How Narrow is the Summit?

There is a particular kind of loneliness that nobody talks about at the top.

It doesn’t look like loneliness from the outside. The calendar is full (often, too full). The phone rings constantly. There’s the constant head-down posture of responding to texts and emails. There’s a board to report to, a C-level team to lead, investors to manage, and advisors for every conceivable professional need. A successful CEO is, by most external measures, one of the least isolated people in any room they enter.

And yet.

The higher you climb, the smaller the circle of people you can speak to honestly. Not because the people around you are dishonest—most aren’t. But because their relationship with you is never fully unconditional. Your board has fiduciary obligations to your investors. Your leadership team has career aspirations (that may include gunning for your job one day). Your investors report to their management committees and LPs. Your spouse or partner has their own emotional stake in your decisions and your wellbeing. Everyone in your life who matters is, to some degree, compromised by their proximity to you. They want things from you, or for you, or because of you. And that wanting—however well-intentioned—makes it nearly impossible for them to tell you the thing you most need to hear.

Most CEOs don’t have anyone who will tell them the truth. That’s one problem. The deeper one is that they have no one to tell their own truth to. And in my experience, the second costs more than the first.

A 2026 survey conducted by Chief Executive and the Mayo Clinic—the first comprehensive study of its kind—surveyed more than 1,000 CEOs, CFOs, and CHROs about their health and wellbeing. The findings are instructive. C-Suite executives report stress levels 26% higher than the national average—a 6.3 out of 10 compared to 5.0 for U.S. adults broadly. And yet 67% report no recent depressive symptoms, and 90% have had a physical exam in the past year compared to just 20% of American adults. On paper, they’re managing. The numbers say they’re fine.

But look closer. Thirteen percent screen positive for potential depression—a figure that, given how rarely high performers acknowledge vulnerability in any formal context, almost certainly understates the reality. The same survey notes that executives are working an average of 53 hours per week—nearly 20 hours more than the national average—while traveling five days per month and carrying stress levels that would concern any physician who looked past the annual physical results. Numbers have a way of describing the surface of things without touching what’s underneath.

That gap—between the managed presentation and the unmanaged reality—is where the real cost lies.

I was never a CEO. What I was, for three decades on Wall Street, was the person some of them called when they couldn’t call anyone else.

I took calls at 10 p.m. from leaders running organizations of thousands of people who wanted to talk—off the record, no notes, nothing that would attach to them—about things they couldn’t say in any other context. Whether I could help them think through something they were ashamed of. Whether what they were feeling was normal. Whether the thing they’d been carrying for six months was as serious as it felt at 10 p.m. on a Tuesday.

Those calls told me something no survey could. The isolation at the top is not a perception problem. It is a structural one. The more consequential your position, the more carefully everyone around you manages what they say to you—and the less access you have to the kind of honest, uncalculated conversation that actually clarifies things. You become, in a very real sense, the last person in any room to know what people are actually thinking. And often, the last person to know what you are actually feeling.

The question nobody asks their CEO is the simplest one: how are you actually doing?

Not the performance review version. Not the investor update version. The unfiltered one. The one that includes what’s keeping you up at night, what conversation you’ve been avoiding for months, what you said in a meeting last week that you wish you could take back, and what you’re most afraid of in the version of your life that exists five years from now.

That question almost never gets asked. And when it does, it almost never gets answered honestly—because the person asking it is almost never in a position to receive the answer without consequence.

The irony is precise and painful: the more successful you become, the more you need honest counsel, and the harder it is to find.

What fills the gap is usually inadequate. Executive coaches address performance but rarely touch the personal. Therapists address the personal but rarely understand the professional context at the level that actually matters. Boards are structurally unsuited to the kind of candid, ongoing conversation that moves the needle on anything other than governance or corporate performance. Friends who knew you before you had the title are often intimidated by it. Friends who know you only in the context of the title don’t really know you at all.

The result is a kind of managed existence—high functioning, externally impressive, and quietly starved of the one thing that would actually help. Honest, experienced, unconditional counsel from someone who has nothing to gain from telling you what you want to hear.

Childhood is where most of us first learn our relational patterns. The boardroom is where we perform them. And the space between those two things—the gap between who you actually are and who you’re required to appear to be—is where the most important work of a leader’s life either gets done or doesn’t.

The most important conversations of your career probably haven’t happened yet. Not because you haven’t had access to smart people. Because you haven’t had access to the right kind of conversation.

That’s the one nobody schedules. That’s the one that changes everything.