"That Would Be Great"

Bridging Generations at Work with Pop Culture—and a Movie Lunch

There’s a moment in every professional’s life when they drop a perfectly timed pop culture reference into a meeting… and it lands with a thud. Blank stares. Polite smiles. Someone typing under the table (probably Googling what you just said). That moment happened to me for what felt like the hundredth time when I made a crack about a TPS report and “channeling my inner Lumbergh.” Crickets. That’s when I realized: my pop culture isn’t their pop culture.

Like many professionals of my generation, I’ve carried certain cultural touchstones with me throughout my career. One of my most well-worn references has long been the 1999 cult classic Office Space. It’s a workplace satire so spot-on, it almost feels like a documentary. Over the years, I’ve sprinkled quotes from it into emails, used it to lighten the mood in tense meetings, and joked about smashing a temperamental printer à la the movie’s infamous slo-mo baseball bat scene.

But my team—filled with bright, capable, mostly Millennial and Gen Z colleagues—often didn’t follow. To them, Office Space is a vaguely familiar title, a meme source at best, not the formative workplace gospel it was for Gen X and older Millennials. They didn’t know about flair. They’d never met Milton. They certainly didn’t grasp the life-affirming joy of a good case of “not gonna work here anymore.”

After yet another one of my Office Space references fell flat, one of my managers offered a helpful—and slightly daring—suggestion: why not turn one of our monthly team meetings into a lunch gathering and screen the movie? I decided it was time. We scheduled a (long) lunch hour, invited everyone to brown bag it, and turned our conference room into a makeshift movie theater. No slides, no updates, no agendas—just some popcorn, shared laughs, and 90 minutes of pure late-’90s corporate catharsis. It was a simple shift, but it created space for something we didn’t know we needed: a communal pause, a cultural reset, and a little bit of fun in the middle of a workday.

And something unexpected happened.

They loved it. They laughed. They exchanged “ohhhh, now I get it” glances during scenes they’d heard me reference countless times. More importantly, it became a shared experience. We started speaking the same language—not just mine, not just theirs, but something in between. It broke down barriers. Suddenly, jokes landed. Google Chat channels lit up with GIFs of Lumbergh and his coffee mug. We even started referring to standard daily and weekly reports as “TPS” reports.

But beyond the inside jokes, it created a subtle but powerful shift. We found common ground in a place none of us expected: a 25-year-old movie about cubicle life. It sparked conversations about how workplaces have changed (and how much they haven’t), what autonomy and burnout look like across generations, and how humor can be a survival tool in any era of work.

I don’t expect Office Space to become a required part of onboarding. And I still make a conscious effort to engage with the pop culture that resonates with my team today (yes, I know who Olivia Rodrigo is, and no, I don’t fully get TikTok). But sharing that piece of my own cultural foundation helped me show up as a more human version of “the boss.” And it helped my team see me as more than just the person who schedules meetings and signs off on budgets.

Pop culture can be a bridge—but only if we’re willing to build it together.

Not long after our movie lunch, I made the decision to step away from my role and begin a new chapter in my career. Even with that change on the horizon, I was grateful for the chance to create one more meaningful moment with my team. Watching them laugh, connect, and rally together reminded me of what’s most enduring in any workplace: relationships, shared experiences, and the small moments that bring people closer.

So if you're ever tempted to reference an old movie or a band you think “everyone” knows, pause for a moment. Better yet, invite your team to share in the experience. You might just find that a little bit of nostalgia—served with popcorn—can go a long way in building trust, camaraderie, and even a few inside jokes that live on long after you’ve moved on.

And if they still don’t get it?

Well, at least you tried. And that would be grreeeeat.

Review

Office Space
directed by Mike Judge

My rating 4½ of 5 stars

In the grand pantheon of movies about work, Office Space exists in a perfect little cubicle of its own—one where fluorescent lights hum, printers jam for sport, and the scent of burnt coffee hovers permanently in the breakroom. Directed by Mike Judge (yes, the Beavis and Butt-Head guy, but stay with me), this 1999 sleeper hit manages to turn the beige banality of office life into something surreal, absurd, and ultimately cathartic. The premise is simple: a burned-out programmer starts ignoring all the rules and somehow gets promoted for it. But beneath that surface-level rebellion lies a sharp, weirdly comforting look at how modern work quietly gnaws away at the soul.

Ron Livingston plays Peter Gibbons, a man so beaten down by memos, traffic, and middle management that even his therapist gives up on him (okay, technically it’s a hypnotherapist who dies mid-session, but you get the idea). I’ve liked Livingston ever since he showed up in HBO’s Band of Brothers as Captain Lewis Nixon—a performance layered with understated depth and a heavy pour of scotch. He played Nixon like a guy who’s seen too much and says too little, which—now that I think of it—isn’t a bad description of Peter Gibbons either. In Office Space, Livingston’s dry delivery and quiet exasperation make him the perfect everyman for a world where showing up five minutes late can trigger a full-scale HR intervention. He’s not flashy, and that’s exactly why he works—both as a character and as a stand-in for all of us who’ve ever contemplated setting our inboxes on fire.

Which brings me to the true villain of this movie: the report. Specifically, the TPS report, with its mandatory cover sheet and the looming specter of a passive-aggressive follow-up from eight different managers. The absurdity of this detail struck a familiar chord with me—and probably will for anyone who’s spent time navigating a sea of weekly status updates, productivity dashboards, or systems that require a password change every 11 days. I once wrote about my nostalgia for green-bar paper and fixed-pitch fonts on this very blog (here, for the curious). There was something wonderfully simple about those old-school reports—clunky, yes, but they didn’t pretend to be anything they weren’t. Today’s reports? They’re like soulless performance art, and Office Space captures that disconnect beautifully. It’s not just that the bureaucracy is overbearing—it’s that it’s completely detached from the reality of the work itself. And when Peter decides to opt out, it feels, for a brief, glorious moment, like he’s achieved workplace nirvana.

Of course, no discussion of Office Space would be complete without Milton—the stapler-obsessed, softly mumbling tragic hero played to perfection by Stephen Root. Or the Bobs, those interchangeable consultants with MBA smugness and bad intentions. Or the printer, whose ultimate fate remains one of the most satisfying acts of vigilante justice ever captured on film. Judge populates this universe with characters so exaggerated they shouldn’t feel real, but somehow do. Maybe because we’ve met them. Maybe because we’ve been them.

Office Space didn’t set the box office on fire in 1999, but it’s lived a rich second life as a cult favorite—passed around on DVD, quoted in breakrooms, referenced whenever someone mentions “flair” with a straight face. It’s a satire that’s both deeply specific and weirdly timeless. Corporate culture has evolved (sort of), but the core truth remains: people want their work to mean something, or at the very least, not to actively erode their will to live.

In short, if you’ve ever wanted to do a slow-motion beatdown of a malfunctioning printer in a field while Still by Geto Boys plays in the background, this one’s for you.

Wanting to Be Snoopy, Feeling Like Charlie Brown

Lately, I've been thinking a lot about Peanuts. Not just the Sunday comics or the TV specials we all grew up with, but the deeper psychology behind Charles Schulz's simple genius. It's amazing how much truth he packed into those four-panel strips—truth about human nature, loneliness, imagination, and the quiet struggle to keep showing up.

If I'm honest, most days I feel like Charlie Brown.

There's something so painfully relatable about Charlie Brown—the kid who tries and fails, who organizes the baseball game no one wants to play in, who never kicks the football but always runs toward it anyway. He's the eternal optimist living under a rain cloud, and I think that's why so many of us see ourselves in him. But the genius of Peanuts lies in its cast of characters who don't just support Charlie Brown, but actively challenge him. Lucy, for instance, is more of an antagonist than a friend. She's confident and outspoken—with a streak of bully in her personality—and she delights in pulling the football away just as Charlie Brown is about to kick it. Her actions aren't meant to help or encourage; they're meant to knock him down, test his limits, and sometimes mock his persistence. Yet, what makes Charlie Brown so endearing is that he keeps running toward that football anyway. His perseverance isn't because of Lucy's encouragement—it's despite her attempts to trip him up. Lucy embodies those voices in our lives that push back, that doubt us, or that challenge our optimism. Charlie Brown's struggle against her reminds me that resilience often means standing strong not with the help of others, but in defiance of those trying to hold us back.

But then... there's Snoopy.

Snoopy is everything we want to be. Confident. Cool. Imaginative. Unbothered. He reinvents himself daily: Joe Cool, World War I Flying Ace, bestselling novelist. While Charlie Brown is down in the mud, Snoopy's dancing on the doghouse. He doesn't worry about fitting in or getting it right—he just is. And isn't that the dream?We all want to be Snoopy. But most of us walk around feeling like Charlie Brown.

I've noticed this theme popping up in my own writing more than I realized. In The Unfinished Work, I stood on the battlefield at Gettysburg, grappling with Lincoln's call to continue the work of democracy—wrestling with whether we're living up to the sacrifices made there, whether our civic understanding is strong enough to sustain what so many died to preserve. That kind of deep reckoning—questioning whether I'm doing enough as a citizen, whether we're all worthy of what we've inherited—feels very Charlie Brown to me. It's earnest. A little anxious. Overwhelmed by the weight of history and responsibility. But it's also rooted in hope, in the belief that showing up matters even when the task feels impossibly large.

Still, there's a part of me that longs for Snoopy's spirit. His creative energy. His ability to turn a boring afternoon into a full-blown saga. As I look back at older posts—from travel reflections to musings on leadership or family—I see flashes of that spirit. Those are the moments when I'm trying to channel Snoopy. When I let my imagination run, when I let humor or curiosity lead, when I step out of the box long enough to ask bigger questions.

But inevitably, I come back to Charlie Brown. I come back to doubt, to duty, to the desire to do better even when the odds aren't great. And maybe that's okay. Maybe the goal isn't to be Snoopy, but to let his spirit visit us when we need it most—to balance the worry with a little wonder, the failure with some flair.

This tension... surfaced deeply in my Christmas reflections from 2010. I admitted to dreading a certain kind of Christmas—the one filled with "lasts." Last Christmas with all the kids at home. Last Christmas with a true believer before the Elf era began. That felt very much like a Charlie Brown moment: the melancholy, the ache of change, the worry that the magic might fade.

But then came the Snoopy side of that Christmas—the passing of the torch. Inviting my youngest into the quiet fraternity of Christmas elves, just as my mom once did for me. That difficult but hopeful conversation wasn't a moment of loss, but of legacy. We talked about belief—not just in Santa, but in something deeper: the enduring magic of generosity, wonder, and love passed down through generations. That's pure Snoopy—the imaginative spark that turns endings into new beginnings, that celebrates mystery and keeps the magic alive.

And it's the same dynamic in Trains, Presidents, and Baseball, my account of a cross-country road trip with my daughter. What started as a practical move to Philadelphia for medical school became a journey of reconnection. We shared national parks, presidential history, and ballgames, but it was the quiet, in-between moments—the misfires, the museum closures, the unexpected laughs—that brought us back to each other. That felt like Charlie Brown's honest longing for connection paired with Snoopy's joyful improvisation. It reminded me that relationships, like life, don't come wrapped up perfectly—they unfold in fits and starts, with hope and humor intertwined.

All of these reflections—ranging from solemn civic duty to family celebrations and travel adventures—trace the emotional arc between Charlie Brown and Snoopy that runs through my life and writing. They remind me that we don't live fully at either extreme, but somewhere in between. We ache, we aspire, we stumble, we imagine. That's what makes the journey real.

What Schulz understood—and what I'm starting to accept—is that we contain both: the melancholy and the magic. We are Charlie Brown with a little bit of Snoopy inside, trying to break free.

So I'll keep chasing the football. I'll keep pitching no matter the score. I'll keep showing up. And maybe, just maybe, I'll dance on top of the doghouse every once in a while too.