In 2008, I had 38 weddings on the books. I’d been building my photography business for three years, things were gaining momentum, and I thought I’d finally figured this out. Then the housing market collapsed.
Six of those weddings cancelled. New inquiries dried up almost overnight. And I’d just gotten married myself that same year — so the timing was, let’s say, not ideal.
A lot of you learned the technical side of photography through my courses. But nobody teaches you what comes after — how to turn those skills into a business that actually sustains you. That’s what I want to talk about today.
I survived that season because I’d been shooting real estate walkthrough videos on the side. When wedding revenue dropped, that work filled the gap. But it taught me something I wouldn’t fully understand for another decade: relying on one type of client for one type of work is a fragile way to build a business.
The Real Cost of Inconsistency
Getting married that year made something else painfully clear. It wasn’t just me anymore. The busy months were great — summer and fall were packed with weddings and the income was solid. But surviving winter could get genuinely stressful. December, January, February — you’re watching the account drain and hoping the inquiries pick back up before things get tight. That cycle is exhausting when it’s just you. When you have a spouse counting on you, it hits different.
I knew I needed something closer to an actual paycheck. Something I could count on showing up every month regardless of the season.
The Weekend Problem
A few years into our marriage, our oldest son started preschool, and I had one of those clarity moments that changes how you see everything. I realized that if I kept building my business around weddings, I was choosing to spend the majority of my weekends working — for the foreseeable future. The weekends my kid was home. The weekends that were supposed to be the whole point of being self-employed in the first place.
So I made a decision. I started looking for photography work I could do during school hours on weekdays. That led me to commercial work — and it opened a door I didn’t even know was there.
The Conference That Changed Everything
That same year, I attended a search engine marketing conference and brought my camera along. Not because anyone hired me to — just because that’s what I do. After the event, I shared some photos with the organizer. They hired me for their next conference.
That single relationship turned into 3–5 events per year for the next 12 years. Consistent. Predictable. Work I enjoyed, on a schedule that made sense for my family.
And then COVID hit, and conferences disappeared.
Again — the model I’d built was disrupted by something completely outside my control. Again — I had to adapt.
The Shift to Retainers
Around that same time, I’d taken some product photos for a client. Standard one-off job. But then they needed lifestyle photos for social media. And then more. They wanted to be aggressive with their content, posting consistently, and they didn’t want to renegotiate a new project every time they needed something.
So we set up a retainer. $2,400 a month for photography and video social media content creation. That relationship lasted four years.
I’d had short-term retainer relationships before — three-month engagements averaging around $300 a month. Helpful, but not life-changing. This was different. This was a real, recurring revenue stream that I could build around.
And here’s the part I didn’t expect. Once my income from recurring revenue was enough to cover my base living expenses, I felt the stress I’d been carrying for years physically leave. I’m not exaggerating. That weight — the constant low-grade anxiety of “will next month be okay?” — it just lifted. I wasn’t waking up wondering where the next client would come from. I wasn’t refreshing my inbox hoping for an inquiry. I had a foundation I could count on, and everything I booked on top of that was a bonus rather than a necessity.
What I Wish Someone Had Told Me
Looking back across 20+ years of professional photography, the pattern is obvious. Every time I was in trouble — the 2008 crash, the weekend trap, COVID — the answer was never “get more of the same kind of clients.” It was always “find a different way to use the skills I already have.”
And the retainer model is the clearest version of that lesson. There are businesses in every town — restaurants, salons, gyms, boutiques, real estate offices, service companies — that need fresh visual content every single month. Most of them are doing it badly or not at all. They don’t need a one-time photoshoot. They need a photographer who shows up consistently and delivers content they can actually use.
That’s work you already know how to do. You just might not have thought about packaging it this way.
A Free Workshop
I’m hosting a free live workshop on Wednesday, February 18 at 2:00 PM MST where I’m going to walk through exactly how this works — how to identify businesses in your area that need this, how to pitch a retainer relationship, and how to structure it so it actually sticks.
I’m also going to run a live exercise during the workshop where you’ll audit your own local market and start spotting opportunities you’re probably walking past right now.
If anything in this post resonated — if you know the feast-or-famine cycle, if you’re tired of starting over from zero every month, if you’ve ever wondered whether there’s a more sustainable way to do this — I’d love to have you there.
No pitch, no pressure. Just the playbook I wish someone had handed me 15 years ago.
