Lessons from the Lonely Side of Entrepreneurship

The loneliest time of my life, ironically, was when I was surrounded by the most people. It was about five years ago, I was co-owner of a brewery, married to the love of my life, I had a big circle of meaningful friendships, I was close with my family, and I had a lot of wonderful and happy customers.?

I wasn’t alone, but I was lonely. I felt isolated, disconnected from others.?What's up with that?

“It’s lonely at the top,” they say, often painting it with broad brushstrokes. While there can be some truth in that, I believe the experience is more nuanced and context-dependent. At least for me, leadership and entrepreneurship carried moments of a deeper loneliness that isn’t as simple as the proverbial "top."

As I reflect on that period of isolation, I realize the disconnection came down to two things:

1. Navigating a significant life change, and
2. Having a support network that no longer fit the shape of my journey.

The Significant Life Change

In 2012, I co-founded a craft brewery with two partners. My purpose was simple: bring people together to connect in the present moment. For a time, I felt like my work was living into that purpose. It fueled me, inspired me, and drove our team to accomplish incredible things.

But as time passed, I started to see a more complex truth. The beer we made brought people together, yes, but it also had the potential to pull them apart. I realized that the very thing I had built held two opposing forces: connection and disconnection. This paradox started a complex inner dialogue that I couldn’t just crunch some numbers and analyze my way out of.

Through reflection, uncertainty, and a feeling of wandering through foggy forest with no clear trail, I came to terms with the fact that I no longer wanted to work in the beer industry. That meant stepping away from the business I had poured my heart into. It meant, that for me, it was over.

When I acknowledged that, loneliness struck me like a brick wall. But to understand the full weight of that loneliness, you need to understand who I was relying on for my support network.

When the Support Network No Longer Fits

For the longest time, my two business partners were my professional support and backbone. They were brilliant, creative, and experienced… which made it easy for me to lean on them. On any given day, they wore multiple hats—business partner, advisor, coach, therapist. In hindsight, that’s a lot to put on two people... a lot of eggs in two baskets.

When I realized I needed to leave, the loneliness appeared because I didn’t feel like I could lean on them for support as I figured out how to navigate the transition—not because I didn’t trust them, but because we had competing commitments and interests. As business owners, their own responsibilities to the business, our remaining investor, employees, and personal interests complicated things. The decisions I’d make would drastically effect them one way or another, which would skew their ability to provide the support I was looking for. I changed the situation, and because of that, I found it difficult to be vulnerable with them.?

The support network I had relied on was no longer the appropriate support network to guide me through this new, uncharted path. It was like I put all my eggs in one basket, and then realized that I was choosing to go in a different direction from the basket.?

I also wasn’t able to have these conversations with employees and other colleagues, for similar reasons, and the need for confidentiality.

Suddenly, I was navigating the biggest change of my life without the people who I’d looked to before.?

I wasn’t alone, but I was lonely. I felt lonely because I was navigating this transition without someone who had been there before or truly understood what I was going through, from both the human and entrepreneur’s perspective.?

Lessons from the Path

I’d be lying if I said the path from there was smooth or painless. In truth, it was a rollercoaster—full of rumination, fear of failure, sunk-cost fallacy, big emotions, mistakes, tough conversations, sleepless 3 a.m. wake-ups, and ultimately, a period of grief. It was more painful than it needed to be.?

I’d be lying if I told you I made the change I knew I needed to make in an effective, efficient, and productive way. It took much longer than it needed to.?

And I’d be lying if I said loneliness was a necessary part of this journey. It isn’t. Instead, I think the loneliness made it much harder to navigate this transition.

I see now how this experience has shaped me into who I am today, and why I’m now dedicated to supporting other leaders and entrepreneurs as an executive coach. I know and believe that you don’t need to be alone as you navigate those unknown transitions. I find meaning and joy in supporting you and others in navigating those spaces that can often feel lonely.??

You don’t need to walk this path alone, because, you are not alone.

- Alex Wallash

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Photo: Johannes Plenio