Playing it safe cost me, not in losses—but in missed opportunities

Playing it safe cost me, not in losses—but in missed opportunities.

I’ve always been someone who works hard.

I put in the hours in school, studied relentlessly, and earned solid grades.

But I was never the top student.

In sports, I played on great teams and was often one of the top players—but rarely the best.

Even now, in pickleball, I’ve trained, taken lessons, and worked my way into the top 100 players in my state.

But I see younger players, former college tennis players, stepping in and surpassing me with what looks like half the effort.

The same has been true in business.

I’ve built a strong reputation, landed great clients, and created momentum.

But when I look at my revenue growth, it’s not accelerating at the pace I want.

Throughout my life, I’ve taken smart, calculated risks.

Bootstrap.

Reinvest.

Look for positive signals before doubling down.

But the gains have been incremental, not exponential.

And that’s when I started to ask myself:

What’s holding me back?

The truth is, I’ve always believed that if I work hard enough, I will achieve a breakthrough.

But maybe that’s the wrong mindset.

Maybe the difference between the top 10% and the top 1% isn’t effort—it’s leverage.

It’s not about just working harder.

It’s about playing a bigger game.

So now I’m thinking differently.

Maybe it’s time to go all in.

Maybe it’s a bold move—making a key hire, securing an investment, or pivoting into a higher-value market.

Maybe it’s something I haven’t even considered yet.

And maybe you’re in the same position.

Grinding away, putting in the hours, seeing success—but not breakthrough success.

If that’s the case, ask yourself this:

What’s the move you’re afraid to make?

Because if you keep playing it safe, you’ll keep getting what you’ve always gotten.

The next level won’t come from doubling your effort but from betting on yourself at a higher level.

If you risk nothing, then you risk everything.