Retire Often Why the Best Leaders Take Halftime Seriously: with Jillian Johnsrud

Jillian Johnsrud has taken thirteen mini retirements (sabbaticals) over the last twenty years. She's raised five kids (three adopted), built and renovated rental properties that changed her family's financial trajectory, and coached hundreds of leaders through their own sabbaticals. Her new book Retire Often might be the most practical and philosophically rich thing written on the subject.

She joins Alan Briggs for a conversation about something most leaders get wrong: the assumption that caring about your work means never stepping away from it.

Who this episode is for

If you're a leader who runs hard and assumes the operation falls apart without you. If you've watched peers burn out and quietly wondered when it's coming for you. If you're caught between a 60-year-old generation that grinds and a 25-year-old generation that won't, and you're trying to figure out a third way. If your identity is so wrapped up in what you do that you're not sure what's underneath it. This one is for you.

What you'll take away

The halftime analogy that reframes extended rest as competitive strategy, not indulgence, and why the leaders running sprints through their break aren't the ones winning long term

A clear three-part definition of a mini retirement (one month or longer, away from your primary profession, focused on something meaningful) and how that differs from a vacation

How to address the four objections that stop almost every leader from doing this: money, work obligations, "what would I even do," and "what if it goes badly"

Why "my whole identity is my work" isn't a badge of honor, it's a problem to solve before it solves itself

The "spring cleaning" effect on your business or team when you step away, and why most leaders come back to a tidier, more efficient operation than the one they left

Why your sabbatical plan is a hypothesis and your sabbatical reality is an experiment, and how that one reframe eliminates the emotional suffering most leaders inflict on themselves

What Jillian thinks AI is about to change about leadership, and why the companies that figure rest out are going to dominate the next twenty years