Ambition vs. Entitlement

May 29, 20252 min read

I found myself, yet again, thrust into deep thought deep thought about something deceptively simple but incredibly powerful: the line between ambition and entitlement.

It started with a quote from James Clear that hit a little too close to home:

“Ambition is when you expect yourself to close the gap between what you have and what you want. Entitlement is when you expect others to close the gap between what you have and what you want.”

It stopped me in my tracks.

Because as a business owner, coach, and parent, I’ve definitely found myself slipping into entitlement mode now and then. It’s usually hiding in plain sight, sneaking into sentences that start with “should.”

I should have more clients.

They should want to work with me.

My kids should listen the first time.

I shouldn’t have to wait this long for a ride!

These thoughts feel harmless—normal even—but when I look closer, they’re laced with a quiet resentment. And resentment, when left unchecked, starts to chip away at your energy and your joy.

The Problem With “Should”

What those statements have in common is expectation… without ownership. They put the result in someone else’s hands.

That’s not ambition.

That’s entitlement.

And it’s subtle. It doesn’t shout, it whispers.

So I had a word with myself. Because I know better. I’ve always tried to keep a tight grip on my mindset. But the truth is, this realisation crept in around something I hadn’t named properly before:

I’m no longer “up and coming.” I’m 42.

And with that has come an unconscious belief that I should be further ahead than I am.

Despite:

  • Having two amazing kids

  • Having a marriage I’m proud of

  • Leaving a safe career to grow a multi-million pound property portfolio

  • Building multiple businesses with my wife and on my own

  • Becoming a qualified ICF-accredited coach

…there was still a small voice saying: "Yeah, but you should be further on."

Ambition Brings Ownership Back

That’s when I flipped the script.

Instead of thinking “I should ………..” I started asking myself, “what future growth do I actually want and what price am I willing to pay to achieve it?

You see, we trick ourselves into thinking we want the outcomes we see of people on social media but we would probably not want to pay the price to get it.

I see people over in Dubai living it up, and that’s great for them.

And on a dreich Scottish morning, there may be a pang of envy.

But, I now we could move there, if we wanted to, but we don’t, for various reasons.

The point is that to focus on ambition, it has to be right for you, and you have to be willing to pay the price.

Entitlement will only have you looking around at the World to give you what you want.

Instead, figure out what you want and what price you’re willing to pay to get it.

And then go get it done.

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