For years, my photography business was a little bit of everything. I photographed headshots, family sessions, personal brand photos, sports events, one-year cake smash sessions, and the occasional wedding. I even photographed a few bar and bat mitzvahs along the way. I was working, learning, and saying yes to a wide range of jobs.
Then COVID hit in 2020, and the entire photography industry shifted overnight. Things shut down. Businesses closed, and people got cautious. A lot of photographers, myself included, started doing porch portrait sessions because it was something that could still happen safely.
Porch portraits were simple. There was no sales pitch and no long process. The setup looked something like this:
- Clients paid a flat fee.
- I showed up for a quick mini session on their front porch.
- I kept a safe distance.
- I delivered the photos they expected from my brand.
- They purchased prints from my Pic-Time gallery.
I photographed a lot of families that way, and I even did some corporate sessions for businesses outside their storefronts. It kept me moving, but it was not big money. It was more like survival mode for a weird time.
First Proposal
Then something unexpected happened. My brother-in-law asked me to photograph the moment he was going to propose to his now wife. At the time, they were still dating, and he wanted the proposal documented. I immediately said yes, and then I realized I had never photographed a proposal before in my life.
Because I have spent years teaching photographers, blogging, and making YouTube videos, my instinct was to document the process. If I was going to do this, I wanted to do it right. I went all in on planning:
- Coordinating the exact where and when.
- Thinking through the light and the bold contrast I like to shoot.
- Scouting the location using Google Maps, Google Earth, and Street View.
- Using apps like PhotoPills to map everything out.
I treated it like a mission. Honestly, that is what a surprise proposal feels like. Of course, I made mistakes. It was my first one, and there were lessons I could not learn until I was in the thick of it. But I documented everything anyway. I noted what worked, what failed, and what I would change next time. Then I wrote a blog post, made a YouTube video, and hit publish.
Second Proposal
Not long after that, a friend asked me to photograph his proposal. It was a totally different location and a totally different situation. This time, I came in smarter. I left the neck strap at home, relied on my Spider Holster to keep the weight on my hips, and improved my approach. I documented the second one too. Somewhere in the middle of that process, I started realizing this could actually be a thing.
I knew proposal photography existed. People have been photographing proposals forever. But what I did not see in my area of New Jersey was someone going all in on proposals as their main focus. So I started building a system. At first, the system was just internal. I made checklists, planning steps, questions to ask, and notes on how to prepare. I just wanted a repeatable workflow that made me better every time.
The Pivot
Then the leads started coming in. It was not a trickle. It was an actual flow. I booked more proposals, and once I saw the pattern, I made it real. To handle the demand, I set up a proper pipeline:
- I created a dedicated landing page specifically for proposals.
- I built an automated email workflow in Flodesk.
- I streamlined my Pic-Time galleries for quick client delivery.
- I did the unglamorous SEO work, focusing on internal linking and targeted blog content.
Before I knew it, I was getting ten or more leads a day just for proposals. It was more than I could realistically manage as a solo photographer, especially because photography is not even my full-time job.
My full-time job is at Imagen. I do not need photography income to survive. I do it because I love it. Proposals give me something I did not realize I was missing. It is a real adrenaline rush. It is fun, stressful, and high stakes in the best way. There is nothing like trying to capture a once-in-a-lifetime moment without blowing the surprise.
As the content built up, the SEO started working. If you were in New Jersey and searched for surprise proposal photography, I was showing up. If you were traveling here and searched for it, I was showing up. At one point I was ranking number one, and the leads kept coming.
I also did some informal press. I went on podcasts and made other appearances that brought external links back to my site. That helped the SEO even more, and it all started stacking. It was not overnight success. It was momentum. I noticed what was working, and I doubled down. Then I tripled down.
That is really the story. I did not wake up one day and decide to be a proposal photographer. I got asked to photograph something I had never done before. I documented it, improved it, systemized it, and put content out into the world. Then I realized nobody around me was owning that space the way I could, so I went all in. Honestly, I wouldn’t look back.
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