It's somewhat difficult to explain my life from about 1993 to 2003 because it was a blur. But this was not a "fun blur" that you might see in the movies - it was twenty years of career mayhem and side helpings of uncertainty, fear and doubt. This was an extremely stressful time because I couldn't quite figure out where I should be going and had little clue how to get there - wherever "there" actually was! All I knew was that something had to change. Looking back, I kept repeating the same actions, hoping for a different outcome. This is the definition of insanity, and I hope that the following stories resonate if you've found yourself in my position. There is a way out, which comes with knowing yourself first. Unfortunately, it took quite some time for me to do this. If this chapter helps one person avoid the traps I found myself in, I'll consider that a win. A big win.
At the time, I had many plates spinning; I was a husband and a father to three children - all under ten. I tried my best to navigate a career in sales while figuring out a path in the world of skateboarding. I had been bitten by the writing bug and had reignited my passion for skateboarding via longboarding. But the truth was that things were not going well regarding my day job. What was my day job? Sales. It paid well, but I was not doing so great.
Outwardly, most people who meet me would think I'd be a good fit for sales. I am outgoing and gregarious and try to be as attentive as possible. The one thing about top-performing salespeople is that they typically share several critical characteristics. I possess some of these traits, but sadly, not in a way that would make for a stellar career in sales. While this may come off as somewhat masochistic, I feel it's vital that you understand why I was failing in my sales career.
In most companies, 80% of the sales come from 20% of the salespeople. In 1991 when I moved from a job in marketing/sales support to actual sales, I had great intentions, but in truth, I pretty much sucked. This placed me solidly in the 80% of non-performing salespeople. Ugh… Even just writing about this triggers so many horrible memories.
Great salespeople understand that selling is about human connection. These folks invest time in genuinely understanding their prospects' businesses, challenges and goals before pitching a product or service. I am interested in building relationships and forging connections, but things never seemed to gel when I tried to move things forward.
Elite salespeople are great listeners and can ask sincerely probing questions to uncover needs and pain points. I am a good listener and continuously curious, but I couldn't seem to take these skills and make something happen.
You will also find that great salespeople constantly follow up but aren't pushy. I am not pushy, but my follow-up was not so great. Sigh - the truth hurts.
I could list many more attributes that successful salespeople have. I'll leave you with just two: resilience and optimism. Great salespeople maintain positive energy and enthusiasm even during difficult periods. They know that persistence pays off and it’s just a numbers game.
I am going to stop here. I've taken you far enough down the sales rabbit hole. To put it the most succinct way I can, I talked myself into what I thought would be a worthy career in sales and found it very difficult to find a way out. In fact, it took me 13 years to get out.
As I got deeper into the skateboarding world, my 9 to 5 experiences became increasingly complicated. I disliked selling photocopiers, and a larger company swallowed up the company I was working for. The money was good for the little amount of actual work I did. I wasn’t meeting my potential but I was clueless as to where to go. This brought about tremendous turmoil, and I sensed it was time to leave. I felt the new owners were in over their heads. People were being fired from numerous departments - except sales. To my mind, it seemed like things were going nowhere fast. I contacted a headhunter and explained that I needed to leave my current position.
I had a series of meetings, and eventually, I wound up in a job interview with a huge office equipment company. When I assess things almost three decades later, I don't know why I thought this move would really change anything. I was moving from one sales job in office equipment to another selling larger office equipment. I should have recognized that the problem wasn't the career in sales; it was me thinking I could have a career in sales.
I distinctly recall telling the interviewer, "Please don't hire me to go up and down the street selling photocopiers because I do that already." I understood that I'd mainly be focused on selling high-end laser printers. On the surface, I was excited to be joining a much bigger company. But deep down, I knew that I wasn't addressing the elephant in the room - I didn't want to be in sales - I wanted to follow my passion for skateboarding, but this deeply conflicted with the need to pay for things like the mortgage, car lease and groceries. I had gotten myself into a rut of my own making. If you've ever done this, you know just how painful this experience can be and how damaging it can be on your psyche.
I started my new sales position in December 1995 with the best intentions. Outwardly, I was gung ho and was assigned to sell to book publishers. While I did have some initial sales success in early 1996, things quickly went downhill. It turned out that most publishers don't want anything to do with large printing equipment - they prefer to outsource that service. On top of this, most of them didn't wish to buy photocopiers either! I was back to doing something I hated, and my poor sales numbers were reflected spectacularly. Again, in hindsight, I admit some of these book publishers probably could have used new copiers and fax machines, but I didn't possess the sales acumen to make that happen.
When I was hired, I was given a forgivable draw that would eventually be removed within a few months. I'd be covering my salary with commissions based on what I hoped would be my numerous sales. With each passing month the lack of a proper sales funnel meant that things became increasingly stressful. Every second Friday, I'd walk up to the bank machine, praying that the money had been deposited.
Speaking of walking, I did a tremendous amount of walking and covered large areas of Toronto's downtown core. I walked so much that I lost quite a bit of weight (and had to buy a belt for my pants to keep them up!). The increased walking also led to a hole developing in my right shoe. What a spectacular metaphor for a failing career in sales.
I knew I wasn't performing well, and they knew I wasn't hitting my sales targets. The charade of my non-performance went on for months, and it felt like the Sword of Damocles was dangling over my head. I also knew the jig would soon be up - I just didn't know when. Curiously, the company had a policy of working from home, giving me much freedom and flexibility. I could do research for my book while working from home. I confess that it wasn't perhaps the best use of my time from the perspective of selling copiers, but I was very focused on researching the history of skateboarding. Mea culpa!
I would come into the office occasionally, but I knew that eventually, there would be a day of reckoning, which gnawed on my soul for months.
Miraculously, with the help of a grizzled sales rep named Bob, I landed a rather large deal in the early summer of 1997 that kept things going for a few extra months. Through some divine monetary intervention, the customer was approved for a lease larger than its yearly revenues. While the sale counted as part of my revenue, my manager knew it was a fluke and that Bob had done 95% of the work.
In the fall of 1997, my manager left me a voicemail asking for a meeting at the local coffee shop that was on the first floor of our building. This was the call I had dreaded, and I knew my time was up. We met sometime in the afternoon, and I distinctly recall my sales manager sitting down and removing his wristwatch. To this day, I am still not sure if this was some psychological power move or his wrist hurt. I remember sitting there and thinking, "Here it comes - I'm about to get fired, and I am so screwed!"
He began with a sentence that I've never forgotten. "Well, Michael, you're the worst salesperson on the team." As you can imagine, it went downhill from there. The only silver lining was that I was given three months to find a job. This was a lifeline that I did not expect.
It took me about a month, and I found another job - office equipment sales! You read that correctly; I went from the fire into the frying pan and back into the fire again. I remained in this job until May 1999, when I worked for the publisher who published my book. You might be wondering, "What was I hired to do?" It turned out they wanted me to help them sell books. I will admit that selling books differs greatly from selling office equipment, but it's still sales. But I still felt at the time that I was moving in a direction that at least superficially felt right.
I was thrown a big curveball within a few months of being hired. My bosses decided that they were going to outsource their sales requirements. As I had been hired as the salesperson, I would be out of a job. Again, by some miracle, fate intervened. It turned out that the publisher didn't just publish books; they also owned a wine magazine. As I wondered what would happen to me, the magazine salesperson quit. I was asked if I wanted the position. I immediately said "Yes" and started another chapter of my lacklustre sales career.
I stayed at this job for about two years, and it was a mixed bag. I did have some sales success, but nothing to write home about. One of the highlights was attending wine tastings and enjoying samples of wine in the office.
I worked from 9am to 5pm for my day job and from 5pm to 9pm on International Longboarder Magazine. It was a crazy time, and I am still unsure how I did it all. My wife was very supportive, but the hobby quickly became a job.
Things started to become more challenging with my job selling advertising at the wine magazine. I was getting itchy feet and decided to move to another magazine. This was a much larger publication that was bi-weekly. It had quite a large staff, and the owner wanted me to join. I spent about two years there. Again, at the beginning, it was OK. But then, over time, things went sideways. During this time, I decided to launch my magazine, Concrete Wave. I realized that having a partner with International Longboarder would not work out. It was a combination of frustration and a sense that I could do more if I worked alone.
Building interest in Concrete Wave took some time, and I knew I was on the verge of quitting my day job. I started checking my CW mail while at the travel magazine. I wasn't focused on my career in sales from 9 to 5. I was more interested in what was happening from 5 to 9. My only goal was to match what I was making at my day job. This way, I could quit the day job and work full time on CW.
You don't have to be a genius to determine what happened next. I got busted checking my email at work, and the owner took me out for lunch. He asked me when I wanted to finish up. I said, "Well, how about mid-October?" He replied, "Fine," and my last day on the job was Friday, October 17, 2003.
Ironically, had I not wanted to leave my position at the copier company, I never would have searched out a headhunter. The larger company would not have recruited me. I would not have been given the job of selling to book publishers. I would never have met up with Warwick Publishing. There would have been no book contract, no book, no TV show, and no magazines, and Spin Magazine might have written a story about the lords of ultra marathons… and on and on…
It took me years to escape my prison and finally wind up doing something that I truly loved. Publishing and editing Concrete Wave Magazine remains one of the greatest experiences in my life. I always used to say the worst day running Concrete Wave was better than the best day selling photocopiers. I had freedom and the opportunity to leave a mark on skateboarding in some truly unique ways. It was my dream job and I had created it by myself.
For 16 years (15 of them as a full time job that supported a family of 5) I was in heaven. I travelled throughout North America and Europe. Unfortunately, things started to unravel with the emergence of social media. Ironically, this was the catalyst to create another prison.