The Loneliness Nobody Warns Solo Leaders About

“If leadership feels lonely at the top, you’re probably doing it wrong.” I read that line in Dr. Jes DeShields’ 9 Leader Touchstones and felt the particular sting of a sentence that is completely true and doesn’t quite describe my life.

I hold two roles that keep me in constant contact with people. As the only staff member and Executive Director of a statewide trade association, I regularly speak with board members, agency partners, and the leaders of the organizations I work for. I also co-founded a safari business with a partner in Kenya, which has created a different communication pattern, a different network of relationships, and another world I am developing in real time. I also serve on several boards in leadership roles.

By any outside measure, I am a connected person. I am not sitting alone in a dark office avoiding my team.

And yet, I am lonely—not because I’m isolating myself, but because in both roles, there is no one else doing what I do on the day I’m doing it. No peer down the hall working through the same challenge—no one inside either organization who carries the same weight of the same decision at the same moment.

That is a structural, place-specific kind of loneliness, and it took me a while to understand that it isn’t necessarily a problem to fix so much as a reality to understand correctly.

Two Different Things Wearing the Same Name

Jes’s line about isolation at the top is, in part, about the isolation leaders can create for themselves. It describes leaders who hold decisions too tightly, refuse help, or believe they need to be the smartest person in the room. That version of loneliness can become a culture problem, and it has a culture solution: share leadership, ask better questions, invite others into the work, and let go of the myth that you must have all the answers.

But solo leadership isn’t quite that.

I’m not withholding anything from anyone. There’s simply no one within the trade association or at Complete Safaris doing the same work I do. The structural reality of being one person in one role, or one of two founders building something from nothing, is different from leading a larger organization and choosing not to trust or involve the people around you.

I think there are actually two different things living under the word “lonely” for someone in my position, and it matters to tell them apart: structural loneliness and the desire for solitude.

The first is structural loneliness. It’s the void. No one inside the organization walks quite the same road, so there’s no one to instantly understand the specific texture of a hard call the moment I’ve made it. This doesn’t necessarily resolve through more networking in general because what’s missing isn’t contacts. What’s missing is someone who understands the road.

The second is the desire for solitude, and it is not the same thing at all, even though, at first glance, it might feel similar on the inside. It is a choice, not a void.

After a day spent constantly in relational mode, giving my attention to board members, the boards I serve on, partners, or clients across two ventures, I find myself wanting to be alone. That pull isn’t avoidance. It’s resilience doing exactly what it’s supposed to do: my emotional and spiritual energy wellsprings asking to be refilled.

For a long time, I wondered if desiring alone time meant I wasn’t a people person, that a “real” connector wouldn’t need to retreat. I’ve come to see it differently. Wanting solitude after genuine connection isn’t a symptom. It’s the system working. The signs of healthy solitude are easier to spot than I realized: I return from time alone feeling recharged and more available to others, not withdrawn or unable to re-engage. When solitude feels like strength rather than escape, I know it is meeting a real need. For me, healthy solitude is intentional and nourishing, leaving me more present for the work and relationships that matter.

Confusing it with the first kind of loneliness, the void kind, can make you feel like even your own way of restoring yourself is somehow a failure.

What Actually Helps the Void

Since structural loneliness doesn’t necessarily respond to general networking, it’s worth being specific about what does. The remedies for the void are not the remedies for solitude.

Professional associations built around your actual role matter more than I expected. Other solo executive directors of trade associations understand something that even the most engaged board member can’t, simply because they carry the same kind of job.

The value isn’t always advice. Sometimes it’s recognition.

Leadership retreats with a cohort walking a similar road do something networking can’t. I recently returned from time with the Crescent Leadership Collaborators, and the value wasn’t in any single session. It was in being physically present with people doing parallel, difficult work long enough that the usual performance of “I’ve got this” could drop.

That kind of space matters.

If you’re a leader who has never had that experience, the upcoming Leader-First® Leadership Summit offers an opportunity to step away from the day-to-day demands of leadership and spend sustained time learning and reflecting alongside other leaders.

And then there is the rarer thing: the one right person.

I have a friend who can enter into real dialogue with me about both of my “jobs.” She understands the trade association because she worked part-time for us for a short period. She understands Complete Safaris because she was our very first client. But mostly, she understands because she’s a genuinely good human being who knows how to listen.

I didn’t build that relationship strategically, and I don’t think it can be manufactured on purpose. But when you have someone like that, it’s worth recognizing what they are to you and treating that relationship as the asset it is. The last piece is simpler than it sounds: naming the loneliness out loud to a friend, a business partner, or someone you trust. Not so someone can fix it, but so you’re not carrying the weight in secret.

The relief isn’t always in the solution. Sometimes it’s in the naming.

Its Own Terrain

Solo leadership isn’t a smaller or lonelier version of leading a team. It has its own terrain, with its own specific losses and remedies.

Treating it as the same problem Jes describes when leaders isolate themselves leads to the wrong prescription. More delegation doesn’t help when there’s no one to delegate to. The issue is structural, not self-imposed.

What helps is finding the people who actually know the road, deliberately resting when your energy wellsprings ask for it, and being honest enough to say the quiet thing out loud instead of assuming that a leader who talks to everyone should never feel alone.

Leader-First® Leadership asks us to look first to ourselves. But that doesn’t mean we are meant to carry leadership alone.