Stephen asks, “How do you choose an album or single artwork?”

Great question.

You know, it’s different with albums than it is with singles. To be honest, it’s one part feel, one part marketing.

One time, I asked my old label if we could just use an image without my name or any title on it. This seemed reasonable to me since, with the way people consume music now, the name and title are already listed wherever they’re streaming or downloading. But my label said no because of marketing collateral. They explained that the image would also be used in other places—posters, ads, etc.—and you want the name and title to repeatedly make an impression. Essentially, the album art becomes a kind of billboard. If it doesn’t say which “exit” to take or what kind of “food” is being offered, how is the driver supposed to know where to go—or why they’d even want to go there?

Now that I’m releasing music independently through patrons and self-funding, I’ve been experimenting with things. You might’ve noticed that on my last four releases, I haven’t included any text on the images. Partly, that’s because I like the minimalist aesthetic, but also because I had this idea for Instagram where my homepage would look like a collage of these images—kind of like a visual representation of my music/releases.

It’s hard to say whether it’s working or whether anyone actually cares (spoiler: they don’t), but it’s fun for me to try. And that’s one of the joys of being independent—you get to invent the rules as you go.

If I were to get really nerdy about it (which I often do), here’s how I approach choosing artwork for singles:

How I Choose Artwork for Singles

  1. Ask myself if I already have any images in mind from when I was making the song.
  2. If yes: Find or create those images.
  3. If no: Move to step 2.
  4. Play the song on repeat and open my Photos app.
  5. Search my photos based on keywords in the song. For example, if the song has a line about “country roads,” I’ll search “roads.”
  6. Gauge emotional resonance while listening to the song and looking at potential images.
  7. If nothing clicks: Ask Heidi (my go-to creative sounding board) if she has any ideas.
  8. If Heidi has suggestions: Choose between hers and mine.
  9. If still nothing clicks: Ask my friend Jeff, who takes gorgeous photos.
  10. Don’t overthink it! If I start spiraling into analysis paralysis, I’ll ask three friends for their opinions and choose based on their feedback combined with my gut instinct.

Once I’ve chosen an image, I’ll crop it, tweak the lighting, and decide whether or not to include text (font type, placement, etc.).

Lately, I’ve avoided all that text-related stuff by just not including any text at all.

Occasionally, for bigger projects (like albums) or when I have more budget to work with, I’ll commission a friend. I’m lucky to have so many gifted artist friends—Natalie is one of my favorites! She painted the cover for “Passages,” and we’ve got the original hanging in our house.

I hope that was interesting and answered your question, Stephen! Thanks again for submitting it.

And for anyone else out there who has questions—feel free to ask me anything!