A friend messaged me in March. He asked me if I would paint something as a gift for his wife. I was honored to be asked.

Wait. I need to go back earlier in time. This is not where the story begins.

A friend messaged me in October. She asked me if I would paint something as a gift for her mother. I was honored to be asked.

I said I would love to do it, but I flaked out. I didn’t do it. I had lots of good reasons for the delay in the beginning. We had family visiting in November. The holidays are always busy. Honestly though, I just froze. I have painted many things for friends and family, but somehow painting something by commission felt completely different. What if my painting wasn’t good enough? What if it didn’t match the imagined concept we discussed? How can I paint something for a person I have never met? How could I possibly paint something nice enough to earn MONEY?? It had only been a little more than a year since my first art lesson!

Luckily, my friend is a very kind and understanding person. We talked about how I was feeling, and I apologized for letting her down. She found something else to give her mom. I had been wanting to get back to this project ever since, but I just couldn’t get past whatever was blocking me.

Then, in March, a different friend messaged me. He asked me if he could commission me to paint something for his wife. I thought about it a bit, and decided I really needed to say “yes” to this.

I did things differently this time though. The first big difference is that I know his wife. She’s my friend too. We were in library school together 30 years ago, and have been friends for a long time. Somehow, painting something for a person I know felt less scary.

The second big difference wasn’t something I purposefully chose, but it turned out to be huge for me. My friend said “I don’t care at all what you paint. Whatever you like. You’re the artist.” I did ask him about her favorite colors, but he reiterated that all of that was up to me. We set expectations for the size of the painting and set a deadline, but I could paint whatever I wanted. I can’t tell you how much easier this made things for me!

The deadline was in early May. I spent a lot of time thinking about what she might like, but in the end I just painted something that *I* wanted to paint. I had this idea for a wild spring hare stopping to smell some roses while on a journey across a meadow. I wanted it to have a bit of a Watership Down vibe. Easter was just around the corner, and I’ve been paying a lot of attention to the earthy, non-religious, nature-based turning of the seasons lately. This spring hare felt meaningful to me during this time. I loved how it turned out, and it was the right size, so I sent it to my friend.

He loved it! He gave it to his wife, and she loved it too! Hooray! I did it! I followed through, and I got paid. I earned real money for my art!

I’m not sure if I want to paint something by commission again though. This success doesn’t change the fact that I found it very stressful. I do want to return to the project for my other friend someday soon, just because I hate letting people down, but once I’ve finished that, I think I need to come up with some other model for selling my art.

On the other hand, I love, love, love that friends and family want me to paint things for them. It truly is an honor to be asked! I just don’t know how to build a good model for doing this in a way that works well for me and for the customer every time. Maybe I just need to build up my confidence. Maybe if I do this more often it will start to feel more comfortable.

On another other hand, (hand number 3!) I don’t want to let anyone down or add stress to my life. Painting has been a wonderful therapy for me in a time when I desperately needed a time-consuming outlet for my emotions and creativity. It feels disrespectful to monetize this beautiful thing that I found for myself.

Meh. I don’t know the answer to all of this, and I’m not in a hurry to figure it out. I only have 4 more months until both of my children leave for college. I want to enjoy my time with them. I’ll have plenty of time to figure out what I want to do and how I want to do it once I’m alone in the house with my Lily dog for 11 hours a day, 5 days a week. Necessity is the mother of invention, after all.. or in my case, boredom will be the mother of creation. At the very least, I’ll have something to write about as I try to figure this out!