Going Freelance: The Davy Kesey Secret Master Plan

Three months ago I left my job and went full time as a freelance fashion and portrait photographer. It wasn't an easy decision initially—I had spent over a year working on Overlap, an app I co-founded in 2016 that helps creatives find each other and work together. I continued to work there after graduating in May of last year, but ultimately decided tech wasn't for me.

While I'd been taking photos for roughly seven years, I'd also had little success with it, financially speaking. In fact, my business is at a net loss over the course of its lifetime and has been sustained mostly through non-commercial work, side jobs, and a bundle of savings. Still, having only ever done it on the side, the question nagged me: what would happen if I really, really tried to make it work? So, I decided to find out.

It's too soon to tell if I've "made it work," but it's been delightful so far. I love fashion and portrait photography—fashion because you can be so creative with it and portraits because you get to know a variety of interesting people. More importantly, I believe each of us has a responsibility to serve others with our talents, resources, and general demeanor. I try to do that with photography. Sometimes that's donating photos or amplifying marginalized people groups, but usually it's simply treating everyone on set with cheery kindness, rather than stressed-out crankiness. Photoshoots should be fun. People are more important than ad campaigns or career accomplishments.

Of course, I still intend to set some goals around my newly-adopted profession. Financial stability is a worthy start, but my ultimate goals are to photograph the cover of Vogue before I turn 30 and a president before I turn 35. Will reaching these goals save the world? Of course not. They are, however, wonderful benchmarks. I think every person should strive to be ludicrously good at whatever they do, and I am no exception. 

There is nothing enlightened about shrinking so that other people won’t feel insecure around you. We are all meant to shine, as children do. We were born to make manifest the glory of God that is within us. It’s not just in some of us; it’s in everyone. And as we let our own light shine, we unconsciously give other people permission to do the same. As we are liberated from our own fear, our presence automatically liberates others.
— Marianne Williamson


What The Plan Is Not

With goals like mine, I thought I should write up a plan. It's very simple. What makes it unique is not so much what I'll be doing; it's what I'm not doing. (To be clear, this is not a universal prescription for photographers everywhere. In fact, it would be decidedly unhelpful for many. I think each person's approach should tailor to his or her unique strengths).

The plan is not choosing better hashtags for my photos, doing a giveaway, or getting re-posted. It's very much not trying to get more followers. It's also not trying to "meet the right people" at Instagram meetups, networking events, or parties. It's not obsessively following industry leaders or industry peers. It's not creating an email campaign, Facebook campaign, or Instagram campaign. It's not sending mailers. It's not buying new gear and it's not buying new presets. 

It's not that one should never do those things; it's that they are so unimportant that they should never be higher than 5th priority and certainly aren't worthy of being in The Davy Kesey Secret Master Plan. I'll do a few of them when I have free time, but they're marginally helpful at best, a 2% boost to a career (despite the infinite supply of blog posts that suggest otherwise). None of them will propel me towards my goals as like what I could be doing instead: getting better at my craft and sharing along the way.


The Plan

1. Skill: Focus on getting really, really good.

For me this means slowly working through the rubric of a great photograph and improving my execution for each individual component until I'm exceptional. This means thinking bigger than just the lighting, for instance, and instead taking the time to put intentionality behind every facet of an image—the concept, lighting, posing, location, makeup, styling, art direction, editing, and curation. 

Each of those elements has a whole list of sub-points. Take the concept, for example. One way to develop better concepts is to expand your sources of inspiration. When I first became a photographer, my primary creative inspirations were popular Instagrammers. It was a poor way to grow creatively (not to mention that it doesn't help you stand out), because I wasn't even following the best of the best! I say that not to bash popular Instagram photographers (who are typically delightful, hard-working people), but to point out that a twenty-year-old probably isn't as worthy of emulation as the sixty-eight-year-old Annie Leibovitz, for example.

I actually try to search for interesting sources of inspiration outside of photography, even, for an even fresher perspective. I'm looking at paintings, designs, movies, music, and even tech or business. The goal is to grow a unique voice, and consuming the same content as everyone else isn't a great way to get there. 


Art Direction

Improving the set / art direction has been a big focus for me lately. Creating something entirely unique, like a car covered in wallpaper, was an attempt to grow in this area. I spent three days covering this car in wallpaper hahaha.


Art Direction and Fashion Styling

Here I wanted to grow in my art direction again, filling the room full of leaves we raked up ourselves the previous week (not an easy task in LA)! I also wanted to dress the model fairly conservatively, as more revealing styles are now so widespread it's borderline cliché.This piece is from a designer in Russia.


2. Openness: share my time, images, and experiences freely.


I want to reach my goals, but not at any cost. I'm over the work-a-holic, sacrifice-everything-no-matter-what mentality. Work is not everything, and I reserve the right to get lunch with a friend instead of sending emails. To be clear, I'm not advocating for laziness or passivity. But as someone who naturally gravitates towards the work-a-holic end of the pendulum, I don't think I'm in any danger of getting passive.


I reject the notion that photographers should never do free work. Sometimes it's actually okay. It's a counterintuitive paradox, but I think working for free often produces paid work? Call it karma. Or if you're Christian, think of the whole first-shall-be-last, he-who-wants-to-save-his-life-must-lose-it mentality. Regardless, it's better to give than to receive, and it's crucial to develop the habit of generosity now as a single twenty-something rather than make a habit out of stinginess and expect myself to suddenly start giving back when I've got two kids and a mortgage.

To be clear, it's usually a bad idea to trade work for exposure and I obviously charge in most cases. However, I reserve the right to give away my images without worrying if I'm "destroying the industry."  Proposing I refuse to do free work is as silly as suggesting I should never give money away.


I've never liked "fake it 'til you make it." Not from some sort of moral high ground (though I do think a more transparent approach is typically best), but because I think it's less effective anyways. True self-confidence is openly acknowledging weaknesses and failings because you believe it's a matter of time until they disappear. I intend to be open and transparent about my challenges. 

So, in short:

  1. Get good.
  2. Stay open.