There is something about having a mountain of debt, no inbound leads, no business model, and youth that makes you sit back to reflect upon the compounding dumb decisions you have made up to this point. At least for me, that was the case.
Let me briefly take you through some of those decisions:
At 8 years old I dedicated myself to the pool for I had a dream to play a sport in college. I had been a successful competitive swimmer (All-American in the 100 butterfly as a freshman in High School) and successfully transitioned to water polo. That transition landed me a scholarship to Santa Clara University and became the team captain of my college team for two years.
After graduating undergrad early, which I do not regret what-so-ever, I flew to New Zealand with a single goal “to cycle around the South Island” for 62 days as a graduation gift to myself and to act as a reset to reflect upon the next stage of my life. I did this cheap, in total $5-7k which includes buying a bike set up, plane tickets (which was like $2k), food, no phone, camping almost every night, showers, etc.
Upon returning from NZ, I did a short stint at grad school, this I do regret, and stacked up $40k of debt in a matter of months with the thought I would become a high school math teacher. In California, that would have been a salary of roughly $60-80k a year with a $2k/year “bonus” for having a master’s degree. So, if I would have followed through on that, paying off my master’s degree would have taken roughly 30 years. Not a good investment!
Knowing that I was not aligned, because of the down time cycle New Zealand gave me, I dropped out and “became homeless”. I moved back onto my bicycle and started to work odd jobs like outdoor education, substitute teaching, and picked up a camera.
I tried my hand at writing as well, but I could never really figure that business model out, at the time.
But, I knew living on a bicycle was not a sustainable lifestyle for me. Sure it was cheap, but I wanted to surf, rock climb, and, well, not live in a tent on the side of the road. Don’t get me wrong, I love camping and backpacking, but not really for 365 days a year. It gets old fast.
Lunch time siesta while living on a bicycle somewhere in West Virginia.
At the time I realized I wanted more than a bike and tent I was cycling from the east coast to the west coast somewhere between West Virginia and Kentucky. But, I had no income, no house, no apartment, and no job prospects. In many ways, I was still decompressing from the athlete life which I had been living from 8 years old. Fifteen years later, my mind was still on sport and I didn’t really know myself outside of a pool.
I knew my personal limits and how to break through those.
I knew my mental limits and how to break through those.
But, I didn’t know how to have fun, laugh, play, or do things for no reason.
Then a camera came into my life.
Just before leaving on this attempt to cycle across the country, I was working for an outdoor education school part time in Baltimore. The whole time I was snapping photos for fun and sharing them with the marketing director, Ben Worden, at the end of each trip I taught. Without thinking much about it, Ben would say a few nice words and provide feedback after each submission. Then, towards the end of my three month contract, Ben called me into his office to have a conversation that kinda went like this:
“You know you are a really good photographer.” Ben complimented me.
”Okay, thank you.”
”Like people would pay you for your photography.”
”Okay, but how much do people really make selling photos?” I asked rolling my eyes.
”Um, 10 times what you make per day right now.” Ben quickly responded.
My jaw dropped in disbelief, “Wait, really?”
”Not exactly, but I would certainly pay you double what you are making now, next year, if you wanted to photograph for us.”
”Yes, sign me up. What do I need to do?”
…
From there, Ben gave me a laundry list of things I needed to do for the school to hire me as a freelance photographer come the spring season. It was the end of fall and, at the time, Outward Bound Baltimore was closed for winter. So, as I cycled across the country I kept trying to understand what I had to do, how much it would cost me, and if I could actually make it happen.
Turns out, it wasn’t really that hard, or expensive:
Get some insurance ($50/month)
Create a sole proprietorship ($10-25 depending on your state)
Keep photographing (my time, which I had a lot of).
The only catch, I was still broke, living on a bicycle, and eating Bisquick with mustard for breakfast, lunch, and dinner. Sure I also had the occasional hot dog, but not often.
In somewhat of a stroke of luck, I had some family shit hit the fan and my parents bought me a plane ticket from Ohio back to California to be with them. Upon arriving at their place, they lent me a Mercury Mariner (which I couldn’t afford the gas or insurance), and that car would became my next home. I couldn’t fully lay down in the back, but I could lay down enough to fall asleep.
For a few weeks, I stayed at my parents place and applied to a few jobs, meanwhile photographing every day.
For the most part, I wasn’t really creating anything with my camera, but I was learning and building a work flow. I even tried to do some marketing for photography at a few local spots, but nothing really came around. Eventually, I got a call back for a substitute teaching position in Watsonville, CA, packed the car, and left my parents house with the mindset that had to land the job because I didn’t have enough money to drive to Watsonville and back to my parents without making some money.
With a college suit on, I walked into that interview, on a Tuesday or Wednesday, knowing I was going to do whatever it took to get the job.
The interview was short and sweet. The hiring lady looked over my paperwork and said, “If you want, you can work everyday. We need bodies in classrooms.” I got the message, scanned my finger prints (I passed), and had to take a TB test.
The thing about TB tests is that they take between 48-72 hours, and, because my bank account had less than $500 in it, I couldn’t do anything. So, I parked my car at Pleasure Point in Santa Cruz, CA, surfed, and started taking surfing photographs with the dream that I could make some money while taking photos.
Nothing on day one.
Nothing on day two.
Nothing on day three.
Sure, I made a few friends and kept practicing, but I really couldn’t figure out how to make any money. Surfers exiting the water asked me if I got any images of them and would let them look through the back of my camera to preview what I shot, but I didn’t have a way to get them images, let alone sell the images, or collect any money. I had no idea what I was doing.
So, when my TB test cleared on Friday, I was in set to substitute teach. Monday was my first class.
PHEW!
I still needed to play it safe on fuel and watch my money because substitute teaching paid NET30, so those dwindling 500 bucks had to last me until I got paid, which wasn’t easy because it was between $20-40 in fuel to drive to the school I would be teaching at each morning (the school changed daily), plus I still needed to buy food. Thankfully, I was still accustomed to my Bisquick meals, so that didn’t cost much.
When that first check came in a major sigh of relief came over me. A couple grand after a month of work. I finally had some wiggle room, but winter break for schools came quick and I was back in the same position once I couldn’t work for two weeks.
Again, I started to realize this new path, substitute teaching, would not be sustainable, but I needed to keep teaching, so I could try to figure out this whole photography thing.
There was so much to learn, but I really didn’t know what to do or where to start.
Feeling a bit defeated, headed to a local book store and returned to my college days of “hitting the books”. Buying a book on freelance photography I read that thing cover to cover, twice. It kinda helped, but not very practical. The skinny, market yourself, land work, produce the work, share the work, and do all the legal things correctly otherwise it’ll bite you in the butt. Good to know, but it surely didn’t pay my bills.
So, I kept going to cliffs of Santa Cruz every morning and every evening to take photographs. December came and went. No sales. January came and went. Again, no sales. And February arrived with a random phone call from a phone number based in my home town.
“Hey, been thinking about your photo offer. I need to update my website. We are doing a bike ride this weekend and if you can come here, I can pay you.”
Wow, my first gig! I crunched some numbers, called him back, and landed a $600 job. That was 7x what I was making at the outdoor school, 4x what I was going to make per day as a substitute teacher, and more money than I had in my bank account. So, I bit the bullet, said yes to the shoot, and spent most of my money on fuel driving the 300-something mile round trip back Auburn to photograph the ride.
I pushed my creativity and did my best to take some images I could be proud to share. In the end, I was still a beginner, but the client was happy. I got paid and I immediately spent the money on a zoom lens so I could improve my photography.
With two lenses, covering 16-200mm I had the bare minimum for action sports. But, I still wanted to photograph in the water, so on my next paycheck I spent $250 of it on a cheap water housing so I could take surf photographs from inside the water.
Instantly, this leveled up my photography game while I waited around for Ben to call me and offer me a job. So, I kept shooting everyday. Sometimes in the ocean and other times on the cliffs with my long lens. At the end of each session I had three goals:
sell something
take 1000 images
drain my battery
Usually I accomplished 2 & 3, but almost never sold anything. I did this all winter long.
Turns out, spring had arrived and Ben had not yet called. Worried he might never call, I decided it was time I do something about it and called him to ask for the job.
He picked up, “Hey Dalton! How are you doing?”
“Good, I have been photographing a ton everyday. I try to shoot at least a 1000 images and I’m getting better. Oh, I did all the things you said I needed to do, so maybe I can still photograph for you all soon?”
“Yeah, let’s talk about that. I have a job for you. Could you fly out here for two weeks and photograph a few trips? We can cover your flight and pay you between $3000 and $5000 for the whole trip.”
“I’m in. How do I sign up?”
“Just write me a proposal contract. I’ll send you an email with the dates.”
“Okay…”
A warm summer night with a fire on the east coast during a kayaking expedition along the Potomac River. Turns out my skill with the water housing became very useful for more than just surf photography.
Turns out I had to wait until June to return to the east coast for the assignment, but it worked out in the end. Learning to ask for the work you want was a learning lesson for me right then and there. After that summer, I still substitute taught, but less and less each year as I built my photography career. It took three years before I was able to completely stop teaching and focus full time on photography.
The biggest difference, learning how to sell and submit images. Once I had a large enough network to do this, I was able to sustain myself as a creative.