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My First Year as a Professional Photographer

Making the decision to leave behind my career to try working for myself as a full time professional photographer wasn’t obvious or easy. For years, I waffled and found ways to squish freelance projects into evenings and weekends. Eventually, I was faced with having to say no to a large project I really wanted because it conflicted with my job. I was tired and disillusioned with my work as a Digital Media Manager for a restaurant group and I wanted to fully commit myself to photography so I finally put in my two weeks notice.

Photography Full-Time 

My first month or two of freelancing went surprisingly well. I emailed people to let them know that I was working as a freelance food and travel photographer around Chicago and would be available full-time moving forward. The work trickled in. 

It may have been beginners luck because things quickly dried up. The rollercoaster like existence of working for myself became crystal clear. When I was working and freelancing on the side, I always had my job to fall back on so I never paid much attention to marketing or pitching. Things came my way and I decided whether or not I was interested. Now, as a full time photographer, I didn’t have a job to fall back on and suddenly realized that I also didn’t have the marketing or pitching skills to keep myself steadily busy. It was a stressful realization.

Facing Failure

Summer was supposed to be the busiest season for photographers and instead my first summer  was painfully slow. Very quickly, the worst case scenario of failure seemed very feasible. When I decided to make the jump I had saved up enough to get through about 6 months but I could very clearly see myself getting to the bottom of that well. 

With failure as a real possibility, I became a bit of a recluse, which didn't help my cause. A few months later a friend of mine that seemed extremely busy admitted that he had also had a really rough summer. It’s difficult to be social when you feel like you’re failing. Social media also makes it bizarrely difficult to parse out what is real and what's edited to look better than it actually is. Anyway, it took a lot of mental pep talks but getting out and about ultimately helped me work through my rut. Friends buoyed me emotionally and occasionally hired me to assist. It helped me slowly find my footing.

Also, to be totally transparent, I got a lot of help during this time. It drives me into a slight tizzy when artists, writers and photographers omit the parental support or family inheritance that kept them afloat during hard times from their stories of success. My savings might have gotten me through my struggle phase but my husband, Eli, and I got hit with 2 unexpected tax bills that wiped us out for a little bit and we had to lean on our parents financially for a month. I felt extremely grateful and fortunate for the support but also totally sheepish that I needed it. We got through it and are in a much better place now. 

By the end of the summer, I had a very serious conversation with Eli about quitting or more like unquitting and going back to a regular job. Thankfully, he had a bit more gumption and confidence and convinced me to stick it out for at least one entire year before throwing in the towel. With failure as a real possibility and a time limit on making photography work, I buckled down and ordered a whole lot of self help and business books on Amazon

Feast or Famine 

Counterintuitively, I decided to incorporate. I wanted to create a structure that would help me escape the feast or famine cycle of working for myself.  When I started out I didn’t want to trade in shitty bosses for shitty clients but often I found myself thinking that I couldn’t afford to be picky so I took all the jobs that came my way even when they weren’t a great fit. My work ultimately wasn’t cohesive and I wasn’t particularly happy.

Once I created a corporate structure, I looked through my past 6 months of invoices and picked my worst month and made that my new salary. Even though it was just a structural change, separating my business and personal finances took me out of the feast or famine cycle, created a predictable income and alleviated a lot of my fear. Most months I made more than my low salary and that money became my reserve and investment pool into research and marketing. Without fear as a motivating factor, I was able to approach each potential project much more strategically and start to create a more cohesive body of work. 

These days I work on projects because I really like the people involved, want to make the sort of images I’m being commissioned to create or really believe in the company. It’s a great feeling. 

Getting better

Going off on my own forced me to take a hard look at all of my hang ups. I have been deeply uncomfortable with self-promotion most of my life. Just the thought of sales and marketing made me feel itchy but without it, I wasn’t getting enough work to keep my budding company, afloat. I haven’t exactly figured this out yet but I’ve acknowledged that it’s an arena I need to improve and I’ve started to take the uncomfortable steps to get better. Sometimes it's just taking the simple step of sharing a few images from a trip when I get back home with a few photo editors. It shouldn't be a big deal but I can have a whole 2 hour mental argument with my internal critic about it. 

Also, I hired a photo consultant to help me assess my work and potential projects. That was the starting point for a lot of the successes I would have later on.  Working with someone that pushed me to define my goals clearly and assess each opportunity much more strategically was a huge shift in thinking for me. I started saying no to work that didn’t excite me or resonate with me emotionally or help me get closer to my ultimate goals. I also made the terrifying move of letting go of clients that weren't a good fit for me and left me feeling drained.

Being pickier about projects and clients made it so I felt extraordinarily excited and proud of the projects I did decide to take on. Promoting my work became a lot easier when I felt genuinely excited about the things I worked on. 

Staying with it 

My husband and I agreed that we would reassess whether it made sense for me to continue on my professional photography path at the one year mark. As the date came around, work had picked up enough for me that I could imagine myself continuing on for at least another year. Right around the exact one year mark, I confirmed 2 very large projects that would financially buoy me enough to make it though a 2nd year of working for myself. 

Considering that I tried to jump back into my previous career path at the halfway mark, it was surprisingly easy to decide to stick with photography. 

Making the jump was very scary but I can honestly say that I have never been happier with my work. Figuring out all the business aspects has often felt overwhelming. Dealing with the emotional roller coaster of inconsistent work has also been deeply challenging. Ultimately though I feel like I’ve grown more in the past year than in my entire career up to this point. 

Should you do it? 

A lot of friends and acquaintances have started to ask me if they should go freelance or start their own company. I really don’t have an answer to that. 

This path has been fun but it hasn’t always been easy. While I now see the opportunity of pursuing my own way instead of the fear, I’m still hesitant to recommend it. If you go around looking for a clear sign, years can easily go by and there won't be a clear signal that you should do it. Also, failure is a actual and real possibility and at some point you will have to scramble around like I did last summer. 

If you want to work for yourself or start something, at a certain point you just have to make the decision and go for it. If you can, build up enough savings so can make it through a full year.  Even if you decide to jump back to your career you will learn more about yourself and how things work than you can imagine. 

photo by Ashley Hutchinson of Sed Bona.