Playing With House Money

In 2016, I hired a guy, we'll call him Matt. He left the role. Then in 2018, I was hiring for another team I was building, and I hired him again. If I had the opportunity, I would hire him a third time. He's just one of those guys who is trustworthy, a hard worker, and you can sort of point in the right direction, and he's going to go make things happen.

Then, about a year ago, he told me he was battling cancer. More specifically, he had a tumor the size of a football in his chest. The outlook wasn't great, but after rounds of chemotherapy, a twelve-hour surgery, and several months to heal, he's getting back in action.

So when he called me yesterday, my advice was simple.

"You're playing with house money. You cheated death. So live your life the way you want to live it. Don't let anything hold you back, and go do what makes you happy. Basically, put it all on red every single day."

The question is, how different would you live after an experience like that? How would you approach your career? How would you approach personal relationships? What would you focus on and what would you defer in terms of emotions or challenges? And more importantly, what risks would you take as a result?

Because here's the truth, most people never learn until it's too late: we all think we have time. We treat risk like something we can negotiate with, as if the right moment will eventually present itself when the stars align and the path is clear. We tell ourselves that we'll take the leap after one more promotion, after one more bonus, or once we finally feel ready. But the reality is that the timing is never perfect, and the people who keep waiting for it often wake up years later, realizing they've been living out someone else's version of success rather than their own.

When you've looked your own mortality in the face, that illusion starts to fall apart. The things that used to feel so important — titles, recognition, status, and the opinions of other people — start to lose their weight. You stop chasing what looks good from the outside and start paying attention to what actually feels meaningful on the inside.

When you've faced the possibility of losing everything, the usual fears — failure, rejection, judgment — stop deciding for you. What's left is a kind of quiet clarity about what you actually want, and a deeper conviction to follow through on it while you still have the chance.

That, to me, is what 'playing with house money' really means. It isn't just about luck or survival; it's about permission. Permission to bet on yourself without apology, to live a little louder, and to stop postponing the things that make you come alive.

So even if you haven't faced something as life-altering as a tumor the size of a football, the question still remains: what are you waiting for? You don't need a crisis to start living as though your time matters. You can decide now to stop playing small, to stop overthinking, and to stop assuming that another chance will always be waiting. You already have the gift of being here today, and that alone is more than enough reason to take the next step toward the life you actually want.