Everyone has made mistakes and failed at multiple endeavors, notes Matt Shoup, Fort Collins, Colorado-based entrepreneur, public speaker, and author. What if your biggest mess-ups were actually your most powerful connection points—to new relationships, new clients, new business success?

At Imaging USA 2026, Jan. 11-13, Shoup is scheduled to speak about how to use your uncomfortable moments to build trust and rapport. His session is titled, “Painted Baby,” which also is the name of his 2023 book featuring the same concepts. Ahead of Imaging USA 2026, Shoup granted Professional Photographer permission to include an excerpt of his book, below.

In the book’s introduction, Shoup, then owner of his own residential painting company, is sitting across from a potentially lucrative client back in 2011. The client asked Shoup to describe his worst mistake and how he resolved it. Shoup shared two stories he thought were particularly damning, but the client wasn’t buying it, Shoup writes.

So, there they were—my two worst stories. I’d painted the right house the wrong color, and I’d almost painted the right color on the wrong house. But as much as I had messed up, I’d taken responsibility and done what I could to make everything right too.

Now it was my turn to lean back. Bill had to sign the contract. I waited for his response. The proposal was still sitting between us, on his desk. My shiny marketing brochure was still on the floor. I had to wait for him to make the next move though. Sales 101: Know when to stop selling. Know when to stop talking.

Bill laughed and said, “Whoa, Matt—unbelievable! That’s better than your first story.”

“Yeah, I guess,” I said, a little embarrassed, but relieved that he was laughing—and that he hadn’t thrown me out of his office.

“Okay, then,” I said, “can we do business now? Let’s get your million-dollar baby on the schedule before it gets too cold. You know, they’re calling for an early winter …”

“Not so fast, Matt,” he said. “I feel like you’re holding out on me. All these years in business? All those projects? You’ve got to have something better, and I’d love to hear it. Come on, what’s the worst—I mean, absolute worst—you’ve ever done?” …

I took a deep breath.

“The worst thing I ever did,” I said, “and I can’t believe I’m telling you this, but the worst we ever did was …”

Bill was looking at me, not saying anything, but I had his attention.

I took another deep breath, and then I blurted it out. Those four words I never, ever thought I’d say again.

“We painted a baby!”

Bill leaned across his desk.

“You what?”

“We painted a baby,” I said, “and I’ll tell you the whole story, but if I do, will you sign the contract?”

Bill smirked and said, “I’m not making any promises, but I sure as heck have to hear this story.”

I told Bill my Painted Baby Story—the worst story of my career—and I’ll tell you about it in Chapter 1. First, I want you to know what that story meant to me. It was a turning point in my business, but until that moment with Bill, I had buried it, promising never to tell it to anybody for any reason. Telling it to Bill, and what I did with that story next, changed not only my business, but it changed my life.

* * *

Do you feel a pressure to present and paint a picture of perfection in your business? Do you always feel like you have to present yourself as the perfect, five-star, A+, shiny marketing brochure version of you and your business? While doing so, deep down, do you struggle with knowing that this shiny marketing brochure is tinged with imperfections, two-star, D+ experiences, customer interactions, and outcomes to business interactions and relationships?

Are you afraid to show the real, raw, imperfect version of yourself, fearing that you will be judged, seen as less of a successful leader and business owner, or that you will lose credibility with your clients, team members, and people you serve? Above and beyond that, do you fear that along with losing credibility, you will lose business, revenue, profit, and the fuel that feeds your family? …

I had always been a good student of business, marketing, and sales. I followed the rules. Put your best foot forward. Share your best stories, your proudest achievements, and your greatest successes. Show them your shiny marketing brochure. But I was disconnected from many people, especially my clients, and I didn’t know why. I thought they wanted the shiny marketing brochure and the success stories, and that’s what I had been giving them for years. I was afraid to show the real and imperfect version of myself. In fact, I had become so good at putting not just my best but my perfect foot forward that I had completely ignored, buried, and forgotten about the imperfect parts of my life and how I operated as a business owner. I felt like at every turn, in every interaction, meeting, sales call, and human interaction, it was showtime, and the show I was putting on was the Shiny Marketing Brochure Matt Show.

What I observed that day over a cup of coffee with Bill flipped everything I thought I knew about business, communication, and building relationships in business on its head. I wasn’t willing to be vulnerable and didn’t understand how much of a crutch those stories had become. Some were the right stories told the wrong way. Others were the wrong stories or the easy stories. They told my clients absolutely nothing about me and my team. Those stories didn’t show clients how we dealt with adversity and disaster. They didn’t show how we could truly shine when it mattered.

SSSHHH … YOUR DIRTY LITTLE SECRET

Your best worst story is the story you don’t want to share with anyone. It’s the story that flies in the face of your shiny marketing brochure; in fact, it could very well disprove and invalidate your shiny marketing brochure. It’s the story that you fear could lose your business, crush your credibility, break down trust and connection in a relationship, and have another person judge you harshly and not do business with you. It’s the story that you may be currently mortified to verbalize, write, or communicate in any way.

Your best worst story is your worst moment, your biggest embarrassment, your most massive screw up or letdown. Your super-duper, no good, horrible day in business. It’s a time when you and your business showed up not at your best, but your worst. That story hides within you, safe from the world. It is locked and you have thrown away the key, keeping this story highly guarded, protected, possibly so well that you have even forgotten about or deny its very existence.

Yet, your best worst story is your most powerful tool to building deeper connections. I call that best worst story (or dirty little secret) the Painted Baby Story, or “PBS” for short.

Bill had forced me into a moment of vulnerability. I needed him to sign that contract. My reluctance and fear-filled giving in to that vulnerability unlocked a part of me that I had never shared with my clients, my team members, or many other people in my life.

Unlocking that part of me, that authentic and true part of me that wasn’t perfect, opened the door to connection and trust. I just needed to walk through it.

CONNECTION THROUGH STORY

I started my painting business almost 20 years ago. Hungry and motivated to build my company as quickly as possible, I took on as many projects as I could manage. Work harder and work more was my motto. I wasn’t focused on efficiency. I didn’t think about getting bigger projects for less effort or creating connections that drove repeat business. My business grew, but it didn’t scale, and I was burning out.

Every entrepreneur I know has days when they ask themselves, “Why am I doing this? Is it even worth it?” Those days pass, and the next day is better, and we press on. That day in Bill’s home, I was at one of those low points and needed to turn it around quickly. …

What I observed that day was counterintuitive. It went against everything I thought I knew about business, sales, marketing, leadership, and ultimately, life. By telling Bill my story, and by him hearing it, we connected on a different level. That conversation taught me that how much and how well I was willing and able to connect with people on a deeper level determined my success. But connecting, I learned, took vulnerability. It took putting myself out there in a way I never had. This was a language I did not speak, nor understand.

Putting myself out there had nothing to do with putting on an air of confidence, telling my success stories, or using clever closes to get the business. And it had absolutely nothing to do with my shiny marketing brochure. Connecting with people and earning their trust started with giving of myself, my real self. I had to let down my guard and show them who I was, and the way to do that was with a story. Not just any story, but a story I never thought I’d tell anyone. My best worst story. My Painted Baby Story. 

©Matt Shoup, “Painted Baby: Connect with Clients Through Brave and Vulnerable Storytelling” (Lioncrest Publishing, 2023). Printed with permission.