The decision to sell your work at a street festival is not an easy one. It is expensive. It makes for some long days. The weather could be bad. And if you are new to selling your work, you have no idea if your stuff will sell. I’ve worked a handful of street festivals selling limited edition prints in Chicago the past few years, and I believe I have a handle on what to expect now. So, if you are looking to sell your artwork, here are 10 tips to help you out:

1. Make sure you have something cool to sell. I know this might seem obvious, but you don’t want to drop hundreds of dollars on products, registrations and supplies without the ability to make some of that money back. I had the chance to sell my first poster to many friends, co-workers and acquaintances. The response to my work was very positive so I knew I was on to something. If you don’t have that kind of outlet, get the opinion of people you trust.

2. If you can, start small. I was fortunate enough to work an indoor concert in December for my first experience selling artwork. The only expenses were my products and a manageable registration fee. Overall, I just barely recovered the costs of the registration fee. However, I was able to gauge how people received my work and it gave me the confidence to register for more festivals.

3. Make your work ready to frame. I have learned a hard lesson with this one. Some of my first posters and prints were not standard frame sizes. While I could sell them as is, it made sense to cut mattes so they were ready to be framed. While this has allowed me to make some money off the mattes, the act of cutting them is laborious. I would much rather be making art. From now on, I decide on the dimensions before starting the illustration.

4. Have items at different price points. I figured this one out by chance. Most of my prints I sell now are $20 and up. This has a tendency to scare people off. On the other hand, I do offer a $8 poster. I have seen many people gravitate toward this poster because of the price. In turn, I end up selling a number of these at each festival. One side note…that doesn’t mean that it was hastily made just to have something cheap. It is an illustration I worked a long time on. Since I had 500 printed, I am able to offer the lower price.

5. For outdoor festivals, prepare to spend a decent amount in start-up costs. You will spend between $200 and $300 on just the canopy if you go with an inexpensive option. The registrations in Chicago hover around $300. You might also need to buy tables, packing materials, mattes, tools, etc. It gets pricey fast. This is a good time to look at a long term plan. To make it worth your while, you will want to go to more than one festival. It is the only way to ease the financial hit of all the start-up costs.

6. Decide if you want to negotiate or not. The best case scenario for any purchase is they buy it as they see it. Once in a while, though, you will have someone who wants to negotiate. I decided early on that I would not negotiate and stick to it. My reason for doing this comes down to two things. One, I don’t want to get that reputation. Two, if most people are willing to pay the advertised price, why should I negotiate? It can be difficult to pass up a potential sale, but it could hurt you in the long run. Just make sure you decide before someone asks you.

7. You can’t think of everything. Inevitably, you will get questions from people asking about items you don’t have. I have gotten questions about prints in different sizes and different colors. I have gotten questions about mattes in different colors. And since I don’t use bags, I have gotten questions about whether or not I have a bag. The fact is…you can’t have it all figured out. The best thing you can do is take all that information in and decide how you will use it at the next festival or for the next artwork.

8. If you can, have someone help you out. If you have a friend, family member or spouse who is willing to relieve you during the day…take them up on their offer. It will make your day a lot more comfortable if you can step away to use the bathroom, get something to eat or just walk around.

9. Art buying is personal…let them look. I think that buying art is very personal. Many people will stand and look and talk out loud about how it will look in their home. That is a good feeling for you! You are better off just letting them look and decide on their own whether or not they want to buy it. I think it is in poor form to give them the hard sell. If they ask a question, answer it as simply as possible. Don’t push them into making a decision.

10. Take pride in the people who tell you that your work is cool, but don’t buy anything. This is the most important tip. The simple fact is that a small percentage of people who look at your work will buy it. The failure rate can be pretty high at a festival with thousands of people. So, you have to celebrate the successes. People might just take your business card or signup for your newsletter or compliment your work. While it might not be money, you never know what it might lead to. I make it a point to thank them and keep that positive energy going. It makes those long days go by a lot quicker.

  • Really cool and insightful write up. I’m not thinking of selling any art, but it was interesting to hear what needs to be considered by those that do.

    By the way, how did the Roscoe Festival turn out? In your previous post, you mention a goal for selling the Roscoe Village print – I was hoping you would have added an update to say whether or not you sold at least half of the 50 printed… don’t leave us twisting in the wind.

  • I guess I left that little tidbit out. Including an online order, I sold 20. I would have liked a few more, but selling 20 of any print over 2 days is pretty good. I think I will still be able to sell some online and there is always next year. It is a small neighborhood so I should probably have even better luck if I do a map of Lincoln Park or Wicker Park/Bucktown.

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