There is something about a crisp Sunday morning that stirs up the imagination. For us Gen Xers, imagination often came with a dose of time travel. We grew up with Marty McFly, Bill and Ted, Josh Baskin, Phil Connors, and John Connor. A whole cast of characters who made us believe we could bend time if we only tried hard enough. We could be our own HG Wells if we wanted to.
Just a Chicago guy juggling fatherhood and bachelorhood. An old trading floor broker raising three kids and living in a flat by the river. These stories are life lessons meant to make you laugh, cry, and think. The “Chalkboard” is my daily post, scribbled on the blackboard in my kitchen—a ritual, a bit of therapy, and a small win to start the day. All Chalkheads are welcome to ride along.
Sunday, October 26, 2025
October 26th, 2025
When I think of imagination, I think of the Oldman. Saturday mornings, there were errands and diners, hardware stores and barbershops. After the chores, he’d point the Cadillac to nowhere in particular. We would wind up at a bakery, a butcher, a hotdog joint, a newspaper stand or an old antique shop off the beaten path.
Sometimes, we would make our way to Maxwell Street…
… a new toolbox in one hand, a pork chop sandwich in the other. The only fast food chain the Oldman tolerated was White Castle. I can still hear him hollering when I left grilled onions on his dashboard.
By the time we got home, the Oldman would nap, and I’d drift into my own little world. I used to imagine that when we drove under the Halsted viaduct south of Maxwell Street, we’d come out in 1932, maybe even 1922.
The “Dadillac” was our time machine, dropping us into a Chicago thick with soot, jazz and prohibition whispers. We’d look at each other dumbfounded, trying to figure out how to hide a twenty-foot car from the future. The Oldman would find work on the railroad, and I’d land on the floor of the Chicago Board of Trade. Him in the glory of steam and me shouting in the corn pit on the old trading floor. Which was actually a new trading floor at the time. Just a father and son, stuck in time, perfectly fine with it.
These days, my imagination has been traded in make-believe for what ifs.
What if Nixon beat Kennedy like he should’ve in ’60?
What if Ross Perot hadn’t split the ticket in ’92?
What if O.B. had the Irish flu on that September Tuesday?
What if I moved to New Orleans at the turn of the millennium?
Well, if Nixon won, men might still wear suits to the ballgame. If Perot stayed home, Monica Lewinsky wouldn’t have had to explain the cigar. If O.B. stayed home, a dad from Park Slope would have watched his kids grow up.
And if took the Illinois Central to NOLA, I wouldn’t have the Shepkids and I would have probably been trapped by Katrina.
So yeah, imagination still has its place, it just looks different now. Today, it is what keeps me grateful for where the road did take me. Time travel isn’t always backward. Sometimes it is standing in the kitchen on a Sunday morning, flipping pancakes for three imaginations left for me to nurture.
Be true to your team today. Cheer proud and loud. It is the last week of October…
…rock it with gusto and astonishment.
