When I take inventory of my career successes and failures, I often reflect back on formative experiences that significantly shaped who I am and where I am today. These are only things we can understand in retrospect. At the time, they only seem to be momentary or temporary. Only in the long-view can we understand the significance.

I’ve looked back at various points in my career in previous blog articles. I chronicled my educational journey. I reminisced about my first tech job. My very first blog post was about a major career catastrophe that I survived. Today, I’m reaching back even further. I can trace much of my work habit development to my very first job. When I was 13, I got a paper route.

As a 13-year-old kid, I was pretty lazy. I didn’t have a whole lot of drive in my life at that time. I remember hearing that the local paperboy was quitting the job and looking for someone to take it over. When I brought the idea to my parents, they tried to talk me out of it. I think this really spoke to who I was back then. They thought, if I get a paper route, it will really become their paper route. It was somewhat commonplace for paperboys to get bailed out by their parents, and they wanted none of that. Furthermore, my overall lack of ambition and responsibility didn’t instill much confidence that I was up to the challenge.

I had recently quit piano lessons, which I had pursued for eight long years and I needed a new challenge. I needed this paper route. I made a verbal contract with my parents. This was going to be my paper route. I would under no circumstances solicit their help or ask them to drive me. Not if I was sick. Not if there was a blizzard. Not if I was going on vacation. If I needed a replacement, it was my job to find one, train them, and make the arrangements. If my customers gave me grief, or failed to pay me, that was also my problem. I agreed to all of this, and they agreed to let me get the paper route.

Lesson 1: Customer Service is King

I delivered newspapers seven days a week, but Sunday was the big day. I could deliver my daily route in about 30-45 minutes in a single trip. Because Sunday papers are huge, I needed to take six separate trips, which made it a three-hour ordeal, preceded by an hour of wrapping. My very first Sunday, I got up very early, but not early enough. I delivered my last paper close to eight o’clock. Within an hour of coming home, my phone rang. One of my customers canceled his subscription on the spot, citing the late paper for the reason.

My first response was to feel like a failure. It was my first big day of my first job, and I already lost a customer. Maybe I wasn’t cut out for this. My parents encouraged me to call back the customer and find out what it would take to earn back his business. I was pretty shy, and hated the idea of calling customers, especially ones that I knew were unhappy with me, but I made myself do it. I reworked my entire paper route to put him at the beginning (and also started the whole thing earlier). I kept this customer for the entire five years I held the job. He also was a great tipper around Christmas time. In his Christmas card to me every year he wrote, “thanks for the early deliveries.”

Lesson 2: Leverage Technology and Systems

When I cross-trained with the previous paperboy, he handed me a written route list. It included each subscriber by name and address, and identified their preferred delivery location: driveway, mailbox, front porch, or newspaper tube. Within a few days of running the route, I realized that it changed constantly. People went on vacation hold. New subscribers joined and some stopped. Others changed their preferences for delivery location.

I maintained these changes on the original paper sheet by hand for a bit, but that soon became untenable. I spent a few hours computerizing the schedule in whatever spreadsheet program pre-dated Excel. This gave me clarity and efficiency. It also gave me the ability to hand-off a fully documented route to a substitute whenever I needed it.

Lesson 3: Overcome Adversity

Over-time, the basics of the route delivery became routine and easy, but challenges still came my way. I once got hit with 30-inches of snow over a weekend. I couldn’t ride my bike through it, so I walked my route through the snow with frozen feet.

I had to deal with a neighborhood kid that repeatedly stole my bike. (I knew where he lived and took it back). I called the cops to report it, and they looked at me and said, “What do you want me to do? I’m not going to arrest a kid. I know the house. His parents are criminals, and this kid will probably grow up to be one too.” Justice went unserved.

Several times I got bit by dogs. One of these dogs was named “Chopper.” It seemed fitting. All of these experiences toughened me and enabled me to grow up. I delivered the paper every day for five years. I don’t know the average tenure of a paperboy, but I think five years is pretty long. I learned to be loyal to a job and stick with it when it got tough.

Lesson 4: People Can Be Jerks

A paperboy is technically an independent business owner. I bought the papers from the company at wholesale and sold them to my subscribers at retail. I had the job of collecting the bills. I had people that ordered the paper, but evaded me at collection time. Who would stiff a kid? People did. One time, during a governor-declared, county-wide snow shutdown, it was illegal for anyone to drive anywhere unless you were an emergency vehicle or a snow plow. I didn’t get my paper drop. The next day, when the driving ban was lifted, I delivered two days of papers.

I got several calls from irate customers that refused to pay for day-old news. My skin started to thicken a bit. This was a skill I needed to survive work-life in the real world. Fortunately, the nice people far outweighed the bad.

Lesson 5: Leverage Subcontractors to Gain Efficiency

About a year into my job, my older brother got his license and a car. While I couldn’t solicit my parents to drive me around on Sunday mornings, I could hire my brother to do it. I earned $30 on a Sunday morning. I paid my brother $10 of it. I got up early to wrap the papers and load them into my brother’s massive 1978 Buick LaSabre. Once it was loaded and ready to go, I woke him up and he drove while I delivered. I cut down my delivery time from three hours to one hour. It was a good deal for both of us. A couple of years later my brother left for college, but I had my own car by then (bought with the money I earned from this job).

From Paperboy to IT Leader

I think it is easy to downplay the importance of your first teenager job, but I learned fantastic personal leadership lessons that serve me to this day. I’m grateful for my parents, who not only allowed me to do the job, but coached me along the way, and allowed me to succeed and fail on my own. That built my confidence, resourcefulness, responsibility, and resilience.

I think it’s a shame that there really isn’t such a thing as a paperboy any more. The job has gone the way of the milk man. The few newspapers that are delivered anymore are done by adults in cars. As my kids approach the age where they will hold their first jobs, I wonder what opportunities they will have to learn these valuable lessons.

Any other paperboys out there? Any first job experiences you found formative? Please share your stories in the comments below.