Flying or Crashing: The Reality of Building Work By Davey
Some days, I feel like I’m about to take off.
Other days, I feel like I’m about to crash and burn.
That’s what building Work By Davey has been like — being a solo entrepreneur, especially in a creative field, is a constant balancing act between ambition and reality. You wake up ready to work, but you don’t always know what you need that day to move forward. And even when you figure it out, there’s the money barrier.
The last thing I bought was a 9.8” SmallRig magic arm, a cold shoe, and 1/4 20 screw attachments for my Canon R8 cage. I hooked up my FeelWorld monitor and RODE shotgun mic, and for a moment, I felt like everything clicked into place — like I was finally building the rig I needed. But that high doesn’t last long, because the list never ends.
Right now, I’m $1,600 away from having the lenses and stabilizer I know will take my work to the next level: an RF 85mm, a Zhiyun Weebil 3S, and an RF 15–30mm. And it’s not just gear. It’s upgrading how I present myself — the clothes, the glasses, the business cards, the flyers, the stickers. It’s a whole shift in how I want the world to see me.
When I wake up, I try to focus on ambition. The feeling that I’m building on what I have, whether that’s adding equipment or working on ideas and projects. My small wins come when I’m out shooting video — not working construction or doing something just for a paycheck, but actually learning my equipment, creating something for Instagram or YouTube, and feeling like I’m in my lane.
But there are crash-and-burn days, too.
Like last week, at the Lawrenceville Art Crawl. I had my camera, but I didn’t know how to use the control ring, and almost everything I shot was out of focus. Expensive gear, wasted opportunity. That’s when the self-doubt creeps in: What am I even doing if I can’t get this right? It wasn’t just frustrating — it was a reminder that I have to spend more time learning before I step into certain spaces.
Most days, I’m on my computer: doing design work, updating the Work By Davey website, researching equipment, planning out projects. The hardest skill so far hasn’t been anything creative — it’s been learning how to network. The art of walking up to a stranger and saying, “Hey, can I take your picture?” without feeling like I’m bothering them.
And yes — starting out means spending way more than you make. That’s just the truth. If I had $5,000 tomorrow, I’d get the lenses, the stabilizer, some better lighting, invest in advertising, and save the rest. Because for me, flying means being in the right rooms, networking, and making money from client work all over Pittsburgh — from events to small businesses — and proving to myself that the $4,200 I’ve already invested wasn’t a mistake.
Crashing? That would mean staying stuck.
Not making money.
Not growing.
Letting my own fear and overthinking keep me from being present in my community.
The truth is, I don’t think I’m going to crash.
I think I just need to keep building the plane while I’m flying it. And that means showing up, gear in hand, ready to create — even if I’m still figuring it out.
If you’re in Pittsburgh and you want your story told by someone who’s chasing the real moments — not just the perfect ones — let’s make it happen. Because flying or crashing, I’m still in the air.
