Lessons From the Street (Fairs)

Last year I decided to dip my toe into the street fair pool. I signed up for three different events around the city, and showed up with about a dozen reasonably priced paintings to sell along with boxes of other odds and ends. I thought I was ready for anything—sun, wind, rain, bugs, long days without a potty break, and no place to buy a bottle of water for less than five bucks—but there were still quite a few surprises.

I had prepared to tell my story—how I came to be an artist, what I love about painting, and what I hope to communicate. In anticipation of blooming conversations about my work, I had also developed anecdotes to share about each piece, some funny, some interesting, and some emotionally touching. But what I wasn’t prepared for were questions about my sales policies. There I was, assuming the role of salesperson without having thought all that through. I was on the spot making snap decisions, which is never a good place to be, right?

So if you’re thinking of taking initiative and selling your own work sometime in the future, here are some questions you should be ready to answer:

What forms of payment do you accept? If you’re only just exploring self-sales, you may not be ready to set up a Square account or something similar that gives you a device for charging credit cards through your smartphone. But keep in mind that hardly anyone carries cash, so if your pieces are more than $50, people may ask if you'll take a personal check. Are you willing to take a chance on a bounced check? Decide what’s comfortable for you in advance.

Can I pay you in installments? Even if you’re selling at a street fair, your bigger pieces might go for several hundred or more. So it’s possible that someone might fall in love but not have the means to pay you all at once. Knowing it’s a one-of-a-kind item and this may be the only chance to get it, he or she might ask for installment payments. Does that work for you? Again, decide how you feel and what you think a reasonable plan would be. Also decide who gets to keep the artwork until the final payment is made. For example, you could ask for a deposit (refundable? nonrefundable?) to hold the work until the balance is paid on a certain date. Whatever you agree on, get it in writing before your buyer leaves your booth with the piece.


Do you offer a discount? Try not to be insulted by this one—it’s not a reflection on your work. The people who ask for discounts do it because they just love to feel like they’re getting a bargain whenever they can. So how do you feel about discounting your prices? If you agree to offer them, the law says you have to be consistent in your policies. So decide up front when and why you’re willing to grant discounts, such as 10% when someone buys two or more pieces or 5% for paying in cash.

Can I return it if it’s not working for me/doesn’t match the sofa/my spouse flips out over how much I spent when I get home? This one’s tricky. It’s tempting to say yes because you want to start building positive relationships with buyers, but how will you feel about refunding money on a work of art that’s coming back to you damaged or broken? If you agree to accept returns, make it clear you’ll only take something back if it’s returned in the same condition as when it was sold. It might even be wise to print out some receipts with that policy on it that you can tuck in with the artwork before handing it over to the new owner.

And finally, do you take commissions? Before you agree, you need to ask yourself if you really want to be at someone else’s direction when you’re creating. You should also ask the person what he or she wants you to create. People don’t really understand that artists have specialties, so they’re likely to ask you to do something you’ve never done before, like paint a pet portrait when you’re a landscape painter. If you do decide to take on the commission challenge, what will your process and payment plan be? Most artists do a preliminary sketch and get approval before creating the final work, and the payments are often split up to align with those milestones.

Now, if there are any street fair or open studio veterans out there, I’d love to hear from you. What other questions do we need to be prepared to answer when we're selling our own art? Let’s connect!

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