It's a Major Award!

There’s a great scene in A Christmas Story where “the old man” wins something. He has entered some kind of sweepstakes where solving crossword puzzles qualifies you to be entered for a drawing, maybe—those details aren’t terribly important.

The old man is proud of his prize! In a tense scene, he puts it front and center in his home for all his neighbors to see, much to the chagrin of Mother.

I once won a major award myself.

This was during my days delivering newspapers, which was one of the ways I made money during middle school. The pay structure was interesting to me, and I found it enticing: we would be paid very little for the actual job of delivering the newspapers, but considerably more based on what we collected from people.

Here’s how I described this in Paperboy:

That’s right—we were paid a pittance from the newspaper for doing all that labor on their behalf, and it probably worked out to something like $1 an hour… unless you got more by asking. In language that would make George Orwell proud, we called it “voluntary pay week”, and mentioned that as we went on to explain that we would like to know if they’d like to give a dollar to their impoverished newspaper delivery person.

From a business owner’s perspective, I get it. Collecting money is icky for most people, so incentivizing doing the part of the job where the newspaper might make more money is important.

This went well enough for me most of the time. I might collect an extra $20 a month by hustling, and that $20 bought a lot of comic books or Paula Abdul tapes.

Finally, since it was a weekly paper, the “voluntary pay week” came about once a month, so it was important to have a careful process to make sure to knock on every door, hopefully at a time when you can get an answer. I might have written the “not homes” down on a little notepad for a return visit, or I might have just remembered the houses… I really can’t remember.

Besides having a robust process, those sales skills I mentioned earlier—having the tenacity to walk right up to someone and ask for money, for crying out loud—they came in very handy years later, when I was running a business and looking for customers. Between the process of developing my own logistical plan and asking for money, I had some very good future-business-owner DNA at a young age.

One day in 1989, the newspaper incentivized us kids to collect even more pay by offering us a big monetary incentive. All kids who collected the most payments during the week of the contest would be entered to win a top prize of $100, and there were smaller prizes given out, too. I figured I was going to do the work anyway, and if I hustled a little extra, I’d make an extra dollar or two anyway.

Here is the insert they gave us paper carriers (this feels like a museum relic to me):

I don’t need to tell you this, but $100 was a lot of money in 1989. I was pretty good at math for a kid my age, so I understood that the probability wasn’t incredibly high that I would win, even if I worked extra hard—although it was evident that collecting more meant more entries to win.

Turns out: I won. This felt amazing—it was the first time I had received such a large sum of cash at once, and I felt like it gave me a little nest egg I could build on. They even published my grinning mug in the next weekly edition:

Last week, I shared this picture with a friend I grew up with, who immediately commented on the T-shirt all the carriers were wearing that day. The quote on the shirt says, “We Do It Once A Week.”

It was kind of okay for tween and teen kids to be the butts of sex jokes for grown-ups. That was just the world I grew up in, folks. Of course, we kids embraced this PG-13 humor since it was edgy and cool, or at least it was something we weren’t supposed to laugh at.

What about you—have you won any major awards in your life?