The Bonus Round: Crafting a Meaningful Post-Work Chapter

When life feels like freefall, most of us scramble for certainty. MIT lecturer and artist Aithan Shapira invites us to do something braver: treat uncertainty as a creative practice.

Join us for a live virtual conversation with both a painter and leadership advisor who coaches NASA teams, governments, and heads of state while teaching at MIT’s Sloan School of Management. He sees the practice of painting and the practice of inner growth as the same discipline: getting a perspective on your own perspective, and learning what to let go.

We’ll look at midlife as a “cubist painting,” the art of deep listening, and the capacity to let go when old identities have stopped being true.

MEA CEO Derek Gehl sits down with gerontologist and longevity advocate Barbara Waxman for a real-world conversation about what actually matters when it comes to living longer – and better.

We’re living in a moment flooded with longevity advice: supplements, protocols, biohacks, and bold claims. But beneath the noise, a more important question often gets lost: how can we age well in a way that’s personal and sustainable?

In this session, Derek and Barbara explore what it means to become “a study of one” – how to tune into your own signals, make smarter choices, and move forward with clarity instead of overwhelm.

For anyone navigating midlife who wants a more grounded, personalized approach to longevity.

MEA founder Chip Conley sits down with sociologist, master coach, and bestselling author Martha Beck to explore what it really means to live in integrity in midlife and beyond.

Drawing from Martha’s book The Way of Integrity and her upcoming MEA workshop, they’ll unpack how we drift out of alignment through people-pleasing, cultural “shoulds,” and stale identities – and how to begin the gentle work of coming back to what’s true.

You’ll hear practical insights on reading your inner signals, questioning inherited beliefs, and making small shifts that bring your outer life closer to your inner knowing. This live virtual session is for anyone who’s curious about a more honest, joyful next chapter.

If there’s a book in you – even just a messy draft or an idea you keep coming back to – this one’s worth showing up for.

Derek’s sitting down for a virtual chat with Kelly Notaras, who’s edited more than 200 books over 25 years, a few of them New York Times bestsellers. She wrote The Book You Were Born to Write and founded KN Literary Arts. And she’s unusually good at seeing what a book wants to be before its writer does.

They’ll get into why writers stall out even when they know what they want to say – and how you keep moving without waiting for some mythical free time to open up. Plus the honest version of how a pile of scattered pages becomes a finished manuscript.