Career Transition Episodes

During times of change, uncertainty can create fear about the future and whether the job you have today will be there tomorrow. That fear is compounded by a job market that can make even confident professionals feel powerless: you apply, you wait, and the silence starts to feel like a verdict. I dig into why that “stuck” feeling is showing up everywhere right now, from political upheaval and social tribalism to the looming uncertainty of artificial intelligence and the future of work. If you are anxious about what happens next to your role, your industry, or your professional identity, you are not alone, and you are not imagining the ground moving.

“Write a book, and you’ll become an authority” sounds like solid advice until you do the math on time, money, attention, and what that book is actually supposed to achieve. Host Eric Dickmann is joined by Ally Machate, a former Simon & Schuster editor and the founder of The Writer’s Ally, to pressure-test the myth that expertise automatically means you should write a book. We dig into why a book is a tool, not a trophy, and why it’s often the wrong next step when your business is still taking shape.

You can “win” your career, sell the business, and still wake up wondering who you are without the role. Host Eric Dickmann talks with Jack Calhoun, founder of Encore Career Lab, to get honest about the emotional and practical mechanics of a second act after a big professional exit. Jack had something many people don’t: financial runway. What he didn’t have was instant clarity, and that gap is where the real reinvention work begins.

A big title and a steady paycheck can still come with a surprising emotion: grief. When you wake up one day and realize you’ve outgrown the career that made you “successful,” it can feel disorienting, and even embarrassing, to admit that you want something different. I unpack why that misalignment happens, how it builds slowly over years, and why so many high-achieving professionals feel oddly guilty for not feeling more satisfied. We trace how career paths often start with a practical first jo...

Getting fired can punch a hole straight through your identity, especially when your career has been the proof that you’re “doing fine.” Mary Korn’s story cuts through that illusion. She had the title, the money, and the corporate ladder momentum, yet privately felt misaligned and depleted. Then she gets fired from a job she took in desperation and suddenly has to answer the scariest question of all: what now, with kids to support and no clear runway?

Success can look flawless on LinkedIn while still feeling wrong in your body. That tension is exactly where my conversation with Yvonne Furneaux begins and where it gets most useful for anyone thinking about identity reinvention, career change, or a second chapter beyond a corporate title. Yvonne spent more than 25 years in corporate communications, employee experience, HR, and DEI leadership, and she shares what she learned from working within large systems that don’t treat everyone the same.

A career can look successful and still feel strangely unfamiliar. Joe Arno spent decades building in sales, real estate leadership, and recruiting, only to realize that the work he was doing no longer matched the life he wanted to live. After a move, a bout with cancer, and one too many “shiny new” opportunities that didn’t fix the underlying problem, the misalignment became impossible to ignore.

Two widowmaker heart attacks will either break your story or rewrite it. I sit down with Adrian “AJ” Jones, a longtime financial services leader who had to confront the question most high performers avoid until something forces it: what if the life you built no longer matches who you are? AJ walks me through the early twists that pulled him from international relations into finance, how comfort can become a trap, and how “fine” can mask deep misalignment.

The strangest career clue is not burnout, it's relief. When concert cellist Kate Kayaian watched her entire performance calendar vanish during COVID, she expected panic. What she felt instead was a weight lifted, and that single emotional moment forced a bigger question: if the “dream” disappears and you feel freer, what does that say about your identity?

A layoff. A cross-country move. A booming coaching practice. Then a stroke that forced a hard pause. Chip Scholz’s story is a sharp reminder that career and identity reinvention rarely unfold as we script them, and that “success” can still quietly pull us away from the life we actually want.

Your job title can make introductions easier, but it can also quietly take over your identity. In this episode, I’m digging into what happens when we tie our self-worth to corporate roles, company logos, and the status that comes with them, then suddenly realize it feels unsettling or empty. After leaving the corporate world and starting my own solo consulting business as a fractional CMO, I ran straight into a strange reality: without the corporate infrastructure around me, my title didn’t car...

Your career can provide you with status, structure, and a straightforward answer to the question “Who are you?” Then one day, that answer stops working. Maybe you’re tired of climbing the corporate ladder. Maybe your role disappears in a layoff, merger, or firing. Or perhaps you decide to walk away. Whatever the reason, you might find yourself in a strange middle ground. No longer where you used to be, but not yet where you want to go. I’m Eric Dickmann, a former corporate executive who spent o...