The life lessons I learned from leaving the entrepreneurial life

I left the entrepreneurial life.

It started on a whim. I’d grown tired of making other people wealthy while staying in the same place and decided I needed to do this for myself. I was between jobs and had just moved back to the Austin area, so I started a kitchen-table graphic design company with the help of my daughter, who is also a designer. In two years, we were a four-person team, with clients ranging from Travel Texas to TGI Fridays.

We worked remotely, were family-friendly, had a four-day work week, and had the luxury of taking on projects that we loved. It was ideal but fragile. There were feast or famine moments, and while we officially only worked four days a week, business development and strategy was my round-the-clock obligation.

We hung in there for nearly eight years. When my daughter received an opportunity of a lifetime to work abroad, she grabbed it. Around the same time, my biggest client decided to take their art department in-house, so we lost half of our annual revenue. It was a big loss. I tried a rebrand, a partnership, and a few podcasts, but my little agency was treading water.

Major clients turned into gigs, and money was tight. I had to find a job.

There’s a language you speak with other entrepreneurs, and a certain reverence is reserved for those who have succeeded. They have clout, grit, moxy, and chops. They are brave enough to go toe-to-toe on a job with companies that possess fat bank accounts, strategists, and actual creative departments. It’s an amazing feeling to be at the helm, to see your work in major media, and to see your clients thrive. To leave that for the safety of a steady paycheck and healthcare is at once a great relief, and terribly heartbreaking.

When searching for a job as a former entrepreneur, you’re seen as a bit of a renegade.

You have the skills and experience they’re looking for, but lack the pedigree of a big agency, and the civility of corporate life.

You’re too bossy or crafty to be an associate, but too rough around the edges to be a leader. You’re in a bit of a no-man’s land, which sort of only resonates with other entrepreneurs or start-ups. And working for those guys is why you left office life in the first place.

Six months later, we all entered the Covid era, and I was and remain glad to have a good job. I still do one or two gigs a year. I say that it’s to keep my agency’s portfolio active, but I imagine it’s mostly because I still wish I had a piece of that life.