Third Time's the Charm? My Journey Behind the Camera

I've loved taking photographs since middle school, although back then my experience was pretty much limited to disposable cameras. Most of which, if I'm being honest, were never actually developed.

It wasn't until high school that I finally got my first digital camera: the Fujifilm FinePix S3100.

This thing was slow, had a laughably low megapixel count by today's standards, and looked like a DSLR without actually being one. But I loved it. I used the absolute crap out of that camera until it finally gave up during my sophomore year.

For the next several years, photography took a back seat to other important teenage priorities. Things like puberty, learning how to play guitar, relationships, and whatever else seemed more important at the time.

My First DSLR (And Absolutely No Idea What I Was Doing)

Fast-forward to college, when my mom surprised me with my first DSLR for Christmas: the Canon Rebel T1i. She was eager to help me rekindle my interest in photography, although realistically, it was still just a hobby.

Compared to the old Fujifilm, this camera was completely alien to me. That little "M" on the mode dial supposedly stood for Manual. As far as I was concerned, it stood for "Must be dumb to think I can use that."

The problem? I had absolutely no idea what I was doing.

After years away from photography, I suddenly had a camera with more buttons, settings, and capabilities than I knew what to do with. I didn't have anyone showing me the ropes, either. It was mostly trial and error, with a lot more error than trial.

I even picked up a Vivitar 283 flash on eBay, thinking I'd found myself a proper lighting setup. It was practically unusable, and I only recently learned that certain older versions could potentially damage a modern camera's hot shoe electronics.

So, in hindsight, that was probably not my smartest purchase.

Still, I kept taking pictures.

Old girlfriends, friends' bands playing outside a local Starbucks, and random black-and-white photographs during walks through the wetlands of South Florida. If something caught my attention, I'd try to photograph it.

Not that the results were always particularly good.

Eventually, photography took another back seat. There was family drama, parties, and a brief period of experimenting with things that probably weren't doing me any favors.

But something stuck with me during those years.

I'd see the same photographers showing up at events, working parties, traveling to festivals, and seemingly making a living doing exactly what I wanted to do.

And I'll admit it. I was jealous.

Not necessarily of their equipment or even their photographs. I was jealous that they were out there doing it while I was watching from the sidelines.

The Canon 60D: My First Serious Attempt

In 2013, I met the woman who would eventually become my wife.

We'd talk about her artwork, and I'd talk about photography. Thankfully, after showing her some of my work, she encouraged me to follow my passion. Those conversations also helped me believe that maybe I had at least a little talent worth developing.

She even helped me buy a Canon 60D, a camera I still own today.

And that was when I made my first serious attempt at doing something with photography.

I started photographing friends' businesses, local bands, car gangs at track days, and whatever opportunities came my way. A lot of those band performances were in dark venues with terrible lighting, which was unfortunate because I still wasn't particularly good at working in low light.

Some of those photographs were rough.

Really rough.

But I was enjoying photography again, and for the first time I wasn't just taking pictures because I liked taking pictures. I wanted to see if I could actually make something out of it.

Unfortunately, most of those early projects didn't turn into paying work.

The Canon 5D Mark III: Attempt Number Two

About two years later, I made what felt like an enormous investment.

I bought a Canon 5D Mark III.

For anyone who remembers the days when DSLRs ruled the photography world, the 5D series was a serious piece of equipment. It was one of those cameras I'd admired for years, and finally owning one felt like a milestone.

I made myself another promise: this time I was really going to make something happen. With a camera like this, surely equipment wasn't going to be what held me back.

I was going to get paid bookings, build a portfolio, grow an audience, and hopefully get published somewhere along the way.

And for a little while, things actually started moving.

I managed to land a few paid projects, built a very small following on Instagram back when the platform was mostly about sharing photographs, and started feeling like I might finally be getting somewhere.

But not nearly enough to pay off my initial investment. Not by a long shot.

Then, slowly, as my friends' bands began breaking up or going on hiatus and I found myself working two jobs just to make ends meet, photography started fading into the background again.

Only this time, the break wasn't a year or two.

It was a decade.

Third Time's the Charm?

Which brings us to today.

Here I am, making my third serious attempt at turning photography into something more than a hobby.

And this time, I've got a little more than enthusiasm working in my favor. I've built up a pretty serious arsenal of photography gear and business tools, along with the skills to do much of the work independently.

And, of course, I still have the love and support of my wife, who's had a front-row seat to all the ups and downs of this journey. She's watched me get excited about photography, chase opportunities, lose momentum, and eventually find my way back to it. More than once.

I've spent years developing sales skills, learning how businesses operate, and understanding that being a good photographer and running a successful photography business are two very different things.

I've also moved into mirrorless photography with the Panasonic Lumix S5 II, my first mirrorless camera, and started building High Trail Media into an actual business rather than another attempt at making a few dollars with a camera.

Technology has changed quite a bit since my earlier attempts, too.

I can now build applications and automate tasks that used to eat up hours of my time. Things like scheduling social media posts, managing content, organizing metadata, and working on website SEO.

All the stuff I either didn't have time for or didn't even know I needed to worry about the first two times around.

But the biggest difference is that I'm actually getting out there and doing the work.

I've taken on more paid photography projects than at any other point in my life. I've developed relationships with clients who call me when they need new photographs. I've been able to explore hospitality, commercial, and real estate photography, and work on projects that would have seemed pretty far out of reach when I was shooting bands outside Starbucks.

And perhaps most importantly, I'm taking more photographs than ever before.

Not just for clients, either.

I'm making time to experiment, travel, photograph interesting places, and work on the creative side of photography that got me interested in the first place.

I'm still learning, still experimenting, and occasionally questioning whether I truly know what I'm doing.

But unlike the first two attempts, I'm building something with a clearer direction and the experience to understand what it takes to keep it going.

So, Why Start a Blog?

Partly because I finally have things worth talking about.

I want somewhere to share the work I'm doing, the techniques I'm learning, the equipment I'm experimenting with, and the occasional lessons that come from getting something completely wrong.

I also want to document the process of building High Trail Media, including the challenges that don't necessarily make it onto Instagram.

I don't know exactly where this third attempt will take me.

But compared to the first two, I'm better equipped, a little more experienced, and considerably more aware of what it actually takes to make a business work.

It's already been a fun ride.

And this time, I'd really like to see where it goes.