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Why Thinking Harder Makes It Worse

clarity
Chris Lippincott·Oct 20, 2026· 3 minutes

When you’re facing an important decision about your career, your relationships, your money, or your future, thinking harder feels like the responsible thing to do.

But what happens when all that thinking leaves you more confused, more overwhelmed, and more afraid of making a mistake?

After 30 years making high-stakes investment decisions on Wall Street, I learned something that took me an embarrassingly long time to accept. More information doesn’t always lead to better decisions. Sometimes it just gives us more ways to worry.

That’s what this week’s episode of Spirits Beside Us is about. Here’s what you’ll take away from it:

Why overthinking makes decisions harder. Fear, stress, and overwhelm change what you see. Your 3 a.m. thinking and your next-morning thinking can land in completely different places, even though nothing about your situation changed.

How fear disguises itself as useful information. Facts, predictions, assumptions, and plain mental noise all sound equally convincing. I’ll show you how to tell them apart.

The one question that exposes unproductive thinking. Am I learning something new, or am I just finding more things to worry about? Both feel like careful thinking. Only one gives you something you can use.

How to stop overthinking with Pause, Label, Listen. This is a simple three-step method from my C.L.A.R.I.T.Y. framework. First you notice the state you’re in, then you name what kind of thought you’re having, then you listen for what’s left once things settle.

How to move forward without knowing the future. You can understand the real risks, explore your options, and take a meaningful step without demanding a guarantee.

I also share what happened with a client I call Valerie. She didn’t suddenly know the perfect answer. She started separating what she knew from what she feared, and that changed which worries deserved her attention. The biggest surprise for her was that she didn’t want to leave her field after all. She wanted to change the kind of work she did inside it.

Listen to the episode on Spotify or Apple Podcasts.

Want ongoing support building clarity and trust in your own inner guidance? Join us inside the Soul Growth Circle membership, where you’ll move step by step through The Inner Clarity Bridge, at your own pace.

And if you’d like to start sorting the useful thoughts from the noise on your own decision right now, the free Decision Clarity Challenge is a good place to begin.

Wishing you clarity,
Chris

Prefer to watch? Find the episode on YouTube.

Next Why Do the Same Patterns Keep Showing Up in Your Life?

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