How to Make Better Decisions with Less Overthinking
If you have ever joined a digital project meeting, you know the scene. The meeting starts with a clear goal. It feels simple in the first minutes. But then someone asks for more data. Another brings up a risk. A third says, “What if…?” and suddenly the talk goes in circles.
I have seen this many times. The energy goes down, people take notes, faces look serious, and when the meeting ends, there is a sense that work was done. But the project has not moved at all.
This is overthinking. It looks like caution, but it is only a delay. It looks like leadership, but often it is fear. Fear of being wrong, fear of making a choice, fear of moving forward when the future is never certain.
And leaders often fool themselves. They believe that more thinking will protect them from mistakes. But it only creates another mistake: paralysis. Nothing happens, time passes, and the cost of inaction grows quietly in the background.
The strange part is that people still feel proud because they were “thorough.” Careful talk, careful notes, but no decisions.
That is the trap.
The Hidden Price of Endless Analysis
It is important to be clear: the problem is not the analysis itself.
Careful thought is part of any serious job. The problem arises when analysis becomes a shield against responsibility.
When leaders avoid decisions by drowning themselves in extra data, they are not protecting the organization; they are exposing it to risk.
Teams feel this cost first. People need direction. When decisions are delayed in the name of more reflection, clarity fades. Priorities become uncertain. Projects lose rhythm. Stakeholders begin to doubt if leadership is capable of guiding the work.
The most dangerous situation is not a wrong decision, but no decision at all.
We rarely measure this cost directly. A project delayed for months does not always appear as a financial loss in the short term. Yet the damage is there: opportunities missed, morale reduced, competitors moving faster.
Every delayed decision is also a decision, because by not acting, you choose to keep the status quo. And the status quo often carries a higher cost than the risk of action.
Why Leaders Fall into the Trap
Psychology gives us one explanation. Daniel Kahneman and Amos Tversky, in their work on Prospect Theory, showed that people are more sensitive to losses than to gains.
Losing one hundred dollars feels worse than winning one hundred dollars feels good.
This is called loss aversion. Leaders, like everyone else, bring this bias into their decisions.
They see the possible downside of action more strongly than the possible upside, so they delay, searching for more certainty.
We like to pretend that in digital work, one day, clarity will finally arrive. That if we just wait long enough, gather enough reports, or attend one more meeting, the fog will lift and the right path will shine in front of us like a highway sign.
The problem? It never happens. Markets shift in months, technologies in weeks, customers in days. Certainty is not part of the package.
Still, I catch myself falling for the same trap. “Let’s just wait a bit, maybe we will know more tomorrow.” As if tomorrow was holding a golden envelope with the exact answer inside. Spoiler: it never comes. By the time things look calm, the opportunity has already passed. It’s like standing on the beach saying, “I will only learn to swim when the sea is as flat as glass.” When the sea finally looks safe, the tide is gone.
And here’s the funny part: this is not even a modern problem. People in history faced the same dilemma. Do I move now with what I know, or do I wait for perfection? Strategy has always punished hesitation.
General George S. Patton had a brutal way of saying it: a good plan now is better than a perfect plan next week. At first, it sounds reckless, almost irresponsible. But if you think about it, it is pure realism. He was not saying “run blindly.” He was saying: Waiting has a cost. Delay looks safe, but it quietly eats away at your chance.
I have felt this many times in projects. The endless analysis, the careful conversations, the weeks of waiting for just one more piece of data. And then we realize the moment is gone. The competitor moved. The team lost energy. The window closed.
Perfection is slow. If it comes at all, it usually comes too late. Progress belongs to the ones who accept that some questions will always remain open, who move with timing, with discipline, and with enough courage to act while the fog is still there.
And honestly, if I look back, the mistakes that hurt most were rarely from acting with an imperfect plan. They were from waiting too long.
What Decision Science Teaches
Kahneman’s book Thinking, Fast and Slow describes two systems of thought:
System 1 is fast, intuitive, and automatic.
System 2 is slow, deliberate, and effortful.
Most organizations lean heavily on what Daniel Kahneman called System 2 thinking, the slow and deliberate mode that examines details and builds arguments step by step, believing this brings rigor and safety. Yet when leaders rely only on this slower path, bottlenecks appear everywhere, because careful thought without closure becomes an obstacle rather than a safeguard.
The most effective decision makers are not those who abandon analysis, but those who know how to combine it with intuition, drawing on years of experience to guide direction while using structured analysis to verify the critical points their intuition might miss.
Herbert Simon added depth to this understanding by introducing the idea of satisficing, the recognition that in complex environments it is more useful to aim for a solution that is good enough than to waste time searching for the perfect one.
Perfection in such contexts is not only unreachable but also dangerous, because the time spent chasing it often outweighs any benefit it could bring. What matters is to define beforehand the threshold that will be sufficient, and once that level is reached, to act, instead of allowing the search for more certainty to consume weeks or months that the organization cannot afford.
Behavioral research has reinforced this point by showing that in many uncertain situations, simple heuristics and timely decisions perform just as well as, and often better than, complex analyses that arrive too late.
Gerd Gigerenzer and his colleagues have studied how so-called fast and frugal heuristics work precisely because they ignore much of the noise, forcing closure at a point when extra information would add little but confusion.
In practice, this means that deciding with a clear rule at the right moment can outperform a decision delayed by excessive calculation.
A similar distinction was drawn by Jeff Bezos in his 2015 letter to Amazon shareholders, where he described two kinds of decisions: Type 1, which he compared to one-way doors, hard to reverse and therefore requiring more care, and Type 2, which are two-way doors, reversible and easy to adjust if wrong.
The mistake, Bezos argued, is when leaders treat Type 2 decisions as if they were Type 1, overanalyzing reversible choices as if they carried irreversible consequences.
The result is unnecessary delay. Recognizing the difference allows organizations to move faster where they can afford to, while reserving deeper analysis for the choices that truly demand it.
A Simple Model for Better Decisions
Knowing the psychology and the theory is not enough. Leaders need clear practices to stop overthinking and make close decisions in time.
A simple model can be built from the insights above:
Define the horizon of the decision: Is it a one-way door or a two-way door? If it is reversible, decide faster. If it is irreversible, take more care, but still set limits.
Set the level of good enough: Before starting the analysis, define what minimum criteria would already be acceptable. This applies Simon’s principle of satisficing and protects against perfectionism.
Time-box the process: Unlimited time creates the illusion that one more piece of data will bring certainty. Setting a deadline forces closure and creates discipline.
At this stage, the familiar objection always arises: what if we are wrong?
Let’s be honest: mistakes will happen. No leader, no matter how many years of experience, gets every decision right. The real game is not about avoiding all errors. It is about making them smaller, quicker, and easier to recover from.
I like how digital product teams remind us of this. They run experiments, sometimes messy, sometimes rushed, but always with one purpose: move fast enough that the mistakes show up early, when they are still cheap to fix. A bug caught in week one is annoying. The same bug caught in month twelve can kill the project.
The difference is timing. Leaders who decide and act reduce the weight of their mistakes. Leaders who wait, who hold back for the illusion of certainty, often discover the same mistake later, only bigger, more expensive, and much harder to explain.
I ask myself this often: how many decisions am I still carrying around, waiting for “perfect clarity”? How many chances have quietly faded while I told myself I was just being careful? It feels safe to wait. But each day of delay has its own price tag, even if you never see it on a spreadsheet. Lost time means lost trust, weaker momentum, and ground surrendered to someone who didn’t wait.
Better decisions don’t come from endless reflection. They come from courage to act under uncertainty, discipline to know when to stop thinking, and the wisdom to say “this is good enough, let’s move.” That is not recklessness. That is realism.
The leaders who move, learn, and adjust are the ones who make progress. The rest? They are still waiting for the sea to calm before they dare to swim.
Inspirations
Kahneman, D., & Tversky, A. (1979). Prospect Theory: An Analysis of Decision under Risk. Econometrica.
Kahneman, D. (2011). Thinking, Fast and Slow. Farrar, Straus and Giroux.
Simon, H. A. (1956). Rational Choice and the Structure of the Environment. Psychological Review.
Gigerenzer, G., Todd, P. M., & the ABC Research Group (1999). Simple Heuristics That Make Us Smart. Oxford University Press.
Bezos, J. (2015). 2015 Letter to Shareholders. Amazon.
Patton, G. S. (1947). War As I Knew It. Houghton Mifflin.
Ries, E. (2011). The Lean Startup. Crown Business.