The other day, I was flying back to San Francisco from a week of meetings on the East Coast. I had a quick connection two terminals away, and was bobbing and weaving through meandering roller-board suitcases like a pro. I arrived at my gate slightly out of breath, in plenty of time for boarding, and happened to see someone I knew.
Standing amidst a group of laughing coworkers was a classmate of mine from business school who I remembered was working as a consultant. As I contemplated whether I had the energy to go say hi and to make small talk, boarding started. She and her coworkers gathered up their briefcases and strode aboard into their first class seats. There was something about that moment that made me feel very alone.
There are a thousand things that are fabulous about starting and running your own startup (in my case, the nonprofit CODE2040). But there is one thing that stands out to me as being particularly hard: the loneliness that comes with being a founder-CEO.
This is never more apparent than when I’m traveling, which I do often, and don’t have any of my other teammates around me. I travel to the different geographies in which we have programming, I travel to conferences and speaking engagements, I travel for fundraising meetings. And almost always when I travel I’m alone.
There is one thing that stands out to me as being particularly hard: the loneliness that comes with being a founder-CEO.
This leaves a lot of time for reflecting on what’s going well, what’s going less-well, what’s making me tired, or stressed. And every now and again it affords a glimpse into the alternatives. What if instead of striking out on my own I had pursued a job at a well-capitalized, prestigious firm where clients flew me first class? Where I worked with peers as part of a team as opposed to leading one?
I don’t regret starting a company, but it hasn’t been easy, and I do sometimes find myself coveting the road more traveled. And when I think about what it would have been like to join a company instead of start one, I think most often of what it would be like to feel a sense of security, of being ensconced in a peer group, tackling challenges together, sharing not just a vision but a vantage point.
Instead, in my darkest moments, I see my company’s org chart reflect the shape of a mountain, with me alone on the windy peak.
I’ve yet to find a way to make myself feel less alone, or more competent or successful in these moments. But a couple years ago I read an old blog post by one of my board members, venture capitalist Ben Horowitz, called What’s the Most Difficult CEO Skill? Managing Your Own Psychology. I remember clearly the feeling of wonder and relief, the feeling of realizing that I might not ever feel less alone or more competent but that there was a third option: acceptance that these were the natural struggles of the role.
Being a founder-CEO may still feel like being adrift at sea on a creaky ship, but the relative calm that comes from stabilizing yourself by swaying with the pitching and rolling, rather than by clutching the rail for dear life, is magical in its own way.