Why I Stopped Waiting to Feel Ready

Why I Stopped Waiting to Feel Ready

I like to think I’m fairly calculated in my decision-making.

I trust my judgement. I’m reasonable. I think through worst-case scenarios and plan for them accordingly. I don’t jump without looking. I don’t send it completely blind.

And to be fair—this has served me well.

I remember early in my career, standing on the edge of a move that would’ve been easy to rush into. Bigger pay, shiny title, all the external validation stuff. But something felt off. The role wasn’t aligned, the lifestyle trade-offs were heavy, and the risk wasn’t the good kind. I slowed it down. Asked better questions. Played the tape forward.
I passed.

A few months later, the project fell over, redundancies followed, and I dodged a bullet without even knowing one was coming.

That’s the upside of being calculated.
Sometimes patience is the play.

When Caution Turns Into Comfort

But here’s the flip side no one really talks about.

That same ability to think deeply—to analyse, to plan, to stress-test—can quietly turn into overthinking. Paralysis by analysis. Waiting for the stars to align. Waiting to feel ready.

I’ve caught myself doing it plenty of times.

Sitting on ideas too long. Waiting for more certainty. More confidence. More information.
Spoiler: those things rarely show up when you want them to.

At some point, “being sensible” becomes a convenient excuse for staying comfortable.

Becoming an Action Taker (Imperfectly)

These days, I’m trying to move differently.

Still thoughtful—but faster.
Still aware—but less hesitant.

I’ve leaned more into action, even when the path isn’t crystal clear. As Machiavelli put it: “Make mistakes of ambition, not mistakes of sloth.” That line stuck with me because it hits a nerve.

I’d rather screw up trying to build something than play it safe and wonder what if.

Investing Without a Crystal Ball

This mindset shift has been huge for investing.

We’ve got four properties in our portfolio, bought into a pretty depressed New Zealand market. The headlines aren’t rosy. The economy’s tight. Interest rates bite. No one can say with certainty how it’ll all shake out.

And honestly? That’s uncomfortable.

But that’s also the deal.

Life is uncertain by default. We fear the unknown, and psychologically we weight potential losses far heavier than potential gains. Losing feels worse than winning feels good—so we hesitate.

Yet every investment worth making lives on the other side of that discomfort.

You don’t know it’ll work out.
You just decide that the risk of doing nothing is worse.

Most Good Things Came From “Sending It”

As I’ve gotten older—and taken the time to properly reflect—I’ve noticed a pattern.

Most of the good stuff in my life didn’t come from waiting until I felt bulletproof. It came from giving it a crack.

There was some thinking. Some risk assessment. Enough to not be reckless.
But not so much that it killed momentum.

Then—bam—I sent it.

Career moves. Investments. Relationships. Even starting this blog. None of it felt perfectly timed or fully baked. It just felt worth a shot.

Final Thought

Fortune doesn’t favour the smartest person in the room.
It favours the one who moves.

If you’re waiting to feel ready, here’s the truth: you probably never will. And that’s fine.

Think it through—but not forever.
Respect the risk—but don’t worship it.
Take the step.

Make mistakes of ambition. Not of sloth.

So, what decisions are you sitting that need an answer?