Back Together for Season 3: Friendship, Fresh Starts & Fall Transitions

After a long summer break, we’re back with Season 3 of Messy Middlescence! This first episode feels a bit like gathering at the kitchen table to catch up after being apart — we swap summer stories, reflect on the bittersweetness of how quickly it all went, and look ahead to the fresh start that fall always seems to bring.

One of the highlights: Tina shares her experience of completing her first-ever triathlon. It pushed her outside her comfort zone and reminded both of us how often, in midlife, we shy away from new challenges. Her story is a lesson in trying something different, facing nerves, and the joy of doing it alongside a friend.

That spirit of connection is what led us to choose our theme for Season 3: friendship and connection. We’ll be exploring the many ways relationships shift in midlife — how they deepen, how they sometimes fade, and why nurturing them matters so much as we move through this stage of life.

We’d love to hear from you, too: What role do friendships play in your life right now? Have you tried something new recently that surprised you? We would love to hear your answers to these questions.

In this episode you’ll hear:

• • Why summer can feel both precious and pressured — and what that means in midlife
  • How the school year can offer a fresh start for everyone, not just kids
  • Tina’s reflections on her first triathlon and the lessons it taught about trying new things, facing fears, and leaning on friends
  • Our reveal of Season 3’s theme — friendship and connection — and a look at the conversations to come