Why Changing Careers in Midlife Is So Hard (and Worth It)
Updated: 6 days ago
The program Scott McCue ran was on the cover of The Economist. A few years later, when he tried to start over in a new field, he spent eighteen months applying for jobs and couldn't get past the front door.
Most of the leaders I coach would recognize some part of that. When I ask a new client to tell me about themselves, most of them start with their job: the title, the company, what they've built. I did the same thing for most of my career, and it took me years to see how much of who I thought I was depended on what I happened to be running at the time.
Scott founded an organization when he was twenty-eight, hired every person who worked there, and ran it for ten years. It was a school, Boston Prep in Boston, and he was in the building by six every morning to shake hands with every student as they got off the bus. "This is the job I'm gonna do forever," he told me, "because it's who I am."
Eventually he decided the school was ready for new leadership, stepped away, and spent the next eight years running a program that trained new teachers. In 2020 he left education altogether to work on climate and nature, figuring it would take three or four months to find his way in. The people hiring for environmental jobs kept asking some version of "So you were like a school principal?" and it ended up taking eighteen months. "I knew I was gonna have to tell a complicated story," he said, "but I don't think I anticipated the silence."
I've heard that same question in other forms from a wealth management executive trying to move outside financial services and from a former CFO talking to startups. I see it with almost every leader I coach through a pivot. They can learn the new work, but going from someone everyone knows to someone nobody has heard of is a lot harder, and at some point they start asking themselves why they walked away from a place where they knew exactly who they were.
Scott still feels that pull. He went back to visit his old school recently and came home glowing, and his wife told him, "That is your existential safe place. You know who you are there." Most of us have a place like that, the old firm, the alumni dinner, the conference where everyone still knows your name. He still believes leaving was the right decision, so I asked him who he is now, without the school. I'll let you hear his answer from him.
There's one more story from Scott that I won't try to retell. Before Boston Prep, he worked at another school, and he spent most of a year chasing one student around the building. Years later, during the worst week of his life, he walked into a hospital elevator and there she was.
My full conversation with Scott is on the latest Midlife Remix, and the elevator story starts about seven minutes in. Link in the first comment.
Do you have a place like that, where you know exactly who you are? And what would it take for you to leave it?
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