Why Startup Leadership Feels So Lonely
And what to do about it
Hi! I’m Molly. I write about what it actually takes to lead inside growing, changing companies: the frameworks that help, the honest truth about what it feels like, and the messy work of shaping a career that actually fits.
Lessons is where those ideas live — both the writing and the conversations around it. (If you want to learn more about how Lessons and the community work, you can read more here.)
This Friday (Dec 12), we’re going to try an experiment. I really want to hear your thoughts, so we’re going to do an Ask-Me-Anything in our (new! shiny!) Subscriber chat from 9-10am PT. I’ll use a couple of our recent Lessons Mailbag submissions to kick it off, but I would love to hear from anyone who has a burning question or a problem they want help thinking through. If it’s fun, we might do more of them! So block your calendar and come hang out on Fri, Dec 12 from 9-10am PT.
We got a question in the Lessons Mailbag recently that hit me right in the gut.
“I’m in a small startup that’s starting to grow and I’m responsible for a lot of things — HR, compliance, ops. I feel really alone in it. No real team and no peers to bounce ideas off of. I’m working a ton and often feel afraid that I’m messing things up. Is this normal?”
If you’ve ever led anything inside a startup, you probably felt your shoulders drop reading that. Yep. Been there. Many times.
What this reminds me of, very specifically, is my early days at Quip.
After we launched Quip, there were weeks where everything looked great on the outside. Press, buzz, momentum. But internally? I felt completely untethered. Unsure, second-guessing every instinct I had; convinced parts of the business were a mess and I was somehow making it worse. And underneath that was something simpler and harder to admit:
I felt lonely.
Not “I wish I had more friends at work” lonely — but the lonely that comes from carrying responsibility without anyone to talk to about it.
About a month into this, I went to lunch with a friend who had been through the startup blender a few times. I unloaded everything, half expecting him to tell me I was screwing it all up. Instead, he shrugged and said, “Oh yeah. Welcome to startups.”
It was like someone opened a window. Nothing changed about my workload, but suddenly I wasn’t wrong or broken; I was just experiencing something incredibly normal that no one tells you about.
So let me say this directly to the person who wrote in (and anyone else who needs to hear it):
If you’re in a leadership role or at a startup and you’re feeling lonely, that is normal.
Startups are lonely. Leadership is lonely. It often feels like you’re crazy and there’s no one to turn to, no one you can be honest with, no one who will really understand. That is how so many of us feel. AND:
At some point in your leadership journey, you have to build your own support structure.
The only thing that will make you feel less lonely is having someone or something to turn to that helps you make sense of it all.
When you work at bigger companies or when you’re earlier in your career, support tends to show up naturally — peers at your level, colleagues who are going through similar things, people to grab coffee with and say “Is this nuts?” But if you’re at a small company, that peer set often doesn’t exist. And the more senior you get — even at big companies — that natural support shrinks. You’re less and less able to be fully honest inside your own walls.
If you’re at a startup or in a leadership role, you HAVE to build your own support.
The Breakfast Club — the thing that inspired Glue Club — started because a friend and I were drowning in our COO jobs and realized we had nowhere to talk honestly about how hard it all was. We had breakfast one morning and decided we should do it regularly. Then we invited a few more leaders. Then a few more. We met monthly for five years. That group got me through restructurings, layoffs, acquisitions, new leadership roles, hiring mistakes, board drama, founder spirals — all of it.
Here’s what I’ve come to believe based on that experience and from building Glue Club for the last three years:
