The Work of Being an Artistic Entrepreneur

The Work of Being an Artistic Entrepreneur

SUMMARY: Buddy Brad reminds me that making a living from one’s “art” is hard work, but once you get something working you should continue to do it until it’s exhausted. It makes sense, but there are a few mental hangups that I need to overcome as well. One is preciousness, and the other is perfectionism.My illustrator buddy Brad Fitzpatrick left a timely comment on yesterday’s post about staying focused on what works, in the context of being an art-based entrepreneur:

Find something that works and repeat it over and over again until it’s exhausted. THEN (and only then) move on to your next great idea.

Although this looks simple on the surface, it’s fraught with unseen difficulties that I’m all too familiar with.

First, consider the act of finding what works. One barrier is that it can be incredibly difficult if you are the type of person that looks for meaning in what you do. The meaning becomes precious, and this preciousness prevents us from selling out. As noble as that is, it also is one of the curses that prevents us from making our own success. By comparison, the business-oriented mindset has a much easier time of it: just go see where people are going to solve their problems, and then you insert yourself into the middle of that value chain. Make a great big sign that says THIS WILL FIX YOUR PROBLEM, and apply a bit of insight into the human psychology of want to your materials, set a price that makes sense, and you have the beginnings of an actual revenue. The difficulty for me is to reconcile the “preciousness” of what I do with the “need to make a living”. This is seemingly an intractable problem until you find a way to protect the preciousness while vigorously pursuing the almighty dollar.

For someone like me, it has taken a lot of a tremendous reframing of my value system to even think about making money in a way that doesn’t feel like I’m somehow selling out or walking the wrong life path. I am tremendously concerned about disrupting the purity of what I’m doing. In the context of work, there is an additional value system that I have when it comes to selling something:

  • Whatever I do, it’s got to work
  • Whatever I do, I have to understand WHY it works
  • Whatever I give, it has to be guaranteed to be useful
  • Whatever I make, it has to be imbued with my original
  • Whatever I claim to do must be 100% credible, demonstrable, and ready-to-go on demand
  • I should do everything in my power to prevent people from being mislead or having hopes falsely raised
  • Whatever I do or make has to be the best I can make it, original, innovative, and effective
  • If people don’t intuitively understand what I’ve done for them, then I have failed to meet their expectations

I find it difficult to find fault with any of the above in principle. However, I know that there are very high levels of expectation that I haven’t, which calls to mind the John Updike qote (truncated here) perfectionism is the enemy of creation.

The next part of Brad’s comment is the idea of repeating something over and over again until its potential has been exhausted. As a seeker of the novel and new, this is the kind of advice I usually don’t like to hear; by the time I finish something out, I’m rarin’ to go on to something else. However, that means I’m probably leaving fruitful opportunities on the table. Creating new things is fulfilling for me, but the reward comes when we push to get that thing out in the world in a form where people can actually see it. I’m pretty sure that there’s some way to reframe the “boring” aspect of this into a game, and I think that game is probably learning how to read revenue reports that result from one’s business activities.


  1. Brad Fitzpatrick 13 years ago

    I’d like to have time to comment on how flattered I am by this post and how I’d like to alter the Updike quote to say “Perfectionism is the enemy of PASSIVE INCOME” and how I think that being a purist is an impossibility… but I’m *right* in the middle of drawing a camel that will solve somebody’s problem someday. ;)

  2. jimmydddd 13 years ago

    Regarding “repeating something over and over again until its potential has been exhausted,” and being “a seeker of the novel and new,” it’s common in the startup world to have serial start-up entrepreneurs who continuously get a new venture going, then pass it to those better at managing, and then start a new venture.  Maybe you could experiment with some form of passing off a (not too precious) project to a manager type.  (I think you are sort of doing this by consulting with people who have manager skill sets).  Of course, this would conflict with your autonomy.

  3. Ashish 13 years ago was good seeing you yesterday and today.

    Your “whatever I do..” list makes me think that you want to have too much control.  I think life is too random for that.  That’s not to say that one should drift.  I guess, for myself, I have narrowed it down to “Always do your best”(agreement four)

    “If people don’t intuitively understand what I’ve done for them, then I have failed to meet their expectations”

    huh?  Might as well take a knife and slit your wrists now.  Everyone(including myself) are caught up in their own dream/illusion to be aware.  You are caught up in your dream, too.  One thing that I have learned the hard way..and am still learning to accept…“I have no control over other people’s reactions”

    You can do the best that you can..and you can fulfill everything on your “Whatever I do” list..but it doesn’t guarantee anything.

    Perhaps I should loan you my Bhagavad Gita(…which references doing your duty without expectation of any rewards.  I realize that rewards you are seeking are not personal nor selfish, however they are still rewards in a self-deceptive way.

    “but the reward comes when we push to get that thing out in the world in a form where people can actually see it”

    are you implying that you wouldn’t do anything if no one else wasn’t around to see it or appreciate it?  I seriously doubt it.  I don’t think true artist create things for others to see it or even to appreciate it.  Why give others control over your art?  Or, yourself, for that matter?


  4. Tammy Hildreth 13 years ago

    Hi Dave,  Although it’s great to have lofty goals about your work/art, and I am a true believer in asking way too much of oneself, I think your value system doesn’t give enough credit to the consumer. 
    By consumer I don’t mean everyone.  I mean the target consumer – the people who understand enough and can empathize enough to see the value in your art.  Your target audience is intelligent.  They can take a concept and run with it.  They can use a good product, a decent idea, as a launching point for their own creative uses. In short, they “get” you.
    You don’t need to be perfect to provide value to your target consumers.  To use a gardening analogy, you just need to have the seed of an idea and cultivate it enough to show that it grows a plant.  You don’t have to give us bouquets, or even blossoms…just evidence of some budding.
    Isn’t that where most creativity begins?  Don’t we often take someone else’s idea and add our own twist to it?  I think you should consider that, and recognize the value you are providing even when your product is short of perfection.

  5. Dave Seah 13 years ago

    Brad: Heh, you are the master!

    jimmydddd: That’s an idea…I’ve often wondered if I’m an “early-stage” guy. However, the rewards go to the guy who can see things through to the end…that’s where the real profits are. That said, I think it’s important to have people that one can work with and complement each other with the right skills and interests. I’m actively trying to find those kind of connections.

    Ashish: Those are good challenging statements. As I said, but did not make as explicit as I could have, was that I’m challenging my expectations. It’s hard for me not to look beyond the “control issues” I’ve listed…these are expectations I’ve developed over the years that I’m trying to overcome. As I say at the end, “perfectionism is the enemy of creation.”

    As for “true artists”, I’m not one of those. I think it’s a false argument to raise the idea of “true art” in the context of my use of the term. I do things that are for my own reasons, and one of those reasons is to see what happens after I make them. I love seeing what happens, and effecting changes through my actions. The “art” part of it is challenging myself to do it despite my tendency to expect mastery before public practice. I think most people have this in some form, and I am highly aware of it in myself and others.

    Tammy: Wow…that’s a great insight! It took me a few moments to really get it, but yes, I probably am not giving enough credit to the consumer. Or another way of putting it: I am taking too much responsibility for providing for everything because I want the experience to go perfectly too.  I’m not sure where that desire comes from…it is probably why I am an honorary Virgo in some circles :-)

  6. Stephen Smith 13 years ago

    Tammy has a great point Dave, one that I think we could have talked about more in the KES meeting. Namely, what are you selling?

    My idea for a “custom”, or unlocked, PCEO matches Tammy’s point of providing a plant for the customer to make into their own bouquet.  Let’s talk about this more at the April summit.

  7. Kristine Spengler 13 years ago

    Thanks for the great article! I find myself getting stuck in non-productive ruts as a result of looking for the perfect idea that will revolutionize everything and everyone in the world. Then I remind myself that there’s truly no such thing as perfection and that it’s a rare, and probably even impossible, feat to create/write/develop something that works for all people all of the time. Most of the time it’s better to just start, somewhere, anywhere, rather than look for the perfect solution. As the saying goes, you eat an elephant one bite at a time.

  8. Emily Wilkinson 13 years ago

    I think there’s something in repeating the same formula over and over again if it works, but does it have to be exhausted? If you allow your practice to evolve organically (with some strategic direction) then surely you take what works and keep using that but continually review and drop what doesn’t work, whilst adding new elements and trying different things to keep your creativity and spirit alive.

    If we can find ways of working that allow this more evolutionary approach then maybe we wouldn’t feel bored or exhausted. I for one need to believe that this is possible, which might sound idealistic but maybe it’s just sustainable and practical for others and yourself?

  9. Jarrod 13 years ago

    Just as the definition of insanity is doing the same thing over and over again achieving no results we must focus on doing the right thing over and over again.

    Those things that work for us, that are learning experiences and that are progressing us in life, are the things we should be focusing our time, thoughts and efforts on.

    Great post!