I was twenty eight years old when I got landed the job that became my career. It wasn’t so much that I had landed the job, it was more that I had been handed the job. My Dad was an independent sales representative for a company that sold caps and gowns, class rings, graduation announcements, diplomas and other high school graduation products. His territory covered large swaths of western and central Michigan. In the spring of 2001, he came to me with a job offer.
At first, I wore the badge of sales associate. Day to day that meant that I would drive around to schools in our territory to take orders during lunches and in the evenings. I sat for long hours at cafeteria tables helping students and their parents fallout paperwork to order class rings and graduation regalia. The work itself was fine. I enjoyed interacting with customers for the most part, and hanging with seniors who were getting ready to celebrate was usually a fun experience.
Not yet thirty and with a pair of small kids at home, the job provided some security and stability for our family. I wasn't making great money, but I was working toward the opportunity for a genuine career, and eventually - if things went well, a very nice living. I worked long, hard hours, but I also inflected joy and enthusiasm into my work and my life. It felt exciting to be helping families celebrate something so important, and I wanted other folks to remember the joy and importance of the moment we were selling.
My territory and the value of my business hit a peak in the winter of 2016. Little did I know that things would take a downward turn, more than once over the next seven or so years. In the spring of 2016, a plant closure designed to save a couple of million dollars sent our production teams into a spiral of late deliveries, shoddy workmanship, and long periods of uncertainty as to whether pr not product would arrive in time at all for graduation. The summer after our delivery nightmare, I lost 30% of my business in less than a month. Fifteen years of growth wiped out in an instant.
In addition to the financial toll, there was the exhaustion and mental anguish of it all. For the first time in my career I couldn't be sure if I would be able to keep the promises that I made. Each account lost was not only money gone from the budget, but a stain upon my reputation and character. Still, I trudged on, but my heart was no longer in it.
The next few years saw fits and starts and more mismanagement at the corporate level. By the time Covid ravaged our already battered company, my enthusiasm for the job was completely
gone. I was exhausted, bleeding customers, and heartbroken that I could no longer hold my head high with my schools and my peers. My mental health took a serious downward turn. For several years, I endured bouts of regular panic attacks, sleepless nights, nausea, cramps, and suicidal nightmares due to my stress at work. My choice of employment was no longer an inconvenience or a job that I dreaded going to, it had become a genuine health risk. In the winter of 2023, I made the decision to walk away from my career and my business.
If you’ve been paying attention to this space in the 18 months since it launched, you’ll know that after my official career ended, I leapt headlong into a life of independent creativity. In the fourteen months since my last day on the job, I have largely looked back upon my time in the field with scorn and resentment. Lately though, I am beginning to take stock of what I learned at my big boy job and the things I learned to master from twenty three years of running my own business each day.
While I cannot imagine having to go back to that life, I am growing more grateful for the opportunities and experiences that my career allowed me to have, specifically the way that it prepared me to be a touring musician responsible for fulfilling each and every task that is required to do that work.
Working for a company as an independent contractor is wholly different from being a direct employee. In this case, I was responsible for my own taxes, health insurance, retirement, and so on. Additionally, I was not assigned to a certain set of tasks. I was given a territory with a list of schools that were potential or existing customers and I was largely left to do what I could to grow it.
For all intents and purposes, I was a one man band. There were times when I had help, but we were always an independent operation, and even in the best of times, support from our corporate office was not something on which one could rely consistently. Largely, this left our office on its own as we worked with thousands of families each year celebrating graduation. This meant managing my own schedule, setting my own pricing, designing marketing materials and presenting to seniors. From accounting to order taking and delivery to trash duty, we did everything except actual production of gowns, announcements and rings, in-house.
I loved the variety of the work. In a given day, I might present to a group of seniors in the morning, work with a group of student leaders at lunch, and then design a marketing piece for cold calls in the afternoon once I got back to the office. Student assemblies were my favorite part of the job. It was part tutorial, part stand-up, and part salesmanship as I walked these young folks through the process of celebrating graduation. I got them excited, I gently nudged for them to buy a few key items that they would use and that I could make my living on.
Elements of the job allowed me the creative freedom to practice my design skills and hone my public speaking chops. I got pretty damned good at handling a crowd. I knew how to get a laugh, how to keep them in line, and I learned to see when I had lost a crowd, and then learned how to win them back.
I have always been good at thinking on my feet, but senior assemblies and sales pitches made me a master. I became adept at finding interesting bits of conversation in a sea of varying interests. Over time, I learned that questions always lead to more interesting places in a conversation, and I worked hard at small talk with a sense of purpose to it.
From as early as I can remember, I have been comfortable in social situations. Two decades as an independent sales rep forced me to face the situations where even a social animal like me would feel awkward, and out of place. In those moments, I learned a greater confidence in myself. Spending time in myriad social and business situations with a huge swath of folks from varying walks of life taught me more about my value and my abilities than anything else in my life. It allowed me not only to see the areas in which I was deficient, but it also displayed for me the areas where I was ahead of the curve.
Making cold calls and asking for business is a difficult and even demeaning part of the work, but it is crucial to success. My Dad used to say, “The harder I work, the luckier I get.”
Of course he meant that luck is questionable but hard work is tangible, but he also meant that fortune favors the bold. It’s the same idea as believing that you’ll never get a date if you don’t ask her out. Learning to go out and ask for business meant learning to hear No for an answer. It meant learning how to turn that No into a Yes, and how to avoid the next administrator from ever saying No. Dealing with that rejection was a huge challenge for me, but it taught me a pragmatism that I lacked until that point in my life. In the harsh reality of Yes versus No, it was hard not to take the rejection personally, but over time each No got less difficult to hear. Eventually, I reached a point where the No was implied and I was only focused on the possibility of Yes.
Whatever skills and talents were improved during my career, I also learned that I stopped believing wholeheartedly in what we were selling, because I no longer felt that I could live up to my commitments. Now, I am able to take those refined skills and put them to use as I work to build a life as an independent musician, writer, and designer. From scheduling to written communication, and pitching to venues to printing up t-shirts, it’s all work I have done a thousand times before.
Working on your own, with full agency and accountability is liberating and intoxicating, but it can also be terrifying. It is now plain for me to see that as I have moved forward from my old job to my new life, I have taken a whole host of skills and talents that I had honed out of necessity for my “career” and applied them to the work that I know now I should have always been doing.
It’s still painful to think about what my last few years on the job were like, but I am able to focus more these days on what I gained from the experience than I am on what it took from me. I know that I am working harder, smarter, and more effectively than ever before. Much of that is from learning on the job at a gig I eventually fell out of love with, and that damn near killed me.
It sure feels good to be putting these talents in a place where they are deserved and appreciated.
Cheers,
Matty C
Really nice story! It's great to hear that you got something from a job that became underwhelming. Congrats for having lasted as long as you did!