A lesson on Justin Sung's newsletter about overthinking

Don't think less. Think about the right things.

Overthinking isn't too much thinking. It's the same few thoughts running in circles. The way out is to change what you're asking, and to decide in advance what “enough” looks like.

Start with why it matters and the map. Each section after that is tagged by importance (1 is the core idea) and ends with something to try.

why me again? what if it goes wrong? what's the best call? the same thoughts, in circles what can Icontrol?
Why this matters

Hours of thinking that don't go anywhere

1

It costs you sleep

Justin describes nights where it took him 2, 3, even 4 hours to fall asleep. Most of that time wasn't real problem solving. It was the same few thoughts on repeat.

2

It isn't harmless

That looping has a name, rumination. Justin points to research linking unchecked rumination to depression and anxiety. So it's not just wasted time.

3

The obvious fix doesn't work

If the problem were too much thinking, the fix would be to think less. But you can't just switch thoughts off, and the thinking itself was never the problem.

The problem isn't how much you think. It's what you think about. Change that, and the same time starts going somewhere.

The big picture

One core idea, a loop, and two ways out

Click any box to see what it is, why it matters, and how it connects to the others.

● what keeps the loop going● ways out of itDashed ring: the loop itself

It's the wrong thinking, not too much

Why this comes firstHow you name the problem decides what you try. Call it “too much thinking” and you try to stop, which doesn't work. Call it “thinking about the wrong things” and you have something you can actually do: point your thinking somewhere else.

Justin's description of his own sleepless nights is the key detail. His brain wasn't solving anything. It was running the same few thoughts in circles, as if thinking the same thing again would lead to a new conclusion.

That's rumination: going over the same ground again and again and expecting something new. Notice what's missing. It isn't effort or time. It's any new input. Loop the same thoughts and you'll get the same answers.

Same ten minutes, two nights
Both nights have the same worry: whether to ask for a deadline extension. Press play and watch what each night produces.
Night A · looping
    Night B · concrete questions

      Trap: treating a long night of thinking as proof you took the problem seriously. Time spent isn't the measure. The measure is whether you reached anything you didn't know before.

      Swap endless questions for answerable ones

      Why it mattersSome questions have no answer you can ever be sure of. Ask one of those and your brain keeps going back to it, second-guessing every answer it finds. Ask a question that has a reasonable answer, and you can answer it and move on.

      Endless (abstract)
      • Why did this happen to me again?
      • Why did this person do that to me?
      • What's the best decision? What if it goes wrong?
      Answerable (concrete)
      • What can and can't I control here?
      • What specifically am I worried about?
      • What's the real outcome I want?
      • What could I do that would give me more clarity?

      The difference isn't whether a question is about something big or small. It's whether you need certainty to answer it. With endless questions, there's no definite answer, and even when you reach one you can't be sure it's true. Concrete questions don't need certainty. As Justin puts it, their answers are “just sensible, logical steps in any situation.”

      “Often, seeking certainty is an impossible game to win, because certainty does not exist in the first place.”

      Two details are easy to miss:

      • Starting abstract is fine. “Why did this happen?” is a natural first reaction. The problem is staying there when it isn't giving you more clarity.
      • The four questions build on each other. Control narrows the field, the specific worry names the real problem, the outcome gives you a direction, and the clarity question turns all of it into a next step.
      Endless or answerable?
      Test: could you give a sensible answer right now, without needing to be certain? Sort each question.
      Translate the loop
      Pick a situation. Then go through the four concrete questions one at a time.
      Your turn: something on your mind

      What you type stays on this page. Nothing is saved or sent.

      Overthinking is often avoidance

      Why it mattersIf you believe your overthinking is you being responsible, you'll defend it. Seeing it as avoidance explains why you keep doing it: it feels like working on the problem, without making you face the part that's uncomfortable.

      Justin calls this an uncomfortable truth he had to accept: his overthinking wasn't about being productive, being responsible, or “doing the right thing.” It was avoidance.

      He points to research that treats repetitive thinking as an avoidance mechanism. It lets you feel like you're “untangling the mess” without actually getting into the specific, uncomfortable, actionable parts of it.

      That's why the concrete questions from the last section help. They aim straight at the specific and actionable parts, which are exactly what the loop lets you avoid.

      Spot what's being avoided

      It's 1 a.m. Your report is going to be a week late, and you haven't told your manager yet. These are the thoughts keeping you up.

      Click each thought: is it circling the problem, or touching the uncomfortable part you can act on?

      Decide what “enough” thinking is

      Why it mattersA loop with no end point can run all night. If you decide what conclusion would let you stop, you can tell when you've reached it, and when more thinking won't get you there.

      Some industries call this the Definition of Done: the point where any more thinking is no longer productive or useful. Justin gets there with three questions:

      • Why do I keep thinking about this? This is where you catch avoidance.
      • What conclusion do I feel I need to reach before I can stop? This names the finish line.
      • Is it realistic to actually reach that conclusion? If not, what do I need to do to make progress? This is where certainty-seeking gets caught, because a conclusion like “I'm sure it won't go wrong” can never be reached.

      The third question connects back to the concrete questions. When the honest answer is “no, I can't reach that by thinking,” the next move is an action, the same kind of step as “what could I do that gives me more clarity?”

      Set your Definition of Done
      Use something real, or
      1
      Why do I keep thinking about this?
      Be honest. Is part of it putting off something uncomfortable?
      2
      What conclusion do I feel I need to reach to stop?
      3
      Is it realistic to actually reach that conclusion?
      If it needs certainty about the future or about other people's minds, it probably isn't.
      Check yourself

      Use it, don't just remember it

      Six situations. Each answer links back to the section it comes from.

      Takeaway

      How it fits together

      Endless questions keep the loop running, and avoidance makes the loop feel worth staying in. Concrete questions give your thinking something it can finish, and a Definition of Done tells you when it's finished.

      When you notice the loop

      Ask something answerable

      1. What can and can't I control?
      2. What specifically am I worried about?
      3. What's the real outcome I want?
      4. What could I do that gives me more clarity?
      When you're not sure you're done

      Check your Definition of Done

      1. Why do I keep thinking about this?
      2. What conclusion do I need to reach to stop?
      3. Is that realistic? If not, what do I need to do to make progress?