Failure is Not a Tattoo (Money Monday)

03/16/25 • 11 min

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One of the most vivid memories from my childhood was the day I was bucked off of my pony. The pony’s name was Macaroni and I was six. We were in an arena where my mother was giving me my very first riding lessons. Macaroni was stung by a bee, and she reacted by bucking. I couldn’t hang on and I landed hard on my back. It knocked the breath out of me. I gasped for air. Then as I finally caught my breath, I started bawling at the shock of being involuntarily dismounted. My mom caught the pony, led her back over to me, and gently told me to dust myself off and get back on. But by this time I was sobbing the way kids do when they’ve cried so hard that they can’t stop. Failure is Just a Bruise I shook my head and refused to get back on the pony. My mother tried her best to calm me down and reason with me but I still refused to get back on. Then she took a different tact and got tough. Her stern, direct tone of voice made it clear that she was not asking me to get back on the pony—she was telling me. That's what I remember the most because my mom had never talked to me like that before and has rarely ever used that tone and directness since. “Get up, and get back on that pony now!” she admonished. She was unmovable. Like Teflon. My tears and pleading made no difference. I knew I had no choice so I stood up, shaking, still trying to catch my breath and she helped me get back on the pony. Right there in the riding ring, at six years old, I experienced one of the most pivotal lessons of my life. My mother taught me that failure is just a bruise, not a tattoo. She wasn’t being cruel; she was being protective—protective of my future self, the one who might otherwise have carried an irrational fear of horses, or an ingrained habit of backing down at the first taste of adversity into the rest of my life. She knew that if she had let me off the hook and let me walk away from that pony that there was a good chance that I’d never get back on again. That the fear I felt when I landed on my back in the sand would grow and gain a life of its own. That I would vow to never let the pain and embarrassment of falling off happen to me again and with that, my brush with failure would become permanent. Failure Can't Really Bite You The truth is, failure is usually a short-lived event. Yes, it’s jarring, unexpected, and can momentarily knock the breath out of you. But it doesn’t have to be the defining chapter of your story. That’s what my mother understood so well in that riding ring. She insisted that I face my fear, effectively telling me, “Hey, the worst part’s over. Now that you’ve experienced fear and failure, get back on and prove to yourself you can handle it.” Because once you push through that initial sting, you discover that the fear can’t really bite you unless you give it teeth in your own mind. When Failure Becomes Permanent For far too many people, though, the pain of failure does become permanent. Instead of allowing themselves a moment to dust off and try again, they walk away in defeat—often without fully grasping the long-term impact of that decision. Rather than letting the bruise fade, they opt to memorialize failure in their minds, assigning it more meaning than it deserves. They replay the embarrassment and pain over and over, until it becomes an unspoken vow: “Never again.” And in that single choice, a brief setback can morph into a defining moment in which they forfeit the chance to learn, grow and eventually experience the sweetness of victory. Think about how this scenario plays out in everyday life. Maybe you dream of learning a new skill—painting, playing guitar, writing a book, starting a podcast—but in your first attempt, you falter or feel foolish. Rather than chalking it up to “beginner’s missteps,” you decide: “I’m terrible at this; I’ll never try again.” And that small bruise becomes a tattoo right there, on the spot. You miss out on the personal growth,

Previous Episode

Leverage the PASTOR Pitch to Sell More

How many times have you gotten to the meeting but your pitch fell flat? You went in guns blazing, thinking the hard part was over and you’d land the deal—but instead you face-planted. It’s not your product or your pricing. It’s your messaging that’s failing you—and blocking you from a sale. A Framework to Tap Into Your Prospect’s Pain So what’s missing? A framework that actually speaks to your prospect’s pain, builds urgency, and moves them toward a ‘yes.’ As The Sales Gravy Podcast guest Mike Malloy points out, the PASTOR messaging method can solve that disconnect. You tap into your customer’s pain points and you close. https://www.youtube.com/watch?v=BkML4D0BPIU The PASTOR Method Created by renowned copywriter Ray Edwards, the word “PASTOR’ is about guiding your prospect through the process with messaging that grabs attention and prompts action. As a salesperson, you lead your potential client toward a solution. True sales relationships aren’t forced—it’s natural and authentic. You’re not stereotypically pushy or desperate. You have the magic answer to a customer’s problem. Think of it like leading a prospect down a sales path where they see the problem clearly, understand the solution, and feel confident saying ‘YES’ to a deal. P - Problem & Pain An eventual ‘Yes’ stems from pain—pain from stalled business, lost revenue, or missed quotas. Until you unearth the problem, there’s no need for you or your solution. Translation: No sale. Your job is to identify the pain point and get your prospect to acknowledge that, yeah, it’s ruining their business, too. Don’t gloss over the pain—lean into it. Show you understand. Your understanding will connect with the customer and start building your relationship—a relationship that leads to closing. A - Amplify the Consequences Don’t be afraid to twist the knife. This isn’t just a little problem. It’s debilitating—costing the customer time and money. It’s a huge pain point. What will the prospect’s life be next quarter, next year, if they don’t solve it this minute? How much worse will it get? Fear of loss is a powerful motivator. Prospects need to feel the urgency to fix the problem now. S - Story, Solution, System This is where you offer the solution—but don’t just drop a pitch. Tell a story. Give your prospect an example that they can hold on to and that helps them connect. Tom’s sales team was floundering. They couldn’t make quota. Then they found our [your service]. Jill’s company needed a new distributor. Her current distributor was often late, goods were damaged and it was hurting her bottom line. Then she learned about [your service]. Make it clear that hiring you isn’t just smart—it’s the game-changer they’ve been looking for. Show them you get it. Lay out a clear, systematic solution that wipes out their pain—once they see you’ve got the answer, the deal’s as good as closed. T - Transformation & Testimony And what does it look like when all that pain goes away? Paint the picture. You highlighted all the real and future pain not hiring you would cause. Now, tell your prospect what life will be like after they embrace your solution. People don’t buy products—they buy results. They need to see exactly how they’ll save time, make money, and come out ahead. Show them the win, and they’ll say yes. This is also where you leverage testimonials to build credibility. Personal accounts from past customers who can bolster your position. When they believe others have succeeded, they’ll trust they can too. They’ll be signing with you before you know it. O - Offer Your offer isn't just about price—it’s about making the value so clear that saying 'no' feels like a mistake. Remove any friction to the deal by emphasizing the ease of transition and fast onboarding. Your offer needs to entice with solid, actionable steps to cutting out their pain points. There’s no room for waffling here.

Next Episode

How to Get New Sales Reps Cold Calling and Building Pipe Faster (Ask Jeb)

Gaius, who runs an insurance brokerage in Ohio wants to know how to get his new sales agents cold calling and building pipeline earlier in their training cycle, without making them feel overwhelmed and sabotaging their confidence. If you’ve ever hired a sales class or tried to ramp up new hires in an industry with complex products or strict guidelines, you’ll relate to Gaius’s dilemma. Below, you’ll find the key takeaways from our conversation on accelerating new rep success, establishing realistic expectations, and blending company marketing with individual agent prospecting efforts. The Challenge: New Hires, Big Learning Curves Gaius plans to hire new property-casualty agents in classes of four, each going through about 3–4 months of training. During that time, they have to learn multiple carriers, underwriting guidelines, and compliance rules so they don’t accidentally write poor-fit policies or lose deals over technicalities. It’s crucial they build confidence before being “thrown to the wolves.” But here’s the catch: If new hires only focus on product and system knowledge for months, their pipeline remains empty. By the time they’re “ready” to sell, they’ll be way behind on prospecting —and might even lose that DAy One enthusiasm for building relationships. The question is, how soon can they start generating leads and setting up sales conversations? Why Pipeline Activities Can’t Wait As I shared with Gaius, I’ve seen many companies assume new reps aren’t “ready” to prospect until they’ve absorbed the entire knowledge library. Yet waiting too long to do real sales activities can backfire. Early Wins Boost Confidence If new hires can set even a few appointments or pass warm leads to experienced agents, it gives them a sense of accomplishment. That momentum helps them stick with the grind of more complex training. Practical Learning Beats Textbook Learning In industries with loads of carriers and underwriting rules, real-life sales scenarios actually teach new reps faster than purely theoretical training. Once they’ve got a potential client on the hook, the rep has motivation to find the answers. Improved Onboarding Speed Companies that mix early pipeline-building with supported team selling often see new hires reach quota faster—sometimes shaving weeks or months off the usual ramp-up. And yes, there’s a risk of missteps. But that’s where a collaborative culture (“sell as a team”) ensures mistakes become teachable moments, not deal-killers. The Team-Selling Approach When new agents don’t have full carrier knowledge, they’ll naturally hit roadblocks. How do you keep them from burning deals (and morale)? Encourage “Hand-Raises” If a new rep snags an interested customer, let them wave the flag: “Hey, I have a lead who needs home and auto coverage. Here’s what they’re telling me. What do I do?” Then a veteran agent or manager steps in to guide the quote or finalize the sale, with the rookie learning through an actual client scenario. Shared Commissions Make sure new reps see a direct benefit. If they hand off a deal, they might get a partial commission or spiff for their contribution. Over time, they’ll rely less on help—but they’re still building pipeline from Day One. Hands-On Coaching Each real conversation is a goldmine for coaching. The rep sees how an experienced teammate answers tricky questions, navigates underwriting guidelines, and pivots between carriers. It’s in-the-field training, not just theoretical. Structuring Training + Prospecting Gaius is worried that his new agents need a full 3–4 months before picking up the phone. The short answer is no. They can start small while still in training. Here’s how: A Few Leads a Day Instead of waiting for them to finish product modules, drip leads early. Let them call 5 or 10 leads each morning, focusing on booking appointments (rather than doing in-depth quoting). This keeps them from drowning in complexity,