing a flat?

I wrote FOG OFF partly for people like this, myself included. A wide-ranging mind can turn a stationery purchase into a philosophical inquiry. The notebook asks one blunt question each day: what is the smallest next action, and can you do it before your coffee goes cold?

Not because notebooks matter that much. Because a busy mind, given a choice and a quiet afternoon, will happily build a spreadsheet, a weighting system and a small philosophical treatise on paper quality.

If you are reading this, I suspect yours does something similar.

Overthinking decisions is one of the most common things I see in the people I work with: founders, managers, expats deciding whether to stay or go, brilliant professionals who can solve anyone's problem except their own next step. And almost none of them are short on intelligence. That is exactly the trouble.

Overthinking is not a thinking problem. It is a stopping problem.

Why do smart people overthink decisions?

Here is the uncomfortable part. A strong analytical mind is a machine that produces reasons. Give it a question and it will keep producing them, for and against, long after the useful ones have run out.

I call this the Unopposed Mind: a brilliant mind with no one left to disagree with it. When you are the smartest voice in your own head, every doubt sounds convincing because it is phrased so well. Your inner critic went to a good university.

There is research behind this, and it is a little humbling. In 1991, Timothy Wilson and Jonathan Schooler published a study in the Journal of Personality and Social Psychology with the wonderfully honest title "Thinking Too Much." They asked students to rate strawberry jams. Some simply tasted. Others were asked to analyze why they liked or disliked each jam. The analyzers' preferences matched expert ratings far less well than the people who just tasted.

Read that again. Explaining their reasons made them worse at knowing what they liked.

The point is not that thinking is bad. The point is that some decisions live partly in a part of us that does not speak in bullet points, and when we force everything into words, we start optimizing for what is easy to articulate rather than what actually matters.

What is analysis paralysis, really?

Analysis paralysis is what happens when the cost of deciding feels higher than the cost of waiting. So we wait. And we call the waiting "research."

Barry Schwartz and colleagues described two styles of choosing in a 2002 paper, also in the Journal of Personality and Social Psychology. Maximizers try to find the best possible option. Satisficers look for one that is good enough by their own standards, then stop. In their studies, people who scored high on maximizing reported less happiness and optimism, and more regret and depression, than satisficers.

Maximizers often make objectively "better" choices on paper. They just feel worse about them.

"Le mieux est l'ennemi du bien." The better is the enemy of the good. (Voltaire, La Bégueule, 1772, citing an Italian proverb)

I find this deeply relieving. It means the endless search is not buying you the satisfaction you think it is. You are paying in hours and sleep for a feeling that, statistically, is not waiting for you at the end.

The perfect option is usually a story we tell ourselves to avoid the discomfort of choosing.

Why does overthinking feel so productive?

Because it looks like work. You open tabs. You make lists. You ask five friends and then a sixth to break the tie. Your nervous system gets a small hit of "I am handling this" without ever having to handle anything.

Psychologist Susan Nolen-Hoeksema spent much of her career studying rumination, the habit of repetitively focusing on problems and their causes without moving toward solutions. Her research linked it with prolonged low mood and poorer problem solving. Rumination masquerades as reflection. The difference is direction. Reflection goes somewhere. Rumination walks in circles in very expensive shoes.

Watch any episode of Severance and you see a beautiful metaphor for this: people endlessly sorting numbers on a screen because the numbers "feel scary," with no idea what the work is for. Overthinking can be our private Lumon. Busy, meticulous and strangely disconnected from the actual life outside.

In Creative Solutions for Ordinary Problems, I treat this as a muscle problem, not a character flaw. One of the experiments I love is the deliberately imperfect start: do the first ten minutes of the task badly, on purpose. Lumon loses its grip the moment real work begins.

Is AI making overthinking worse?

Possibly, yes. We now carry a machine in our pocket that can generate ten more options, twenty more pros and cons, and a comparison table in seconds. For an overthinker, this is like handing a gambler an infinite bank account.

I keep returning to a line I use in my work:

The machine gives answers. The human chooses the question.

If you ask AI "what are all the things that could go wrong if I take this job?", you will get a long and articulate list. That list is not wisdom. It is supply. The real skill is knowing which question deserves your attention and when you have enough to act.

How do you know when you have enough information?

Jeff Bezos, in his 2016 letter to Amazon shareholders, wrote that most decisions should probably be made with somewhere around 70% of the information you wish you had. Wait for 90%, he argued, and in most cases you are being slow.

In an earlier letter (2015) he described "Type 1" decisions, which are consequential and nearly irreversible, one-way doors, and "Type 2" decisions, which are two-way doors you can walk back through. His warning was that big organizations tend to treat every decision like a one-way door. So do overthinkers.

Most of the doors you are agonizing over swing both ways.

The new city can be left. The course can be quit. The email can be followed by another email. Even a career change is rarely the cliff it looks like from the inside; it is more often a staircase with landings.

"Life can only be understood backwards; but it must be lived forwards." (Søren Kierkegaard, Journals, 1843)

Kierkegaard saw the trap nearly two centuries ago. We want the clarity of hindsight before we have done the thing that would give us hindsight. That clarity is only available on the other side of moving.

How to stop overthinking a decision: small experiments

I am not going to give you ten steps. Overthinkers collect steps the way some people collect houseplants, and then worry about watering them. Instead, here are a few questions and small experiments. Try one, not all.

1. Name the door. Before anything else, ask: Is this a one-way door or a two-way door? If it is two-way, give yourself a deadline in days, not weeks. If it is truly one-way, give it more care, but still a date.

2. Define "good enough" before you look. Satisficers decide their criteria first, then stop at the first option that meets them. Write down three things that would make an option acceptable. When something meets all three, you are done. Not "done for now." Done.

3. Ask what the waiting is protecting you from. Very often overthinking is not about the decision at all. It is about the feeling that comes after: disappointing someone, looking foolish, being responsible. What would you have to feel if you decided today? That answer is usually more useful than another spreadsheet.

4. Run a two-week trial. Treat the choice as an experiment instead of a verdict. "For the next two weeks I will act as if I chose X, and notice what I notice." Data from living beats data from imagining.

5. Give your Unopposed Mind an opponent. Tell one person you trust your decision before you feel ready, and ask them to argue the other side for five minutes. Hearing a counterargument out loud from someone else is strangely calming. It turns a fog of doubts into one position you can actually weigh.

6. Taste the jam. Remember Wilson and Schooler. For decisions involving taste, people or places, notice your first gut reaction and write it down before you start analyzing. Then check whether your reasoning is leading you somewhere better, or just somewhere more defensible.

What if I choose wrong?

You might. I have. Everyone you admire has.

But here is something I believe after years of working with very bright, very stuck people: an imperfect decision you act on teaches you more than a perfect decision you never make. Movement creates information. Stillness only creates more thinking.

And thinking, beautiful as it is, was never meant to replace living. It was meant to serve it.

So I will leave you with one question to carry around this week:

If you knew this decision could be undone, what would you have chosen already?

With love,

Gizem

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