The aroma of bacon and coffee wafts through the air, a stark contrast to the weighty conversations unfolding around me.

It’s July 2024, I’m sitting in a large conference room with endless round tables eating a hot breakfast alongside mediocre, hotel-calibre coffee.

Sitting next to me is a ~40 year-old man named Toby. Toby sold his business for over $400m three years ago.

I’m sharing my experience building a social media audience, what it was like getting started, and how it’s changed my life. 

He tells me that he’s starting a family office to buy new businesses. He wants to build his own social media audience to support entrepreneurs and win deals for the family office. But, he’s got a problem. He’s insecure about sharing openly online. He’s worried he’ll be judged. He’s worried people won’t find what he has to say interesting.

I resonate deeply with this: “Wow, that’s exactly how I felt when I started.”

It’s 3 hours later, I’m seated in a breakout room listening to another man, similar age, called Michael. He sold his business two years prior for over $200m, fully bootstrapped. It’s a champagne problem, of course, but he’s talking about what it was like to put his heart and soul into something for 10 years before practically having nothing to do overnight.

He shares why he started. He shares why he sold. He shares that all the way along, he struggled deeply with insecurity. 

When he was getting started: insecurity. 

When he was hiring impressive people: insecurity. 

When he sold his business: insecurity. 

A pervasive feeling of not being ‘enough’ has never left him.

Neither of these were a surprise to me. They confirmed a pattern I’ve observed the more time I’ve spent with people that I admire and who have done great things.

They have insecurity just like everyone else. Often more.

The difference is: they proceed in spite of their insecurity. They put themselves in environments that challenge them to become a greater version of themself.

Because they know a fundamental truth: to be insecure is to be human.

Tim Ferriss so eloquently describes this:

“If you are insecure, guess what? The rest of the world is, too. Do not overestimate the competition and underestimate yourself. You are better than you think. The fishing is best where the fewest go, and the collective insecurity of the world makes it easy for people to hit home runs while everyone else is aiming for base hits. There is just less competition for bigger goals.”

The next time you’re putting something off because you’re insecure, remember this: insecurity is a sign that you’re doing something that actually matters to you. Stepping out of your comfort zone. Putting yourself in the firing line of rejection. Stepping up to give yourself a better life than the one you have now. 

The alternative is comfort all the way along. Never stepping outside your existing boundaries. 

What a shame it would be to live your life that way.