Episode 69: Free Yourself from the Fear of Failure

When a creative has launched out on their own, they’ve entered the path of entrepreneurship. Being an entrepreneur is not for the faint of heart. Entrepreneurship involves risk. Even a simple solo-preneur freelance practice assumes all the risks associated with being in business for yourself. The ultimate risk you take is simply that you might fail. There are potential serious implications in failing, especially if you unwisely leverage yourself with debt in the process, but even if you avoid debt, the idea of failure itself can be terrifying. For some people it’s paralyzing. But if you’re going to make it as an entrepreneur, you’ll have to overcome your fear and courageously face the possibility of failure.

Are you ready to take the struggle out of finding new clients?

The very first iteration of my career as a creative entrepreneur involved freelance illustration and producing fine print broadsides, cards, and invitations. My focus in art school was letterpress printing and wood engraving, and right out of school I got an opportunity to buy my own Vandercook proof press and several cases of metal type. For about a year I produced a line of limited edition, signed, hand-printed greeting cards. I succeeded in making them, and utterly failed to sell them. I still have boxes of beautiful cards in my closet.

That first business was a failure. I wasted an enormous amount of time, and money. But I also learned some important lessons. Many of those helped me when I started my first company with actual employees and office space. But I was not done learning. That company did end up succeeding, but not without many failures along the way.

As I look back on all the mistakes I’ve made over the decades, I sometimes shudder at how close I came to complete failure, so many times. But instead I learned my lessons, patched up my business, and made it stronger for the future. The expression, “whatever doesn’t kill you makes you stronger,” is quite fitting in life, but it’s especially applicable to business. But only if you learn from those failures.

Over time, when you’ve studied long enough in the school of hard knocks, you stop being so terrified of failure. And once you’ve had the opportunity to experience the pain of failure a few times, and survived to enjoy the benefits that accompany those painful lessons, you can almost lose that fear entirely. Almost.

Failures take many forms. You can fail to manage client relationships. You can drop the ball in communication. You can make assumptions in estimating work and end up providing quotes and estimates that are way off. You can simply fail to deliver great work, or miss the mark in your strategy. You can make bad hires, fail to market yourself effectively, enter into unwise contracts or partnerships—there are potential failures and landmines everywhere.

The most painful kinds of failure are the ones directly attributable to our own faulty decisions. Whether we make them out of ignorance, or just make a bad call—those failures sting the most. Especially when they result in having to reduce staff. Never a good time.

When we evaluate our failures in hindsight we often give ourselves a head slap. But as creative entrepreneurs we can’t afford to beat ourselves up forever. You will make mistakes. Sometimes costly mistakes. Try not to repeat them, but don’t set impossible standards for yourself. You’re going to make mistakes. Learn from them, get up, dust yourself off, and move forward.

Of course there are also failures that are not your fault at all. This past year has seen many small businesses shuttered due to governmental decisions that unilaterally closed restaurants, decimated travel, ended live entertainment, and cancelled in-person conferences world wide. Sometimes situations completely outside your control can mean failure. And you have to be okay with those risks as well.

Failure is a part of life, and a part of business. As an entrepreneur you are signing up for a roller coaster ride of learning through failures. Success in business is not the result of avoiding failure, it’s what you do in the face of them that matters.

Until next week: don’t let the business of creativity overwhelm your creative business.