The Freedom to Thrive: What I Learned from a $500M CEO

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At 10:30 am every second Tuesday, I interview the CEO and Creative Director of a $500M brand.

Two hours in his calendar, every month. My only job is to ask questions.

It’s intense.

We’ve met like this since November 2023. Our conversations range wildly - from why luxury fashion is good for the world to why mainstream media thrives on fear and negativity.

But last week? Things got real.

We were reviewing 2024—one of his company’s most successful years to date. I tossed out a question I thought would require deep reflection:

“What’s been the key to your success this year?”

I expected silence, a long pause, maybe a contemplative stare out the window.

Instead, his answer was instant, sharp, and completely unfiltered:

“Doing exactly what I want to do.”

He let it hang in the air for a moment before continuing:

“My desire is to do things the way I feel, the way I want. Then I surround myself with the people I want to work with.”

At first, his response felt jarring. Simplistic. Self-centred. Arrogant, almost.

But deep down, I knew it struck a nerve because it mirrored the very reason I became a solopreneur:

To do exactly what I want to do.

I pressed him further, and he elaborated:

“Not everything I do works. It's normal not to succeed in everything. So, what’s important is to do what I like and not listen too much to others.”

He paused a beat, then added:

“Listening too much to others leads to failure.”

Those words flipped a switch in my head.

I care a lot about what others think of me. Too much, in fact. At my worst, I crave recognition from people I respect—sometimes more than the success itself. It’s why I listen to so much advice, absorb so many opinions. People-pleasing 101.

But lately?

I’ve been leaning into my freedom.
Leaning into doing exactly what I want.

It’s liberating. It’s terrifying. And it’s transforming me as both a creative person and a business owner.

For the first time, I’m doing and creating things I used to only dream about.

So I had to ask him one last question:

“Where does your self-confidence come from?”

His answer surprised me again:

“I’m confident in myself, but at the same time, I doubt myself constantly.”

It’s comforting to know I’m not the only one.

When was the last time you did exactly what you want to do?

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