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Artist vs. Entrepreneur: When should you wear each hat?

artist vs entrepreneur

You know in cartoons or movies when the main character is trying to make a decision and there’s a little angel and devil perched on their shoulder taunting or encouraging them in either direction?

That’s your life as a creative entrepreneur.

And on your shoulder sit both Creative You and Entrepreneur You.

Constantly having to switch between your “creative” self and your “entrepreneurial” self is tough and can be exhausting.

Sometimes they overlap, yes. But for the most part, they tend to have different goals and values.

Consider, for example, some scenarios you’ve probably experienced:

Scenario 1: You flat-bid a project and then hit the max number of hours you allotted yourself.

Entrepreneur You would finish up the project as quickly as possible to save margin.

Creative You might justify working a few more hours on the project even though it means lower profitability and delay on other projects. Better to get it right.

Then again, Entrepreneur You could justify it as a marketing or branding expense: “If I really knock this project out of the park, this client will come back and might even refer their friends.”

See the dilemma?

Or how about this scenario?

Scenario 2: You feel like your work is getting stale so you search the web for some inspiration.

Creative You loves this process. Everything you take in contributes to the work you create yourself.

Entrepreneur You knows this kind of “work” doesn’t pay the bills and constantly nags at Creative You to “get back to work.”

When you finally do get “back to work,” Creative You gives Entrepreneur You a “told you so” because your work really has improved, you feel happier, and you put out more work that you’re proud of.

It’s enough for anyone to start to feel like they have multiple personalities.

So how do you know when to listen to Creative You and when to listen to Entrepreneur You?

The first step is to realize you have to wear both hats at some point if you want to run your own creative business. If you’re going solo at this, you can’t always wear your entrepreneurial hat or you’ll never get any solid creative work done. And you can’t just wear your creative hat all the time or you’ll never succeed at business.

(One small caveat: I realize that to be a successful entrepreneur, you also have to constantly be thinking creatively. This is more about the kind of work you do. Running a business vs. doing the work that your business is all about. For example: finding clients vs. designing web sites.)

Here’s what I recommend:

Take time each day, week, or month (find what works best for you) and put on your entrepreneurial hat. In this moment, you’re thinking 100% about your business: margins, profitability, growth, plans, etc.

Then take off the entrepreneurial hat, put on the creative hat and get to work doing whatever it is that lights you up.

There will be moments when Creative You wants to stick it to Entrepreneur You and watch endless cat videos on YouTube.

If you’re a pro, you’ll stick to the plan Entrepreneur You made.

Soon, you’ll find both Creative You and Entrepreneur You are happily satisfied with your business.

Entrepreneur You gets to focus on increasing profits, feeding your family, and building a business instead of just another job.

And Creative You gets to do enjoyable, creative, interesting and important work.

Everyone wins.

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Written by Preston Lee

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Preston Lee is the founder of Millo where he and his team have been helping freelancers thrive for over a decade. His advice has been featured by Entrepreneur, Inc, Forbes, Adobe, and many more.

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  1. Shana Haynie says:

    This post kind of reminds me of the post I wrote for you guys back in September called Sell out or Starve: How to Reconcile Your Inner Artist and Inner Marketer (

    Actually, I’d say this post is pretty similar in a lot of ways, but I like how you’re coming at it from an entrepreneurial angle. Entrepreneurs are famous for having to wear a lot of hats, (believe me, I know), and especially as a creative entrepreneur, there’s a ton of hats that don’t…quite…. fit.

    Ultimately, you shouldn’t have to sacrifice creativity in order to “pay the bills.” It just boils down to remaining focused on the big picture, and taking time to feed your starving inner artist along the way.

    1. Preston D Lee says:

      Shana, I agree absolutely. What a great post you wrote for us! And thanks for your additional comments here on this post. Have a great day!

  2. Joan Manuel Santos says:

    I like it 🙂
    Thanks Preston

    1. Preston D Lee says:

      Glad you enjoyed it, Joan. Thanks for reading!

  3. Joe Tantillo says:

    There’s one more hat to mention. The “update your skills” you. This demon on your shoulder is much harder to do if you are no longer full-time because, no one is asking you to do new technologies and giving you lessons and software as needed. You have to keep up on the new trends, which are moving so fast and keep your skill seriously up-to-date. Sometimes making a new project for yourself, will satisfy the “Entrepreneur You, and you can add a credential to your social media. It’s really hard work to break and learn something new every few weeks or months, but it’s really a necessity to staying in business. Also keeping your website up-to-date, (I’m one to talk, it’s been over a years) is part of this as an up-to-date website, with new technology shows you’re current.

    1. Preston D Lee says:

      Joe, great addition. Thanks! To me, it seems like this one lies right in the middle of the two. “Entrepreneur You” knows that you need new skills and an up-to-date website in order to stay relevant and appealing to new clients. But learning new skills is also a favorite task of “Creative You”—sometimes learning new skills you don’t necessarily need yet. Wonderful comment. Thanks!