I hear some version of this almost every week…
“I’m good at what I do, but it’s not what I love. I want to go in a different direction. I just don’t know if that’s even possible at this point.”
It is.
But the fear of change, the anticipation of being told what will go wrong or what you will ‘lose’, holds most people back from even trying.
Let’s look at it differently.
The years you’ve spent becoming excellent at something or building a career in a certain direction, they don’t disappear when you pivot. They travel with you.
I think about a CFO I’ve heard about, someone who spent years building companies, helping them grow and get sold, then quietly wondering, “Now what?” His real love had always been designing jewelry. An art he’d set aside because someone told him it wasn’t a safe bet. He’d never make money at it. He’d always be a ‘starving artist’.
When he finally gave himself permission to pursue it, he walked into retailers to pitch his work. He didn’t talk about the stones or the colors or the artistry. He talked about margins. He spoke the language of the corporate buyers who would be selling his jewelry, because he’d spent a career speaking it.
His background wasn’t his obstacle. It was the advantage.
I know this territory personally. I left a great corporate career to build my company. People tried to talk me out of it. And honestly, I felt the fear of failure. But two things got me through: 1) I believed in myself, and 2) my family said “go for it.” That kind of support is so important. The absence of support is what holds more people back than fear ever could.
The CFO had it. I had it. And when I work with people who are ready to make that kind of change, part of what I’m doing is becoming that person in their corner.
If you’re the marketing director who wants to open a food business, those twenty years of brand strategy are how you’ll tell that story better than anyone else. If you’re the operations leader who wants to teach, you’ve spent years figuring out how people actually learn. You’re already more prepared than you think.
The question isn’t “how do you leave what you’ve built behind?” It’s “how do you take it with you?”
Before we ever get to resumes or job titles or business plans, I ask even simpler questions: “What did you love doing when you were 8, 12, 15 years old?” “What do you find yourself doing in your free time now, or wishing you were doing?” “What shows do you watch, what books do you pick up, what conversations make you lose track of time?”
Those answers aren’t nostalgia. They’re data. They point toward something real about who you are, and often, they point toward where you could be going.
The logistics—the money, the ramp-up time, the fear of starting over—those are real, and we’ll get to them. But the plan comes after the direction, not before.
If you’re wondering whether a new direction is even possible for you, start there. What did you love before anyone told you it wasn’t practical or possible?