Someone asked me recently how they would know if they were thinking something through properly or just going round in circles.
I did not have a tidy answer ready, which is usually a sign the question is a good one. I have since found a test that actually works, and it is simpler than I expected.
It is not about how long you spend on something. It is about whether anything new is arriving while you spend it.
TL;DR
Thinking moves. Overthinking loops. The test is whether new information is arriving each time you go over something, or whether you are running the same lap with the same facts and just feeling worse. Thinking leaves you calmer and closer to a decision. Overthinking leaves you more tired and no closer than when you started. The fix is not to think harder or think less. It is to notice the loop, let the feeling driving it settle, then ask what you would actually need to know to move, rather than what would make you feel certain. Certainty is a feeling, not information, and more laps will not produce it.
In this article
What Thinking Actually Looks Like
Proper thinking has a direction. You start somewhere, you learn something, and the next lap looks different from the last one because you now know more than you did.
It also tends to feel calmer than people expect. Not exciting, not urgent, just steady. You are working towards an answer, so each pass narrows things down rather than opening them back up again.
Thinking usually ends. That sounds obvious, but it is the clearest marker. At some point you have enough to decide, even if the decision is not perfect, and you stop.
What Overthinking Actually Looks Like
Overthinking has no direction. You go over the same handful of facts again and again, and the tenth pass looks almost identical to the first.
It feels worse the longer it goes on, not better. Calm gives way to a low hum of anxiety, and the anxiety is doing most of the driving, not the actual question.
Overthinking rarely ends on its own. It gets interrupted, by tiredness, by someone asking you a different question, by the deadline finally forcing a choice. Left alone, it just continues.
I notice it most reliably late at night, lying in bed going over something that had a perfectly ordinary answer earlier in the day. Nothing about the situation has changed between six in the evening and midnight. What has changed is that I am tired, and tiredness seems to make the loop louder without making it any more useful.
The Test I Actually Use
Here is the question I ask myself now, and it takes about two seconds. Has anything new arrived since the last time I went over this?
If yes, that is thinking. Keep going, you are making progress.
If no, and I am simply replaying the same handful of facts with the same worry attached, that is overthinking. Nothing further will arrive by doing another lap, because there is nothing left to find. The facts are already all in the room.
This single question has saved me more time than any productivity trick I have tried, mostly because it is honest rather than clever. It does not ask you to think positively or stop worrying. It just asks what is actually happening.
I use it at work too, since I get plenty of decisions to make on the spot. If a colleague asks my opinion and I notice myself giving the same non-answer a third time, I can usually tell within a second whether I am still weighing something up or simply avoiding committing to it.
Why This Test Works Better Than Time Spent
Most advice on this measures the wrong thing. It counts minutes, as though twenty minutes of consideration is always fine and two hours is always a problem.
Time is not the tell. A genuinely complicated decision might need real hours of proper thinking, gathering facts, talking to people, checking assumptions. A trivial decision can tip into overthinking in about ninety seconds if the right feeling is attached to it.
What decides which one you are in is not the clock. It is whether the activity is still producing anything. This matters because it stops you feeling guilty for thinking carefully about something that deserves it, while still catching the loop on something small that has quietly taken over an entire evening.
Underneath most overthinking loops sits a want for certainty, and certainty is a feeling rather than a fact you can gather. That is why more thinking cannot deliver it. You are trying to feel your way to something that only ever arrives through evidence gathered by actually deciding and seeing what happens.
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Get the Free Email SeriesWhat I Do Once I Catch a Loop
Catching it is most of the job. Once I notice I am on the third or fourth identical lap, I stop trying to think my way out, because thinking is exactly the tool that got me stuck.
Instead I go to where the feeling actually sits. Usually my chest or stomach, depending on what is driving it. I stay there rather than arguing with it, the same way I would with any other feeling, and I let it settle before I go anywhere near the decision again.
Once it has settled, I ask a different question. Not "what would make me feel sure", but "what is the smallest thing I could actually do that would tell me something new". Send the message. Ask the question. Try the small version. That produces real information. Another lap in my head does not.
I still slip into this more than I would like, particularly with decisions that have no clear deadline attached. A deadline forces the loop to end. Without one, I have sat on things for weeks that a single honest conversation would have settled in ten minutes.
What helps most, oddly, is writing the loop down rather than running it in my head. Seeing the same three facts on paper, over and over, makes it far more obvious that nothing new is arriving. In my head it can disguise itself as fresh thinking almost indefinitely.
When It Is Not This Simple
I want to be fair to the harder cases. Sometimes a decision genuinely needs more information, and going back to check something twice is not the same as looping.
The difference is whether the second pass has a specific target. "I need to check whether the numbers still hold" is thinking. "I need to feel okay about this before I decide" is not, because feeling okay is not information, and it will not show up no matter how many times you check.
It is also worth saying that some loops are not really about the decision in front of you at all. They are the mind defending a need to be right, or a need to stay in control of how something turns out, dressed up as diligence. If that sounds familiar, the fuller picture of what usually sits underneath a stuck decision is in why your choices get worse by evening, and the specific trap of treating a feeling of certainty as evidence is covered in trusting your gut instead of overthinking.
If the loop tends to land specifically on small, low stakes choices rather than the big ones, that is its own pattern with its own fix, and I go through it in how to stop overthinking small decisions.
I would also say this gently to anyone reading this and thinking they should now be able to spot a loop instantly every time. You will not, and neither do I. Some days I am three laps in before I even notice, and the test only works once you remember to actually ask it. Noticing sooner is the whole skill, and it improves gradually rather than arriving all at once.
Stuck on the same decision for days?
Working out whether you are still thinking or just looping is usually the first thing we do in overthinking and decision coaching. No sales script, just a real reply from me.
Contact MeCommon Questions
What is the simplest way to tell thinking and overthinking apart?
Ask whether anything new has arrived since the last time you went over it. If yes, you are still thinking. If you are replaying the same facts with the same worry attached, that is overthinking, and another lap will not add anything new.
Is spending a long time on a decision always overthinking?
No. Genuinely complicated decisions can need real hours of proper thinking. Time is not the tell. Whether the activity is still producing anything new is the tell, and a long, productive process is not the same as a short, repetitive loop.
Why does overthinking feel worse the longer it goes on?
Because a feeling, usually the want for certainty, is driving it rather than the facts. Feelings that are not let go of tend to build rather than resolve themselves, so the anxiety increases even though nothing about the actual decision has changed.
Can you ever think your way out of overthinking?
Rarely, in my experience. Thinking is the tool that produced the loop, so using more of it tends to extend the loop rather than end it. Letting the underlying feeling settle first, then asking what would actually produce new information, works far more often.
Does a deadline actually help with overthinking?
Often, yes, because it forces the loop to end somewhere. I notice I loop longest on decisions with no deadline attached. Setting yourself an artificial one, even an arbitrary end of day, can do the job a real deadline would have done.
What should I do the moment I notice I am looping?
Stop thinking about the decision and go to the feeling instead. Notice where it sits, let it settle without arguing with it, then ask what small action would actually produce new information, rather than trying to think your way to feeling certain.
Written by Harry
Not a trained life coach or counsellor, just sharing what has helped me on my own journey. For more free guides on confidence, self-belief and letting go, visit the blog. To read the full story, see the about page.