Nonlinear Leadership: Why Straight Career Paths Don’t Lead to the C-Suite

The best career advice I ever received came from my mentor, a Chief of Staff, who told me to stop trying to make my path straight.

I was 24, working at the Governor’s Division of Medicaid, with my five-year plan mapped out clean, linear, predictable.

She listened, paused, and said, “No. Try again.”

So I did.

Same answer.

By the third attempt, I finally said, “Clearly, you see something I don’t. So tell me.”

She laughed.

Then she said something I’ve carried for more than two decades:

Stop trying to make your career path linear. Evaluate the risk in front of you.

Opt in when it matters, and don’t stay inside the box.

She told me that if she had stayed linear, she never would have reached the level she did. The defining moves weren’t forward. They were sideways, backward, and into unfamiliar territory.

I took that seriously.

Twenty-two years into my healthcare career, I stepped into the role of Director of Marketing at Hartsfield-Jackson Atlanta International Airport, the world’s busiest airport.

It wasn’t a straight move.

It was the right one.

The roles that define your career rarely look logical on paper. They make sense in hindsight. The discipline is knowing when to step into something that stretches you before you feel ready.

And the higher you go, the more true it becomes.

Leadership doesn’t always move up.

Often, it moves across.

The most important moves in my career didn’t look straight. They were intentional.

And they changed everything.

The career you’re trying to map perfectly right now may be the one holding you back.

Where in your career are you forcing something to be linear?