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7 Questions that Shape Your Art/Work Life

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Please Write this Book: The Freelancer’s Attitude Kit

I’m working out new ways to present the freelance life to college writing students. They are interested in this independent life but not clear about all it entails. They wonder: is there more to it than sitting around in your underwear all day?


I’d like to present them with a textbook that answers these seven questions. Because these are seven questions that freelancers and other independents continually ask and occasionally even answer. These questions are useful for anyone trying to figure out the relationships between work, craft, art and employment.

  1. How do I balance art, craft and economics? Is it even possible? Because there is stuff I want to do that has no audience. There is stuff I’m less interested in that has a larger audience. And there is stuff I can do to pay the bills, which frankly doesn’t engage me much. I feel less fulfilled when I do that third category of stuff. Then again, I feel pretty fulfilled when I cash the check from that third category. Part of the answer has to do with what your time in life allows. Part of the answer has to do with the economic choices you make.
  2. Is it me or is it you? What does it mean to care for others with my work? Is it possible to use my art or craft or skill to truly look after the needs of another—or perhaps to look after the needs of an organization? One point I’ve made repeatedly to students is that while introspection is one way to sort out who you are—and our creative lore pegs introspection as the main work of writers and artists—there is another way. And that way is finding places and people to work alongside and, well, serve. Sometimes we begin to sort out who we are as we seek to help others. Sometimes our collaborator and our collaborative processes reveal more than we could ever sort when isolated at our desk or easel.WhatIsArt-04302015
  3. What unseen forces are at work? I am a copywriter who also believes that God answers prayer. I am a copywriter who is also comfortable with artists who say the universe provides. My point is that the independent person has a better perspective when convinced there is more going on than what they can muster on their own. For example: every client I called last week said “No.” But then two new calls came in from completely unexpected sources. And these calls said “Yes.” Coincidence? Faith of one kind or another plays a role in this life—especially if a spouse/children/mortgage are part of the picture.
  4. Where does my ladder lean? Aiming for the approval of your boss is not bad, just limited. Bosses change—and sometimes very quickly. Better to climb toward a larger goal. In corporate life, we climb toward this position or that responsibility. In freelance, we climb toward this kind of project or that kind of project. Freelance does not have titles and offices that automatically designate how important you are. Are you ready for that? Freelance depends on intrinsic motivation—the stuff that bubbles out from inside. In fact—it turns out—that corporate life does too. The intrinsically-motivated colleagues are far and away the happiest, because they do the work out of willingness and mission. Just like freelancers.
  5. What do I look like, an entrepreneur? In fact you do, if you are someone who sees a need and starts to figure ways to meet that need. One textbook defines entrepreneur this way:

Entrepreneurship is the process of identifying opportunities for which marketable needs exist and assuming the risk of creating an organization to satisfy them.

–Hatten, Timothy S. Small Business Management, Entrepreneurship and Beyond (New York: Houghton Mifflin Company, 2003)

There is risk with the approach: you might fail. It might take a long, long time. This approach requires turning that intrinsic motivation into an engine that chugs along every single day. That can be exhausting, especially when met with a daily chorus of “No.”

  1. What’s sharing go to do with it? Today artists and writers and crafters and tribe members find each other online. Not exclusively, but frequently. Part of the independent life has to do with finding generous ways to talk about your passion. This is not shilling for work, this is giving away good stuff. Good stuff that people can use. It turns out that clients just might find you this way as well
  2. What if people knew how weird I was? That’s right, you are strange. Really strange. But everyone is. Freelance capitalizes on weird by you doing what you do in the way you do it. Freelance is the opposite of cookie-cutter. It is niche-building with much of your weirdness intact (not all, people will run from you).

That’s the book I want to use as a text. Some books I’ve read come close.

What questions shape your work life? Tell me if you’ve read this book.


Image and dumb sketch credit: Kirk Livingston

Written by kirkistan

September 30, 2015 at 10:13 am

12 Responses

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  1. Great post Kirk! Loved it all, but definitely prescribe to 3 & 6. When I’ve freelanced it always seems like opportunities come from exactly where I wasn’t actively looking for them.

  2. Wow, that’s a lot to think about. But good to pose the questions for your students.
    I needed to work and also raise children so I just did it. But I’m glad I had a full time job for a number of years first. Good to learn the day-to-day discipline and not-perfectness of making a living and it also gave me the connections I needed to make it work. (K)


    September 30, 2015 at 9:00 pm

    • Good point. Thanks, Kerfe. It is a lot, that’s why I want a entire book to walk through each part.


      September 30, 2015 at 10:27 pm

      • So write it!


        October 1, 2015 at 4:59 am

      • That’s what I’m thinking. Thanks.


        October 1, 2015 at 6:44 am

      • I don’t know anything about the college textbook industry, but there’s certainly a need to be filled.


        October 1, 2015 at 11:08 am

  3. Yeah. Write it, Kirk. Really enjoyed the article. I need more time to respond. I’m on the cusp of hopefully opening an art business in addition to my small tax practice, and there’s a lot to consider. But your article spoke to me, particularly the weirdness part. That was such a great point, and IMO, college students NEED to hear that. There are way too many sheep in our society and world, and particularly among the young. Here is a way they can truly be themselves AND contribute and rake in some green too. Win win win. Nice post!!

    Laura (Createarteveryday)

    October 1, 2015 at 7:36 am

    • Thanks, Laura.I’m glad you are thinking about opening an art business.


      October 1, 2015 at 7:40 am

      • Thanks! Sometimes I wonder if I have the energy, hehe. But it seems Christmas shopping season would be the time to do it, if ever there was a time.

        Laura (Createarteveryday)

        October 1, 2015 at 8:32 am

      • Thanks, Laura.I’m glad you are thinking about opening an art business.


        October 1, 2015 at 8:46 am

  4. […] Seven critical questions help frame how we progress in our quest to balance work, art and economics in real life. One of those questions has to do with where we aim all our efforts: “Where does my ladder lean?” Common assumptions about work include the notion that you want the corner office and the big stock options that come with the high-octane positions. Of course you do: money and power are on everyone’s radar. Writers and artists want fame and money. Athletes want wins and fat contracts. Televangelists want souls with wallets. We all aim at something because that’s how we motivate ourselves. […]

  5. […] thinking of my next book. It may be something related to the seven essential questions that shape our expectations about work and life. It may be something completely different. But I am […]

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