I showed up for my first day of work on my Specialized Stumpjumper hard tail mountain bike, where I was to be trained by the most senior messenger at City Bike, Kevin. I tailed him for a few days, and there were moments where I felt like maybe he was either trying to drop me or at least serve me with a wake up call regarding the whole "riding around in the big city" thing. The only specific thing that I can remember vividly was accidentally jumping into the swirly doors with him... and I mean "with him." An awkward moment with a stranger, but a lesson in keeping my head out of my ass for sure.
The look on his face tho... Sorry, Kevin.
Two days of training later, and I showed up at work to hear the news. Kevin just up and quit. No more training for me. I was on the job officially.
I still didn't know north from south or east from west. All I had was a printed out map of the Center City that the Chamber of Commerce gave out for free. We were required to wear all black, all the time. Fortunately, I had a black helmet. Unfortunately, I had no black shorts. I was handed some denim cargo shorts with a built-in chamois.... used by a previous messenger. I was issued a bag and a giant radio that had to be picked up and dropped off every day at the main office. The strangest thing being that we had to have our gear on us and be uptown fourteen blocks away to start our day on time... and we couldn't leave uptown and head back to the office until it was time to leave. Essentially, we were adding 50-60 minutes to our work week... unpaid. Once again, I was a grown ass adult, and I chose to do this.
There were only two bike messenger companies in town back in '96, City Bike and Mercury Messengers... which was really just one guy, Holt. He had an incredible red mullet that hung out the back of his Shoei helmet and a certain bow-legged way of pedaling his bike about town. My boss at the time told me that guy wasn't gonna make it in this "conservative corporate world."
To put it bluntly, the job sucked at least a little bit. I was too poor to buy proper gear, and I was starting right at the sharp end of winter. Yeth, a Charlotte winter as opposed to all those other winters of my life in Ohio, but staying inside was not an option as it was in the "just kill me" state. I stuck it out through that winter and made it to the blessed spring and then on to summer.
That's the first time it all fell apart.
My boss had a disagreement with someone higher up at our largest client. They didn't like that, so they decided to drop us. Strangely enough, they would end up being my employer a whole bunch of years later and still currently.
Anyways, things didn't go so well after that. They were a huge part of our business. When they dropped us, you could hear the air coming out of our tires. There were only two bike messengers working by that point (and a couple car drivers), and it got to where one of us was sent home halfway through each day. We would take turns taking the financial punch in the wallet.
That doesn't work out so well when you're sometimes paying for daycare.
So as much sense as it never made for me to take the job, it made all the sense in the world for me to quit.
And I did so in August '97.