Christopher Gallego
June 5, 2019Â Â Â Â 12 Comments
The Things We Most Regret in Life
are the Things We Never Tried.
Oh do I disagree with that one.
Disagree because the older I get the more I lament over all the moronic, humiliating, devastating blunders I committed as a young artist.
Things that I never should have tried but did anyway, emboldened by the rationale, Ah, what the hell.
I can hear the consoling voices now…
But we learn from our mistakes.
Nothing ventured, nothing gained,
and so on.
Agreed, but I believe we learn a helluva lot more from achievement. Which is wonderful to experience and just as nice to reflect on.
Or as the holiday advertisers say, It’s the gift that keeps on giving.
So if you’re launching an art career of your own, I invite you to learn from some of my costlier mistakes.
This in the hope that you won’t have to go and make them all yourself only to learn that you shouldn’t have made them to begin with.
Besides, you’ll have your own whoppers to learn from.
Mistake #1.
Thinking Your Gallery is Your Friend
It’s easy to delude yourself into believing the artist-gallery relationship is a friendship. Especially when you’re new on the scene and everyone in the place is going nuts over your work.
Heads up–
Your gallery is not your friend. Doesn’t matter how friendly they are.
Not unless you’re a veteran enjoying a 10 to 20-year run with the same gallery. In which case you’re probably on firm enough ground for a friendship to blossom and survive a few challenges.
Otherwise, it’s nothing more than a business partnership.
But your gallery isn’t your enemy either. They want you to flourish. They want you to be happy and productive. And they want to profit from your work.
So don’t ask them for favors and don’t burden them with whatever tales of woe you might have, and we all have em.
Failed romances, financial troubles, health issues, are to be discussed with close friends or life partners, not with the gallery management or staff. An artist’s troubles, particularly, can be seen as signs of instability, flagging you as a risky investment.
And to a gallery, every artist is a good or a bad investment.
Mistake #2.
Anticipating Collectors’ Tastes
Painting what you expect others to love is another great way to self-sabotage.
For example, everyone loves flowers. So beautiful floral paintings should be an easy sell, yes?
No, not if you suck at them.
Never sold a floral in my life (haven’t done so many either). Because my heart just isn’t into painting them. So how can I possibly compete with some of the freakishly-talented masters of the genre out there?
Lucian Freud, Reflection (Self-Portrait), 1986
Oil on canvas, Private Collection, Ireland
Another example: how many people do you suppose are turned off by Lucian Freud’s paintings?
I don’t know either, but I’d guess quite a few.
And how successful was he?
Point is, what matters most is your passion for your subject. That’s what enlivens your work. That’s what sets you apart. If the passion is missing because you’re painting what you should the work will go flat.
So scan your surroundings for the things you love. Then paint the hell out of them, no matter how unusual they seem, no matter how exposed you might feel.
And don’t ever fear the naysayers or the critics. Because the stronger your work, the stronger the reaction to it, positive and negative.
Rubber Gloves, 2005
Oil on wood panel, 8 x 13 in.
Private Collection, Dallas, TX
Mistake #3.
Not Preparing for an Artist Talk
Few things are more traumatic than showing up for an artist talk, brimming with confidence you’re going to knock it out of the park, and then going completely blank.
What happened?
How did you lose the ability to speak?
Why did your IQ drop 30 points?
Here’s why:
You’re on unfamiliar turf.
Cold, expressionless faces staring at you, adrenaline racing through your system, and worst of all, the haunting echo of your own voice. Which suddenly sounds like the voice of a stranger.
The solution?
Over prepare.
If you’re giving a one-hour talk, prepare for two.
Rehearsing will make you sound stale, but do know your material backward and forward. This way if you forget something, and guaranteed you will, you can always grab hold of something else. You’ll sound more relaxed and natural when you’re overflowing with information.
Artist talks are a great way to get involved and build your career, so don’t shy away from them. But unless you’re an experienced public speaker, don’t try to wing them.
Mistake #4.
Overpricing or Underpricing Your Work
A director at Hirschl and Adler Galleries once said that overpricing one’s art shows a lack of confidence. Which actually makes sense.
Because if you feel you can’t surpass your best work you might hold on with an unreasonable price. Or agonize over finding the perfect dollar figure.
Chuck Close likened his paintings to grown children leaving the nest and getting lives of their own.
And, like your children, your art will always be yours, no matter where it lives. Clinging is the sign of an amateur, and will hold you back professionally.
Underpricing also stems from feeling unworthy. Make it a habit, and unworthiness become ingrained. Same goes for giving too much of your art away.
I find the best pricing strategy has no emotion to it– not the rush of chasing the jackpot nor the comfort of the easy sale. Find that unremarkable middle zone. Do some research and stay in line with the competition. You can always adjust the numbers later.
Let Your Art be Extraordinary.
Let Your Prices be Typical.
Mistake #5.
Saying Yes to Every Opportunity

Tenth Avenue Crosswalk # 4
Charcoal and graphite on paper
18 x 20.5 in.
Why would you turn down a collector willing to pay good money for that “special” art project, just because the project is out of your realm?
Here’s why:
It could be a lousy fit. Lousy and doomed to failure.
Someone wants you to paint their swimming pool filled with inflatable toys.
Or their high school sweetheart from an old yearbook photo.
Or their dog wearing pajamas and a hat.
Should you do it? Should anyone do it?
No, not unless your heart is truly into the project. Otherwise, you’re asking for trouble and likely to disappoint the collector. You’ll hate the project and you’ll kick yourself for accepting it.
You’ll feel underpaid too.
Sometimes, you just have to say No, without the guilt over being fussy.
But here’s the good news…
A high-quality no is empowering. You’ll feel your confidence rise when the wrong commitments are off your plate, and you’ll be dying to get into your other projects.
Just about everyone in the workforce has a specialty. Find yours, work like crazy at it, and do it better than anyone. Only then will the right opportunities find you.
Final Thought–
Resilience is King
If you’re like most of us, your first attempts at painting were probably humbling. Putting yourself out there is no different.
You’ll feel lost at first and you’ll get knocked down a few times. Even the big names can fail miserably, and they have big reputations on the line.
But no setback is permanent, not for any artist.
And while you can’t avoid all mistakes, you can minimize them, and take years off your career-building time.
More artists than ever are becoming successful, even before becoming household names.
So why not avoid some of the pitfalls? Why not get there a little faster?
Don’t worry if you haven’t paid your dues yet. You can pay them later on.
12 thoughts on “Five Dumb Mistakes to Avoid in Your Art Career”
Thanks a lot for sharing your enlightening thoughts, much appreciated =)
Thank You!
I just like your writing. I personally believe what you write can be applied to any part of one’s life, period.
Thank You, Marlene!
Thanks Christopher. As always to the point, relevant and very useful.
Always nice hearing from you, Lynn!
I enjoyed your writing and the suggestions for commissions made me laugh, definitely making it clearer to stay on track with what one is passionate about and to determine what are good fits before saying yes to tempting “opportunities” …It came to mind that a level of fun could be an added bonus in some cases…ie the swimming pool filled with toys commission could be quiet “refreshing” if negotiated well. Great Post – Thank You.
Thank You, Jane. Yes, the inflatable toy commission is starting to sound like fun. Happy to hear your thoughts!
What a great post. I’ve done it and been there, even after only 2 years of painting. I mostly refuse to paint things for people when they ask. Either they like what I’m painting, or go find another artist. I also find as a new artist, that having monthly goals or ‘projects’ will inspire me to paint. But most of my best paintings have had no expectations at all . . .
Thanks, Al. Yes, everything changes when you’re painting for someone else, even if it’s something you love. Some artists are great at it, but not all.
Hi Christopher, I just wanted to say thanks for this post. It’s great advice! And advice that is worthwhile for me to keep in mind even though I’ve been making my living as an artist for over 20 years.
Looking forward to reading more!
-Scott
Thanks very much, Scott, for the comment(s)! Glad to know some of it is worthwhile for you.