The loneliness of leadership, and how to fix it

They tell you leadership is lonely. What they don’t tell you is how literal that gets, or how subtly it happens. There are more meetings, more messages, more people asking for your time than ever. But the conversations get thinner. The ones where you can say, "I don't know. What do you think?" without it landing as a problem.

I felt it most clearly on an ordinary Tuesday. A demanding meeting had run long, an urgent decision was sitting in my inbox, and a strategy I had championed was starting to wobble in ways only I could see. I made the calls I needed to make. Then I closed my laptop and realized there was no one I could turn to and ask the only question that mattered: was that right?

I have a team I trust, and a hugely supportive boss, whom I admire and respect. But there’s a whole category of thought that simply has no home inside your own organization.

The conversations you cannot have at work

Seniority comes with a strange tax. The more your judgment is worth, the less you’re allowed to be unsure of it out loud.

You can’t process a painful restructuring with the people it touches. You can’t admit doubt about a direction to the team you’re asking to run at it full speed. You can’t test your read of a boardroom with anyone who answers to that same board.

The role asks you to be the steady one in the room, every room, and performing steadiness all day leaves you with no room for uncertainty. Nowhere to be wrong on the way to being right.

And then there’s the part of promotion no one prepares you for. You step up, and some of the people around you change. A peer who was warm last quarter is suddenly cooler, more scrutinizing, quietly waiting for you to stumble.

The role makes you a target in ways that have nothing to do with the work, and everything to do with where you now sit. You can’t name that internally without sounding paranoid or ungracious, so you absorb it. You tell yourself you’re imagining it. Usually, you’re not.

So you carry it. You get good at carrying it. And you start to mistake the carrying for the job itself.

I did that for longer than I would like to admit. I told myself the isolation was simply what leadership cost, the price of the view from up here. It took me a while to understand that I had it backwards. The loneliness was not the cost of doing the job well. It was quietly making me worse at it.

Decisions made entirely in your own head start to calcify. You lose the friction that good thinking needs. You begin confusing "no one is challenging me" with "I must be right," which is one of the most expensive mistakes a leader can make.

What a mentor cannot give you

The standard advice is to find a mentor, and mentors are valuable. But a mentor is usually looking back at a stage they have already left. They can tell you how it looked from where they stood, which is not the same as standing beside you in the weather you’re in right now.

What was missing wasn’t wisdom from above; it was connections at eye level. People facing the same kind of decisions, at the same altitude, in the same week, with the outcome still unknown to all of us. Not someone who’s solved it, someone still in it.

The circle

I found what I was looking for through a leadership program in Germany that does something deceptively simple: it connects you with a small, closed circle and then mostly gets out of the way. Mine was four women in senior marketing roles, all from completely different industries. Four worlds with almost nothing in common on paper, which turned out to be exactly the point.

The cross-industry part is the quiet genius of it. None of us competes with the others, so there’s no awkwardness, no sense that we’re rivals comparing notes. We never share anything confidential, but we can talk freely about how a decision is weighing on us, how we’re thinking through a problem, and what we would do differently, without the guardedness that creeps in when the person across from you operates in your market.

And because we come from different worlds, no one reaches for the same tired playbook. Someone in a completely unrelated sector sees my problem through a lens I would never have found on my own. The distance is exactly what makes the insight land.

The program ended more than seven months ago. The circle did not. We still meet once a month, and somewhere along the way those calls stopped being professional development and became something closer to a standing therapy session, in the best sense of the phrase.

And it’s not only work that has no outlet. The people closest to you – a partner, family, friends – love you but generally can’t follow you into the specifics. They haven’t sat where you sit. Lean on them too heavily and you either watch their eyes glaze or turn your evenings into an extension of the office. There are things you can’t say at work and things you shouldn’t keep bringing home, and that narrow gap between the two is exactly where this circle lives.

There’s something else, harder to name. Four women talking openly about leadership does something a mixed room rarely allows. We can be honest about the parts of the job that are gendered without having to caveat or explain them first: the second-guessing we’ve each been trained into, the way authority is read differently on us, the quiet calculation of how much certainty is too much. We don’t have to make the case that any of it is real. We just start from there. That shared shorthand is its own kind of healing.

" Four women talking openly about leadership does something a mixed room rarely allows. We can be honest about the parts of the job that are gendered without having to caveat or explain them first." – Felicitas Sommer VP Marketing & Communications, PriceHubble

We bring the things that have no other home. The decision one of us is quietly second-guessing. The conflict someone handled badly and is still wincing about. The offer on the table that looks golden from the outside and feels like a trap from within. The morning you woke up genuinely unsure you were good enough for the role you fought to get. Nobody performs in that room. Nobody is selling. There’s no polished version of any of us that needs maintaining for an hour, and the relief of that is hard to overstate.

Some months we solve something concrete. Some months we just hold each other's uncertainty for a while and send each other back out steadier. Both are valuable.

Why it works

I’ve watched plenty of networks dissolve into nothing, so I’ve thought about why this one held. These are the reasons our leadership circle works:

It’s small and fixed: The same four people, every time. Trust compounds when the group does not churn, and you never spend the first twenty minutes re-explaining your life.
There’s no competitive tension: Because none of us operates in the same market, there’s no rivalry in the room and no instinct to hold back. It’s never about trading sensitive details. I can think out loud about the “how” of the job without wondering how it lands with someone on the same playing field.
Its slot in the calendar is sacred: Once a month, protected, not quietly sacrificed to the first thing that comes up. That reliability lets the heavier conversations surface, because you know there’s always a next time to pick the thread back up.
It has no agenda: We’re not there to trade introductions or swap vendor lists. The moment a circle like this becomes useful in the transactional sense, it stops being able to do the one thing it’s actually for, which is to let you think honestly with people who understand the exact shape of your job.

If you recognize yourself in this

You don’t need a formal program to build your own peer group, though that’s how I stumbled into mine. You need two or three people at roughly your level, ideally outside your industry, and a genuine commitment to keep showing up.

Keep it small. Protect the time like you would protect a board meeting. And resist, hard, the urge to make it productive, because the instant it turns into networking it loses the only thing that made it matter.

The loneliness at the top is real, but it is not a law of physics. It is not the price you have to pay for the title. The answer turned out to be smaller and simpler than I expected: the right few people, once a month, and the honesty to use the hour well.

I walked into that program looking for a sharper strategy. I walked out with three women I now cannot imagine doing this job without. They know who they are, and they know what they have given me. This one’s for them.

If you’re ready to build a peer network of your very own, CMO Alliance’s Slack community is a great place to start. Connect with thousands of fellow marketing leaders, so you can grow together.

The loneliness of leadership: How I built a peer network that actually helped