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Image turned thirty years old this April. As we reflect on what’s ahead, we asked fifteen visual artists and two singer-songwriters to tell us what they learned and how they changed after turning thirty. Click here for the full collection.

I’m a little jealous of my thirty-year-old self. I miss how cute she thought she was. Her goal was to play as much as possible, for whomever, whenever, mostly solo because it was cheaper. She had plenty of okay songs on CDs in boxes in the back of a Dodge Grand Caravan (that broke down twice). She never really stopped to think about where this was all going. She just knew she was getting stuff done.

She had a hard time trusting herself, though. When Night Air was released, one reviewer called it a bit too earnest. She assumed he was right.

At gigs, she felt an unrelenting desire to please audiences, which too often insured she didn’t please herself, or them. She fretted over set lists and tried to work in more “upbeat” songs, which is pretty hard when you have titles like “Old Woman,” “Oh My,” and “Man of Sorrows.” When a music executive commented on her demo, “You may want to vary the tempo a little more,” she figured he was right.

I would handle that guy differently now. I know more what I’m about and why I’m doing this. I’m learning to trust the meandering and sometimes unruly creative process, and I try to look at a performance as an opportunity to meet people where they are. People walk through the doors of whatever venue I’m playing with all kinds of struggles, so Lord help me not to waste their time. They could’ve stayed home and watched Netflix.

Lately, whether it’s a recording project or a performance or even a co-write, I see the benefits of just getting the right people in the room. I’m grateful to have had good collaborators over the last twenty years. Doing gigs and records completely solo doesn’t interest me so much now. I love the dynamic that comes when you bring other people on board who hear and phrase notes differently than you do.

Some of the people in the room may even be my children. In the last few months, I’ve learned to take guitar solos and not worry if I mess up. Part of this has come because my fourteen-year-old son, who is learning to play drums, will often ask, “Mom, want to jam?” When your teenager asks you to jam, you do it. He experiments with drum fills, and I play some guitar riffs. I’d like to take that same exploratory vibe, that playfulness, from the garage out into the wider world.

I think about this in terms of David Byrne’s metaphor for artistic vulnerability: I’m trying to embrace the parts of my work where I go out on the tightrope and take heart from the crowd cheering me on. I wish to say to myself: Hey, don’t just endure the tightrope. Enjoy it. You don’t get that view every day.

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The Image archive is supported in part by an award from the National Endowment for the Arts.

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