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This is a guest post from the amazing Melissa Dinwiddie. I've been working with her off and on for several months and I think her story is instructive to many artists. This is the second post in a series on how her art evolved into a thriving full-time business that supports her mortgage.

In Part 1 of this series, I shared my story of how I became an artist and grew a business from my art.

In a nutshell, I fell in love with the art of calligraphy, and fell into the business of creating custom artworks for clients, primarily ketubot (Jewish marriage contracts) for engaged couples.

At first it was all sweetness and light: I was making art, trying new things, and getting paid for it! What could be better, right?

But after my divorce, when I really had to make a living, the hard kicked in. For a number of years I worked like a dog to build up my line of ketubah prints, while at the same time accepting client commissions because I couldn't afford not to. As my line of prints grew and I spent more time processing orders, I found myself effectively working double-time.

The commissions were inevitably squeezed into overtime hours, and always with a hard deadline to meet — somebody's wedding! For a number of years my mantra was "I wish I could afford to stop doing commissions."

In 2005 my line of ketubah prints was bringing in a decent income, and I designed a line of invitations and stationery to match, which brought in a bit more (and also started a trend in the highly competitive ketubah "industry"). Late that year, after three months solid of all-work-and-no-play, I crunched the numbers, took a long, hard look at my life, and realized that not only could I probably afford to stop accepting commissions and live on print sales alone, but I couldn't afford not to.

I was running myself into an early grave.

How had this happened? I got into the art business because I loved making art, and wanted a career that would allow me the freedom to do the things I love. Instead, the business side of my art business sucked up most of my time and energy, and I got so burned out that when I did have free time, I didn't spend it making art.

My art had become "just a job."

Money changes everything

One of the problems with turning your passion into your income source is that money has a dangerous tendency to color relationships — let's face it, to poison them — including the artist's relationship with her art.

When I got started as an artist, I lacked the imagination and confidence to think I could make whatever my muse inspired me to make, and then find an audience to buy it. (In my defense, this was even harder to do back then, when the internet was still in its infancy.) Instead, I took what seemed to be the path of least resistance, and I made the kind of art that I already knew clients were looking for.

In and of itself, this is not a bad thing. However, over time I stopped thinking in terms of "what does my soul want me to create?" and got stuck thinking "what can I do that will make me money?"

And when everything becomes about money, it just stops being fun.

Gradually, I found that my soul was no longer getting the nourishment from my art that it used to. When I had free time, I no longer turned to my drafting table for my fun, creative thing.

(On a side note, there was a surprising silver lining to this sad state of affairs. Because sitting at my drafting table felt like a busman's holiday, I started making music during my free moments, and discovered a new creative passion. Over time this evolved into a second art career as a jazz singer/songwriter! I will admit, though, that I'm hyper-vigilant about not wanting money to poison my relationship to my music. I'm very clear I don't ever want to depend on my music to pay my mortgage, which may be part of why I haven't pushed my music career as hard as I might have.)

Here I was, making my living as an artist (in expensive Silicon Valley, no less!), but spending very little time actually creating new art. I was a working artist, but I wasn't very happy.

With the benefit of hindsight, I can see that my business model had a number of weaknesses as a path for my long-term happiness.

1) I wasn't following my true passion

When I first took up calligraphy, making a ketubah was a big, exciting goal. And getting paid for it was a dream come true! I was proud and eager to wear the label ketubah artist.

But although I still enjoy making ketubot, my real passion was never ketubot, or weddings. My initial groove turned into a rut, and I got stuck in it.

Whereas some people are happy to dive into one thing and stick with it for a lifetime, I've always been multi-passionate, and my creative impulses wanted to forge new artistic paths, try new things. Because the ketubah and custom calligraphy business was paying the bills, though, I "followed the money," rather than following my bliss. And although I pushed the envelope of ketubah design, working in a variety of styles and media, it still wasn't enough to fully satisfy my artistic needs.

2) I didn't have clear goals

Looking back, I can see now that my biggest problem was that I literally just kind of stumbled into the ketubah business, rather than starting with a clear picture of what I really, really wanted, and then working to build it. To paraphrase Steven Covey, author of Seven Habits of Highly Effective People, I climbed the ladder of success, only to discover it was leaning against the wrong wall!

3) What goals I did have were set way too low

Artist and coach Ann Rea says that the biggest problem most artists have is in not setting their goals high enough. This was certainly a problem for me.

I was cowed by the "starving artist" myth, and couldn't envision success as an artist doing what I really wanted to do, so I settled for what felt possible, doing work that I enjoyed but wasn't passionate about.

It's worth noting here that I also set my financial goals too low. I couldn't envision myself making a lot of money, so I settled for a goal of "just enough to get by."

The thing about goals is that whatever goals you do set are what you're programming yourself to achieve. Sure enough, I created a business that made just enough to get by, doing work that I enjoyed but wasn't passionate about.

Better than working in a cubicle, for sure, but not the best I could get.

4) I didn't set set clear limits for myself

Not having a clear vision of alternative ways that I might consciously create an art business, I fell into the business of doing private — and heavily art-directed — commissions.

At first it was exciting to be paid to use my artistic talents, but not only did I soon tire of being underpaid, I also chafed at having to fulfill my clients' vision instead of my own. Don't get me wrong — taking commissions is not all bad; I enjoy the challenge of realizing a client's vision, and it has pushed me to create artwork that I never would have created otherwise, of which I'm very proud.

However, I got into art because of an internal desire to create, to feed my soul. And I will not kid you: the commissioned pieces I was making could be fun and satisfying in some ways, but they weren't the art I was aching to create. Plus, although a lot of my clients were a pleasure to deal with, some were… um… not.

(I have since encountered artists with a completely different model of commissions, in which the artwork is entirely the artist's artistic vision, and no art direction by the client is involved. But back when I got started, for whatever reason, I was simply unable to imagine that this might be a viable possibility for me.)

Setting limits was especially hard for me when money was tight.

To this day, whenever I feel scared about my money situation, I tend to fall into the trap of taking every job that comes my way (usually for much less money than it's worth). This is always a mistake. Not only do I end up resenting the jobs, but I probably scare away more sales than I attract.

My attempt at a solution: streamlining

Although I was increasingly dissatisfied with my art life, my business was steadily growing (and without a lot of active marketing efforts on my part). Success is validating, and it seemed only logical to keep heading in the same direction.

After years of busting my butt, though, I was burned out and desperate for a break. Print sales were good, so I decided to spend a year "coasting." I consciously "retired" from commissions and let the business chug along without any new input on my part: I actually set an intention to create nothing new for the business for a full year, in the hopes that it would get me back to creating for me, to feed my soul.

It all seemed so logical: if I could simply liberate my energy away from the custom work and streamline my business as much as possible, the less time I'd have to spend in the business, and the more time I'd have for my creative things.

The surprising result: boredom!

As it turns out, my "year of coasting" evolved into two and a half years, and the results were not at all what I expected. At first, it was a huge relief to coast for a bit and not create anything new. But after awhile I realized that now, with the exception of designing proofs for client review, my business was 100% drudge work, with very little creative benefit to me at all.

It's true I worked for myself, in my own home, but I wasn't doing anything fun or creative.

I wasn't truly satisfied, but my situation wasn't uncomfortable enough for me to make a change. I had a nagging sense that I wanted to make things different, but couldn't figure out what or how. Besides, business was going great, and I was feeding my creative needs with my music, so why complain?

I see now that I was stuck thinking in a box. I bought into the lie that it's not possible to do what you really love and make a living from it. I settled for the standard vision that a job is a job, that the goal is to spend as little time as possible at it, to allow as much time as possible away from it to do what you really want.

Then the unexpected: the Crash

From the day I officially formed my business in 1996, it had grown steadily upwards. 2007 was my best year yet, and I was sure I would hit my personal income target the following year.

Instead, 2008 happened: the economy crashed, and my business dropped dramatically. Around the same time, I discovered that without realizing it, I'd been spending more money than I brought in, using savings to make tax payments and IRA contributions when I didn't have the cash in my checking account. Oops…

The universe effectively walloped me upside the head with a 2×4. I was heading for an implosion.

Next up: more mistakes, more wallops upside the head by the universe, and finally, a renaissance (coming soon)

Melissa DinwiddieMelissa DinwiddieAs an artist/designer, freelance writer, jazz singer/songwriter, and teacher/coach, Melissa Dinwiddie likes to call herself a Multi-Passionate Creative ARTrepreneur. She combines her varied passions on her blog, Living A Creative Life. Melissa's current project, the Thriving Artists Project, is an online course for anyone who aspires to turn their art or creative thing into a full-time career.

Cory HuffThis article is courtesy of
Cory Huff is a digital strategist specializing in helping artists learn to sell their art online. His Big Hairy Audacious Goal: help 1000 artists create a full-time living from their art. You can view more blog posts like these and get a free gift for ArtPal artists here: window