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...