You Can’t Fake Experience: Learning the Hard Way in Photography and Business
I help photographers and creative entrepreneurs over 40 reclaim their confidence, cut through the noise, and build bold, independent lives through no-BS insight, experience, and action. Welcome to my Substack. I am glad you are here.
Why Losing is the Fastest Path to Winning
You can’t fake experience. And you can’t skip the part where you mess things up.
There’s really no “Crossroads” for photographers. That mythical place where we can meet the devil and trade our souls for instant excellence doesn’t exist. (And if it did, I wouldn’t be allowed to talk about it so let’s just leave it right there, OK?)
So we have to face the fact that practice pays off. And the word practice automatically includes failure. Nobody gets it right the first time.
The goal is, of course, to master what we are working on. Whether it be rock guitar, writing a newsletter, or photography, we want to master the ability to do what we want with a level of excellence.
That takes a lot of failing.
But it has its rewards.
You know, like in this immortal scene:
Eugene didn’t want to do all those classical exercises. He wanted to just do what he wanted. And he was quite good at doing that. But there comes a time when the hard work of scales, runs, and perfectly executed string work becomes a superpower.
There comes a moment when his life is genuinely saved by all his experience at working hard, failing, and working harder.
Dangerous ideas are circulating in certain creative circles, suggesting that if you possess talent, everything will simply fall into place. But the problem is that ‘good’ just isn’t a high enough bar these days.
There’s this idea that achieving real success is a natural result of hope, inspiration, and some kind of divine alignment between you and the universe.
Well, that’s nonsense, total hogswaller.
(You can see the meaning of hogswaller here, if you are curious.)
The magic we call talent is a result of the effort we expend to nurture that seed of possibility. And it doesn’t come easy to most of us.
Of course, there are a few that find themselves instantly at the top of their game. Call it luck, fate, or a visit to the ol’ crossroads. Whatever it is, it’s rare.
For the rest of us, screwing up is what teaches us the most and what really pushes us forward.
Not in the romantic, Instagram-fails-to-inspire-me kind of way, but in the gut-wrenching, ego-crushing form that makes you hear your breathing and cry loudly inside. You know what I’m talking about.
When you walk out of a meeting knowing you blew it. The kind where the image you worked on for days falls flat, and not because the client “doesn’t get it,” but because it’s just not good enough.
Yet.
Wins can be lovely, but they’re truly mediocre teachers. You’ve already won them over. They are pleased, and we move on with a big ol’ dumb smile.
But failure?
Failure makes you stop.
Failure makes you analyze.
Failure asks the uncomfortable questions.
Failure forces a kind of clarity you’ll never get from applause.
Here are three failures that did more for my career than most of my wins ever did.
The “Fun” Gig That Got Away
I was on a go-see with my book. The art director was into it. She brought in the creative director, who liked my work as well.
“I’m in,” I thought to myself, barely holding back a Cheshire grin.
They began talking about a specific campaign and how I might fit.
Yeah, that’s me, baby, rockstar!!!
Then came the question:
“Why do you think you’re the right one to shoot this?”
I smiled. I said something like:
“Honestly, I think it would be a lot of fun — and I know I’d do a good job.”
Silence. Smiles all around.
Friendly smiles, but flat.
And just like that, the conversation died, and I left.
I didn’t get the job.
Here’s what I had to understand: clients aren’t hiring me for my enthusiasm, although enthusiasm is good.
They’re hiring me to solve a problem.
I should’ve talked about how I’d manage talent, how I’d work with their team, how I’d pull their brand emotion through the models, styling, and the shoot. Maybe talk a little bit about how I had done this before, and what I can bring to the shoot.
Instead, I made it about me having a good time.
Lesson: Clients don’t care if it’s fun for you.
They want to know if you’ll nail it for them.
2. The Soap Shot That Nearly Went Down the Drain
Big client.
Big brand.
Big paycheck.
Possibly more of the same.
We’re photographing their line of soap. You’ve probably used it when you’re totally dialed in.
I’m in the zone, building sets, shaping light, adding shadow, chasing visual drama like it’s Cannes and I am going for “most incredibly lit product shot, ever”.
I don’t know if that is a real category, but it sounds legit.
Only one small problem.
They didn’t want drama. They didn’t want the image to win some sort of photo award, that was NOT their need.
They wanted the soap — the product — to look elegant, luxurious, like something you’d be proud to see next to a spotless porcelain sink.
But what I delivered to them initially was:
Overstyled.
Overly dramatic.
A little too “clever.”
They didn’t say no.
They didn’t say anything.
And that was a huge no for me.
So we stripped it back.
Cleaned the set.
Focused on simple, illuminating light.
Finessed every surface.
The final image was simple, but it was elegant and perfect… for what they needed.
And it just worked.
Lesson for me: My job isn’t to impress with complexity.
It’s to communicate with clarity. Sometimes that means dialing it way, way down.
3. The Portfolio That Didn’t Sell
After a few years shooting a lot of editorial, I wanted to break into advertising.
I started pitching — and getting nowhere.
I knew my book was good, but I couldn’t figure out why it wasn’t connecting.
Off I go to meet with a consultant from L.A. A skilled and well-connected consultant who had helped a few shooters I knew fix their approach.
She looked through my book and didn’t sugarcoat it.
“This is good editorial work. But ad agencies want more polish. Production value. Confidence. These feel like you shot them on the fly, and they won’t trust you with a six-figure campaign based on this. You’ve got to really step up your game.”
That stung. A little.
But she was right.
I’d been showing the wrong kind of work to that kind of client.
It didn’t matter how good the images were, they weren’t speaking the right language for that audience.
Ii went to work.
I overhauled the book.
Shot and reshot.
Edited and re-edited.
Asked for a portfolio review from the LA consultant.
Took notes.
Took action.
Shot some more.
And more.
Then…
Pitched to a few agencies.
Got feedback.
Refined the work.
Pitched again.
And this time, it worked.
I spent nearly 6 months and over $10,000 on film, props, stylists, talent, and tools, but it paid off.
I needed that re-focus, that redesign in my head.
I needed that clarity.
If your work isn’t landing, it’s not always because it’s bad — it may just be saying the wrong thing to the right people.
Failure’s Not the Opposite of Success, Failure Is the Road to Excellence
Here’s another way of thinking about it.
In baseball, to hit more home runs, you have to be willing to strike out more often.
And they are not necessarily failures.
They are the price of learning.
You swing, miss, recalibrate.
You swing, miss, recalibrate.
You swing, miss, recalibrate.
You swing, miss, recalibrate.
And each time you miss, you work harder to find a way to get that ball to fly.
And then you hit that sucker.
Because you took all those swings and kept on going, earning the hit.
It’s the same with photography.
To make one outstanding image, you’ll shoot a dozen, or more, mediocre ones.
But if you’re paying attention, you’ll start to see the process unfolding.
You begin to understand what is happening when…
Composition,
Gesture,
Light,
Timing,
Production value,
Syling,
Post…
All come together.
You’ll see the difference.
Hell, you can feel the difference.
And then you’ll grow.
But if you turn away from even the possibility of failure or just accept mediocre work as “good enough,” your growth gets derailed.
Don’t run from the reps… they are so incredibly important.
Of course, success feels good. It’s satisfying.
But failure teaches us how to be better.
If we let it.
Your Turn
Look at the last five images you made.
Pick the weakest one.
Now ask yourself — and answer honestly:
What makes this image fall short?
What were you thinking when you shot it?
What would’ve made it a stronger image?
Now, look at 5 of your best images.
Pick the best one.
And ask…
What makes this image work for you?
What were you thinking when you made the shot?
Could it have been made better? How?
What can you do to make another one like it?
If you can do that, without excuses, without ego, you’re already ahead of most people holding cameras.
New Business Post:
Stop Being the Best Photographer No One Knows About
— Mentor’s Corner.
There is a lot more at The Mentor’s Corner.
Including a deep document on pricing.
AI Corner.
I believe it is imperative, even a responsibility, to keep up with AI. You may not like AI, or think of it in a good light, but it is not going anywhere soon. I spend 15-30 minutes a day keeping up with it. And I am not talking about generating ‘photos’, I am talking about the myriad of other things that it can do. Many of them are hugely beneficial to photographers and small businesses.
I would suggest joining at least one AI-focused newsletter to stay up-to-date with the latest developments. The Rundown is one of those newsletters I read every morning, check out their links, and keep myself in the know. There are many newsletters about AI available, but this is one of the best for staying up-to-date. Check it out here.
Never Trust Any Visual From This Day Forward > Kontext
Adobe releases “Boards”.
Now, this I can get behind a bit. As you know, I do not generate ‘photographic’ images. I don’t see any point in it. However, I do utilize AI for many things. I have generated architectural renderings for our hacienda, our garden, and other little things, but I am not interested in visual AI stuff.
This tool can be used to sketch out, design, and produce mood boards, storyboards, and a variety of inspirational art to help you pitch to clients and create effective tools for your work. From product to story ideas, Boards is something you should look into.
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If you’re over 40 and still hungry to make, build, and create, stick around. This space is for people who aren’t done yet (and never will be). I’ve got five decades of wins, failures, comebacks, and creative battles under my belt, and I’m sharing everything that still works—and burning the rest.
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I have been telling friends of mine recently that everything I've learned on the camera I've learned the hard way. I don't have any formal art education. Yet, that hasn't stopped me from chasing the 10,000 hours to excellence. This was a great read and advice that everyone can benefit from. Thanks for writing and sharing 💪🏻
Great stuff as usual, and I had to stop and watch the guitar battle, which I'd never seen before. Fantastic.