Stride Stories: 10 freelance learnings from pro photographer Nathan Welton

[Nathan is a Stride customer and ambassador, professional photographer, and instagram inspiration]

Stride: What did you do before you were a photographer? 

Nathan: I got my masters degree in journalism and began working in newspapers covering health policy and science. I started at a small paper that was so understaffed that I started shooting every story I wrote. My career drifted toward photography afterward because I just liked the process of photography a lot more than writing.

Stride: How did you find your creative side?

Nathan: I’m a weird mix — I have my creative side, and I also have a very literal/scientific side. Part scientist, part artist. In graduate school I wrote a story about the artist in residence at MIT Biology, and realized those two sides were actually not that separate. The sciences are super data-driven, but exist due to the creativity of scientists. And photography really benefits from a technical mastery.

Stride: How did you start supporting yourself as a freelance photographer?

Nathan: I slowly built my business while working in newspapers – I carefully reinvested all my money while I still had a regular job. Every dime I made, I put right back into buying new gear and equipment, making sure that when I quit the newspaper world I’d have all the necessary tools to become a photographer.

When I quit, I decided that if I couldn’t pay my rent 12 months later, I’d go back to newspapers. Thankfully I made it. The biggest hurdle was deciding exactly how to focus — did I want to pursue adventure photography and nothing else, or did I want to diversify? I chose to diversify, and now I shoot weddings and adventure sports.

Stride: How do you differentiate yourself in the crowded field of adventure photography?

Nathan: One of the things that I’m strangely thankful for as a wedding photographer is the absolutely terrible lighting conditions I encounter. To shoot wedding receptions well, you have to be fluid with your equipment and vision. So when I’m faced with an outdoor adventure shoot that requires me to set up lighting in two minutes and nail a shot immediately, I’m very quick at having a vision and executing it with minimal fuss. I wouldn’t have built those skills as solidly if I didn’t shoot weddings.

Stride: What’s your biggest weakness as a photographer?

Nathan: A powerful photo takes lots of abstract ideas like beauty or love or determination and describes them without words. The images that make me stop and stare almost always involve people. I struggle to capture intimacy the most. It’s a continual challenge to create an image that allows the viewer to understand how the subject is feeling… I imagine I will feel the same way for the next 40 years.

Stride: Where do you struggle most on the business side of being a freelancer?

Nathan: Ha! I struggle with everything on the business side. It sucks! One thing that makes me nervous is never having any idea what finances will look like in six months. This continual uncertainty makes it super hard for me to spend money on outsourcing – which is critical to maintain my sanity, provide good customer service, and stay creatively inspired. Outsourcing work is a huge step towards freelance sustainability. 

Stride: What’s your best photography tip for the amateur photographer? 

Nathan: Shoot a lot and then put words on what you like and don’t like about an image. This forces you to think critically about photography in a way most of us never do. Do the same thing with images you see on Instagram. After a while you’ll start to understand what kind of images resonate, and you can incorporate all that into your own photography.

Stride: What is the craziest thing you’ve ever experienced in your profession?

Nathan: A couple of years ago I had been out shooting all day, and I came home late and got to editing. It was a hot summer night at my house, which is in a rural area near a National Park. I left the front door and my sliding door open in order to get some cross breeze and became completely absorbed in the images. After a few minutes, I heard a grunting noise behind me and swung my office chair around to see a pretty large brown bear pawing around in my closet. I hadn’t heard it wander in, and it hadn’t noticed me editing.

I screamed like a little kid and jumped up on my chair, nearly falling off onto a glass table. The bear was super startled, and in its attempt to run out the door, it ran headfirst into the wall. I screamed even more. Then the bear looked at me, found the door, and bolted up the steps… they are surprisingly fast. I don’t think that would ever happen at an office job.

Stride: What’s the best thing about being freelance?

Nathan: Hands down, the best part is having the freedom to choose when and where I want to work. If I want to wake up and go climbing and work in the evening, I can. If I want to wake up and work at 6am, I can. To me, this is priceless. I never want to go to an office again.  

Stride: What is your favorite aspect of Stride? 

Nathan: During this open enrollment, I went back and forth between all the options that were available to me. After a day of crunching numbers and analyzing every possible option out there, I wound up buying the insurance plan that Stride selected for me in the first place. It was pretty revealing that the suggestion Stride gave me after 5 minutes was actually spot on. My favorite part of Stride is that it really does simplify the system.