08/31/2026
THE MONDAY REFLECTION
Before There Was AI, There Was a Bowling Ball Coming at My Head
Last Monday, I wrote about growing up in Lindsay, Ontario, and asked a question that stayed with me longer than I expected: What did that place, those people and that time give me that I’ve carried all these years?
A lot of you shared your own memories. Different towns, different people, different stories, but there was something familiar running through many of them. We weren’t necessarily longing to go backward. We were trying to understand what we brought forward.
So I kept thinking about it.
And somehow I ended up back at a bowling alley in Lindsay with a bowling ball coming directly at my head.
Welcome to the second Monday Reflection.
I grew up at a time when a kid’s first job wasn’t necessarily designed to build a résumé. It was usually about putting a few bucks in your pocket and learning, fairly quickly, what it meant to show up and do the work.
One of my first jobs was at a local bowling alley. Not working the counter. Not handing out shoes. I set the pins. By hand.
There was no machine sweeping the lane and magically resetting everything. There was me behind those pins, listening for the crash, jumping in to reset them and getting the hell out of the way before somebody sent another bowling ball down the lane.
It sounds a little insane today. At the time, it was just a job.
And that’s probably what I remember most about those early jobs. Nobody talked to us about career paths or personal brands. You showed up, figured out what needed doing and tried not to screw it up too badly. In my case, one of the first professional skills I developed was apparently knowing when to move quickly.
Years later, that skill came in handy. Unfortunately, it did nothing to improve my ability to eat a hot dog before an important job interview.
I had just finished grad school and landed an interview with a prestigious firm. I was running late, skipped breakfast and grabbed a street hot dog with mustard on the way. I raced into the office, did the interview, shook hands and walked out feeling pretty damn good about myself.
Then the elevator doors started closing and I caught my reflection.
Mustard on my lapel, tie and white shirt.
Nobody had said a word. Somehow, I got the job anyway.
Both stories still make me laugh. But now I see something in them I certainly didn’t see then. Funny how much of life turns out to be figuring things out after the original plan goes sideways.
And those of us who grew up in that era have had a fair amount of practice.
Last week I wrote about Gen X being the analog kids who became digital adults. We went from rotary phones and paper maps to the internet, smartphones, social media and now AI. But the bigger transformation wasn’t technological. We changed too.
Somewhere along the way came careers, recessions, relationships, kids, aging parents, friendships that lasted, others that didn’t, successes we celebrated and failures we definitely didn’t post about. There were also more than a few moments when the life plan apparently got lost in the mail.
Some things we handled well. Some we absolutely did not. We changed our minds, learned new things, occasionally learned the same lesson twice and kept going.
Maybe that’s something we don’t give ourselves enough credit for after 50.
There’s plenty of conversation about what supposedly gets harder as we age. I’m becoming much more interested in the other side of that equation:
What have decades of living made us better at?
I certainly don’t think we have all the answers. In fact, getting older has mostly taught me to be suspicious of people who claim they do.
But we have stories. Lots of them.
And sometimes the ridiculous little stories explain more about who we became than anything on a résumé ever could.
THIS WEEK’S REFLECTION
Last week I asked you to think about where you came from and what you carried forward.
This week, take me back to your first real job.
Not the impressive one. Not the one that eventually appeared on your executive bio. The real first one. The unglamorous one. The weird one. The one that put a few dollars in your pocket, exhausted you, embarrassed you or quietly taught you something you didn’t realize you were learning.
What was your first job?
Tell us the story in the comments. Bonus points if the job would raise a few eyebrows today.
Mine?
Keep your eye on the bowling ball.
And go easy on the mustard.
That’s The Monday Reflection. Each week at RestlessUrban, we’re taking one question about life after 50 and seeing where the conversation takes us. No instructions about how we’re supposed to age. No pretending we have it all figured out. Just stories, questions and a community comparing notes about what we’ve learned and what might come next.
If that sounds like your kind of conversation, follow RestlessUrban and join us again next Monday.
Live curious. Age boldly.
See you next week.
