A MEMOIR
Roll With It (an excerpt)
A Trip Back to the ’90s — Gen X Style
From the back cover
More than just a strange but true sports story, Roll With It is a love letter to Generation X. A time machine to the ’90s, the memoir captures a snapshot of humanity’s final Slacker-friendly years before a technological tidal wave would render things utterly unrecognizable.
It’s 1990, and the author comes of age and chases his childhood dream of working in sports. Through an unlikely sequence of events, he gets drafted as General Manager of a professional roller hockey team in the up-start Roller Hockey International, completely out of his depth.
Flashbacks to road trips, dive bars, locker rooms, Dead shows, and blind dates celebrate the improvisational superpower an entire generation utilized to MacGyver our way through a world that transmogrified beneath our feet.
But, it’s cool. We rolled with it.
(Questionable choice for book club.)
Below is an excerpt from the March 24, 2025 release of Roll With It: A Trip Back to the ’90s — Gen X Style.
Prologue: “Pregame Show”
I’ve moved seven times in the past 30 years. Every move is a chance to get rid of my junk. No matter how diligently I purge, one box of treasures that harbors an assortment of keepsakes always survives. Ticket stubs. A thumb drive with God knows what on it. A beer koozie from JazzFest. A pair of my grandfather’s cufflinks.
My most prized memento in that box is a ring — the blinged-out kind sports teams get for winning world championships. I’ve worn the ring maybe a dozen times tops over the past three decades. Sometimes it goes missing, and I can’t find it. Most of the time, I just forget. I tend to wear it to formal events, as it pairs nicely with a tux, gaudy in all the right ways. At first, no one notices, but eventually, it catches someone’s eye.
“Hey, man, what’s with the ring?”
The barely gold 10-karat band is adorned with all sorts of imprinted words and images, customized for each recipient. One of a kind, it’s a real conversation starter.
“What, this ring?”
The band was sized for my ring finger. My left one’s taken, so I wear it on my right. It’s terrifying when I shake hands, as the oversized band becomes a bone crusher whenever my undersized hand misses its mark. One night, when I used to bite my nails like a savage, a couple of well-heeled dames at a fancy fundraiser came in tight for an inspection, unexpectedly getting a close-up of a gory cuticle. I soon learned to yank the ring off, pass it over, and thrust my hands back into my pockets. Frankly, the clunky ring is not all that comfortable anyway, and by the end of the night, it too has typically disappeared into a stray pocket, only to go missing again.
The ring is an artifact of a team championship, and I’ll get to that later. More so, the ring doubles as a relic for an entire generation and celebrates the unique moment in time that was the 1990s.
Generation X stands alone in human history as the only generation to have straddled both sides of the technological wave that irreversibly transformed the world. Okay, I’ll include Gen Jonesers (you know who you are).
Like a well-spun 45, we found our groove on both sides. Side A: We grew up, came of age, and became young adults during the technical dark ages in the 20th Century. Side B: We worked, raised families, and lived as adults while adapting to the constantly changing technology-dominated world that arrived with the new millennium.
We are generational time travelers — Back to the Future style. If my 20-year-old self were suddenly dropped into today’s modern world, I would have agreed with Keanu Reeves in Bill & Ted’s Excellent Adventure. Strange things are afoot at the Circle K.
Born in 1968, I land in the slightly older end of the Gen X age distribution curve — widely defined as those born from 1965 through 1980. My generational peers will concede that we grew up in times of bad hair, questionable fashion, iffy food, and the looming fear of either getting AIDS on the one hand or getting nuked on the other. As punk rockers Suicidal Tendencies repeatedly reminded us on MTV, “It doesn’t matter, I’ll probably get hit by a car anyways.”
Why the angst? Because, even if our generational timing was experientially auspicious, our market timing was crap. We were the first generation in several who had things worse off than our parents. We graduated into an economic recession. Our education and training, rooted in the old world, soon became obsolete. We were ill-equipped to ride the technical wave that Gordon Moore’s law accurately predicted. The number of silicon chips that can fit on a motherboard did double every 18 months, with unimaginable implications for the world around us.
We’ve been called the “latchkey generation.” The moniker is apt. The 2:40 p.m. school bell announced it was time for me and Rajan to meander our way home, kicking a rock down the center stripe of Raimundo Way (speed limit 35 MPH). I’d let myself into an empty house, let the dog out, warm up a can of Chef Boyardee, and practice some basketball trick shots in the driveway before plopping in a beanbag in front of the TV until the grown-ups turned up — that is unless it was my night of the week to cook dinner (today’s special: pigs in a blanket). I was ten.
Left alone, we learned to improvise.
The Cambridge Dictionary defines improvisation as “the activity of making or doing something that you have not planned, using whatever you find.” I like this definition. The latchkey generation embraced life without plans and made use of whatever we found. Faced with a changing world, uncertain prospects, and minimal resources, ours became a generation of improvisational masters. Scrappy and proudly so. The uber-resourceful MacGyver, who could reliably save the day by cobbling together common household items, became our hero.
We got labeled “slackers” — in a nod to Richard Linklater’s resonant cult indie flick Slacker, which came out in 1991 and was made Gen X style on a $23,000 budget. The plot, or lack thereof, followed everyday bohemians in Austin, Texas, from one pedestrian scene to the next in a daisy chain format, with a rotating cast and without a cohesive narrative. The absence of a plotline was the plotline. Its indie irreverence resonated with a cohort of would-be adults ready to graduate from The Breakfast Club but lacking a clear roadmap to do so.
But are we slackers? Or are we just the forgotten, misunderstood, and slightly derailed middle child who became undeniably resilient, competent, and able to take care of ourselves in the face of a world that sucker-punched us? The triple whammy of being worse off than our parents, graduating into a recession, and being trained for the old world on the eve of a new one was headwinds at best and derailed us at worst. We rolled with it, though, and did so without fanfare. We learned to be resourceful, extracting utility from whatever was within arm’s length. We didn’t need much attention as we soldiered through. The capable yet invisible middle child never does.
By the early 1990s, we were full-fledged adults unwittingly in the dawn of the coming technological transmogrification. E-mail barely existed at the beginning of the decade and was still not mainstream by the time Y2K bookended the millennium with a whimper. Pagers were novel. Voicemail was exciting. Pausing live TV was science fiction, years before anyone had dreamed of TiVo. VCRs that incessantly blinked 12:00 were game-changers.
Perhaps more defining than the “low-tech” living in the ’90s was the lack of connectivity and limited methods we had to keep in touch with each other. We didn’t know any different, so it didn’t bother us. Sometimes, you got ahold of people. Sometimes, you got a busy signal. Whatever. Poor connectivity led to spontaneity, serendipity, chance meetings if you were paying attention (“Hey, there’s Matt!”), and near misses if you weren’t (“I was also at that show. I can’t believe I didn’t see you.”)
As kids, our generation went through school the old-fashioned way, sniffing mimeographs, huffing magic markers, taking bubble tests, and drafting homework assignments longhand before gingerly tapping out the final copy on an electric typewriter accompanied by a crusty bottle of Liquid Paper™. Now, in mid-life, we’ve fully crossed over. We’ve not all thrived, per se, but we’ve persevered. No one prepared us for it, but we figured it out.
And wasn’t the latchkey generation the perfect group to navigate the uncertainty of a world in transition? Predisposed to our scrappy disposition from our childhoods, as young adults, we were unfazed by the improv required to cross that chasm, which only enhanced our superpowers of making or doing something unplanned using what we found. Wonder twin powers, activate.
The 1990s were heady times. Life was starting to modernize, but things were still clunky. So much changed in the subsequent years that it is easy to forget what life was like during that pre-transitional decade. Everyday life, during years that were just not that long ago, is now utterly inconceivable to anyone who has not lived in both worlds.
Is that the sound of eyes rolling inside my Generation Z sons’ skulls? Admittedly, this “Ours is the most unique generation” declaration could very easily be dismissed as nothing more than self-orientation and the normal generational cycle of life. But how could they possibly relate to what life was actually like when everyone wasn’t 100% connected at all times? With folded maps, unhealthy recipes prepared from geriatric index cards, communication limited to the mailbox and a landline shared by five people, and a bookshelf stocked with a set of out-of-date Encyclopedias as our source of truth for those of us lucky enough to have parents with a willingness and the largess to over-pay for a set. Our substitute for porn was, at best, stealing Wexler’s older brother’s dog-eared Penthouse Forum and, at worst, greedily flipping through last year’s Sports Illustrated swimsuit edition.
OK, you get it. Another old guy nostalgic for simpler times when he drank out of the garden hose? Guilty. But this book is more than just nostalgia. It’s a desire to capture, preserve, and pay homage to the absurdity and sometimes hilarity of ordinary life in the 1990s — a decade that already seems impossibly distant in the rear-view mirror and yet was hardly a cosmic blink of an eye ago. And to remember, recognize, and appreciate the hustle and can-do mindset that life required of an entire generation to improvise and roll with it.
This book started as a rescue mission for a long-lost document. In early September 1995, I holed up for a weekend with my Auntie Suie and Uncle Art in a remote lodge in central California and spent the better part of two days journaling the chaotic whirlwind of the prior 18 months. I was on the eve of embarking on a life change, two weeks before starting graduate school. I had just completed a frenetic and unlikely stint working in professional sports. Seeking catharsis and closure, I captured the nutty and mundane things that happened on a borrowed laptop. By the end of the weekend, I’d brain-dumped some 20-odd pages of raw and unpolished stories, thus defragmenting my brain, making head space for the life chapter ahead. A quarter of a century later, I can find neither those floppiest of floppy disks nor the hard copy once printed and possibly tucked away in a box in a storage unit near some scrub brush somewhere. A lost artifact.
So many times, I’ve fantasized about coming across that hot mess of a manuscript. I still harbor hope that one day I will. But like that gut punch when your desktop IBM went all “blue screen of death” on you when you hadn’t saved your work, it seemed to me the document was gone forever, along with the stories that went with it. My last recourse was to declare bankruptcy and see if I could still excavate the memories from my own cranial storage unit.
So, in the early stages of the global pandemic, I opened the blank page of a new document and started over. Once I began, the memories came in waves and the stories practically wrote themselves. This narrative zooms into a five-year timeline when I worked in the world of professional sports, between my college graduation in 1990 and the beginning of graduate school in 1995. But wait, this is not just a sports story. No, it’s a romp through life in the early ‘90s.
With this book, my dream is to notch a hat trick by tallying three goals. The first is to resuscitate bygone stories and memories before they are lost forever. Goal number two is to time travel and recount day-to-day life in the early ’90s as a unique moment in time — humanity’s final years preceding its irreversible transformation. The third goal is to honor a generation who improvised and MacGyvered our way through an era and figured life out as we went.
“So, what’s with the ring?”
Crack yourself a Zima, set the Wayback Machine to 1990, and I’ll tell you all about it.
Roll With It is available on Amazon, Barnes & Noble, Apple Books, and other places you buy books.
