Chapter 41: The Paradox Of Ambition

How many people do you admire whose lives you wouldn’t actually trade places with?

Andrew Wilkinson has this great line about high achievers:

Ambition is a gift.

But left unchecked, it becomes a curse.

The Curse of the Insecure Overachiever

High achievers want to collapse timelines.

To squeeze a decade of progress into three months.

And sure, urgency can get you far.

But grind yourself to the bone long enough, and you’ll end up hating the process.

When I moved to Portugal, I made this mistake.

I put insane pressure on the first project I worked on to be my “life’s work.”

Think about that: demanding perfection from something I didn’t even have the skill for yet. No wonder I was miserable.

But what I’ve learned is this:

If you’re truly committed to the vision, you’re going to get there anyway.

The only question is, how?

You have two options:

1. Make yourself miserable, white-knuckle through it, and arrive exhausted — only to realize it was never about “getting the thing.”

2. Or do the work, trust the process, and maybe even enjoy the ride.

The destination is the same.

But the way you travel is up to you.

The Illusion of Control

When faced with challenges, the insecure overachiever grips tighter.

They think if they can force certainty, they’ll finally feel safe.

But the more you chase certainty, the more fear you create.

Because certainty doesn’t exist.

Life is chaotic. Plans fall apart. & Things change.

That’s not the exception — it’s the rule.

And clinging to control only makes the sting sharper when reality doesn’t cooperate.

Real Freedom

Real freedom comes from loosening your grip.

From realizing uncertainty isn’t the exception — it’s the natural state of life.

The thing you’re looking for won’t come from forcing outcomes.

It’ll come from trusting you can handle whatever wave comes your way.

And ironically…

When you stop clinging so hard to the outcomes, the work becomes fun again.

And remember … that's the goal … to be challenged, in pursuit, and having FUN.

Wrapping Up

Ambition isn’t your enemy.

But insecurity-fueled ambition will eat you alive.

So the next time you feel yourself gripping tighter…

Remember:

You don’t need more control.

You just need to trust the process.

The work will get done and you’ll get where you’re going.

The only question is — will you enjoy the ride?

Rooting for ya,
—Dodds