Why Taking the Road Less Traveled Can Skyrocket Your Career and Fulfillment - Excerpt from THE SHOW MUST GO ON

The Show Must Go On, AVAILABLE NOW! serves as the comprehensive follow-up to Salesman on Fire : an extensive guide on sales strategies, personal development, and leadership.

It provides insights into building a successful sales career, overcoming obstacles, and achieving personal and professional growth en route to the story of how LinkedIn, AI and a Moneyball approach to sales has generated over $1B in revenue.

Carson V. Heady discusses the significance of personal branding and how it can differentiate a salesperson in a competitive market, the role of a leader in fostering a collaborative and empowering environment for team members, strategies for dealing with setbacks and failures, and methods for effective prospecting, including leveraging social media, AI and personalized messaging to connect with potential clients.

Pick up your copy of THE SHOW MUST GO ON here:

Take the Path Less Traveled

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When people ask me why I do what I do, carrying a quota instead of starting my own company or consultant firm, and comment on what a unicorn I am with my books, shows and podcasts while still being in the field, I tell them I would not have it any other way. I love everything about what I am blessed to be able to do.

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Don’t ever feel compelled to fit in or allow your unique superpowers to be stifled.

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If 50%+ of sales professionals miss goal, why do so many embrace a formulaic, comfortable way of mediocrity or failing?

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Why do people accept that they are in dead end jobs where they hate their lives and choose not to risk their unhappy state for the potential for more?

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I get it. It’s not that easy. With every risk or change comes the chance that the outcome is inferior to the current path. Many of us have responsibilities outside of just maintaining and managing ourselves. We have mortgages, car payments, kids to send to school and needs and wants.

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But where you can, stand out.

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Years ago, I saw the YouTube video of Richard Goodall, a janitor at a school who sang “Don’t Stop Believin’” to the students every year. Since that time, he went on to win America’s Got Talent and sang with Journey. Whatever your role, you can own it and make it yours.

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Remember how you presented yourself when you applied for that job and interviewed? On that day, you pledged to give your best self to the organization and the hiring manager. Have you lived up to that promise?

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When you enter into a role, you commit to being the person you were on interview day while the company makes the pledge to provide you with the infrastructure for success: training, ongoing support and whatever tools and resources you need in order to do the job.

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Do companies sometimes fail us when it comes to this commitment? Yes. Have we used their failure to follow through as a reason or excuse to mail it in and not give our best?

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I made a decision a long time ago that no matter what, if there was a number next to my name, I was going to ensure it would be indicative of my absolute best.

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My friend Matt Berra says that all great sellers have a chip on their shoulder. Where does it come from? We have talked about the “why” and there are a variety of factors that can influence this: upbringing, parents, role models, who we associate with, surroundings and environment, and experiences. It may be one thing when you start out in your formative years and it can change as you choose a partner and have children. But your “why” or chip on your shoulder can be a blessing or a curse.

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I didn’t choose sales. Sales chose me. Time and time again. Even when I tried to leave it, it pulled me back in.

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Choosing a career path is seldom a straightforward decision. I’ve talked to a lot of accidental salespeople.

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The things I’ve achieved can literally be achieved by anyone. I’ve had plenty of blessings but also seized lots of opportunities; not always the right way, but I have gotten better over time.

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I was born November 1, 1978. It was a Wednesday.

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The U.S. President was Jimmy Carter, the global population was 4.3 billion, minimum wage was $2.65 per hour and the slang of the day was “far out” and “dream on.”

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The film Superman: The Movie was released, which was a childhood favorite. There was a box of Cheerios on the table at the Kent farm. As I’ve always said about my favorite cereal, if it’s good enough for Superman, it’s good enough for me. I also grew up on Kent Street.

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Also born that year: Kobe Bryant, Rachel McAdams, Usher and John Legend.

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Musically, the Bee Gees dominated the charts while on television, shows like "Different Strokes" and "Three's Company" took center stage. Fashion trends included polyester flared trousers and platform shoes for women, while men rocked V-neck velour shirts and chest hair.

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The year also saw a big blizzard just weeks after I was born, and I was baptized in December.

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My family ancestry is predominantly Irish and German, with some French on my mother’s side.

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My Mom grew up on a farm with her 3 brothers and a sister who passed away just prior to her fifth birthday.

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She spent much of her day preparing food with my Grandma for the boys who worked out on the farm all day. By the time they finished making meals and went to meet them, it was time to go back and prepare the next.

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I vividly remember the backroads to get there, the one long street in the town of population 191. The spot on the corner where my grandparents went dancing, going fishing and hunting on the property, the extremely smoky front room where the men would talk and puff on their cigarettes while the women prepared meals, the pool table downstairs and the field where my cousin and I would play “war.”

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My Mom spent her career as a teacher and instilled in me an unwavering work ethic and ability to pivot and get through any situation no matter how grueling.

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My Dad is exactly 8 years, 8 months, 8 days and 8 hours older than my Mom. My lucky number? 8. I wore it multiple years playing basketball and loved it when Bo Jackson made his comeback to baseball after his career-ending football injury wearing the number for the White Sox.

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My paternal grandparents passed away before I was born. My Dad grew up with two unique, eclectic sisters, was a great athlete and spent most of his career in retail management. I remember going on trips in my Dad’s truck to his company offsites.

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My Dad instilled in me a deep faith and reverence for God. He coached my sports, was involved with my Scouts troops and was always available to do whatever I wanted.

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I never needed or wanted for anything.

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We had a beagle named Charlie. I loved to read and write. I started journaling at age 7 and it’s a helpful habit I continue to this day.

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Writing stories was a passion, and even though I was my worst critic, I enjoyed creating imaginative tales, incorporating classmates into the narratives.

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A significant event in my life was skipping second grade. It reshaped the entire trajectory of my academic and social experiences, from the people I interacted with in school to the classes I attended, sports and when I entered and graduated high school. For a long time, I pondered the “what-if’s” and the alternate paths that might have unfolded had I stayed in my original class. It’s fascinating sometimes to reflect on how a single event can set the course for numerous aspects of life.

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I mention this because the vast majority of my friends were in the class I left behind. Had I stayed in that class, I would have been with them in sports and clubs throughout high school.

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Overall, high school was an experience I did not enjoy. I showed up 5’7” and 140 pounds with straight reddish hair, glasses and braces. While I was eventually the Treasurer, then President of Future Business Leaders of America (my friend talked me into joining so I could hang out with the girls in their business attire), played sports and lost the glasses and braces while my hair got lighter, I never forged a bond with my class. Two particularly horrible classmates picked on me. They added to the chip on my shoulder.

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I’ve had a lot of fuel to perform. I remember the people who made fun of me in grade school and the things they said. I remember being made to feel less than by bullies; even though I smarted off to them and rarely showed emotion, the words stuck with me. I’ve been lied to, cheated on, mistreated, targeted, slandered, stolen from, shunned by people I thought were my friends. I’ve lost many people I cared for. I’ve had the screws put to me in my career multiple times. But I just keep getting up. I’m unstoppable.

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In the book Think and Grow Rich, Napoleon Hill tells us that success comes after the point when most people would have given up.

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One of my favorite scenes in any film is in Rocky, in the fight with Apollo Creed where Rocky Balboa, a nobody who gets a million-to-one title shot and literally just wants to go the distance with him so he doesn’t feel like a bum, is in the 14th round with the champ and the announcers marvel at how he’s even still standing. “What is keeping him up, Phil?” “I don’t know.” “He can’t even get his gloves up to protect his face.” Apollo sends Rocky to the mat, where even his trainer Mickey tells him to stay down but to the disbelief of everyone including Apollo, he climbs back up for one more round.

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My Mom, a meticulous and process-oriented, goal-driven and selfless individual, instilled in me a drive for success and an unwavering commitment to get things done while ensuring I made everyone around me better. She is diligent, disciplined, she manages everything dispassionately and just keeps going no matter what.

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My Dad is well respected and is just good to everyone. He taught me how to be a faith-based, humble, selfless husband and Dad who leads by example, is a doer, gets involved, and is a good friend and role model.

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These lessons were not a completed product in me when I left home, but they continue to be my personal north star. Both sets of attributes have served me well.

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I had a lot of pivotal moments in my life, but the most important was the birth of my oldest daughter.

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Because I had great difficulty determining what I wanted to do with my life in school and my career, there was friction with my parents. They wanted what was best for me, but I didn’t really want to hear advice or guidance from anyone. I knew I wanted to be a Dad, however. There were some significant relationship breakups in my late teens and twenties plus a failed engagement (thankfully), but as I got older as a successful salesman and sales manager I relished the reward but was extremely lonely beyond that. I did not lack for companionship, but love was rarely in the cards.

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When my oldest daughter was born, it changed everything. My relationship with my parents became wonderful; they are perfect grandparents and them seeing me loving fatherhood changed the dynamic between us. My daughter became my #1 focus, instead of myself or my work. Prioritizing her needs over my intense work schedule became a newfound needed discipline. I learned more patience and a greater concern for others’ thoughts and feelings. I understood the plight of parents on my team.

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My life has since been enriched by marriage (as my daughter’s mother and I finally made it work), gaining family members, having more kids and re-discovering faith as my career has further rewarded me.

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My faith evolved from a fluctuating aspect of my life to a central and grounding force, especially amidst trials and tribulations, losses and crippling uncertainty.

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My pastor shared with me how the leadership qualities displayed by Christ are the definitive display; I’ve learned much (and still have much to learn) by studying the Gospels again each year.

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I’m a nobody. Just a small-town Midwest guy who likes sales, who had no idea what he wanted to do with his life until well after college and bounced around avoiding commitments for a long, long time.

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We all have an educational career and hopes and dreams, some of which we may eventually bring to fruition. We’ve all had jobs and managers we loved and loathed.

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We can’t connect the dots forward, but we can certainly connect them backwards.

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Hindsight is 20/20 – the serendipity makes a lot more sense and is a lot more incredible when you look back at the great things that came as a result of pain, loss or setbacks. It makes it all the more awesome. God is truly the greatest screenwriter there could ever be.

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You get to choose the path less traveled. I’ve never tried to do what’s easy nor have I had any desire to. Is it easy to get up every morning before anybody else in the house is up to work out? Is it easy to bring my best self into every call, back-to-back throughout each work day only to walk out the door and be a husband and Dad with no rest? Is it easy to be dealt unforeseen, crippling defeats, be treated unfairly or counted out, only to get up time and time again and give it everything you’ve got?

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No. But it’s worth it.

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Is it easy to “put yourself out there?” Is it easy to stand out?

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As I’ve mentioned, speech class was one of my least favorites. I never enjoyed getting up in front of people to speak when the focus was on me and me alone. Oddly, however, I was frequently in prominent roles in plays for many years of my life; I was a performer who could be unleashed, but it had to be in situations where I could drown out or ignore my surroundings – something I still do to this day.

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Getting dressed down by a customer executive can be daunting and draining. Negotiating a multi-million dollar deal can be nerve-wracking if you really let what you’re doing sink in. I just try not to.

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Realizing the people you are talking to are people and not getting lost in the title can help you when you connect with practically anyone; I’ve walked up to and presented to the senior-most people in my organization, have walked up to and met celebrities and try not to think about it in the moment only to look back and relish how cool it was after the fact. If you over-think something, it can lead to the regret of not having done it, which is far worse than the nervousness or awkwardness.

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A friend of mine in high school taught me to identify a negative thought, feeling or emotion, acknowledge it and dismiss it. I got really good at it. I often come off as indifferent or numb to many things that could deter or derail me. It doesn’t mean I don’t care, but I won’t let anything stop me or keep me down, and this tactic has been invaluable.

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I never enjoyed being in front of people until 2007.

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Between my growing mastery of discarding emotions and consistent over-achievement in sales results and career promotions, I was developing significant confidence. Too much, in hindsight.

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When I ran a call center, the experience of getting up in front of 200 salespeople every day and delivering Wolf of Wall Street style (more PG-13 versions) speeches to standing ovations was exhilarating. I relished it. Thrived on it. It felt like a peak of sorts because I was “the guy,” and in addition to the speeches, I mapped out the markets we would call from our assignments, wrote up notes on them plus calling scripts, and I wouldn’t hesitate to hop on the phone for a sales rep in need and close the business.

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The sheer electricity of giving those speeches and knowing I was in the zone as my sellers got fired up and cheered for me made me feel euphoric.

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Too often, I was a bull in a China shop—wild, undisciplined, doing things my way, and it worked for a long time. I was a corporate leader's nightmare, but I loved it. I loved getting in front of people, feeling like a rock star, and conducting myself in a way that was authentic to me.

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It's fascinating how times have changed. Going from addressing hundreds in person in the middle of a call center during stand-ups and division meetings to creating and delivering virtual training and video and podcasts to thousands upon thousands of audience members globally has been a tremendous evolution of influence.

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Despite an earlier disdain for getting up in front of people in my insecure, younger days, I learned to embrace my skill in this arena and adapt to the different roles I needed to play to get to where I wanted to be. Much of this required me shutting off or controlling my emotions so that little could faze me. Note, I did not say “nothing,” as there were still personal and professional challenges that got the better of me from time to time.

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Public speaking became a necessary evil, but I got good at it by squashing the nerves, emotions, and focusing on what I need to do.

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I get more nerves when I read a story in front of my middle daughter’s classmates or serve in church – not from a lack of confidence but a strong desire not to falter.

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These developing attributes helped me tremendously in what would become my calling. Throughout my youth and for what seemed like the longest time, I had little clarity if any about what I wanted to be. Like a lot of kids, I thought about being an astronaut, perhaps some kind of scientist. I did always want to be a writer. Maybe a movie director or producer.

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Sales happened by accident, but my goals also shifted dramatically. At first, it was about survival, then success. Then it was all about climbing the corporate ladder. Everything seemed so clear cut; manager to senior manager to director to general manager to vice president. As I’ve gotten older and hopefully wiser, it’s far less about titles than it is about relationships, reputation, enriching experiences and a constant quest for growth.

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Looking back, I have always been adept at surveying the scene and uncovering the opportunity. In those one-call close call center days, the customer was a means to an end. Flipping customer phone packages around became the name of the game. So much so that I grew to wonder if I could actually ever sell anything or was cut out for real sales. This wasn’t sales; it was answering questions, navigating systems and making changes to accounts that benefited you without crossing any ethical lines.

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Then, I was leading a team of 6 people doing that role. Later 20. Later 36. Later 45. I wanted and needed more and more challenge.

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The exponential leap in earnings felt profound, from the grocery store to the sales arena, and it just kept climbing.

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The ability to study and understand and master new playing fields has always served me well. While everyone else was doing it a certain way, I would seek out a way to win and I’d find the people who were already winning so I could learn what they were doing.

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Over time, I developed into the problem eliminator. I listen – to the problems, challenges, gaps or opportunities our leadership talks about, what my teams talk about, and I go about finding a way to address or fix them. We need more of this widget? I’ll figure out the reason we’re not selling it, write a script to ensure we do, and develop a process to make sure we land it. We need better customer executive relationships? We take to LinkedIn and Sales Navigator and any tool that will help us find them and message them and engage them more regularly.

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I’ve bet it all on people and process, and never worried about a result a day in my life.

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If you shoot for the stars, turn over every stone and leave it all on the field consistently while continuing to bring your best to everything you do, you cannot be stopped.

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However, that is easier said than done. I’ve seen many have immediate or early success only to fizzle out after setbacks or when they were told they weren’t yet ready for promotion. I’ve seen others who have longer term success, but the nature of life and career breaks them and they never recover. I could have very easily been one of those people. Life and career will deal you some unimaginable, unforeseen challenges and it’s up to you to somehow keep your cool, endure and stay the course. ?

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There’s also something to be said for strategic risk-taking. I talk to a lot of people who are weighing making moves in their career, leaving a role or company to go to another or who lament the fact they cannot move up so they want to leave.

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First, the adage that you are always interviewing for your next role is true; the experiences and relationships you are forming right now impact whatever you do next.

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Second, you can always infuse your passions and skills into what you do currently, and you can seek out stretch roles and assignments that give you greater visibility and help bolster your case that you are the obvious choice for whatever is next.

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Third, you are always going to have to pay dues, and you will not get what you believe you deserve on your timetable.

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You can absolutely look to make a move away from your company or role, but you have to be very careful and thoughtful in how you do it. Exploring is encouraged. Some people do not know how to strategically explore; it’s all about the new relationships you create, radars you get on and conversations you have to further your knowledge of what’s out there. Until there’s an offer on the table, you have no decision to make. Explore and discover your worth in the market.

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One of the best things that happened in my career was when a competitor very aggressively recruited me; I went down the path, even flew to Dallas for a day of interviews, got an offer that was considerably more than I made at the time, and out of respect for my leadership I told them about my offer I could not refuse. My favorite manager I’ve ever had stopped what she was doing, called me on my cell, asked me what would keep me, told me to give her 24 hours; she came back with a PowerPoint presentation of the Top 10 reasons I should stay (David Letterman style) ending with a significant retention bonus, promotion and stock award.

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This was valuable for a few reasons: it helped me understand my worth in the market, but also showed that my leader was serious about keeping me and the company supported it.

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I’ve been very close to making moves before, but it comes down to this: exploration is healthy. Explore it all, even if you’re not 100% sure you want the other path. If you’re not sure you want the new job, it doesn’t matter until there is an offer on the table. Get to a position where you have a decision to make. Furthermore, you never know when you may want or need the new relationships you are creating.

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Even once there is an offer on the table, you have to judge if the sum of the parts of the new destination is superior to your current one.

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Something that has helped me is opening Excel and creating a scorecard of the two roles. Ranking certain important facets like career growth, who I would be working with or for, benefits, pay, fulfillment, etc. is a great place to start.

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I can tell you that I verbally committed once to a new company and role with vastly superior base salary and a lot of potential for earnings that actually fared better on my scorecard, but when it came down to it, I backed out and stayed put. There were too many unknowns and there was not enough compelling me to leave. I’m so glad I made that decision.

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I can also tell you that once I left a hellish, thankless team and organization to make a foray into a completely unknown situation where I was completely hoodwinked about the pay and possibilities and wound up having to ask my old employer to take me back after I already burned the bridge. They declined (and I can’t blame them considering the content of my exit interview). ?

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It’s all about learning and growth. There are few moves you could make that would forever derail or destroy your career or life. Despite many ups and downs in my own, I can perfectly trace back how each move led to the next and the one after that. If I had not made even one of those moves, I would not be where I am today.

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Do it your way. Be unique. Stand out. Reflecting on the entire journey thus far, that has been a common theme for me along with gradually learning and becoming more disciplined over time.

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It was important for me to realize that I did not need nor want to be the smartest person in the room. My real talent has lied in orchestrating relationships and experiences, storytelling and delivering outcomes and wins for everyone I meet.

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Along the way, there have been long, arduous court battles with eventual victory, loneliness, managers who counted me out and didn’t believe in me, lack of loyalty, fierce rivals and uncertainty, doubt, burnout and exhaustion, but my career highlight is the present moment. I reached a point I once would have considered unattainable. The unpredictable outcomes have also been rewarding.

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The years of hard work, perseverance, and continuous learning have led to this pinnacle of fulfillment.

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Now, with a wealth of experience and a polished skill set, I appreciate the journey that brought me here.

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I do admit I get asked a lot how I do it all. From an outsider’s perspective, I probably appear to be everywhere – LinkedIn, Facebook with my family, showing up on my own shows and the shows of others while working tirelessly and finding time to exercise.

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My admission: I don’t know sometimes. Sometimes, I look at the day ahead and wonder how in the world I’m going to do it. I’m exhausted, and what’s the payoff? More experiences or podcasts that I’ll someday look back on and be proud of while I hope my wife and kids are grateful for what I provided?

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I’ve made this analogy before and I’ll make it again: sometimes I feel at the end of the day like Rocky Balboa in Rocky IV after his fight with Ivan Drago – punch after punch, knockdown after knockdown. But he won that fight.

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Doing it differently is something I relish.

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Whether it was the flair I brought to what could have been boring call center roles to taking a completely different approach in every tech sales role I’ve been in, standing apart and bringing unique value has been my superpower.

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In my first tech sales role, I led business results for a region, including a prominent retail store and its team along with whatever I could conjure up myself. Let’s call it a player-coach role.

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As I’ve stated, without being remotely technically savvy, not really being a prototypical tech seller nor a retail veteran, I far from fit the mold of even being there. The manager who recruited me knew I would find a way to be successful.

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I’m glad he saw it, because I wasn’t sure I did at first.

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In the early days of a job or a significant shift of your role, it’s important to be a sponge and I took a lot of notes. I still remember the first sale I made in that role! It was for $2,000.

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While every role is different, many variables are the same – I learn from others around me what’s working and what’s not, study the process in place and determine how it is currently yielding or not yielding the desired outcomes, and then determine what should be done to create more at bats, more connections, more conversations.

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We wanted the store to be a destination. There were lots of attractive things about doing so, like training and events and other offerings. We built out new events and worked diligently to build community around what we did.

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I mined the CRM for who had already purchased from the store from a business perspective. We coached the team on better qualifying customers to determine if they were shopping for business; once we captured them as a lead, they would get our business newsletter and events and be invited to the community.

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My favorite win while doing this role was scoring a meeting with a well-known local organization who had purchased a handful of devices from the store before. I was told, “Don’t bother going to that meeting – they are looking for an arrangement we can’t deliver.”

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I went to the meeting anyway and met the buyer. He had outlined what they were using these devices for – a rewards program – and that they could result in purchases from anywhere. They had signed with a current vendor because of the price point they were given and indicated if we could beat it, they would rather go directly with us anyway. He even alluded to the potential for more of our products.

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So now, it was time to find a way to make it work.

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So much of our important selling is internal selling; this involved reaching out to people in our business who could help get what I was seeking and painting a vision. They needed to understand what was possible for our channel in order to be coaxed into considering my ask. The ask was not unreasonable. And we got it done.

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The inherent challenge was that the arrangement they sought mirrored a resale relationship, which we were not set up to do, but in ensuring that I was receiving the orders and we were sending them to the end customer rather than allowing the customer to warehouse them, my company agreed to do it. It became the largest deal in the channel’s history – several millions of dollars – and because of the number of end customer organizations it touched, this – coupled with our other strong results – made us #1 on the global business scorecard.

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We became a fixture at the #1 spot. It was based on revenue results, total number of unique customers sold to, pipeline generation and lead generation.

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Many others in the channel lobbied to have the rules changed after we were at the top for so long and the leadership agreed to not count the unique customers sold to from this relationship as unique customers anymore.

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We stayed #1.

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But it’s not enough to just be #1; we always have to be learning and growing as well. If you can give and contribute – even better. Building community serves everyone. I realized that we had over 100 regions and store locations globally and we were not talking to each other enough – sharing best practices and learnings, communicating and helping each other out. So, I started Colleague Corner.

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Colleague Corner was a monthly call where we came together as business leaders and illuminated best practices shared from the other teams. Sessions would spotlight specific leaders and teams often, and I included results of polls that would go out to all other business units. In short, it was a conglomeration of best practices and fostered sharing across the channel. It was wildly popular.

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It became so popular that a member of my leadership found out about it and wanted to control it, but they let me run with it because the grassroots campaign had really started something.

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The key to community is it isn’t about you; every month, we would connect, I would solicit for speakers and topics, and we would share. It also offered ability to communicate via e-mails and celebrate wins and learnings. It helped a great deal to forge relationships, which helped out when we needed to work with colleagues around the world to get inventory or they needed ours.

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After nearly two years in a role and never vacating the #1 position, you may start thinking about what’s next. In this case, I was being told by my leadership that I was being groomed for a promotion to a regional leader who would oversee the role I was doing. They were creating the role for me. It took months, but the role finally opened and I interviewed; the interview could not have gone better. The role was given to someone else.

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This was surprising to me, but given the politics and the fact the hiring manager was intimidated by my following and influence, it shouldn’t have been.

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When I looked back and realized that rules were unsuccessfully changed twice to keep me from being #1 and weighed how much I had done and given and delivered to colleagues and this business unit, I realized it was time to make a move. I nearly left the company to work for a partner organization, but fortunately I had successfully sold to so many local customers that when an account executive in the commercial space took a new role and was asked to name her backfill so she could transition out of role sooner, she asked me if I was interested. I said yes.

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I have outlined the ups and downs, but the biggest realization was that I could take these experiences and learnings and concepts and approaches and apply them anywhere. Building community always works. Creating relationships internally and externally is always important. Understanding the processes and their loopholes and limitations is key.

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Significant deals I was closing solely because of LinkedIn outreach showcased my unique skill set. I became known for it and it served me well.

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There have been numerous changes to my role, multiple external opportunities I almost took and a lot of self-doubt and imposter syndrome. I have stayed because I’ve realized and embraced this unique bond I have with my company and there’s still more to do. Despite angst and challenges, I would not change a thing.

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Sometimes a unique value you can deliver your company and your customers is your understanding of the industry, the nuances, and the resources. I can demystify numerous nuances of my organization for customers and bring them resources and experiences they would perhaps never have access to otherwise. This is a benefit as well of becoming better known or influential in your organization – when you can influence as an evangelist for your customer and advocate for your brand, you can achieve remarkable things.

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A stark contrast between my 30-year-old self and my 45-year-old self is real wisdom. Knowing my place, knowing I’m not the smartest person in the room and don’t need to be. I’m an introvert with imposter syndrome who does a bang up job of ignoring it, masking it and succeeding in spite of it.

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I’ve literally had moments where I fear someone realizing I’m a fraud. Because of my insecurities, I over-compensate in what I feel are healthy ways; going above and beyond to really listen to my customers and colleagues, doing everything I can to study and take notes and speak intelligently about the mission even if I don’t understand the technical components. My job is to serve, be available, be responsive, be communicative and be efficient and effective, and I can do all of that. I obsess over it. And constantly throwing myself into everything I can, controlling what I can, often quells my feelings of overwhelm and inadequacy.

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Compliments sometimes make me uncomfortable; often because I have been at such low points I don’t know that I believe them to be true and I just want to move on.

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My past experiences, especially the moments when luck ran out at previous jobs or when I was left for dead, contribute to this feeling. While my approach now is different – disciplined, a team player, serving others above all, steering clear of past mistakes – there's an ever-present fear that the other shoe might drop. The vulnerability experienced during challenging times at the start of my tech journey, coupled with setbacks like the manager who targeted me, are constant reminders that I could be discovered as a fraud at any time.

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Every meeting, connection, or interaction comes with the lurking question – are they seeing through the act? For how long can I keep up this persona and do this much to over-compensate for my glaring inadequacies? The toll the act and the persona take on me is considerable. I try to make time for everything and everyone, wanting them to be happy with me and my contributions.

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Paradoxically, this feeling serves as a motivator. The chip on my shoulder pushes me to work relentlessly, to exceed expectations, and to prove that the perceived excellence and hard work are not just a facade.

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I'm in a perpetual state of staying "on" to ensure that the image I project aligns with the expectations, and that nobody sees anything but dedication and authenticity in my efforts. It's a relentless pursuit, but I know no other way.

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Something that has helped me tremendously, specifically during moments of doubt, is to “land the step.”

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It reminds me of a two week back-packing and camping trip I did with my father-in-law, brother-in-law and friend back in 2018 through Mount Rainier and the Cascades. I’m by no means a hiker or mountain climber; my wife encouraged me to go and it seemed like it would be an adventure.

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The scenery was absolutely beautiful. There is something about standing amidst God’s masterpieces that strikes absolute awe and reverence into me. But when I would occasionally look up to where I was headed or realized the treacherous path ahead, it was daunting and terrifying.

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A couple of examples: there was a moment at a precarious snow field at Sahale in North Cascades where a ravine separated us from where we needed to be. To get across, I literally had to leap toward vegetation on the other side, grab it, cling to it and pull myself up. I felt like Indiana Jones.

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Someone in the prior party had needed a helivac to transport out after a significant fall here. It also felt practically impossible at times to get and secure footing at places where a fall would have led to injury or worse.

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I would look up to the mountain we were climbing and be blown away that I was going to have to do that; filled with self-doubt and a gnawing fear. But if I just landed the step in front of me, over and over and over again, I would look back and not only see the incredible path I had traversed but also even more amazing views as a reward.

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The sheer daunting nature of looking ahead and visualizing the journey can induce anxiety. However, when broken down into smaller, manageable steps, the path becomes clearer. It's the same with imposter syndrome – focusing on one step at a time, slowing down, and emphasizing landing the step in front of you can make whatever you face more manageable.

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In the realms of sales and life, investing in relationships is key. Seeking candid feedback from those who truly understand my strengths, passions, and skills has been invaluable. It's reassuring to know that others, even those highly technical, may harbor their own insecurities. This acknowledgment grounds me and helps in fostering connections beyond surface-level perceptions.

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Working for a large company can easily trigger a lack of confidence, especially surrounded by a lot of brilliant minds – people that are brilliant in ways that I will never be. Comparing myself to others or feeling out of my comfort zone in specialized conversations adds to the complexity. However, reaching a place where I could embrace my unique role and skills as I leverage them to benefit others has been crucial in overcoming self-doubt. Because of me, more customers have been able to hear from our brilliant minds. How can you uniquely serve your colleagues?

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Asking for feedback, be it from mentors, team members, or customers, becomes a powerful tool. The surprising positivity and impact I learn about from others help counteract the internal doubts. It's a constant reminder to focus on my strengths and avoid unproductive comparisons.

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There are a lot of things that can contribute to imposter syndrome, from early life experiences and comparisons in society. We weren’t born with these thoughts or feelings, but something along the way has ingrained them into us – and it’s not all bad. I’m grateful for the chip on my shoulder. It’s made me infinitely better.

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Over time, focusing on what I can control, understanding my unique value and working to add positive influence to every interaction has helped me manage the waves of imposter syndrome.

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If there's one recurring theme in my life, it's perseverance.

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I like to tell others often that what I’ve achieved can literally be done by anyone. I’m willing to put the work in to master my craft and the process that I know will work. Furthermore, I’ve had plenty of unfair and crippling losses; I just refuse to stay on the mat.

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A day will likely never come where we will be required to pay dues to get what we want or closer to it.

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You cannot get lost in the struggle you’re in, nor think you are unique in your struggles – everyone faces them and we all fall down. There’s no such thing as a dream job – they all have positive and negative attributes, things change and we will always be posturing and pivoting.

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Family, friends, our circles – these will change dramatically over time. You will inevitably face many unforeseen events that shake you to your core. It’s what you learn during and from them, what you do next and how you emerge from them differently that counts for everything.

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Many of us spend so many time trying to keep up with the Joneses, but who says the Joneses are happy? We judge happiness by smiles on sporadic social media posts and envy what others appear to have while ignoring creation of our own fulfillment.

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Unconventional, probability-based approaches focused on being at the pulse of the customer prevail. Scrappy, resourceful, resilient sales professionals are the most successful over the long haul.

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Going into any situation with limited or no expectations but a willingness and ability to react and respond as needed has served me very well. Knowing that no deal goes off without a hitch, that I should expect the unexpected and be prepared for it, and never bank on anything until it pays out have been invaluable.

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Salespeople are often presented with prescribed scripts and processes to follow. These tried-and-true methods are designed to increase efficiency and predictability in sales, but they don't always guarantee success. Sales isn’t a cookie cutter program. It’s not one size fits all.

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While salespeople can't control the cards they're dealt, they can control how they play the hand. This analogy highlights the importance of adaptability and resourcefulness in sales. Rather than sticking rigidly to a script, salespeople should pay attention to their customers, adjust their approach based on feedback, and be willing to take calculated risks.

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Study the people and the process above all. By observing customers' actions, listening to their concerns, and anticipating their needs, salespeople can tailor their approach effectively.

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Leadership plays a significant role in fostering a culture of effective sales training. Instead of merely enforcing a rigid process, leaders should encourage salespeople to find their sales voice, empower them to build relationships, and enable them to create a community around their products or services.

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People earned the right to be in the role they are in, so leaders don’t exist to tell them how to do it; they should ensure the team member has the tools and resources with which to be successful, earn their trust and the opportunity to work together to collaborate on a better process that improves outcomes. Often, it’s relatively small tweaks to process that can make all the difference in the world for results. Don’t overhaul your people – help them shore up their gaps and double down on their strengths.

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Sales, like a card game, involves uncertainty, and the ability to adjust, innovate, and take calculated risks can lead to higher success rates.

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It confounds me that when presented with a better way, many sellers will still gravitate toward their comfortable ways of mediocrity or failing. I get it – sometimes people are using the job for the paycheck and benefits and they don’t care about mastering their craft, but then when they can’t get promoted, they wonder why. Lots of people don’t want to make waves or embrace the uncomfortable.

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I’ve often asked salespeople if they are 100% satisfied with their results. Rarely will anyone say they are, unless they are having a great month or quarter and they chuckle when they say it. Because they know what I know to be true – to stay on top, you have to keep grinding, keep sharpening the axe and embrace new avenues that lead to the desired outcomes.

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If we are not 100% satisfied with our results, why would we refuse to gamble those dissatisfactory results for the statistically probable chance of improving?

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I acknowledge that my success in a scripted environment came from deviating from the script. Writing my own, based on the fundamentals but also what I was hearing from customers and encountering in sales situations.

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Being a student of the game, I learned that, while we can't control every aspect of sales, we can control our actions and reactions. Like playing cards—you can't control the cards you're dealt, but you can control how you play them and anticipate your opponents' moves.

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My success has come from being adaptable and continuously learning. I approach each interaction as an opportunity to refine my strategy. If a customer rejects a certain package, I adjust my approach based on their needs. This adaptability has allowed me to forge genuine relationships and win in sales. However, I acknowledge that not everyone approaches sales with the same mindset.

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One significant factor is leadership's role in setting the tone. Effective sales training, coupled with ongoing support, ensures that sellers don't revert to comfortable yet ineffective methods. Leadership should focus on developing a culture of effective sales training rather than merely pushing for more sales without considering the individual voices of the sellers. Providing guidance tailored to individual styles, as opposed to rigid scripts, can make a substantial difference.

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Everyone has to find their own way off the beaten path. It won’t always be comfortable, but if your comfortable way of failing continues your lack of comfort will only intensify. Eventually, we all have to make tough decisions and changes if we value our health and success and the well-being of the ones we love.

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One of my favorite stories about someone on my team was way back in the call center days.

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We would draft teams, and whichever team was in first place got the last choices – this was always me. My fiercest rival in that call center management team had referred a member of his church to the call center, but he would not pick him through multiple rounds of drafting of the new training class. The prognosis on this new seller was not positive; he was monotone, not assertive or confident and the trainers ranked him last in the class on their scorecard. This person wound up on my team.

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His voice and delivery were not what you would envision as the most rousing on a call center sales team. When a lot of people get out of training, they focus on getting the core focuses of their job right – the systems, the ability to answer customer questions, the navigation of screens and the technology – and sales can become an afterthought for some. All of these things were working against him.

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However, I don’t give up on anyone, though many give up on themselves. I know that anyone can find success if they truly want it and are willing to do what it takes to get it.

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It’s important to me when I start working with someone to understand why they’re there, what motivates them, what they need from me and how they like to be coached; like my sales approach, it’s something I’ve used and tweaked in several roles over the years as I survey my new team members.

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This gentleman wanted side by side coaching on his calls; he indicated a desire to be successful. Undoubtedly the fact he was picked last in the draft and even his friend didn’t want him was likely always in his mind. It would have been for me!

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This sales rep was struggling with putting together his delivery during and after handling customer questions and responding, navigating through the systems and call flow and when he was trying to half-heartedly offer something at the end of the call, the customer was ready to go and it ended without him following the flow or really offering anything.

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So I challenged him to write a script in his voice with a handful of parameters and suggestions. It needed to be in his voice because he had the responsibility of weaving it in throughout the call and ensuring he was making strong recommendations. We met, reviewed it, I made some alterations, and then he committed to using it on every call as it was written.

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This rep won Fortune 500 – the top 5% of all salespeople in the company – his first quarter in role.

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Find your own unique sales voice, embrace strategic changes for improvement and always keep people and process at the heart of everything you do and you can’t lose.

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Reluctance to embrace unfamiliar or uncomfortable new paths may stem from a fear of change, a lack of encouragement in the existing system, and the absence of leadership support. To elevate sales success, sellers should challenge the status quo, invest in continuous learning, and be willing to take calculated risks. It's not about seeking a mythical work-life balance but finding a rhythm that allows for personal and professional growth.

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I have always taken the road less traveled. My most rewarding experiences have come not from trying to fit in but embracing my own way, even if and especially when it meant venturing off the beaten path. In fact, when I have tried to fit in, those have been my most miserable and inauthentic experiences.

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Every step of the way—navigating a new sales territory, building community across organizations, or helping team members discover their strengths—I’ve prioritized staying true to myself and valuing the process over simply chasing results. The results are always there.

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It’s all about the impact you create, relationships you build, and the outcomes you deliver.

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I’ve never played it safe, and I hope you don’t either. When you are at a crossroads, take the road less traveled.

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