My Failure as a Freelancer

In 2016 I found myself without a job. The Oakland, CA-based company I worked for merged with a company headquartered in Arizona. With a severance package in hand I felt fortunate to be in a position to try something that always intimidated me. Freelance photography.

I’d like to tell you that this was the beginning of a success story. If we define success by profit margins, it most certainly was not. If we define success as learning something valuable about oneself, well then it’s a different kind of story.

People don’t want to interact with a brand — they want to interact with you.

The blog you’re reading right now is salvaged from the wreckage of a failed freelance career. NeverStark was the original name for the brand I was excited to build for my business. Building brands, after all, was the focus of my corporate life. But shortly after launching the website and printing business cards, I was advised by someone I greatly respect that when you’re a professional photographer, people don’t want to interact with a brand – they want to interact with you. I quickly pivoted to James Jordan Pictures.

The business card with former branding.

Over the next two years, I registered a DBA, leveraged contacts, built proposal and invoice templates, purchased equipment, software and insurance, established a workflow, created a social media presence, adopted a complicated tax process, assisted other photographers that I could learn from, and of course took a lot of pictures.

A look back.

Going into photography full-time was not a random choice. I’d loved taking pictures since childhood and enrolled in a photography class at the local art museum when I was 12 or 13. I remember a bit of wisdom imparted by the middle-aged bohemian teaching the class. “We don’t ‘take‘ pictures,” he explained. “We’re not stealing. We ‘make’ pictures.”

It was a sentiment I appreciated. (I declined to use the phrasing.)

After a couple of photography classes in college, I built a hodgepodge photo studio in my parents’ basement. I had to beg friends to sit for portraits so I could practice.

A 4-megapixel digital camera, a bent music stand, an umbrella painted silver on the inside, cheap halogen shop lamps, poster board, and felt fabric draped over PVC pipes. Turns out you can do a lot with a little.

Years after leaving home and moving to California, I continued to work on portraits and headshots with my first dSLR and an actual off-camera flash to accompany those same halogen shop lamps. (And the same shirt, apparently. That’s embarrassing.)

Between unpaid side projects and acting as the resident headshot guy at companies where I held marketing roles, I amassed a lot of experience. It made sense to try freelancing.

I had a huge advantage starting out.

As mentioned, the company I previously worked for closed its headquarters following a merger. Many of the executives left to start new companies, and when they needed photography or video, they came to me. I was also lucky that they stuck with me, because it took a while to find my stylistic footing. I grew a lot in the years that followed, and I think these examples represent the consistency I cultivated in my corporate headshot work.

I moved a bunch of furniture around to realize this vision for a founders portrait, and I love how it turned out.

Additionally, I’d just started writing sketch comedy for a San Francisco theater group called Killing My Lobster. There, I met a lot of local performers who needed headshots. I was also employed to help promote shows for the group, some of which I’d contributed to as a writer. Here are just a few of many highlights from working with KML:

I’m so proud of these Victorian-style portraits of the cast for KML’s show A Bag of Dickens.

I can’t overemphasize the importance of these early connections. The faith and trust they placed in me was a much needed source of confidence. Without these teams, my freelance career couldn’t have existed.

And yet, things were still difficult.

I think anyone venturing into a creative pursuit can point to two major challenges at the outset.

  • Developing patience and a thick skin.
  • Figuring out what your value is in the marketplace.

I managed both in time, but the latter was the toughest. After years of working for free, I found myself feeling guilty charging for it. This wasn’t a scam — I’d worked hard to learn this craft — but my mindset needed to change. To get around the mental block, I did what anyone would do in that situation: Compared myself to other local freelancers, investigated their rates, and then set something similar and stuck to it.

As opportunities trickled in, I got pretty good at carting a lot of gear to on-site locations. It wasn’t fun, but my system worked. (And it was a workout. I was always sweating during shoots, which didn’t convey the cool, calm demeanor that I wished to present.)

For actor headshots, the only space I had available was my tiny one-bedroom apartment. These were the longer sessions where we’d shoot a range of expressions and clothing styles. I purposely furnished my living room with items that could be picked up and stacked in my bedroom so I could clear enough space to set up a backdrop, lights and reflectors. I put blackout curtains in the windows for light control, and I tried to schedule all my shoots in the mornings because my apartment didn’t have AC and got oppressively hot in the afternoons and evenings.

This work wasn’t glamourous. I often dreamt of having a dedicated studio space with infinite ceilings, massive windows and industrial aesthetics. My equipment would always be set up and ready, and clients would feel confident when they came by for a session. But I’ve always managed to do a lot with a little, and this was no different. I achieved some fantastic pictures working this way. These were challenges I was equipped to overcome.

Which is more than I can say about my biggest hurdle.

I’m a creative, not a business person.

At the end of the day, I wanted to take pictures professionally. But freelancing means managing a business, too. I’d hoped that with enough word-of-mouth exposure from existing clients, I’d end up developing a viable business organically, but the reality is you have to constantly put yourself out there. At a minimum, that means attending networking events, keeping up a strong social media presence, and continually asking for referrals. As an introvert, I wasn’t even hitting minimum.

There’s a very good chance that success as a freelancer could have come if I’d given it more time. I learned a great deal in two years, but that wasn’t enough to find comfort running a business. I was burning through savings to stay afloat and my partner and I eventually made a decision to relocate to Denver, CO. That meant leaving behind the network I had in the SF Bay Area. But the real deciding factor — the reason for ending this pursuit — was that freelancing isn’t for me. I’m a marketer, but I can’t be the product at the same time. I prefer telling stories that aren’t my own. I like being relied upon as part of a team. And I tend to thrive on simplicity. I’m glad I got the chance to learn these things about myself.

There are things I miss about freelancing.

I’m a person who doesn’t like crowds. Large social gatherings are anxiety-inducing, and it’s tough to get me out to one. As a photographer shooting events, I have a reason to stand on the edges of the crowd. I get to capture natural moments between people. I have a purpose that fits my nature, and I can be involved in my own way.

Opportunities to get to know people one-on-one are much better for me. As a photographer shooting headshots, half of the job is making conversation and putting a person at ease so that together, we can capture a moment that feels genuine to both of us. It’s an art that I still have a lot to learn about, but I miss the journey. I miss digging deeper. And I miss hearing the stories.

I was nervous every time I had someone in front of my camera, but the real treasure in my time as a freelancer was overcoming some of those confidence issues and getting to know so many wonderful, interesting people. Here are a few of them.