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Taking chances is not about the rewards. It's about whether or not you can live with the results of not taking the chance.
I'm one of those calculated risk people. I don't mind taking risks. Change doesn't bother me. However, I don't take needless risk where I could permanently harm myself (not a big fan of pain). I remember, in my 30's, when a friend of mine asked me how I could keep asking women out all of the time after I kept getting rejected. It was simple. The alternate was to let luck find someone for me. Not going to happen. If I was going to meet someone, I had to get out there and do it myself. I remember, in my 20's, when I was about to be laid off, my manager said that I could take a job with our consulting firm doing Windows development (in the early 90's) for a guaranteed 3 months or keep doing C++ on Linux systems for the government for a guaranteed 3 more years. I took the 3 month job. I knew that Windows commercial development would be the big thing in the 90's and beyond versus more government work.
So, when I take a risk, I look at my current situation. See if I really need to improve the situation and then figure out the best way to go about making the change. I want to be a full-time artist. Am I going to walk away from my day job this second and just go out and do that? Nope. Some people would. However, that doesn't fit into my risk level. Could I make it? Sure. However, I'm almost 50. I love what I do for a living. I have a responsibility to my wife and dogs to make sure that they currently are comfortable and that they have a good life when we retire. There is no benefit for me to just walk out and become a full-time painter.
However, there are smaller things to take risks on. I signed up for smART School. It's expensive. It's a risk where the outcome of the class may or may not be worth the cost (I've taken lots of classes where I've thought that the class wasn't worth the cost). I need help with my compositions. Plus, the artist that I'm taking the class with, Greg Manchess, has lots of methods for dealing with thumbnails and composition methods. Yes, it's a risk. But, I think that the risk is worth what I would learn.
Every time I create a painting or do a show, I'm showing my work in front of people. They may hate it. They may throw tomatoes at me and tell me never to create art again. This is a risk. Art fairs cost money. I may spend a lot of money on prints and attending the show and come home deeper in debt. Training costs money and time. Art supplies cost money. Every time you put your artwork out there, you are taking a risk for acceptance.
Some of the ways that I minimize risk:
What are the pros and cons of doing this activity? This is your basic list of "Do the benefits outweigh the risk?" It's easy to lie to yourself and weigh in one way versus the other. I know that I do that. If I want to really do something, I'll weigh it more to the pro-side versus the con-side. However, it's important that you weigh it equally. For the smART School, I weighed the fact that it would take a lot of time and is a high cost versus whether I would really learn anything new and solve my issue of compositions at the end of the course.
Does it have to be done now? One of the things that I do when evaluating risk is to determine if I can wait a bit for it. For the smART School, I weighed the option whether I could take the course in the Fall versus this upcoming Spring. In the Spring, I have to do a lot of paintings to make sure that my galleries have enough inventory. In addition, I'll be adding more galleries to the list. In the fall, during my day job, I have a big conference to make sure that my software works for. The Fall is usually extremely busy for me.
What would happen if I don't do it? If I don't take the risk (going out on lots of dates, taking a training course, working constantly on painting), what would happen? Does it improve my life and help me reach any of my goals or am I just wasting time and money? I know that I need composition help. Since I sell my paintings through galleries, this means that the better my compositions are, the better my paintings will be... hence, more sales... which means more money to buy supplies and create more paintings. If I don't work on my compositions, my paintings will probably sell, but not near as fast. I would be doing the same work.... just one year later.
How will this affect the people around me? If I take a risk and become too stressed or am gone all of the time, how does this affect the people around me? I have a wife and dogs. I have a full-time job. Although I love painting and my art business, I would never jeopardize those relationships around me. That's not who I am. That's not what I do. So, for the smART School, I'm already made sure that my wife is good with me working a lot of hours for the class. She understands what my goals are and supports me.
In the end, you are the only one that can decide whether or not the risk you take is worth the changes that you have to make. If you don't take the risk, you, most likely, will not improve and get better. This is extremely true as an artist. For me, there are two situations for my art work. I can just paint for myself and never show my artwork to anybody. No stress. No loss of money from training or art fairs. No rejection. However, I would not see myself improve at a rate that I would view to be acceptable. OR I could put my artwork out there for people to criticize, go into galleries and deal with the rejection by some of them, show my work in art fairs and potentially lose money, and take classes/workshops to potentially improve my work to a professional level... at the cost of time and money. I go for the second method. It's my way to become the best artist that I think that I can be.
Editor's Note: You can view Doug's original post here.