Mike was 40, head of digital strategy and innovation at Bank of America, with a job that looked great on paper. He says that's the moment he realized he had become the corporate version of the person he'd spent his whole life saying he never wanted to be.

Today I’m launching Remix Career. It gives you what I give my coaching clients: a clear read on who you are at this point in your career, where to take it next, and the specific steps to get there. You upload your résumé and walk through a guided reflection in your own words. The AI, trained on my coaching methodology, reads what you wrote and produces a Remix Report with your career archetype, recommended directions, a skills analysis, an AI impact read on each path, and liv

Thomas had that question forced on him in the most extreme way possible. In 2021, he was six months from the exact age his father was when he died, and his grandfather before him. When he had a heart attack.

In a recent podcast conversation, I spoke with contemplative psychotherapist David Redish about how psychedelics and meditation can support people navigating these midlife transitions. Not as escapes, but as tools for awareness and reflection.

We’re living through a moment where the systems many of us relied on, work, institutions, routines, and expectations, feel less stable than they once did. The shift isn’t personal; it’s structural. Technology is accelerating everything, institutions are strained, and the traditional indicators of security no longer apply in the same way. People feel this in their careers, their identities, and the choices they’re being asked to make in midlife.

In this week’s Midlife Remix, I sat down with Paige Scott, Senior Partner and leader of the Asset Management practice at Kingsley Gate, to talk about the crossroads many Gen X leaders are facing: career transition, changing values, multi‑generational teams, and the courage it takes to live and lead from alignment. Below are the core themes from our conversation, the questions I’m asking clients right now, and a simple practice Paige swears by to re‑center your path.

We’re the generation who learned to rewind cassette tapes with a pencil, typed college papers in WordPerfect, and made calls from hallway...