This week, I graduated. In my last blog post, The Graduation Nobody Celebrates, I explored all the different moments in our lives that we “graduate.” This week, I completed another milestone.
After twelve intense weeks in the Goldman Sachs 10,000 Small Businesses program, I stood in a room in New York with the cohort of 150 scholars I’d only ever known through a screen — and we crossed the finish line together. Final classes. Final presentations on our business growth plans. And finally, after three months of virtual sessions, the chance to meet the incredible people who had been in the trenches right alongside me the whole time.
Now I’m sitting at the airport, waiting on my flight home, reflecting on all of it.
Here’s the truth about being an entrepreneur: it’s exciting, it’s terrifying, and far more often than anyone admits, it’s lonely. Even when you have a big team. Even when, like me, you spend your days surrounded by people, in a coworking space full of members and meetings and constant movement. None of that touches the particular loneliness of being the person ultimately responsible for the business. The challenges, the wins, the 2 a.m. worries, there usually isn’t anyone to talk to about those. Not really.
The little boat on a big ocean
Sometimes I feel as if I set out to sea on a tiny sailboat when I started The Village Workspace March 2, 2020.
At first, it’s exhilarating. The horizon is wide open and filled with opportunity. The ocean gives you this incredible feeling of freedom… just you, your boat, and everything you could possibly build out there. That’s the part no one warns you might end.
Because then the weather turns. Storms come up out of nowhere and toss the little boat around, and you realize there’s no one nearby to show you how to adjust the sail. No one to explain how to repair the rips the wind tears into your canvas. You’re bailing water, reading the sky, and gripping the rudder all at the same time. All alone. You don’t want to worry your team or your spouse. You just sit questioning your decision to leave the safety of the shore in the first place.
Being in New York this week reminded me how completely that changes when you’re not actually out there by yourself.
A fleet of sailors, all headed the same way
What I found in that cohort was a fleet. A group of sailors on the same journey, their boats cutting through the same water right alongside mine. We shouted encouragement across the waves. We traded the things that were working for us right now, the real, current, this-is-what’s-helping-me-this-week kind of advice you can’t get from a textbook. We called out warnings about the rocky shores one of us could see that the next boat couldn’t yet.
There is a deep comfort in sitting beside people who are in the water with you. Not above you, offering advice from the safety of the shore, but in it with you, their boats rocking in the very same swells.
By the end of the week, there were tears. Real ones; tears of gratitude and love for the people who had stood beside us through twelve weeks of hard, honest and vulnerable work. There were genuine hugs. There were promises to stay in touch, to keep checking on one another’s journeys as we pointed our boats back toward home and scattered across the country.
What the week in person renewed in me
I already knew the power of community. I build my business around it every single day. But this week, that knowledge was renewed… reinforced right down to my bones.
We all need a group of encouragers. The people who, as I always say, are cheering for us from the balcony when things go right, and reaching down to pull us back up when we fall hard. We need people who have weathered the same kinds of storms and are willing to hand over their hard-won wisdom, so we don’t have to learn every lesson the most painful way.
And here’s the part I most want you to hear, whether you’re twelve weeks into your business or twenty years in: the storms don’t stop coming. They just don’t. The longer you sail, the better you get at reading the sky, but the weather keeps arriving. That’s not a reason to be discouraged. It’s the reason to make sure you’re not sailing alone.
If you’re an entrepreneur reading this and the loneliness I’m describing feels familiar, take it as your sign. Find your fleet. Get into the rooms– virtual or in person– where other people are doing the same brave, terrifying, exhilarating thing you’re doing. Build real relationships with the kind of people who will yell encouragement across the water and warn you about the rocks.
Because the freedom of the open ocean is real. But so are the storms. And the difference between the entrepreneurs who make it and the ones who quietly capsize often isn’t talent, or funding, or timing.
It’s whether or not they had a fleet.
Who is in your fleet? Send them a thank you note and let them know they have helped you sail on. Do you need to find other sailors to cheer you on? Reach out to me. I’d love to connect.