If You Can’t Embrace Uncertainty, Manage It

01: Creativity

It seems like just a few weeks ago I was FaceTiming my parents from Montreal to tell them I’d gotten engaged (it was…), but already, my fiancé and I are buried in wedding prep. Venues, DJs, caterers, photographers…on it goes. Every day, a new quote lands in my inbox—five hundred dollars for four hours of this, twenty five dollars per person for that.

I’m no stranger to quotes. When someone hires me for a writing project, I have to price my services as well. But the advice I’ve heard (and generally follow) when charging for creative work is to price by deliverable rather than the hour.

It’s like that famous story about Picasso:

One morning, he was sketching in the park when a woman confidently approached him. “You’re Pablo Picasso, the great artist!” she said and insisted he draw her a portrait. He studied her face, the gentle curves, the soft nose, and in a single stroke, he perfectly captured her essence. Delighted, the woman asked how much she owed for this treasure.

“5,000 Francs,” the artist said.

The woman was outraged. “5,000 Francs? But it only took you a moment.”

“No Madame,” Picasso shot back, “it took me my whole life.”

Had Picasso charged for his portraiture per hour, he would have left the park without lunch money. Instead, he charged per portrait—5,000 Francs, irrespective of the time it took—because each piece of artwork encapsulated a lifetime spent mastering his craft. Charging by time would have, ironically, punished him for his skill and expertise.

But there’s also another reason I like to charge by deliverable.

Creativity is a flighty force. It doesn’t always show up on a schedule. The writer who asks for $200 to pen a blog post may do so expecting it’ll take him, on average, two hours to complete. But that’s only an average. If the words are flowing, he might complete the assignment in an hour. On a less inspired day, it might take two hours just to get that first sentence down.

Unlike serving drinks at an open bar, a creative person can’t always show up and do the job he’s promised to do, which makes charging by the hour a bit tricky. Why punish yourself if, like Picasso, you get the work done quickly? And why punish clients if the work takes longer than expected? Charging by deliverable ensures everyone’s protected from the uncertainty inherent in creative projects.

02: Improv

I haven’t performed much improv since my Harold team was cut back in July. I’m rusty. Out of practice. That’s why I was a little nervous walking into a workshop this past weekend taught by one of my improv heroes, Liz Allen.

The three-hour intensive was about “world collisions”—the part of the show where the players stop creating new content and start smashing everything together. You know, the fun part of longform.

In four years of performing Harold, I’ve always meticulously managed these “collisions.” During the show, I’d see characters or games I’d want to bring together in the run and find a way to make it happen. But in the workshop, Liz discouraged us from this sort of pre-planning. She asked us to walk out, see who else went with us, and find a way to make some sort of collision happen on the spot.

The uncertainty scared me. What if I couldn’t come up with an idea to tie those two characters together? But I gave it a shot (I kind of had to…I paid for the workshop…). Unsurprisingly, Liz was right. In every instance, my scene partner and I found some way to tie our characters together, often one that was unexpected and funnier than anything we could have planned.

In improv, I’m constantly learning the same lesson over and over—less is more. So many aspects of the performance are shrouded in uncertainty, and I try to manage that by leaving as little to chance as possible. It quiets the fear, but it also weakens the performance. It’s a beginner’s mindset. The professional knows that uncertainty in improv can be good. He knows he has the skills to go out there and make something happen—no matter who he’s paired up with. He knows that going out with less often yields a better result.

03: Life

Uncertainty is a part of life. Will you get the job? Will your friend be mad if you don’t go to their party. Will you have to work late on this mammoth project? We live with uncertainty every day, and yet, it never gets easier.

Uncertainty is scary because it’s shapeless. It’s a blank canvas onto which we’re able to project our greatest fears. And because it’s unknown, we’re not able to use rational thinking effectively.

I’m an expert in this field. There are few people in this world who can work themselves up better than I can. My worries are like a snowball, tumbling down a hill. They start small, but they gather speed and mass until they’re so big that they paralyze me and prevent me from taking action (or doing anything else). But the thing about uncertainty is that doing nothing is the worst thing you can do. Just getting started, taking the smallest step forward, is the greatest cure. Because once you get moving, you start to realize the fear is all in your head.

The task in front of you is never as daunting as you imagine. And once you make even one percent progress, rationality returns. You’re able to think through the steps much more clearly. You can visualize the other ninety-nine percent. And the uncertainty begins to melt away like a snowball in the sun.

Each week, I write a new article helping busy people find meaning and fulfillment through sustainable creative habits. If you enjoyed this week’s letter, you can sign up to get them delivered to your inbox each week by digital carrier pigeon.