| “If you’re not failing, you’re not trying hard enough.” — Joel Grimes |
In photography, failure is easy to see. The blown shot. The missed focus. The gallery with one frame that almost worked and didn’t.
In business, failure is easier to hide — and easier to avoid by never trying anything uncomfortable. You can coast at your current rate indefinitely and never technically “fail” at a pricing conversation, because you never had one that stretched you.
Grimes is describing something more specific: the willingness to attempt things at the edge of your capability, knowing that the edge is where you’ll sometimes fall off. And falling off at the edge of your pricing capability — quoting a rate that a client declines — is not a failure. It’s a data point.
Who Is Joel Grimes?
Joel Grimes is a commercial photographer, educator, and retouching specialist known for his dramatic, high-contrast composite style and his extensive work with athletes and action sports clients. He’s built a significant following as an educator, known particularly for his directness about the real craft and business skills required to succeed as a commercial photographer. His philosophy on failure and risk is central to how he teaches — he consistently pushes students to attempt things they’re not sure they can pull off.
The Business Lesson: The Loss Is Information, Not a Verdict
Most photographers interpret a lost booking as a rejection. The client said my prices are too high, which means my prices are too high, which means I should lower them.
That’s one interpretation. Here’s another: the client said my prices are higher than they were willing to pay. That tells you about that client, not about the market. It tells you what that specific person, at that specific moment, with that specific budget, valued photography at. It tells you almost nothing about whether you’re priced correctly.
When you’re genuinely at your pricing ceiling — when you’re quoting rates that feel like a stretch — you will sometimes fail. A client will say no, and it’ll sting. But if you never fail at a pricing conversation, you’re not at your ceiling. You’re safely in the middle, charging what you know people will say yes to — which is always lower than what some of them would have paid.
The experiment Grimes is implicitly pointing at: quote a rate that you’re genuinely not sure a client will accept. Hold it without hedging. See what happens. Do it ten times. Track the conversion rate. Adjust based on evidence, not fear.
Failing at the ceiling teaches you where the ceiling actually is. Not failing means you’ve never looked up.
Real-World Application: Define Your Failure Rate Target
If 100% of your pricing conversations convert to bookings, you’re almost certainly undercharging. Some loss is a sign of correct pricing.
A healthy conversion rate for most photographers who are priced appropriately is somewhere between 50-70%. That means 30-50% of inquiries don’t book — and that’s fine. Those are the clients whose budget didn’t match your rate.
If your conversion rate is 90%+ and you’re happy with your income, great. If you’re converting nearly everyone and still feel undervalued, that’s the signal to start failing more.
Take the Next Step
The OTODEO Booking Audit Checklist helps you calculate your current conversion rate and identify where in the process you’re losing clients — so you know whether you’re failing for the right reasons. Get it free at otodeo.com/booking-audit-checklist.
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- Quote of the Day – Lindsay Adler on Lighting, Transformation, and What Photographers Get Wrong About Highlighting Their Best Work