Entrepreneurial Loneliness

Up Early Designs

Having been self-employed for over twenty years I can speak to the reality of entrepreneurial loneliness. Though I love the freedom provided by working for myself, it is far from utopia. The loneliness associated with running a small business is very real.

Sure you have staff possibly or perhaps even a partner, but you are still confronted with loneliness. You are still confronted with being the only person with knowledge of all aspects of the business.

And that loneliness is at its apex during slow periods. When sales take those cyclical dips, the pressure of cash flow, employees and more is greatest. You certainly cannot speak about cash flow concerns with staff. Friends may lend an ear but they won’t fully understand nor appreciate what’s going on.

In my retail business I would experience lulls a few times during the year. The worst being November and January. As an outdoor clothing retailer in the northeast I would have plenty of cold weather gear on the tracks during those times. And an invoice loaded locomotive heading towards me. There was a window of time to move that product before the spring line came in. It was scary. And I had no one to share it with.

Fortunately, as was always the case, December and February sales would clean up the tracks and I could avoid the fears I anticipated. I could pay those bills. But it was difficult. Or when you go through periods of staff issues, those are not scary just stressful. Having to let someone go is hard. Especially when the only thing wrong is they can’t sell. Why is it those people are often the nicest and thus the hardest to let go?


For me, I dealt with entrepreneurial loneliness by forming relationships with business owners within my industry. It’s amazing how the knowledge that sales are also slow elsewhere can calm your nerves.  The vacuum in which you felt you lived became smaller. I mean you still have to deal with slow periods for example, but at least you don’t have to keep asking “is it my business only?”

I wouldn’t change the entrepreneurial lifestyle for anything. It has rewarded me great freedom, growth and much reward. But it’s not an easy road. Perhaps that is why the vast majority never end up on this path.