The Fear of Failing

It’s Saturday afternoon, and I’m writing this article because I told myself I would write it today.

I’m 17 years into self-employment. We’re in a good spot. I value what we’ve built, and I’m excited about where we’re going. Yet something as small as leaving this article unfinished can still feel like letting myself down.

That’s how persistent the fear of failing can be. It follows you from wondering whether your business will survive to wondering whether you’ve done enough this week.

The stakes change. The feeling remains.

When I started, I felt like I had to make the business work. There was no Plan B I was willing to consider. In reality, I could have always just gotten a job. But that was the last thing I wanted to do.

I was taking my shot, and I was going to give it everything.

Then I hired people.

You spend hours together every day. You hear about their families. You share stories, work through problems, and build a shared history. Over time, the responsibility of being a boss, an employer, becomes personal. These are people who have trusted you with their careers and livelihoods.

The possibility of failing starts to include all of them.

I worried about letting my family down. I worried about letting employees down. Clients had put their trust in us, too. If I couldn’t figure out how to keep the business working, they would all be impacted if I failed.

Then there were the questions I didn’t want to admit I was asking. What would people think of me? Would the stigma of being failed business follow me into every job interview? Would someone even want to hire me?

My response was to work.

For a long time, work filled nearly every available time slot. What did I do for fun? Work. Entertainment? More work. There was always something to finish, improve, or figure out, and I cared enough to keep going.

That effort helped me build the business. It also came at the expense of other parts of my life.

The difficult part was how completely my identity became tied to the company. When things were going well, I felt successful. When things were going badly, I felt like I was failing as a person. There wasn’t much separation between me, the business owner, and the other parts of my being.

I’ve had stretches when I thought we were failing, and they were frightening. There have been many sleepless nights. I’ve also had stretches when we felt almost invincible.

After enough of both, I’ve learned to be careful about treating either feeling as a barometer of the business.

Today, we have very good people. We continue to improve. We’re on a good trajectory. I can recognize all of that and still find something about the future to worry about.

AI. Automation. Changes in what clients need. I don’t know exactly how those things will affect our agency over time.

Another Saturday at my desk won’t give me certainty.

That’s the part I’m still learning to live with. The same fear that pushed me to work hard can continue to demand more, regardless of how the business is actually doing. There’s no natural stopping point if feeling completely safe is the requirement. Because I never fell complete safe.

I have to come back to what I can influence: our strategy, the people we employ, the clients we choose, and the systems that help us produce consistent results.

Those decisions deserve my attention. They give the company something it can operate on beyond my willingness to keep working.

I feel responsible for the people who depend on this business. I always will. But carrying that responsibility doesn’t mean I can guarantee every outcome, and worrying doesn’t guarantee anything.

Seventeen years in, I’m getting better at acknowledging the fear and asking whether there’s something useful for me to do about it.

Sometimes there is. Sometimes I’ve done what I can for today, and the harder work is allowing that to be enough.

If the fear of letting people down follows you even when business is going well, how do you handle it. Reply directly to me at [email protected]. I look forward to hearing from you.

~ Erik

About
Erik J. Olson is the Founder and CEO of Proxa, where he builds and operates multiple marketing agencies focused on predictable, system-driven growth. He has scaled agencies across multiple markets by replacing fragmented execution with structured systems that drive consistent revenue. Erik is the author of Million Dollar Journey and writes The Business of Agency newsletter. He is building Proxa into a $100M platform with a planned private equity exit.