Why do some people just... go for it?

Hi there,

Recently I was working on a project and I met a 30-year-old realtor who was selling them multi-million dollar homes to some of America’s wealthiest people and making an absolute killing doing it.

He had multiple luxury cars in his driveway, two or three homes, and several million dollar listings… all at 30.

As I stood on his driveway taking it all in and I felt two things at once: genuine awe and something uncomfortable underneath it. Not envy exactly, more like a reckoning. Because standing there looking at his Lamborghini, the thought that hit me wasn't good for him. It was, why have I not let myself dream this big? He wasn’t any different from me. If he can build this, achieve this, and live this — why am I not? And then I thought:

Am I the thing standing in my way?

Talking to him, he said that when he was a kid he had a picture of a Lamborghini on his bedroom wall. He said he looked at that poster every single day knowing, not hoping, knowing that it was going to be his. And then it was.

It was obvious he had ambition, drive, and work ethic. But what was less obvious was that he had a completely different relationship with what he allowed himself to want. And he never made his dream smaller or edited it down to something more reasonable, more modest, or more socially acceptable. He just put it on the poster on the wall and went to work.

Most of us never do that. And I don't think it's because we lack ambition.

What we’re actually afraid of

There's a Marianne Williamson quote that I'm paraphrasing here because my version hits harder for me:

Because who will you be when you get there? The life you have now, the identity you've built, the people around you, the way you fit into your world — all of it shifts when you get bigger. And that is terrifying in a way that's hard to admit out loud because it sounds like you're complaining about succeeding.

I saw this up close once in a way I've never forgotten.

There was a girl I went to high school with who was around 300 pounds. She was withdrawn, always dressed in black, thick eyeliner, sitting alone at lunch sketching in a notebook while everyone else ate and talked and did the things teenagers do.

Then three years later I saw her in the university cafeteria and did a genuine double take.

She was unrecognizable! Not just because of the weight, though she had lost most of it. She was wearing a bright yellow top, the thick black eyeliner was gone, her hair was loose and light around her face, and she was laughing with the people around her. She was taking up space in way she never did in high school.

I went over and we talked, and I told her how happy I was to see her doing well. She told me that in high school she had an identity and felt completely trapped inside it. Everyone knew who she was (the quiet girl, the one who sat alone) and there was no way out of it without someone noticing and making it weird.

But when she moved away for university, nobody knew her old story. Nobody had a version of her they were attached to. So she just decided to become someone different. What she was describing wasn't really a weight loss story. It was an identity transformation.

The Tallest Poppy Syndrome

I used to work with someone from Australia who used the phrase "tall poppy syndrome" and I had no idea what it meant until he explained it. He said it refers to the social tendency to cut down anyone who grows too tall and too successful above the everyone else. And even if nobody around you is actually wielding the shears, we internalize that fear so completely that we do it to ourselves before anyone else gets the chance.

We keep ourselves at a manageable height. We dream at a scale that won't make us too different, too visible, too far from the people we came from. We make ourselves smaller because that feels safer and more comfortable to the existing identity we’ve built for ourselves.

The Golden Handcuffs

I once read that man's greatest burden is unfulfilled potential.

I believe that completely. I have colleagues who are brilliant, educated, accomplished people that who chose the academic path, the corporate path, and the professionally respectable path. And somewhere along the way the path they chose and the path their soul actually wanted quietly diverged. And they feel it. That low hum of internal disquiet that sits underneath the good salary and the impressive title and the LinkedIn profile that looks like everything is going exactly according to plan.

But rather than doing anything about it, they keep plugging away. Because the golden handcuffs of the salary, the prestige, the title, the certainty of knowing exactly what next year looks like is a real thing. And somehow, they get remarkably comfortable for something that is slowly suffocating them.

Leaving all of that to actually dig deep and figure out what lights you up from the inside, what could also sustain you financially, what your soul has been quietly asking for, that requires a kind of courage that a steady paycheck makes very easy to avoid.

Thoreau called it living a life of quiet desperation. Most people nod when they hear that line. Fewer realize they're living it.

Final Thought

A man's greatest burden is unfulfilled potential. Not failure… but, potential. The version of yourself that never got to exist because you kept choosing the safer, smaller, more socially acceptable dream over the real one.

That burden gets heavier every year you carry it.

So put it down.

Let yourself want what you actually want in full volume. Give the dream the wall space it deserves. And then wake up every morning and close the gap between who you are and who you know you're capable of becoming.

The Lamborghini on his wall wasn't a fantasy. It was a promise he made to himself.

What promise are you ready to make?

Catch you next week,

Shakila