How to Tell If You're About to Make a Bad Decision

I’ve made some a sh*t ton of bad decisions in life.

Sometimes it’s because I'm reckless. Most of the time, it’s because I use my brain.

If I look back honestly, most of my worst decisions weren’t made in chaos. They were made while I was thinking. That’s the embarrassing part. A lot. Sitting there, going in circles, telling myself I was being careful, strategic, mature.

And if you’re anything like me, you usually knew exactly what the right move was with hindsight.

You just didn’t want what came with it:

• The uncertainty.

• The discomfort.

• The “oh shit, now I actually have to deal with this” part.

So instead of deciding, I let my brain take over. I let it turn simple things into complex ones. I let it chase certainty that didn’t exist. I let it gather more data, imagine more scenarios, manage outcomes that weren’t manageable anyway.

Which is how smart people avoid action while feeling productive.

Look, 98.6% of the bad decisions I have ever made had the same fingerprints on them: The process before it. The same mental moves, on repeat.

So more recently, I stopped asking, “How do I make better decisions?” And started asking a much more useful question:

How do I avoid the stupid ones?

Charlie Munger calls this inversion. Instead of trying to be brilliant, you focus on not being an idiot. And weirdly enough, that’s when things start working.

So that’s what this is.

Four signals that show up right before you make a bad decision, and a way to catch yourself before your brain hijacks something you already understand.

The First Signal: When Thinking Feels Like Work

You usually know you’re heading toward a bad decision not because the situation is confusing, but because thinking suddenly feels heavy. Not useful thinking. Just..effort.

It’s like you’re forcing something that should not require this much mental power.

That’s when the lists start. Then new versions of the same lists.

Scenarios multiply. You replay the same thoughts with slightly different wording, hoping that this time something will click. You tell yourself you just want to get it right. (right?)

That’s the signal.

When thinking turns into work, it’s rarely because clarity is missing. It’s because your brain is stepping in to block something you don’t want to feel yet: Uncertainty. Discomfort. The fact that once you decide, you actually have to deal with what follows instead of staying safely in your head.

So I don’t try to solve the decision anymore. I stop and ask a different question: “What feeling is all this thinking trying to protect me from?”

I name it as it shows up.

• Fear of being wrong.

• Fear of hurting someone.

• Fear of looking stupid.

Then I let it sit there for a moment without fixing anything.

Most of the time, once that feeling is allowed, the decision stops needing so much effort.

And when it still feels heavy after that, not scary, just heavy, that’s usually the answer too. That’s not a decision trying to be made. That’s one I’ve been trying to avoid.

The Second Signal: The Hunt for Certainty That Doesn’t Exist. (Perfectionists, gather here)

You usually know you’re heading toward a bad decision when the question shifts from “what do I want to do?” to “what’s the safest possible move?”

That’s when the certainty hunt begins, because you start asking questions that sound reasonable and smart.

• “What guarantees the least regret?”

• “What’s objectively best?”

• “What choice can I defend later if this goes wrong?”

You tell yourself you’re just being responsible.

That’s the signal.

Because those questions can’t be answered in real time. Certainty only shows up after the fact, once the decision has already been made and lived. Before that, it’s a mirage, nothing more.

So when you chase certainty, nothing moves. You stay frozen, not because you’re missing information, but because you’re trying to eliminate discomfort before acting. And that never works (trust me, I tried). That’s how decisions drag on for weeks or months while you keep telling yourself you’re “still thinking.”

So I flip the question.

Instead of asking how to avoid regret, I ask what kind of regret I’m already creating.

• Will I regret not doing this more than doing it?

• Will I respect myself if I keep avoiding this?

I don’t try to answer perfectly. I just notice what comes up. I give it a minute. Sometimes less. Sometimes more.

And if nothing shows up after that, if there’s just silence and no pull in either direction, that’s usually the answer too: That’s one I don’t need to make.

The third signal: hiding behind research

This one took me longer to admit, mostly because it let me feel smart while doing nothing..

Whenever a decision made me uncomfortable, I’d suddenly become very curious. I’d read more. Ask more people. Look for better arguments. Convince myself there had to be one more piece of information out there that would make the choice obvious.

I told myself I was being thorough.

In reality, I was stalling.

I can think of decisions where, looking back, I didn’t learn anything new for weeks. I had the same inputs, and same conclusions. I just created more time circling the same territory, pretending I was getting closer to clarity when I was really just avoiding the moment where I’d have to act and deal with the consequences.

That, my friend, is the signal for hiding behind research.

Because when it turns into a reflex (and it does), it’s no longer about understanding. It’s about buying time: Time before you have to feel the guilt, uncertainty, or discomfort of choosing something that closes other doors.

When this happens, I start asking an annoying question: What feeling am I using information to avoid right now?

Once I see that clearly, the next step isn’t to gather more data. It’s to narrow the problem. I look for the ways this decision could be stupid instead of the ways it could be optimal.

• Am I ignoring an obvious red flag?

• Am I betraying something I already know matters to me?

• Am I doing this to be approved of instead of because it’s right?

If more information doesn’t remove one of those, it’s not helping. It’s just helping me stay comfortable.

The question becomes simple again when you trade input for honesty.

The Fourth Signal: Obsessing Over Outcomes Instead of Alignment (trying to future-proof yourself)

This one is sneaky because it sounds grown-up. It shows up when your questions move into the future, like:

• Will this pay off?

• Will this make sense in ten years?

• Will this make me look smart, strong, evolved, like I knew what I was doing all along?

Sure..on the surface, these are reasonable questions.. But most of the time, they’re about control.

This is what I do when I don’t trust myself enough to stand by a decision unless it looks good later: When I’m more concerned with how the story will sound in hindsight than with whether it feels right now. That’s the signal.

Because the moment a decision depends on predicting outcomes, managing optics, or avoiding how it might look if it fails, I’m no longer deciding. I’m negotiating with an imaginary future version of myself.

So what do we do? You guessed it.. We flip it.

Instead of asking whether this will work out, I ask a much harsher question: What version of stupid am I about to commit by abandoning my gut for appearances?

Then I stop projecting forward and sit with what’s actually here. Just whether this choice requires me to override something I already know in order to feel safe or respectable.

If the decision only makes sense as long as I can control unknowns or other people’s opinions, it’s usually the wrong one. Alignment doesn’t come with guarantees. But every time I’ve chosen it anyway, the decisions that followed got a lot simpler, and a whole lot cleaner.

Why This Actually Works (And Why I Wrote It Down)

This isn’t about never making mistakes. I still make them. Probably always will. Some of them are even useful.

What changed is that I got better at catching the moment before the mistake, the moment where my brain starts doing that familiar thing where it tries to protect me from a feeling I haven’t agreed to feel yet.

That’s the common thread running through all of this.

• Overthinking.

• Chasing certainty.

• Hiding behind research.

• Obsessing over outcomes.

These are not separate problems. They’re all variations of the same move: Trying to stay in control.

When you look at it that way, inversion suddenly makes a lot of sense. Instead of asking how to make the perfect decision, I started asking how I usually mess them up. And the answer was almost always the same. I try to outthink discomfort. I try to manage the future. I try to eliminate risk before acting.

My life didn’t get better by adding smarter strategies. It got better by removing these habits. Removing the need to be certain. Removing the need to look good later. Removing the illusion that I can control how things unfold if I just think hard enough.

That’s also why this has less to do with decision-making and more to do with the nervous system than it might seem.

The moment you stop trying to control everything, your body relaxes, but because you’re no longer fighting reality in advance.

Hope this helps,

Benoit

Something I watched last week

I watched the Tony Robbins × Alex Hormozi interview last week. It was a smart conversation. Lots of useful ideas.

But it left me with one clear thought: be careful who you call a guru. Sometimes what’s missing in a conversation matters more than what’s said.

I recorded a short video sharing what stood out to me and why.
Here it is if you want to watch it:

If, after watching, you’d want a deeper breakdown of this through the same lens as today’s email, just reply and let me know.

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P.S.
If this resonated and you want to go deeper, the book Unf*ck Your Thinking is here on Amazon.
And here’s the PDF version if you prefer a format that you can share with your friends and read on any device.