How You Can Learn to Be More Comfortable With the Messy Middle

My painting was so bad.

Somewhere between blank paper and halfway done I’d lost my way. Now, my painting and I were equally confused about what it was meant to be.

My high school art teacher, Mr. Baucom, had a habit of strolling among our desks to watch our progress. He was usually silent as he did this, offering only the occasional guidance.

And that day, as he strolled, he stopped behind me. Not next to me — not where I could see him — but behind me and over my shoulder. I could feel him looming there, letting the moment build.

My painting was so bad.

Then he said “you know, everything goes through a vomit stage.”

His tone was so casual. Such a blunt consolation: like oh, by the way, your art looks like vomit. He moved away to the next table, and while I’ve never been certain I think he hid a smirk behind his full, dark beard.

I forgot about that line for a long time.

When I remembered it, 20 years later and in some career frustration, it made me laugh. Because while don’t think he meant it as general life advice (I can’t be sure?), it has proven to be exactly that.

And humor is a great mnemonic. Maybe the best one.

Labeling is the way

Chris Voss, author of “Never Split the Difference,” describes labeling like this:

What Mr. Baucom had done was to teach me how to label struggle.

Of course I didn’t see it that way at the time, but the years since have proven it true. Because in anything worth doing we will, at some point, find ourselves in a place where things look messy. Not as planned.

Stepping back and labeling it as what it is, is an act of self-empathy. “My painting is so bad” becomes “yep, this painting is 100% in the middle of its vomit stage.”

It’s just the messy middle

I thought of Mr. Baucom’s advice just this month, helping my 10 year-old son paint planets for a solar system project. He’d asked me to paint Jupiter, and it was a right mess . . . until it wasn’t. As I painted I’d hold it away from me, get a good look, and then keep painting.

What I’ve learned, and would share, is this: there is value not just in accepting the vomit stage will happen, but in trusting that it will. Looking out for when it does.

Because it’s just the messy middle.

And once you label it — whatever label you choose — you’re free to see it as just the stage where some of the best things to come are still taking shape.