Sixteen conversations from the show, organized into the eight categories of a thriving next chapter. Listen by what you're working on — not by what came out last.
The Retirement Drift Assessment takes five minutes and surfaces the categories where your week is most at risk. Then come back here and listen by category.
Two conversations with authors Teresa Amabile and Joanne Lipman of the best books I've read on retiring and transitioning. If you've only got time for two, choose these.
Each of the eight categories below has one or two episodes selected as the strongest starting points. Pick the category you're avoiding, not the one you're already good at.
If everything else on this page is the curriculum, these two are the orientation. Listen in either order, both are worth your time.
Wellness, Relationships, Lifelong Learning, and Fun & Rest. These aren't electives. The data is consistent across decades of research — if these four aren't on your week, very little else holds up.
Workouts, sleep, medical care, brain health — the foundation everything else compounds from. The research is annoying in its consistency: people who keep this category active in retirement do better on essentially every other dimension. People who don't, don't.
The two episodes below take different angles. Ezekiel Emanuel pushes back on a lot of the longevity industry's noise; Majid Fotuhi gets specific on cognitive protection. Both are useful.
"If my health drifted 20% over the next year, which dimension would slip first — and what would the early signal be?"
The Harvard Study of Adult Development is now in its ninth decade. The headline finding hasn't moved: the quality of close relationships predicts well-being in later life better than wealth, fame, IQ, or even physical health at midlife.
Marc Schulz is one of the two current directors of that study. Marisa Franco gets practical on the hardest part — making new friends after work no longer provides the scaffold.
"Who are the three friendships I want to be closer to in 12 months than they are today — and what would it actually take?"
The cognitive case for learning in later life is well established. The deeper case is about identity — a learner is someone who is becoming, not just being. In retirement, becoming has to be chosen, because nothing else is going to assign it to you.
Lorraine Besser brings a philosophical frame (interestingness as a third dimension of the good life). Tom Vanderbilt brings the lived experience of awkwardly being a beginner again in your 50s, 60s and beyond.
"What's a question I'm genuinely curious about that I've never had the time — or permission — to actually pursue?"
Without work to rest from, rest stops feeling earned — so it stops happening. Fun has the same problem. Both have to be designed in, or they disappear in plain sight.
Mike Rucker frames fun as a structured practice; Catherine Price distinguishes true fun (connected, playful, flow-inducing) from "fake fun" (passive, screen-mediated). Both episodes are unusually practical. And fun!
"When was the last time I had genuine fun — not the screen kind, the actual kind — and what did the conditions look like?"
Service, Creative Pursuits, Purposeful Work, Personal Growth. The strongest retirements have at least two of these unlocked and active. Not all four. That's overkill. But one or two might be just right for you.
Senior leaders — especially the ones who ran teams of hundreds — feel the loss of being needed at scale more acutely than they expected. Service is how that capacity finds a new outlet without requiring you to start a nonprofit at 65.
Brad Aronson's frame (small acts, sustained) is a counterweight to the "must do something big" instinct that paralyzes capable retirees. Benita Cooper's project shows what's possible when ordinary acts of recognition compound.
"Where is my professional experience most useful to someone who doesn't yet have it, and how could I be a quiet resource to them?"
The "I'm not really creative" objection is, in my experience, the single most reliable predictor that someone needs this Elective specifically. The research on creative engagement is decisive, it has measurable mental health and longevity effects regardless of skill level.
Daisy Fancourt is one of the leading academic researchers on the topic. John Weiss is the practitioner, a former police chief who built a full creative life after a long career in something else entirely.
"What's something I used to make — write, draw, build, cook, play — that I quietly stopped? What would it be like to start again?"
You retire from a job, not from meaningful work. The fastest-growing pattern in retirement isn't full leisure — it's selective, purposeful work on your own terms. Encore careers, advisory roles, board service, consulting, mentoring, teaching.
Chris Farrell gives the macro view from years of economics journalism. Richard Eisenberg gives the honest first-person account of his own "unretirement," the trade-offs included.
"If I were going to do one piece of purposeful work in the next year — paid or unpaid — that uses what I'm best at, what would it be?"
You don't stop growing because you retired. The interior work — what kind of person you're becoming, what you're making peace with, what you're newly able to see — continues whether you attend to it or not. The question is whether you make it deliberate.
Arthur Brooks brings the research framework (Strength to Strength is one of the foundational texts for this entire program). Cynthia Covey Haller brings the philosophy her father Stephen Covey developed in his final decade — that your most important work is always ahead of you.
"In what specific way do I want to be different — more whole, more honest, more skilled at being human — twelve months from today?"
If something on this page surfaced a category worth working on, or a question worth holding, a 30-minute conversation might be the right next step. No pitch — just an honest look at where you are.
Book a Free Conversation