Overthinking

John Bradley "JJ" Jackson

09 Jun 2026 • 2 min read

The owl is wise because the more it sees, the less it talks. (Old African Proverb)

I come from the land of overthinking.

After 23 years at a university, I had a front-row seat to analysis. Faculty members, researchers, students, and administrators all shared a common trait: the desire to think deeply. Thinking is valuable. It helps us understand complex situations, solve difficult problems, and make better decisions.

But there is a point where thinking stops being productive and becomes something else.

Psychologists often use the term rumination to describe the tendency to analyze a situation repeatedly. The mind loops through hypothetical scenarios, conversations, outcomes, and possibilities—whether they are real or imagined. The same thoughts circle around and around, often without producing any meaningful conclusion. Maybe you know what I mean? You go to bed thinking about an issue, replay the scenarios in your head all night, and wake up still thinking about it.

For some people, the roots run deep. If you grew up in an unpredictable environment (IE a dysfunctional family), overthinking may have been a survival skill. You learned to anticipate problems before they happened. You looked for patterns in people's behavior. You tried to make sense of situations that didn't always make sense. Your brain became highly skilled at scanning for risks, opportunities, and hidden meanings.

That skill often carries into adulthood. Many successful entrepreneurs, leaders, teachers, and advisors are excellent at pattern recognition. They can synthesize complex information and see connections others miss. They are often highly empathetic, able to sense what others are feeling or experiencing. These are valuable strengths.

The downside is that the same brain that can spot patterns can embellish or exaggerate them. Not every problem needs another hour of analysis. Not every decision requires perfect information. Not every imagined outcome deserves equal attention. At the supermarket you have a choice: paper or plastic. Pick one.

For some people, overthinking becomes paralysis. All think and no do. Opportunities pass while they gather more data. Decisions are postponed while they seek certainty. Problems are examined from every angle but never acted upon.

The irony is that action often provides the answer that thinking cannot. Entrepreneurs eventually learn that there is a limit to planning. At some point, you must launch the product, make the call, have the conversation, or take the risk.

The challenge for over thinkers is not learning how to think better. They already know how to think. The challenge is learning when to stop and let go. Let things happen. Or better yet, go make things happen. More thinking is not necessarily better.

Sometimes the next step forward is not another thought.

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