There is a version of entrepreneurship we all see from the outside: the polished, highlight-reel version.
It can make it look as though someone has a golden touch and everything they launch automatically succeeds.
But when you only see the wins, it’s easy to create a quiet story in your mind that says, “Of course it worked for her. It always works for her.”
The truth is that, for every big thing that worked in my business, there were at least five to ten things that didn’t!!
Some ideas were expensive mistakes.
Some fizzled quietly.
Some were embarrassing.
And a few left me wondering if I should keep going at all!!
If you’re sitting in your own version of a “flop” right now…
- A price jump no one is booking
- A pivot that isn’t resonating
- A season full of disappointments
I want you to know you’re not alone!
Here are ten things I tried in my business that totally flopped, and the lessons each one left behind.
Why I’m Sharing My Failures
I don’t usually promote my failures, and most people don’t either.
That’s part of the problem. When failures stay hidden, they start to feel like evidence that something is wrong with you rather than simply part of the process.
It becomes too easy to assume that other people just glide through life and business without ever hitting a wall.
Every failure I’m sharing here taught me something, shaped something, or cleared the way for something else.
They were not dead ends!! They were detours that redirected me toward the next right thing.
Failure #1: Katelyn’s Krafts “Starfish” Designs
When I was fifteen, I started a tiny business called Katelyn’s Krafts.
I painted ceramic plates, bowls, mugs, and ornaments, baked them in the oven so they were dishwasher safe, and sold them at craft shows.
My all-star product was a custom snowman plate with the family’s names written in cursive.
People loved them!!!
I once made over a thousand dollars in a single day at a craft show!! This was my first real taste of entrepreneurship and I was hooked. This business was NOT a failure!!!
The failure came when I tried to expand my best seller.
Once everyone in my world had a snowman plate, I created a summer version featuring beach colors and a family of starfish.
Not one single person bought them.
Every craft show felt like crickets!! I literally sat at one for HOURS with my sweet dad and not ONE person stopped by! Talk about a humbling experience.
That failure nudged me to try graphic design, which eventually led to photography, which changed the entire trajectory of my life.
Thankfully my Mom still hangs her snowman family plates with pride during Christmas!! (Along with several other family friends!!)
Failure #2: A Homemade for Hosting
Years later, I launched an Instagram account called A Homemade for Hosting.
I imagined this account would be for sharing interior decorating, our home-building progress, recipes (from my sister!!) and hosting tips. I mean, we literally announced this to the world as a REAL thing. We were going to have recipe series, tablescape designs….We were convinced we were going to build our own sisters version of Joanna Gaines’ empire!
I pulled over fourteen thousand people to that account, and then… I JUST STOPPED SHARING.
Life hit hard!!
I was pregnant with my first baby and still shooting twenty-five weddings a year.
The idea simply wasn’t sustainable and eventually, the excitement faded, and with it, the entire brand.
That experience taught me that even a good idea can become the wrong idea if the season can’t support it! I’m not embarrassed by this failure… but I do sometimes wonder what in the world I was thinking!!! Honestly, that’s a CLASSIC first time pregnant woman thing to do… you have all the dreams and then literal new life happens and it knocks you down a few notches!
Failure #3: The $10,000 Sales Tax Mistake
Early in my career, I misunderstood Virginia’s sales tax rules.
My CPA repeatedly told me I needed to charge sales tax because I included an album in my packages.
I insisted I didn’t because other CPA’s said it wasn’t true. I didn’t know WHAT to believe!!
After ignoring her advice twice, I ended up with ten thousand dollars in penalties.
It was painful, embarrassing, and totally avoidable.
It also taught me to listen to professionals who know more than I do (especially when legal compliance is at stake!!).
Failure #4: Launching a Bestseller That Was Broken (And Illegal!)
In 2020 I launched what is now known as The Preset Process.
At the time, I named it Develop by Katelyn James.
I didn’t want to sell one-click presets, so I turned my Lightroom teaching into a four-step system that gave photographers control and consistency.
The launch exploded!!!
Over a thousand photographers purchased it in a weekend.
And then everything fell apart.
Step three was broken because I had exported the wrong profile.
My sister launched it while I was nine months pregnant and shooting an engagement session hours away from home and I couldn’t help her fix it, and we were both in tears!
Thankfully we pulled it together within hours and got everyone taken care of.
Two days later, a cease and desist arrived. A company had trademarked the sound “develop” in the preset world and I had no idea!!!
Their letter was incredibly kind and we understood, but we still had to rebrand immediately.
That week was chaotic, humbling, and exhausting.
It also left us with one of our best-selling digital products ever…proof that a failure inside a win can still produce long-term success!!
Years later, the KJ Preset Process is used by over 12,000 photographers around the WORLD who were tired of mis-marketed “one-click presets” on RAW files that never delivered!! This isn’t a preset, it’s a PROCESS within Lightroom that gives you steps to find your consistent style!!!
GET YOURS HERE!!!
Failure #5: Don’t Poodle My Doodle
This one makes me laugh every time I talk about it!!
I spent more than a thousand dollars filming a full grooming course where my mom taught doodle owners how to maintain that adorable “forever puppy” teddy bear face without letting groomers shave it into a poodle snout.
We built the domain, the freebie, the draft website, and the entire course.
And then I did absolutely nothing with it.
It’s that wild?! We were SO close! Honestly, if I received 15-20 requests for this business, I would seriously find a way to put it into the world because I was always so proud of the concept AND the content!! Mimi killed it!
Failure #6: Wall in a Box
At one point, I wanted to create a business that sent customers a ready-to-hang wall gallery.
They would send their wall dimensions, choose their frame style, and I would send a paper template with nail marks for perfect placement. It was creative, helpful, and tied beautifully into the photography world!!
But shipping costs, production complexity, and logistics made it unsustainable. The idea never made it off the ground!
This experience reminded me that passion can’t always overcome practicality.
Failure #7: Coaching Groups Across America
I was convinced photographers around the country would sign up for my in-person coaching tour.
I announced multiple cities, set up the plan, and prepared for a full schedule.
Only a handful of people registered….. And yet I still had to go!
I ended up traveling across the country for one or two students at a time, and I hadn’t priced the program high enough to cover travel. I lost so much money on each stop!!
Even though the sessions were meaningful, the business model itself was a flop.
I learned to never let confidence skip over the planning phase again!!
Failure #8: The $6,000 Copywriter
Someone once told me I shouldn’t write all my own emails forever, so I hired a professional copywriter.
At that time, I didn’t understand the brand voice and hadn’t built clear guidelines for anyone to follow.
So naturally, the copy didn’t sound like me and I didn’t catch it…and I sent it out anyway.
So many of our audience replied back to emails saying, “This doesn’t sound like you at all.”
That experience convinced me I could never hire a copywriter again.
It wasn’t true, but I believed it for almost eight years!!
The real failure wasn’t the copy. It was allowing one bad experience to shut a door I should have tried opening again.
Failure #9: Now Teach It
A few years ago, I launched a business called Now Teach It because I wanted to help other educators sell online.
Parts of it were absolutely wonderful!!!
I loved the coaching, the breakthroughs, and the personal transformation I got to witness.
But I didn’t love the systems, funnels, and tech-heavy marketing side.
I realized quickly that I wasn’t trying to become the next Amy Porterfield, and the business faded as soon as that became clear.
It wasn’t a total failure, because it taught me where I come alive: in personal, holistic coaching that helps people uncover deeper issues beneath their business struggles.
Failure #10: The $30,000 Decision I Regret
I once paid thirty thousand dollars for something I thought would make me feel more confident as a business owner.
Deep down I knew it wasn’t right.
I even paused twice, then proceeded anyway because other people said it was the right move.
But it absolutely wasn’t!!
It caused confusion in our brand and led to an expensive lesson in trusting my discernment. One day when I’m further removed from it, I’ll share exactly what I did but for now, just know that all advice isn’t GOOD advice!! Yikes!
What These Failures Reveal When I Look Back
When you’re standing in the middle of a failure, it feels like a dead end. When you look back, you begin to see how everything connects.
One failure leads to a lesson that prepares you for something else.
Another exposes a weakness you need to fix.
Another clarifies a direction you didn’t know you wanted.
None of these failures were wasted!!
Each one shaped something essential about who I am and how I run my business today.
Your Homework: Build Your Impact Web
If I were teaching this as a course, here’s the exercise I’d give you:
- Write down ten failures you’ve experienced.
- Circle each one.
- Draw lines outward from each failure and write down what you learned and where it led.
- Keep tracing the connections until the page is full.
You’ll likely discover that your failures form a map of resilience, growth, and unexpected direction far more than they form a map of disappointment!
If You’re in a Failure Season Right Now
Reflecting on failure can either pull you down or push you forward.
If you already feel discouraged, your brain may use your failures to reinforce old beliefs that aren’t true.
Beliefs like “I’m not good at this,” “I always fail,” or “I’m letting everyone down.”
But your feelings are not facts!! You get to challenge them.
Lean into the discomfort long enough to understand what the failure is trying to teach you.
That process builds resistance to the lies your brain wants to cling to and strengthens you for what comes next.
Final Encouragement
If this blog made you think, “I needed that,” there’s a reason.
Something inside you is asking to be strengthened and clarified.
Don’t stop here!! Keep leaning in.
Your failures are not proof that you’re falling behind.
They are evidence that you are trying, growing, and becoming the kind of entrepreneur who doesn’t quit.
You can flop ten times and still build something beautiful. I’m living proof.
Ps. If you’re an Entrepreneur in a season of floundering, it’s time we get a little clearer on who you actually ARE as a business owner!! Your brand deserves clarity and your audience is desperate for it!!! The KJ Brand Starter Guide is your FIRST STEP and right now it’s only $14!!! Enjoy!
