The short answer is: “I don’t know.” 🙂
There are some things to consider, though. I know that there is a temptation to get to a certain standard of work and then to decide “it’s time”. At that moment, an income and livelihood is riding on it, so many professional artists begin to paint what they think will sell. I’m not convinced that is the right way to go.
For one thing, it tends to cramp the style of the artist and homogenise their output, as they try to second guess the market. In most cases, the artist’s idea of what will sell cannot possibly be grounded in fact and data. At best, all they can know is what previously sold. The artist’s notion of what sells has to be an opinion and what gives anybody the idea that they can guess this correctly the first time out?
Lately, people have begun to ask me when my first exhibition will be and when I will start to seriously market and sell my work. I don’t feel ready. I don’t think I have reached a point where my style is strong enough. People tell me that some of my work is good enough (they’re often just being kind, but equally often quite sincere). I don’t. It’s not fear of falling or lack of confidence, I just don’t feel like my art is “there” yet. It doesn’t yet feel complete.
I think one of the best things about delaying the decision to go pro is that you can explore your own technique and paint the things you like, rather than the things you think will sell. At least that way, you can develop something authentic, that you like to do, which allows you to express yourself, without inhibition. If you pursue that line of being true to yourself and exploring your own aesthetic expression without fear or self-conscious constraint, I think you are more likely to come up with something original. I may be wrong, but that’s how it seems to me.
In contrast, I believe going pro too soon carries the danger of constraining you into creating something derivative, just like all the other works that seem to be selling at the moment. It’s limiting. You might be able to make a decent go of that, but in the end, it must be more like being a juke box than being a composer. What you think sells might not even be the thing you like to paint most. To my way of thinking, you wind up going through the motions and denying your soul, in the long run.
The downside of staying amateur is the difficulty of finding the hours to perfect your art. After all, you would have to earn your living some other way and use only your leisure hours to paint, so that has to slow you down somewhat. On the other hand, going pro and starving seems like a very hard (but all too common) road to travel, to me. At least if you have a job, you’re better placed to afford decent art materials.
Maybe that’s the reason the starving artist has become such a cliché. They’re spending the time necessary to find their own style, but not succeeding in selling anything, because they’re trying to sell to people that may be unprepared and unreceptive to their new way of seeing, at first.
Here is the supreme irony. If you stay amateur, develop your personal style and, by happy chance, come up with something original, it will probably sell, at some point. What people want most is authenticity and originality. That has been demonstrated countless times by history. Van Gogh, famously, undoubtedly came up with something highly original, beloved by millions today, but didn’t manage to sell much during his own lifetime. There’s the rub. You may never earn a professional living from your art while you’re alive.
However, that isn’t always true and I claim that taking your time to develop your own style is worthwhile, because it ultimately produces work that will sell better and command a much higher value than derivative works (even if that takes a lifetime). It also allows you to continue to enjoy the process of making art, without compromise to your inner creative being.
In the end, it’s all about artistic integrity. If you do what you must, as an artist, the work flows out. If you do what you think you should, you might be productive, but you won’t necessarily like what you do or even yourself. Ultimately, that will make even staying productive all the more difficult. You may also consign yourself to the legion of forgotten journeymen artists whose work eventually, but relentlessly, becomes valueless.
So forget the money. Shoot for immortality instead! It might enrich your kids or your grandchildren. 🙂