Jim Moorhead has been in courtrooms, war rooms, and boardrooms ... and the only career advice he ever rejected was "stay put." A former federal prosecutor, Goldman Sachs M&A banker, statewide political candidate, and crisis communications advisor, Jim built a career that looks like it doesn't add up until you understand what was driving it. Range wasn't an accident. It was the strategy.

In this conversation, Jim gets into why generalists are being squeezed out by companies demanding specialists, why leaders default to control, harmony, and being right when things get hard, and why bravery isn't a personality trait — it's a system you build before you need it. He also makes the case that harmony without honesty is just quiet dysfunction, and most organizations are running on exactly that.

For senior executives navigating a career transition or thinking seriously about their next move, Jim's framework on operational courage reframes what leadership reinvention actually requires. This is a conversation about executive career strategy, range, and what separates leaders who thrive from the ones who stall.

Follow Who Moved My Career?! on Spotify or Apple Podcasts and leave a review if this one made you rethink the comfort you've been protecting.

Most executives know how to climb. Nobody teaches them what to do when the ladder moves.

Julian Lighton spent decades running P&Ls at Cisco and Hitachi, advising boards, and watching sharp leaders stall out at the exact moments they should have accelerated. He wrote Navigating Your Next because he kept seeing the same pattern: people who were exceptional at progression — titles, influence, external validation — with no real sense of what they were actually good at or what they wanted next.

Julian breaks down the four career transitions every executive will face, why most people hit stages three and four completely unprepared, and the distinction between progress and progression that changes everything. He also walks through the competence-context-culture framework he uses with coaching clients and why knowing what you want is the only real prerequisite to getting it.

For senior executives navigating career transition, leadership reinvention, or the question of what comes after a big role, this one is worth the hour.

The gap between ambition and self-awareness is where most executive careers get stuck. Julian Lighton has spent 30 years working with senior leaders on executive career strategy, decision-making, and the transitions that define a career.

Follow Who Moved My Career?! on Spotify or Apple Podcasts and leave a review if this one made you think.

Satta Sarmah Hightower quadrupled her salary going freelance. By year seven, she'd crossed seven figures in revenue. By year ten, multi-seven figures. She didn't plan any of it. Two layoffs ended her journalism career during the Great Recession. A cross-country move bought her time. One former colleague hired her for a contract role — and she never went back.

Satta is a B2B tech content marketer, 12-year full-time freelancer, and author of The Forever Freelancer, out in June. In this conversation, we get into the myths — no, it's not just for creatives; no, it's not financially reckless — and the mechanics of finding clients without Fiverr. We also talk about the mindset shift that separates the people who make it from the ones who quit: stop thinking like an employee.

We get into AI as leverage, caregiving, the broken corporate promise, and why if no one is saying no to your proposals, you're undercharging.

For senior executives navigating career transition, Satta makes the financial case for self-employment in concrete terms. Whether you're exploring fractional work, a portfolio career, or a full break from corporate, this episode is a masterclass in career reinvention on your own terms.

Follow Who Moved My Career?! on Spotify or Apple Podcasts — and leave a review if this one made you rethink your options.

He has one question tattooed on his arm: When was the last time you did something for the first time? For Gabriel DeSanti, that's not inspiration — it's infrastructure. He's a full-time content creator and co-founder of Staj who has gone to work across nearly 200 industries, filming two-minute windows into what jobs actually feel like from the inside.

Most of our guests figured out their path after a disruption. Gabriel is building the thing that might have prevented the disruption entirely. He went to a trade school that spent a full year letting students try everything before committing to anything. He never got over how rare that was.

In this episode, we get into why he walked away from a clear engineering path at 19 because one boss change showed him how fragile job satisfaction is, what nearly 200 jobs have actually taught him about what makes work meaningful, and why the first rung on the career ladder being broken might be the best argument for what he's building with Staj.

Every executive we've talked to has a version of the same regret: I wish I'd known sooner. This episode is for that.

Follow Who Moved My Career?! on Spotify or Apple Podcasts. And if this one landed, leave a review.

A "Mack Truck Moment" is the thing that hits you out of nowhere and takes the plan completely off the rails: Job loss. A diagnosis. A market that shifts under your feet. Omar Garriott coined this term and...yeah. Haven't we all been there. Omar has spent 25 years building a career around one filter: impact. Through Apple, Salesforce, LinkedIn, and Qualtrics, when his Mack Truck came, that filter is what held. His point of view on the power of non profits and their essential place in this world will make you rethink the order of the world. Omar is now Executive Director of the Batten Institute at UVA Darden, and in this conversation we get into what to do when the Truck comes for you. We also debate LinkedIn. He wrote the book on it. I still call it the digital sewer, but will admit he makes some valid points!
For senior executives navigating your career, the question isn't whether disruption is coming, it's whether your network and sense of mission are strong enough to hold when it does. This episode covers executive career resilience, mission-driven leadership, and how to really use LinkedIn properly. Follow Who Moved My Career?! on Spotify or Apple Podcasts — and leave a review if this one made you think.

Chuck Hutchinson grew up on a farm in Malvern, Ohio. Baseball was the plan — left-handed pitcher, natural curve — until a fractured elbow at 14 forced a pivot to football. He got knocked around as a freshman. He grew. Woody Hayes showed up at his parents' house, spent three hours with them and five minutes with Chuck, and handed him the 21st — and last — scholarship in the 1966 class.

He became an Ohio State Buckeye (and beat TUN). He played (and started) for two teams in the NFL. Then he wrote a book called Getting My Hands Dirty — part memoir, part reinvention handbook.

In this episode, Chuck and Nicole dig into what his story teaches about building a career in the dark — when the original plan is gone, when the path wasn't yours to choose, and when the only real option is to focus on what's in front of you and do the best you can with what you can control. He's been running that play since he was a kid. It still works!

Astrid Weisseise spent 35 years building a corporate career that looked exactly like success was supposed to look. Titles. Responsibility. A workload that followed her on every vacation she tried to take. Then she did something most executives only think about: she cashed in two years of banked overtime, booked a one-way ticket, and spent months traveling through the U.S., Hawaii, Bali, and South Africa figuring out who she actually was outside of a job title.

What she came home with wasn't a retirement plan. It was a blueprint.

Today Astrid runs The Corporate Escapee — a platform and Solopreneur Playbook helping professionals turn their corporate experience into something they actually own. She coaches. She creates. She's built a significant following on TikTok and Instagram. And she's constructed a genuine portfolio career: multiple income streams, full ownership, none of it dependent on any single employer's org chart.

Call it a lot of things but do not call her an influencer!

In this conversation, Astrid and Nicole dig into what the leap actually looks like from the inside, and what it really means to build a career on your own terms — not as a concept, but as a functioning business.

Traci DiMartini has seen it all. As a senior HR executive across multiple federal agencies, including a tenure leading human resources at the IRS. She spent decades making sure employees were treated with dignity during the hardest moments of their careers. She was the person in the room. The one who knew how it was supposed to go.

Then the rules changed. And she found herself on the other side of the table.

Here's the thing about Traci: she also survived a literal explosion in her apartment. And somewhere in the wreckage, she found something a lot of executives spend years chasing: perspective on what actually matters when everything gets stripped away.

In this episode, Traci and Nicole get into what federal service really looks like from the inside, what job loss does to identity, and why the people dedicated to serving 330 million Americans deserve a hell of a lot more credit than they get. Traci is funny, direct, and completely unbothered by saying the quiet part out loud.

She went through the fire. Her light's still on.

Bill Fitzgerald, CEO of FitzDrake Search, returns for round two.

In this episode, Nicole and Bill get into the realities of the 2026 job market — still brutal for the long-term unemployed — and why most executives are misreading how recruiters actually work. They cover AI's real (and limited) role in job searching, what your resume is failing to communicate, the mechanics of meaningful networking versus transactional networking, and why career pivots are harder than anyone admits.

Bill also shares one deceptively simple tip that most senior candidates overlook entirely. If you're in transition — or plan to be — this is the intel you need before you make your next move.

Jim Chilton didn’t start his career in technology.

He started at Mr. Donut.

In this episode of Who Moved My Career?, Jim shares how discipline, grit, and a healthy chip on your shoulder can shape a career far beyond where you begin.

From early lessons in work ethic to executive leadership in technology and education at Cengage, Jim walks through the pivots that defined his professional growth — and the mentors who helped him along the way.

We discuss:

• Career development and mentorship
• Navigating imposter syndrome
• Why understanding both technology and business matters
• Using Ikigai to align career ambition with personal purpose
• Why “your career is your responsibility”

This conversation is for anyone navigating a career pivot, feeling stuck in their current role, or trying to design a career plan that prepares them for opportunities anywhere — not just inside one company.

Because sometimes a little paranoia keeps you sharp.
And sometimes a chip on your shoulder becomes your edge.

🎙️ Topics: career growth, mentorship, cybersecurity training, leadership development, professional pivots, imposter syndrome, Ikigai, education technology, Cengage