When “Working Wid People” Doesn’t Work: A Hard Lesson in Securing Retainers


So, let me tell you a story, not to shame, but to shed light.


Back in May, I received a booking inquiry for a photoshoot scheduled for July. The client was clear about what they wanted, had the vision in mind and the excitement was mutual. Everything sounded good, except they couldn’t pay the required 50% retainer upfront.


Now, typically, that’s a non-negotiable part of my process. But this time? I made an exception.


Why?


Because the person wasn’t just a potential client, they were a childhood friend. And in true St. Kitts fashion, I figured I’d “wuk wid she,” giving her the chance to lock in her slot and pay the retainer the following month. I even encouraged her to officially book the date to avoid losing the slot to someone else.


Weeks passed… no update, no payment, no communication.

Fast forward, we’re now three days away from July 1st. Still no retainer, no message, just straight crickets. Bare crickets, real Kittitian silence-style... dead quiet.


So I did what I had to do. I followed up.


And then came the response: she wanted to cancel the shoot.


Whew.

I’m not even gonna lie, that one stung bad. A physical pain in my chest kinda sting.


Not just because of the cancellation itself but because it felt like something was taken from me. The possibility of a serious client. The time I blocked off. The energy I started pouring into prep.


And in that moment, it hit me.

I was trying to be understanding.

I was trying to be accessible.

But in the end, being too accessible gave room for me to be exploited.


What’s a Retainer and Why It Matters


A retainer is a non-refundable fee that reserves your session date and signals commitment from both sides.


It also allows me, the photographer, to begin planning with intention (researching locations, curating the mood, organizing logistics, and setting the creative tone for your session).


It’s not “just a deposit.” It’s a mutual agreement that this session is real, and it matters.


The Lesson? Don’t Skip the Non-Negotiables


This was a hard but necessary reminder:


Secure the retainer. No matter who it is.

Friend. Cousin. Your aunty from ‘round the corner.


Because the truth is, business doesn’t run on sentiment. It runs on structure, protection, and respect for your time and talent.


Being kind doesn’t mean being unprotected. And being flexible doesn’t mean being a pushover.


As creatives, especially in small communities, we often want to give people grace, and that’s beautiful. But grace can still have boundaries.


So if you're reading this and you're building something, whether you're a photographer, stylist, makeup artist, or baker, let this be your sign:

Put your systems in place and stick to them. You owe your craft that much.


Here's to honoring your boundaries, protecting your peace, and remembering: the right clients won’t flinch at your policies,  they’ll respect them.