The Man Who Had It All (and Still Felt Stuck)

Met with a client this week

He’s the kind of guy everyone looks at and says, “That’s the dream.”
Beautiful house. Three amazing kids. A wife who’s his best friend. CEO title. Country club weekends. Boat. Beach house. Millions. All of it.

And yet at breakfast this week, after the usual niceties, he said something quietly.
Almost like he didn’t want to hear himself say it.

“I feel like I’ve gotten nowhere professionally in four years.”

He didn’t say it for sympathy. He said it because he knew I’d understand.

And I wasn’t surprised because he has been dropping hints around this for 2+ years and while we have talked about it, he was not yet ready…

Because it’s hard to say that out loud when you’re the one everyone expects to have it together.

He loves his life. The Saturday soccer games. The diner breakfasts. The kids. The memories.
But somewhere between the meetings and the milestones, something shifted.

He started wondering if he’d already done his best work.
If his greatest success might already be behind him. He’s 42.

And that’s when it hit me again, the pattern I’ve seen in so many high achievers.

The quiet burden doesn’t start with failure.
It starts with success that no longer feels like growth.

Why It Hits So Hard

He’s not burned out. He’s not lost. (well, maybe a little). He’s just… no longer fulfilled in the same way.
Because the same playbook that built his first mountain won’t build the next one.
Because he doesn’t want (or is it scared?) to risk what he has built to seek greater fulfilment.

And for people like him. Like us. That’s terrifying.

He knows he’s been blessed.
But he’s also haunted by this whisper: “Is this it?”

That whisper is not ingratitude.
It’s awareness.
It’s the soul reminding you that comfort is not the same as purpose.

Our Conversation

At one point he started listing the reasons things weren’t moving faster.
His team wasn’t quite right. His board wasn’t as sharp as he hoped. The coach he met last year didn’t quite “get him.” The one before that wasn’t seasoned enough. His old boss had blind spots.

It was all true—every person he mentioned was imperfect.
But so was he. So am I. So are you.

I stopped him.

“Listen,” I said, “all I'm hearing this morning is about you spotting imperfections in others. It’s what made you successful—seeing the gap, fixing the system, tightening the bolts. But at this stage, that same instinct is holding you back. You’re not looking for a perfect leader to follow. You’re avoiding the work of leading yourself.”

He looked up.
Quiet. Processing.

“You’ve got to stop looking for someone perfect enough to be worth following,” I said. “There isn’t one. You’ve got to own your part of the imperfection and work on what you can control. Not perfect—just better.”

That’s where progress begins.
Not with the right boss, or board, or coach.
But with ownership.

Perfection isolates.
Ownership transforms.

He admitted he expects perfection from everyone else because he hasn’t figured out how to extend grace to himself. He said it more like this, “I start thinking perhaps I am not good enough.”

He’s successful but insecure. There with the best but feels like an imposter.
He knows he’s gripping too tight on what worked and now feels comfortable but what worked is no longer helping him grow. But doesn’t know how to let go.

So I said what I’ve said to a lot of quietly burdened midlife millionaires lately:

“Stop blaming others. Start owning it.”

Because ownership isn’t about fault, it’s about freedom.
It’s not about doing more. It’s about doing different.
And it’s not about time, it’s about direction.

The Truth

You can’t optimize your way into fulfillment.
You can’t spreadsheet your way into meaning.
And you can’t keep doing what used to work and expect it to feel new.

Progress. Not perfection.
Ownership. Not control.
Release. Not retreat.

That’s the work.
And here’s the secret: it doesn’t actually require more time, but does take time.
It requires letting go of what’s no longer yours to carry. It requires ownership and effort.

Where we are heading

I’m calling the client above The Man Who Had It All.

You have met the Man Who Couldn’t Chill.

I will introduce next week the Midlife Mom Who Gets It, as she will give you hope as a person who has already gone through the early phases of  graduating from the Quietly Burdened Midlife Millionaires Club into the Phase II SocietyTM.

You’ll meet them (and others) again in future letters as each begins the same climb we all face:

The shift from control to ownership, from “what’s next?” to “why next?”

We’ll walk with each as they:

• Rediscover values (the compass)

• Define mission (the map)

• Rebuild rhythm (the 5-1-12-5 framework)

Because for the Quietly Burden Midlife Millionaire, midlife isn’t a decline.
It’s the start of next ascent.