Fellow Substacker Timothy Snyder, an American historian living in Toronto and expert on the Holocaust and antisemitism, posted a few days ago on an unlikely subject: How his plan to run a foot race in Toronto was momentarily derailed. Here’s an excerpt and a footnote to the post itself:

Briefly, what happened is that the runners were scammed. Signed up online, paid the fee, and showed up for the race that wasn’t. Might as well go home, right? But wait; why not just run the race even though the fancy ways of keeping time and deciding rankings was absent? What resulted, as you’ll see when you read his post, is that everybody had a good experience, maybe a good time, too, but that part won’t ever be “official.”

I loved this little story. It reminded me of a book that was popular when I was in college decades ago. The book was called “The Organization Man” by William Whyte. The key point was that by the 1950s businesses and corporations had yielded individual innovation and initiative to organizational structures that imposed boundaries on creative thinking. Whyte saw a situation that could create an “organization man” who subordinates his personal life to the demands of the organization for which he works.

Snyder evidently came to a similar conclusion with his serendipitous running experience when he wrote:

What did we make happen?

We were all fooled by a digital scam that played to our better angels and took our money. The scammers claimed to be helping veterans on Canada’s Remembrance Day. And we fell for it. And then we gathered ourselves up, organized ourselves as much as we needed to be organized, did the thing, and felt better. ... We fell for it. And then we went for it.

I was reminded of my experiences as a boy growing up in Denver and playing endless hours of sandlot baseball. In my long life I’ve seen big changes. As a kid, I played Young America football and Old Timers baseball. My parents drove me to the football games that were too distant to walk to, but the Old Timers baseball games always were at 5th and Federal where a single adult decided which team would play which team and which of the two fields would be used. There were no coaches. We figured out our starting lineup and batting order, and played to our heart’s content. It was special to have uniforms that featured the name of a business that paid for them.

Other games were less formal. Odd things, like somebody’s t-shirt, could be used for bases. We could decide who got to bat first by tossing a bat from one boy to another who had to catch it in the air. Then alternating members of each team would grip the bat until nothing remained except the knob. Whichever team had the top position got to go first. (But there sometimes was a caveat — the bear claw! With this maneuver, one more hand was allowed to perch on top of the knob, thereby becoming the “upper hand.”)

A few years later, I had my own young athletes, two boys who like me loved anything involving a ball. By then, there were more choices for youth sports, more adults involved, and fewer decisions made by the boys themselves. Even so, my youngest boy spent the majority of his summer days playing unsupervised sandlot baseball, often from sunrise to sunset. He turned into a pretty good player, played baseball and football in high school and even played both sports in university. His older brother, equally skilled in sports, was the same. I often wondered if their skills with a grounder had something to do with playing on a field replete with dips and mounds and rocks and weeds.

Whether it’s true that American businesses have become too organized is best debated by the experts in the field (so to speak). But it’s fair to say that wonderful things can happen without planning, or when planning is a hoax, or when planned events simply fall apart. Let innovation carry the day.

As for kids, I say let ‘em play! Let them skin a knee or catch a baseball on the chin. Let them settle a hurt feeling or a debated play without the intervention of a biased parent. This isn’t to say there is no need for guidance and oversight, but for the most part children benefit from unsupervised play. Sitting here now at my keyboard, my eyes glaze over with images of that sandy playground at Valverde Elementary School where many a game unfolded with no planning at all.

As Snyder and his daughter did on a snowy day in Toronto, we also might cherish the delightful serendipity when everything organized falls apart. Disappointment, sure. But wait! Opportunity! Yay!