Play Your Way to a Successful Creative Career: Interview with Melissa Dinwiddie

Have you ever found yourself burned out from making your art?

Play Your Way to a Successful Creative Career

Our guest today has and she’s learned some valuable lessons as a result. Melissa Dinwiddie is is an artist first, and entrepreneur second. She has a great story to share. I loved it so much I included it in my book Real Artists Don’t Starve. Today we’ll hear what I didn’t include in the book and what new endeavors she’s taking on.

Before she was paid as an artist, Melissa wondered whether or not she was worthy of that title. But after her friend paid her $25 for a commissioned piece, Melissa finally believed she was an artist.

That her friend took her seriously enough to pay her made it a very big deal in her mind. Melissa says she needed someone to hold up a mirror and tell her she is an artist before she could make art for a living.

Many of us have experienced this, too. Even though we understand intellectually we don’t need others’ permission to be an artist, there are still moments like Melissa’s that are pivotal to helping us own our inner artist. It doesn’t have to be a gatekeeper like an art dealer or gallery owner, it can be a loved one like it was for Melissa.

Once she began making art for a living, she eventually stopped making art for herself. Soon, Melissa was putting business first, and artistry second. On this episode of The Portfolio Life, she shares why they need to be inverted with art first and entrepreneurship second.

We also talk about why we often get stuck in a rut and how to we can get ourselves out. Finally she tells us about her current business: it’s creative consultancy that shows companies how to be more effective through the use of methodologies like play.

Melissa tells us what that is, how she found it and much more about learning to play in your creative sandbox on today’s The Portfolio Life.

Listen to the podcast

To listen to the show, click the player below (If you’re reading this via email, please click here).

Show highlights

On today’s show, Melissa and I explore:

  • What is paper cutting and why did she combine it with calligraphy?
  • Why did she get burned out making art for pay?
  • What is a ketubah and how was it critical to her evolution as an artist and entrepreneur?
  • How can you keep the fun alive in your creative process?
  • Why is play NOT the opposite of work?

I stopped following the fun, and starting only following the money.

Melissa Dinwiddie

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The choice to make money from art

  • Should a creative person be trying to monetize or not?
  • How much time should you be spending on marketing and commerce for your art?
  • Is making money from art something every artist should pursue? Why or why not?
  • What is her golden formula?
  • What does it mean to think daily and tiny?

There are so many different ways to be a creator.

Melissa Dinwiddie

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What it means to be creative

  • The lesson we can all learn about creativity from my 4-year old.
  • What is the question to ask yourself if you think you are not creative?
  • When did she start believing she was not an artist?
  • What is the comparison-trap gremlin?
  • Why did she stop taking art classes for 15 years?


How are you going to add creative sandbox play to your life? Let us know in the comments.