My pal Chris Guillebeau has a great interview up over at his blog, The Art of Non-Conformity. He recently profiled artist Tsilli Pines (who also happens to be a loyal GRS reader and a customer of my family’s box factory). The interview discusses Tsilli’s development as an artist, her initial steps toward starting her own business, and her decision to make the leap to full-time entrepreneur. Here’s an excerpt from the conversation:

What is your advice to someone who wants to “escape” from traditional work and start something like this?

Find what you love to do, and then do it, even if it doesn’t bring in money at first. Experiment on the side, experiment on the cheap. It’s the single most important concept to grasp if you are looking to build something from scratch.

What worries you?

Everything! I’m a chronic worrier. But there’s a bad way to worry, and a good way.

The bad way of worrying paralyzes you. You worry you won’t make the money side work, and it seems so overwhelming that you decide not to even try. I used to worry in this way, and did nothing.

The good way of worrying keeps you competitive, keeps you striving. For example, I still worry about making the money side work (especially now that I’ve thrown my weight into my own business completely). I still think, “What if all the work dries up? What if a competitor comes into the market that takes away my market share?” But I worry about it differently now. I worry about it by thinking ahead of the curve, recognizing what my strengths are and what I can do to mitigate that risk.

I think this is fascinating. I’ve always admired artists for their passion, but wondered how they could make a living. It’s great to see somebody making a go of it. (Doubly so since Tsilli is a GRS reader!)

You can see some Tsilli’s art at her website; her business is called New Ketubah.

Note: Mr. Guillebeau makes his living producing e-books. One of these is The Unconventional Guide to Art and Money, which teaches artists how to thrive without selling out. From the site: “Here’s a shocking idea: artists are not destined to be poor. If you’re an artist, you can actually make money from your art, feel good about it, and build up a following to support your independent career. Seriously.” I haven’t read this guide, but I’ve heard good things about it.

By the way, I recently did something I’ve always wanted to do: I commissioned an artist to do a painting for me.

Chris’s wife Jolie does whimsical paintings of children’s toys. When my wife’s sister loaned Jolie a stuffed Kermit the Frog to paint, I loved the result, and I knew I had to commission a painting of my very own. Here is a very very J.D. painting, which I plan to display in my Man Room:

It's Not Easy Being a Man
“It’s Not Easy Being a Man” by Jolie Guillebeau

I love Kermit holding his pipe, his glass of Scotch at his side, and sitting on a copy of Your Money or Your Life. The only thing that could make this better would be if he had a stack of comic books by his side.

Speaking of art and entrepreneurship, Jolie is conducting an interesting experiment right now. In order to challenge herself (and perhaps make a little money), she’s creating 100 paintings in 100 days. And she’s selling each of them. For the first painting, she charged $1. For the second, she charged $2. And so on. The 100th painting will go for $100.

Though the money Jolie earns from this will be modest ($5,000 before expenses), it’s a great way for her to get her name out there. It’s a marketing ploy and a money-making project all in one.

Artists are entrepreneurs, too! It’s fun for me to get a small glimpse into their world.

[The Art of Non-Conformity: The Eight-Year Escape Plan: Interview with Tsilli Pines]

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