Last year, my son’s bike got a flat.

No big deal, right? Just replace the tube.

Except it had been decades since I’d fixed one, and I couldn’t remember what kind of tools it needed or which repair kit to buy. So I did what any Five would do: I opened twenty tabs and started researching.

I compared patch materials, valve types, CO₂ inflators vs. hand pumps. I read every review like I was studying for a final exam.

Meanwhile, my son went six months without a bike.

When I finally picked one at random, the repair took five minutes (face palm).

We fixed it together. It was easy. It was fun. And I realized I’d missed out on those moments for months because I was trying to make the perfect choice.

That’s when it hit me: I wasn’t being cautious—I was trying to avoid regret.

As Fives, we don’t struggle with indecision just because we’re unsure. We struggle because we’re trying to eliminate the emotional fallout of getting it wrong.

Today we’re talking about how that protective instinct backfires and how to start making decisions that move life forward again.

The real cost of overthinking

We think indecision protects us from pain. In reality, it quietly drains the life out of us.

Every moment spent “researching one more option” is a moment spent in limbo, neither moving forward nor feeling at peace. The mental tabs stay open long after the browser is closed.

Here’s what indecision actually costs us:

• Momentum. We lose the compounding effect of small, timely actions. The world moves on while we’re still comparing specs.
• Energy. Holding multiple possibilities in our mind burns through mental bandwidth, leaving us fatigued before we’ve even acted.
• Confidence. Each delayed decision trains the brain to associate action with danger, slowly eroding self-trust.
• Connection. Life happens in participation, not observation. When we over-analyze, we miss shared moments that build belonging.

In short, we trade safety for stagnation, and the longer we stay there, the heavier life feels.

The better goal: aligned, not perfect

The goal isn’t to find the decision with zero regret. It’s to make one that’s aligned with your values, your current capacity, and your best available information.

That’s enough.

Here’s how to start breaking the cycle:

• Redefine “right.” Stop chasing “risk-free.” Start asking, “Which choice feels most true to who I want to be?”
• Decide before you’re ready. Set a clear research limit: three options, one evening, then act. Real clarity comes from data gathered through doing.
• Embrace micro-regret. Small mistakes are practice runs. They teach you faster (and cheaper) than overthinking ever will.

The 24-Hour Decision Experiment

This week, try a simple experiment.

1. Pick one decision you’ve been sitting on: something small but real. It could be a purchase, an email, a conversation, or a next step in a project.
2. Give yourself 24 hours to decide. No more research after that.
3. When you act, notice what happens:
   • How much energy returns once it’s off your mind?
   • What did you learn that you couldn’t have learned by thinking alone?
   • Did the “regret” you feared actually happen?

Record what you notice.

This isn’t about reckless action. It’s about proving to yourself that most regret is imagined and that confidence grows through motion, not mastery.

When I finally ordered that repair kit, my son didn’t care what kind of features it had. He cared that we did it together.

Regret shrinks when life expands.