4 MONTHS AGO • 2 MIN READ

I think you ask too many questions...

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Understandings

This newsletter is for people who are not perfect. If you are still figuring out, seeking growth and want to know the game of life a little bit better - this is for you. New issue each Tuesday! Don't miss out.

We question everything.

There is always something else.

Something deeper.

Another way to look at it...

We’ve been taught that thinking things through is smart.

That considering all options prevents failure.
That waiting for the right time leads to better results.

And yet, the more we analyze, the more we hesitate.

The more we hesitate, the more we miss out.

So many people stay stuck not because they don’t have answers, but because they keep asking the same questions.

"What if I fail?"

"What if I regret it?"

"What if I’m not ready?"

But here’s what I’ve learned.

The people who succeed in life aren’t always the smartest, the most prepared, or the most experienced.

They’re just the ones who start.

You don’t have to be great to start, but you have to start to be great.

The problem is, we overthink for one reason - fear. Fear of failure. Fear of rejection. Fear of making the wrong choice.

But fear is sneaky. It doesn’t always show up as panic or anxiety. Instead, it disguises itself as logic.

"I just need to think about it a little more."

"I need to do more research first."

"I’ll start when I feel more confident."

And just like that, hesitation starts to feel like wisdom. But it’s not. It’s just a way to avoid risk while pretending to be responsible.

If you spend too much time thinking about a thing, you’ll never get it done.

Overthinking feels productive. It tricks you into believing you’re making progress. But in reality, you’re just delaying action, avoiding risk, and searching for certainty that doesn’t exist.

Because that’s the truth - certainty doesn’t exist.

You don’t get confidence from thinking. You get it from doing.

You don’t find clarity by waiting. You find it by trying.

You don’t become ready before you start. You become ready by starting.

I’ve always been a cautious person.

I like to think ahead, plan my moves, analyze situations like a game of chess.

I thought that was smart - always looking a few steps ahead, always questioning.

But lately, I’ve noticed something.

The more I analyze, the more stuck I feel.

The more I seek reassurance, the less certain I become.

The more I wait for the “perfect” moment, the more opportunities I miss.

And while I’m still in my head, someone else is already out there figuring things out.

That’s when it hit me.

I wasn’t avoiding failure. I was failing by avoiding.

We don’t realize how much we lose by waiting.

How many chances slip away while we’re busy second-guessing ourselves.

The world moves fast, and hesitation is the quickest way to get left behind.

So what’s the solution?

Set a deadline for action.

Stop giving yourself unlimited time to make a decision.

Give yourself one hour, one day, one week—then commit.

If you keep waiting for the perfect moment, you’ll still be waiting a year from now.

Ask yourself what’s the actual worst-case scenario.

Be brutally honest.

Most of the time, the worst that could happen is an awkward moment, a small failure, a lesson learned.

And what’s the best-case scenario? Growth. Success. A new opportunity.

If you do nothing, the only guarantee is staying exactly where you are.

Trust that action brings clarity. You don’t have to know everything before you start.

You won’t. You can’t.

And you don’t need to.

The people who figure things out aren’t the ones who knew everything beforehand - they’re the ones who took action first and learned along the way.

No one wins by waiting for the perfect moment. No one succeeds by sitting on the sidelines.

The biggest risk isn’t failing. It’s looking back a year from now and realizing you’re still in the exact same place.

So stop overthinking.

Start moving.

This week - Otis Redding

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Understandings

This newsletter is for people who are not perfect. If you are still figuring out, seeking growth and want to know the game of life a little bit better - this is for you. New issue each Tuesday! Don't miss out.