Oct 7, 2026 · 43 min · 11 segments
The first six months of retirement may be the easy part. At first, there may be travel, projects, and long-awaited plans to fill the time. But once the dust settles, retirement can begin to feel…
I think not everyone has that ability or willingness to ask those very deep questions of themselves to really go inside.
You know, 'cause it's like, you know, you, you, you have your marching orders and you go forward, right? And, um, to stop and say, "Hmm," you know-
... "I'm going in, I'm going in this direction because it speaks to me," or it, it's, it's b- becomes an, an obvious answer.
And, and I would argue that that is the best thing about retirement, right? Because it's one of those natural times in life where, you know, the demands might not have been as, as immediate as they were throughout your career, um, but it's a fantastic time to lean into that, those kind of parts of yourself that might have been, you know, pushed a little bit to the shadows, um, and, uh, you know, do a bit of a dive and figure out what fulfillment looks like.
Here you are on the front lines of, you know, work- working with- You know, successful, high achieving men and, and women, I, I, I, I expect.
And what are, what are some of the, the big issues that you're seeing in this demographic? And men especially, since Chapter Ex is really aimed more to men, although, you know, as I can...
as I say all the time, you know, there are women who absolutely fit the same model of difficulty, uh, in that transition, and think the, you know, think the same way, experience the same things.
I think one of the big themes that I'm seeing now, and we may have touched on it the last time, but it's even in the last two years since we spoke, I've- it's sort of played out a lot in the consulting room, the sort of gravitational pull of isolation and loneliness that happens to very sort of successful people, people who've had great careers and, you know, invested really heavily in that success.
And then something happens, right, like they, you know, might either contemplate in giving that up or more usually like in the, not in the very early stages of retirement when they're doing things on their bucket list, but maybe sort of six months in as the dust settles, there's, uh, an experience of isolation.
And as I've worked more in this sort of space, I realize it has pretty deep roots that deserve to be...
They're not really talked about very much, but it's, it's basically the roots go back much earlier, maybe 30 years earlier.
And so getting past that stage involves just taking that out of the shadows, kicking the wheels on it and, and, you know, and moving past it.
I think not everyone has that ability or willingness to ask those very deep questions of themselves to really go inside.
You know, 'cause it's like, you know, you, you, you have your marching orders and you go forward, right? And, um, to stop and say, "Hmm," you know-
... "I'm going in, I'm going in this direction because it speaks to me," or it, it's, it's b- becomes an, an obvious answer.
And, and I would argue that that is the best thing about retirement, right? Because it's one of those natural times in life where, you know, the demands might not have been as, as immediate as they were throughout your career, um, but it's a fantastic time to lean into that, those kind of parts of yourself that might have been, you know, pushed a little bit to the shadows, um, and, uh, you know, do a bit of a dive and figure out what fulfillment looks like.
Here you are on the front lines of, you know, work- working with- You know, successful, high achieving men and, and women, I, I, I, I expect.
And what are, what are some of the, the big issues that you're seeing in this demographic? And men especially, since Chapter Ex is really aimed more to men, although, you know, as I can...
as I say all the time, you know, there are women who absolutely fit the same model of difficulty, uh, in that transition, and think the, you know, think the same way, experience the same things.
I think one of the big themes that I'm seeing now, and we may have touched on it the last time, but it's even in the last two years since we spoke, I've- it's sort of played out a lot in the consulting room, the sort of gravitational pull of isolation and loneliness that happens to very sort of successful people, people who've had great careers and, you know, invested really heavily in that success.
And then something happens, right, like they, you know, might either contemplate in giving that up or more usually like in the, not in the very early stages of retirement when they're doing things on their bucket list, but maybe sort of six months in as the dust settles, there's, uh, an experience of isolation.
And as I've worked more in this sort of space, I realize it has pretty deep roots that deserve to be...
They're not really talked about very much, but it's, it's basically the roots go back much earlier, maybe 30 years earlier.
And so getting past that stage involves just taking that out of the shadows, kicking the wheels on it and, and, you know, and moving past it.
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