The Lonely Leader
You have 50 people reporting to you. You've never felt more alone.
My personal story
The Silence
Nobody talks about CTO loneliness. It’s not in the job description. It’s not in the leadership books. But when I coach CTOs, it comes up constantly. Not in the first session. Usually by the third or fourth, when trust is built. “I feel completely alone in this.”
The higher you climb, the fewer people understand what you’re dealing with. Your team sees the confident leader. The CEO sees the technical expert. Your family sees someone who’s always working. None of them see the full picture.
This isn’t weakness. This is structural. The role creates isolation by design.
The CTO role is very different from any other role the engineer has held before. Before being a CTO, they could talk to peers about their problems, they could bubble up problems they could not solve to their boss. The CTO is the first position they could get fired because the CEO just lost trust - not because of their performance. Political games set in - and you’re alone.
Why Tech Leaders Have It Worse
Every executive faces some isolation. But CTOs carry extra weight.
You speak a different language. Half your job is translation. Explaining technical reality to people who don’t want to hear it. Explaining business constraints to engineers who think product is the enemy. You’re the bridge. Bridges are lonely places.
You can’t share your real problems. Tell your team you’re worried about the architecture? Now they’re worried too. Tell the CEO you’re not sure you can deliver? That’s a career conversation. Tell your spouse about the production incident at 2am? Their eyes glaze over. The problems you carry are yours alone.
The imposter syndrome hits different. Most CTOs got here through technical excellence. Now you’re doing a job you were never trained for. Managing people, navigating politics, presenting to boards. Every day feels like a test you didn’t study for. And you can’t admit it.
Founders and co-founders move on. In startups, you might have had the founder or CEO as a genuine peer. Someone who understood the early chaos. Then the company grows. They get busier. You get busier. That relationship atrophies. Now you’re running a department, not building something together. Founders leave, professionals take over and the VC steps in. None of them share a history with you.
The Burnout Connection
CTO burnout and loneliness feed each other. I’ve seen it several times. Sometimes people come to me too late.
It starts with overwhelm. Too many decisions, too many people, too many fires. You work longer hours to keep up. The longer hours cut into relationships. Fewer relationships means less support. Less support means more stress. More stress means more burnout.
The cycle accelerates. At some point you’re running on fumes, with no one to tell and no energy to reach out even if you wanted to. The isolation becomes complete. And there is no way out of it in sight.
Most CTOs who burn out don’t see it coming. They’re too busy coping to notice the pattern. They think they’re just having a hard quarter. Then a hard year. They think this is just how the CTO job is. Then they’re dropping out of the game.
The warning signs:
- Sunday dread that never lifts
- Anger at interruptions that used to be routine
- Decisions feel impossible, even small ones
- You’ve stopped caring about things you used to love
- You can’t see how to get out of it
- Physical symptoms: sleep problems, headaches, chest tightness
If this list hits close to home, pay attention.
What Actually Helps
I’ve watched CTOs try different things. Some work. Some don’t.
Peer groups work. Other CTOs going through the same thing. No need to explain the context. No risk to your reputation. Just people who get it. The CTO groups I’ve seen work best are small (5-8 people), regular (monthly), and confidential. Finding peers isn’t easy, but it’s worth the search.
Sharing works. Better build relationships and trust with other executives - share with those you trust, ask for advice and listen to them.
One trusted person works. Not someone who reports to you. Not someone you report to. Someone outside the system who can hear the full truth. A coach, a mentor, an old colleague who’s been there. One person who gets the complete picture can break the isolation.
Exercise works, but not for the reasons people think. Yes, endorphins. But the real value is having something that isn’t work. I walk to the beach each morning. Something where you’re just a body, not a CTO. Running, swimming, lifting - doesn’t matter. The mental break is the point.
Boundaries work, eventually. Hardest thing for ambitious people. The work expands to fill all available time. If you don’t protect space for yourself, there won’t be any. This feels selfish. It’s actually survival.
What doesn’t work: Pretending everything’s fine. Working harder. Drinking. Isolation as coping strategy. I’ve tried most of these. None of them helped.
You Don't Have to Carry This Alone
The biggest lie tech leadership tells is that you should handle everything yourself. That needing support is weakness. That isolation is just the price of the job.
It’s not.
The strongest leaders I know have support systems. Coaches. Mentors. Peer groups. Therapists. Someone they can be honest with. Someone who helps them think clearly when the pressure is highest.
If you’re feeling overwhelmed, burned out, or just alone in this role - that’s not a personal failing. That’s a structural problem. And structural problems need structural solutions.
Ready to Talk?
I’ve been the lonely CTO. I know what it feels like. Now I coach tech leaders through exactly this - the isolation, the overwhelm, the burnout risk. Confidentially. Without judgment. If you need someone in your corner who understands the weight - let’s talk.