How I Plan a Year as a Freelance Photographer

Dreaming the path forward, speeding through the dark.

Some of my notebooks from the past few years. Apparently, we are 42% more likely to reach our goals when we write them down.

You’re reading Depth of Field, a newsletter about making a life in photography and beyond. While most of my Substack pieces are free, this is a paid post that offers an in-depth, personal look at my process.

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In the final hours of December, I careened down a dark mountain on skis with a hundred other people, clutching a flaming signal flare attached to a pole. The goal was to appear as a smooth, moving river of lights to a crowd watching from the base of the mountain, but the group of skiers ahead of me were drunk. In the red glow of their torches, their silhouettes swerved on the icy snow, flares hissing and dripping molten fuel. After a few minutes, I sped up to pass them around a corner, and for a moment I was alone on the dark slopes.

There was no moon. The angle of the cold earth pressed up beneath my skis, the tall shadows of the trees reaching up in the starred sky. Out there, birds slept huddled in the branches; bears curled in their dens beneath the earth. By the dim light of my torch, I could only see what was right in front of me. But it was enough to go by, even to keep up speed, seeing only a few feet forward at a time.

It was a lot like living as a freelancer. It was a lot like persevering in a time of uncertainty. It was also a lot like making art.

Self-portrait by starlight. Baffin Island, Canada, 2014.

The idea of January 1st as a bright new beginning can seem absurd in the dead of winter, in Alaska, when nearly everything in nature is dormant. To me, it’s a gentle, introspective time of year, like a plant building strength beneath the soil. These early months are when I create each year’s vision for the path ahead—a private endeavor, for the most part, until now.

This January, I gave a virtual talk to a class of photography students at RISD, where I studied photography a decade ago. In the short span of an hour, I endeavored to explain to a group of hopeful young people that it is, in fact, possible to have a photography career without ever moving to New York City. And the more I tried to articulate my trajectory as an artist—a path that can feel, on the surface, guided by intuition and luck—the more I saw how this “luck” has been the result of consistent planning, goal-setting, and steady efforts to maintain momentum.

In other words: while a freelance life may feel like speeding through the dark, seeing only a few feet ahead at a time, you can get pretty far that way if you have a clear destination.

Today, I want to offer a transparent look at how I plan a creative year as a freelance photographer: an adaptable structure that has kept me moving forward creatively and professionally for the past ten years. While I can’t promise this is the best approach out there—if such a thing exists—it has worked well for me so far.

An ideal year-dreaming environment. Alas, this is not my home office, but a cabin where I once spent a glorious month working at Storyknife Writer’s Retreat in 2021.

Centering personal work.

The first thing I meditate on, every year, is the personal work I most want to bring into being. If a creative life were a physical body, personal work might be its blood: a vital substance that circulates, keeping all the other parts nourished, alive, and in communication with each other.

Personal work refers to the creative projects that, for whatever reason, give me a sense of deep, soul-true fulfillment. To keep myself spiritually alive, I must make time and space for them, even if there is no promise of success or financial reward. That said, because it represents the kind of work I want to be hired to do, it is an investment. When I do it, paid or not, I am building up my portfolio towards the professional artist I want to be.