I was eleven years old when I got my first newspaper route. That experience taught me lessons I’ll carry to my grave.
The minimum age for paperboys was twelve, but I figured I could say I was twelve because the Arizona Republic wanted paperboys, I wanted to work, and my birthday was only a little more than eleven months away. And, so through all of sixth and the first half of seventh grade, I got up before sunrise, seven days per week, and delivered newspapers. After my family moved to Minnesota, I delivered the Minneapolis Tribune until the start of eighth grade.
Paperboys were independent contractors, which meant we bought our papers at wholesale and sold them at retail. Which also meant, if I wanted to get paid, I had to collect the money from customers. I collected every Thursday, riding my bicycle to every customer, knocking on the door, and collecting a payment in return for a tear-off coupon receipt. The problem was, some customers were never home and others just didn’t like to pay, and this meant I had to keep coming out day after day to knock on doors.
One time, I knocked on a door on a Saturday and the customer turned me away, claiming Saturday was their Sabbath. That was forty-nine years ago and I still get mad when I think about it. I got up every morning and delivered this guy’s newspaper, even on my Sabbath. Seems to me, he should have been happy to pay, no matter what day of the week it was.
If I could go back in time, I would tell my younger self to bring that up with this customer, even though he was an adult and I was a scrawny kid. If you don’t care enough about getting paid to stand up for yourself, why should anyone else? This lesson came in handy a few times when I was an independent IT consultant.
I tried to collect from another customer who was never home. Finally, I knocked on his door at 4 A.M. one day when I delivered his newspaper. He was unhappy to crawl out of bed at that hour, but he paid me and never gave me any problems paying after that.
After we moved to Minnesota, I also became a golf caddy.
The golf club where I worked offered “A” caddies and “B” caddies. “B” caddies made $4 for eighteen holes. “A” caddies made $5. Plus tips. Prospective caddies waited on a platform on the other side of the putting green from the clubhouse for attendants to match golfers with caddies, and so caddies who curried favor with the attendants became “A” caddies the fastest and got the best tippers. As a scrawny twelve and thirteen-year-old newly arrived in Minnesota, I didn’t curry much favor with those guys.
There was a prestigious amateur golf tournament coming up and the guys in the clubhouse made it clear they would assign caddies to golfers in whatever manner they saw fit. I didn’t like that at all, because I had no clue who they would assign me.
The morning of the tournament, I went out to the parking lot and looked for golfers who looked nice, and offered to carry their bags into the clubhouse. And the first golfer I found who looked like she needed a caddy, I was the man for the job.
That was a mistake. I spent four hours in the sun, watching her get more and more frustrated with her game. I tried to offer some advice on one hole, since I’d walked that course dozens of times, but all I did was make her mad. I kept my mouth shut after that. She paid me the standard “B” caddy rate of $4. Not one penny for a tip.
I learned another lesson that day; no matter how desperate I am, don’t always jump on the very first offer, because it might not be the best offer.
It turned out I was more popular in the clubhouse than I thought. The next day, the clubhouse attendants told me they had picked out a top golfer for me, but were flabbergasted when I matched myself with that lady in the parking lot. If I’d only been a little more patient, I could have caddied for one of the top golfers in the event and probably gone home with more money and status.
I never did understand how caddies became “A” caddies, but during my second summer, I figured I’d paid my dues and I was ready. One day on the way home, I happened to fall in step with Bob Olds, the club golf pro.
“Hey Bob, I think I’m ready to be an ‘A’ caddy. Can I be one?”
“Sure. You’ve been here a while now. You’ll make a little more money. Okay, you’re an ‘A’ caddy.”
And that was it. Next day, I told the guys in the clubhouse I was an “A” caddy and nobody objected. Sometimes you just gotta ask.