Last month Robert and I were down in Washington DC for a presentation on my career. At the end we took questions from the audience and one in particular struck me. The question was “What are your biggest mistakes or worst choices you’ve made in your career thus far?”

I’ve done a handful of talks and interviews and this was the first time a question like this has ever come up. Originally we were going to focus on a few questions from the Q&A after the presentation, but this one deserves some focus.

Going back to the question itself and to my failures, I think one of the mis-steps along the way would be when, in 2007, I made a transition from working at Wonderful Machine to being independent photographer. Before this transition I was growing my work and expanding my skills. The pictures had seen big jumps every year from 2004 to 2005 and I think I was in a really great place in 2006 to transition out of assisting and studio managing and into being an independent photographer.

Consciously though, I don’t think I realized the weight of the responsibilities in managing all aspects of my business being an independent photographer and as a result creatively I was trying to do things that were a step back – almost analog to a point. I was trying to work more minimally and had stopped thinking about photography from a progressive point of view. I had stopped pushing myself and stopped growing my skill set and in that sense I was working backwards. It took a while for me, almost until mid 2008 before I started to realize I’ve been heading in the wrong direction and not really making the next steps for my work. That was one a big one. That’s why I tend to call 2007 my “lost year.”

Another choice I made that I think may have been a mistake relates to a photo I made of Michael Vick, the Philadelphia Eagles quarterback. Soon after it was released in Philadelphia Magazine, one of the major network channels was covering a football game in Philly the next week and contacted me wanting to use that photo and talk about it during the broadcast of the Eagles game. I asked for photo credit after they said they had no money to pay for the usage, but they explained that wasn’t part of their process. Ultimately the value of national exposure with that photo verses the monetary worth of five or ten seconds of broadcast would have balanced out – in retrospect I think that’s one I should have just given away.

One more mistake I think I’ve made in my career has to do with my landscape photography. Going back to day one of Photo 101 in college, it has always been something I’ve been drawn to and interested in. When I started shooting more portraiture, I think that I abandoned the landscape work.

Jumping ahead a few years to when I was actually making money through photography and was able to travel and take trips to great places like Madrid, Barcelona, Buenos Aires, and all these beautiful places. When I would go on some of these trips – I think if I was on vacation I’d want to abandon my work. Now, I should say that it’s always nice to take a break, but this job is not always a job and if you’re in a wonderful place you need to take advantage of the opportunities in front of you, which is not what I did. On a few of those trips I didn’t even bring my camera and missed out on a few amazing opportunities. It wasn’t until 2010, coincidentally on my honeymoon, that I returned to making landscapes when I travel. I haven’t looked back since.

Speaking literally, there have been some falls in my career. In 2011 when working in Maui on the Travaasa Hana shoot, we were shooting on a pool at the base of a waterfall and I slipped and fell into the water, taking a 1Ds MK III and 24-70mm lens with me. That was certainly a mistake.

Last but not least – I don’t know if this qualifies as a mistake, but it certainly can feel like a failure in the short term. For some projects and larger advertising campaigns, we will often go to great lengths to prepare for the job. In the initial creative and bidding process we’ll go to great lengths to express our desire and drive to be part of the job. Sometimes we might spend a weeks worth of time trying to win a project – and when you know that you’re the right person for the shoot and you’re 100% engaged with the job, everything lines up and you know your numbers are fine then you don’t get the job, well it’s a big hit. Sometimes it takes a little while to shake it. When that happens though, you just have to persevere. You have to keep working and keep putting yourself out there and showing the world that next time, you’re the right guy for the job.