From finance to freelance :: lessons learned & failing up

How did you decide to change careers to become a freelance photographer? 

In the twelve months since I left finance for a career in food, travel & lifestyle photography that is the question I get asked most often.  After repeatedly having this conversation via email exchanges with readers, at dinner parties and even to a total stranger while riding the London Underground, I now realize the crux of that question, what people are really asking, is where did you find the courage to do it. 

Since Joanna Yee Photography just turned one, I thought I’d share how I decided to take the leap from finance to freelance and what I’ve learned by failing up.

The backstory
Three years ago I participated on a social photography project called Project 365, where participants aim to photograph and post one picture a day for 365 days.  Despite enjoying my day job (seriously, it was the best gig ever) I yearned for a creative outlet.. and an excuse to buy a new camera.  The project itself wasn’t a great success, I made it to 300 days and the pictures were so unremarkable I took them offline. But it sparked an all consuming desire in me to lead a creative life and to make my living as a photographer. 

The confession
At first I failed. When I was in between jobs during the summer of 2012 I attempted to become a freelancer full time.  It was a hot mess. I had no focus, strategy, support system/network in place and only a very limited skill set.  When I finally gathered the courage to email potential clients and fellow photographers not one of them responded. Six months later I panicked and told myself I’m not cut out for creative work, I can’t hack it, so I swooped back into the safe and financially seductive arms of finance.

Immediately I realized I made the wrong decision.  Self doubt got the best of me and led me back to the safety zone.  As soon as I recognized this self preservation tactic for what it was I started preparing as much as I could to avoid the same mistakes I made before.  During the year that I continued to work full time at my desk job, I assigned myself projects and started shooting more often, invested in workshops such as this one & this one and gradually began to build a network of likeminded people who have all at one time or another faced the same struggles (which made me realize just how desperately alone I felt the first time around).  


The takeaways
Up until the moment I decided to quit my cushy job in the finance industry for good I battled relentlessly with uncertainty.  Lurking not far behind was the what if I end up homeless scenario or Can I really do this? Do I have what it takes.  Sometimes the fears and doubt still tend to playback in loop one year later but the intensity of it has mellowed. I’ve already failed once and it wasn’t the end of the world, in fact it was a learning process.

These are the takeaways I’ve gathered over the last year on navigating the creative/freelance life and what I would recommend wholeheartedly to those who are considering this path:

–  Plan ahead. This applies to everything but especially when it comes to finance.   I needed to get rid of my major financial shackles so I could focus on the work itself and worry less.  As someone who has been financially independent since the age of 19, making sure I’m not going to be a financial burden to the Brit or my family felt especially important.  It’s not lost on me that I am lucky enough to have someone I can lean on. The issue is, not only do I dislike asking for help, I do not like to accept help because ultimately that leads to being vulnerable (and financial vulnerability is THE WORST).  This way of thinking is one of my worst traits and continues to baffle the Brit but I digress… 



To prepare myself for the very real prospect of not making any income for at least 6 months I worked towards two goals while I was working my desk job: save enough for twelve months of expenses and pay off my student loans (which at its peak nearly reached 6 figures) before I could be in the mindset to start this creative venture again. 

Put yourself out there,  Nobody will know you’re available for work unless you put it out there.  I spent those six miserable months hoping someone would miraculously notice my work and hire me.  And as soon as I gained the courage to meekly announce myself and got zero responses from it I accepted it as a failure and closed down shop. Sometimes I look back and am mildly amused, did I really think it was going to be that easy?

The majority of my current clients came to me through recommendations.  My growing network of friends/contacts now know I’m a working photographer and are happy to send people my way – which leads to my next point.

Be kind.  You probably already are but I can’t stress the importance of this enough. We are all a little vulnerable in this journey, let’s help each other.  Besides, it is a lot easier to find yourself in a supportive environment when people like you and gain repeat clients if they enjoy working with you.  I get random emails from people I don’t know asking to meet so they can pick my brain or network.  I’m not always able to meet in person but I will take the time to respond and offer some kind of assistance.  And you know what? I’ve gotten work this way.  Karma is real.

– Keep at it. Keep creating.  It is like a muscle, the more you do the stronger you become.  Do you sometimes fear your work is not good enough? I do, all the damn time. Regardless on whether I’m too hard on myself, I know this – my work isn’t going to get better if I don’t keep working on it.  This video skillfully explains my point (don’t skip this, it’ll be the best 2 minutes you spend today):

 So this is my story of finding courage, failing up and how I worked past it.  It has taken me 5 days write this post because I wanted it to come from an honest place without the vulnerability.  I finally realized it’s not possible so here you go, vulnerability and all.  


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