for creative entrepreneurs

Episode 68: Are You Cut Out for Creative Entrepreneurship?

Back in my art school days I took dozens of classes in drawing, painting, and design. We studied our craft intensely. And as senior year approached we all started working diligently on our portfolios, getting ready to make the transition from student to creative professional. We all felt tremendous excitement and anticipation, and no small amount of anxiety as we contemplated facing the real world. As I looked around me, considering the fact that my peers were about to become my competitors, I began to look at their work from a different perspective. Frankly, many of my classmates had much more talent than I did. But I also noticed that the overwhelming majority were terrified, and ill equipped to face the business aspects of what laid ahead.

There are some creative disciplines that have a direct path to a full time job. If you study architecture, or graphic design you may very well end up with a staff position you love. But if you’re a fine artist, or illustrator, or designer who prefers the freelance path you’re going to need to build a freelance practice. And that means running a small company, even if it’s a company of one. But when you’re studying painting and illustration, you’re not thinking about cash flow, marketing, or writing contacts. You think of yourself as an artist, not an entrepreneur. And so you end up being cast into the world of entrepreneurship without ever considering whether or not you’re even cut out for that path. Sadly, many of my classmates never made that transition, and frankly their amazing portfolios didn’t help them when they had to make a radical career change to pay the bills.

Art school can produce well trained artists but it doesn’t equip entrepreneurs. It provides focused critique on artistic skills, but never assesses an individual’s temperament, or their general fit for running a business. Maybe you’ve been struggling to run your creative practice, not only for lack of preparedness, but maybe because it’s just not your calling. Are there any ways of assessing whether or not you’re cut out for creative entrepreneurship?

There are some indicators that can help you determine if creative entrepreneurship is the right path for you. But before I list some of these, don’t ever confuse the simple fact that being an entrepreneur is hard work, and that it can be exhausting even when you’re perfectly cut out for it. So don’t be too quick to rule this path out, just because you’re facing troubles along the way.

The first characteristic you need to have, as an entrepreneur, is a “never give up” attitude. You will face challenges, and if you’re too easily overwhelmed you’re not going to get over those hills. That’s not to say that there’s never a time to call it quits—you don’t want to wear yourself out by pressing on when you’re heading in the wrong direction. Nevertheless you have to have deep resolve to make it in business.

One characteristic of the creative entrepreneurs is a general comfort with risk taking. There’s no business venture that does not involve risk. And there are a thousand small decisions involved in running a business. If you belabor your decision making process, or wring your hands over every tough choice, you’re going to drive yourself crazy. Part of being a risk taker is not blind optimism, or confidence that you are always making the right decision. It’s the ability to make the best decision you can, with the information at hand, and being okay with the possibility that you might be wrong, and have to deal with the consequences.

At a practical level, if you’re going to run your own business, you need to cultivate a broader set of skills than just your core artistic talents. You’re going to need to budget your money and your time more efficiently. So consider how you do with your personal finances, and your personal calendar? Do you manage your money well, and keep track of meetings? Or do you bounce checks and miss appointments with some degree of frequency?

Not everyone is cut out for creative entrepreneurship. If you’d like to evaluate yourself in a bit more detail check out my freelance suitability survey available at It’s one thing to endure the struggles of running a creative business, it’s another to swim upstream against the current of a temperament that’s just not suited to this kind of life.

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

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