Portrait and Headshot Photography: Five Years On

Five years ago today I submitted my resignation at my day job to do freelance portrait and headshot photography full time. It was a big move, but one my family and I had prepared for. Over the years we’ve had our ups and downs in the business. I often think owning a business feels like sailing on the ocean: it’s a fun adventure but you never know what lies beyond the horizon. At first this uncertainty was a source of stress, but I’ve learned to embrace it. While I do have some slow spots, the business is working, and I am happy I made this career move.

Here are a few things I’ve learned since going out on my own:

– Consider what you really need to be happy and shape your life around it. In both business and hobbies, it really helps to narrow your focus.

– Pay off your debt! You’ve got enough to worry about without compounding it with interest.

– Get help! Naomi (my wife) does most of my bookkeeping, but we leave tax prep to the pros. There are quite a few considerations that we absolutely would have missed without our tax man. We also get marketing help from the amazing people at Fresh Figs Marketing. They’ve been a great client of mine for years and now help me keep the business rolling in.

– Business can be surprisingly variable. There have been a good few months where I thought I’d made it, I couldn’t have been busier, but those months were sometimes followed by dead ones. Make sure you plan for those ebbs and flows.

– Learn from mistakes. This is a tough one. One of the drawbacks of being a freelancer is that you’re easy to fire. Not that I’ve had many blunders, but there have been (unfortunate) times when clients were not entirely satisfied with the images we’ve made. Unless he or she is a dedicated client it is unlikely you will be called again. I make every effort to shape my work process around ensuring my clients are happy with the photography we produce.

– Don’t forget the real world connections! As an introvert it’s easy for me to just stay at home doing my thing, but real-world networking works. I attend meetings at a great BNI chapter and try to get out to a few social media gatherings a month.

I really do love my life now; the 9-5 world was just not for me. The mix of new and repeat jobs provide a bit of stability and variety in my day-to-day life. Not everything is the same, not everything is different.

Looking back it is abundantly clear that I could not have made it these five years without the incredible support of family, friends, clients, and business partners. Thanks everyone!