Saturday morning, I walk to the farmers market with a list in my head: salad, tomatoes, kale, cheese, sausage, enough food for the week. I'm moving fast, eyes scanning stalls the way I'd scan a grocery aisle, and I get everything on the list in about twelve minutes. It's efficient. I also walk right past a little New Orleans-style jazz ensemble playing near the entrance without really hearing them, and I don't see a single person the whole time. If you've spent years buildin

I was standing in the San Francisco airport when my left arm and neck went numb, my heart started racing, and I was sure I was having a heart attack. The EKG came back normal. My doctor told me that if I didn't learn to reduce my stress, the next one would be real. That was the cost of decades of working hard on terms I had never stopped to examine. Last week, a 22-year-old described what I was missing better than I ever have: "Our generation recognizes a bad deal when

"AI amplifies what the leader brings. If the leader brings confusion, you get confusion at speed. You get chaos. If the leader brings clarity, you get clarity and execution at speed." That's Jack Swift, back on the Midlife Remix this week. If a leader walks into Monday's meeting confused about what it's even for, everyone goes back to their desks, opens Claude or Copilot, and starts querying from that confusion. The leader's inner state has become a business variable.

Last night, I almost turned off the game that became the biggest comeback in NBA Finals history. That urge to skip the hard part is one I know well at work and in my career, and one I watch the leaders I coach give in to all the time, usually right when it matters most.

It’s a reasonable bet, and until this year it was a safe one. Then Meta cut about 8,000 jobs this May, a tenth of the company, and Groupon roughly a quarter of its workforce, both to move the money into AI, and the people cut were largely experienced, well-paid, and supposedly untouchable. Being competent but no longer engaged doesn’t protect you the way it once did.

Most of the leaders I coach describe themselves as driven, strategic, maybe a little intense. But underneath the drive, there's often a vigilance that never turns off, a background calculation running before every decision: what could go wrong here, what am I exposed to. It doesn't feel like fear, it feels like being thorough.

For twenty years, I did what most driven leaders do: I worked harder, earned more, rose higher, and assumed I’d eventually arrive at a life that felt right. And by most measures, it worked. I had the career I’d been building toward since my twenties.

I've been noticing something in myself lately, and I wonder if it's true for you too. My days are full. Work, kids, aging parents, and the constant demand for everything that needs attention. I'm rarely alone. And yet, something's missing. I think it might be loneliness. Not the kind where no one's around. The kind where you're surrounded by people but not really with any of them.

In my coaching practice, I work with capable, emotionally intelligent leaders who are often overlooked, not because they lack results, but because they don’t dominate meetings or make everything about themselves. Many of them work for narcissistic bosses, leaders who avoid responsibility, take credit for others’ work, and care more about optics than outcomes.

We spend our lives chasing success; climbing the corporate ladder, making more money, and proving ourselves. In midlife, we question what to do once we achieve it, or why we keep pursuing it when we haven’t.