What If the Bigger Risk Is Staying Where You Are?

We talk about risk as if it only exists when we make a change.

Leaving the job is risky. Starting over is risky. Going back to school is risky. Walking away from a career you’ve spent decades building is definitely risky.

But we rarely talk about the risk on the other side of that decision: staying.

I kept thinking about this during my conversation with Captain Carole Hopson.

Carole had wanted to fly airplanes since she was four years old. But like so many dreams we have when we’re young, life happened around it. She built a successful career. She got married. She became a mother. And becoming a pilot remained this thing she wanted to do someday.

Then, at 50, “someday” started to feel a little more urgent.

She knew exactly what starting an airline career at 50 would mean. She would be beginning again at an age when most people are being told they should be protecting everything they’ve already built. She’d be older than many of the people training alongside her. There were financial realities to consider and absolutely no guarantee that it would work out the way she hoped.

But Carole realized something that I think a lot of us miss when we’re trying to make a big decision.

Not doing it had a cost too.

She told me, “I was more afraid not to than to do it.”

That stopped me.

Because how often do we calculate risk by looking only at what could go wrong if we move?

What if I lose money? What if I fail? What if I look ridiculous starting at this age? What if I leave something stable and regret it?

Those are legitimate questions. But there’s another set we don’t ask nearly enough.

What if I’m sitting in exactly the same place five years from now? What if I never find out whether I could have done it? What if the thing I’m protecting so carefully is also the thing keeping me from the life I actually want?

Carole didn’t recklessly blow up her life. That might be my favorite part of her story. She planned. She figured out what the dream would cost. She saved. She surrounded herself with people who could help her think through it. She gave the dream a date.

And then life still didn’t cooperate.

Her path into aviation was interrupted by 9/11. She became a mother. Years passed. The timeline she originally imagined disappeared.

She could have taken all of that as proof that she had missed her chance.

Instead, at 50, she decided it was now or never.

Today, at 62, she’s a Boeing 737 captain.

I don’t think the lesson here is that everyone should quit their job and chase the dream they had when they were four. Sometimes staying is the right decision. Sometimes the financial reality really does mean not yet. Sometimes the dream itself changes.

But I do think we owe ourselves a more complete definition of risk.

Because staying somewhere simply because it’s familiar isn’t automatically the safe choice. There can be a cost to postponing the life you keep thinking about. There can be a cost to waiting until you feel completely ready. And there can absolutely be a cost to assuming your age has made the decision for you.

Carole said something else during our conversation that I wrote down immediately:

“The difference between a dream and a goal is a date.”

So maybe the question isn’t, Am I too old to do this?

Maybe it’s: If I still want this, what would it actually take to begin?

And perhaps the most important one:

Which scares me more, trying or never knowing?

My full conversation with Captain Carole Hopson is out now on The Tamsen Show. Listen to it here or watch it here.

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