There's Old, Then There's Bold [TMR #067]

You know the saying: "There are old pilots and bold pilots, but no old, bold pilots."

I've been thinking about this a lot lately.

And honestly? I think there's truth to it.

Not because being bold kills you, but because most of us stop being truly bold over time.

We think we're being bold. We take the "safe" risks. We make the calculated moves that feel scary but aren't really.

But the big, life-changing bold moves? The ones that actually matter?

Most of us chicken out.

I know I have.

There have been so many times I played it safe when I should have gone all in. Times I chose comfort over growth. Times I let fear disguise itself as "being responsible."

The Two Types of Bold

Here's what I've learned:

There's "business bold" and then there's "life bold."

Business bold is easier. It's launching that product, making that hire, investing in that marketing campaign. These feel risky, but they're not life-altering if they fail.

Business bold is easy to fake.

Life bold? That's different.

Life bold is having the conversation that could change your marriage. Picking up your family and moving across the country for something bigger than yourself. Cutting ties with people who are holding you back. Pursuing something you're passionate about even when everyone thinks you're crazy.

Most of us are pretty good at business bold.

We sometimes suck at life bold.

What Playing It Safe Really Costs

The thing about playing it safe is that it feels responsible in the moment.

But here's what I've learned: The biggest risk is not taking one.

Every time I've played it safe, I've paid for it later.

In missed opportunities.

You know what's actually risky? The regrest if looking back and realizing you spent decades just preparing...

Stop Waiting for Permission

You don't need permission to live boldly.

You don't need to wait for the right time. You don't need more money, more experience, or more certainty.

You need to decide that your life is worth more than your comfort zone and there is a much larger purpose than just business.

That conversation you've been avoiding? Have it this week. That place you've always wanted to live? Start making a plan. That relationship that's draining you? Address it or end it. That dream you keep talking about? Stop talking and start doing.

The people in your life need you to be bold too. Your family needs to see you take risks and fight for what matters. Your friends need to see what's possible when someone stops making excuses and starts making moves.

Your Move

I'm not writing this from some mountaintop of perfect decision-making.

Part of this is for me.

But here's the good news: It's not too late. For you or for me.

This week, pick one thing you've been playing it safe with.

Not the small stuff. The big stuff.

The life-changing, relationship-altering, future-defining stuff.

And do something about it.

Make the call. Book the flight. Have the conversation. Take the leap.

Your future self will thank you.

And more importantly, the people who love you will see what's possible when someone stops playing it safe and starts playing to win.

There are old people and there are bold people.

Which one are you going to be?