What happens when you’re 45, 55, or even 65… and career change isn’t a choice—it’s forced?

In this episode, Kevin and Joe break down the real psychology behind midlife career transitions, especially when other people depend on you. If you’ve been feeling restless, drained, boxed in, or secretly craving a second chapter… this conversation will hit home.

Kevin and Joe bring a grounded mix of midlife coaching insight + real lived experience, including firsthand experience with layoffs, career pivots, and rebuilding identity after a major professional reset.

“It’s not something somebody could flippantly advise… you got a lot more concerns than just, ‘I look dumb here.’”

“The task of midlife is not to look outside for answers, but to look within…”

“The most important person in the world is watching everything that you do—and that’s yourself.”

“You don’t need to be stuck in this thing of something that you said you didn’t want in the first place.”

“We are not here to fit in… We are here to become ourselves.”

1. Midlife career changes after 45: why they’re rising.
2. Provider pressure + identity crisis in men.
3. Fear of incompetence and sunk-cost fallacy.
4. Family expectations and lifestyle resistance.
5. How layoffs can become a “calling”.
6. Finding alignment vs forcing discipline.
7. Transferable skills and resume reframing.
8. Blue-collar opportunities and buying businesses.
9. Why communication with your spouse is crucial.

1. Midlife career change isn’t only professional, it’s personal identity.
2. Don’t ignore the inner restlessness—explore before you’re forced.
3. Look for the through-line: what wants to come to life in you now?
4. You’re more qualified than you think—your experience contains transferable skills.
5. Discipline without alignment becomes misery. Alignment creates discipline naturally.
6. If your marriage can’t handle these conversations, fix that first.

1. James Hollis - The Middle Passage.
2. Carl Jung (unlived life concept).

If this episode inspired you to reconnect with joy and curiosity, please...