"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.

Theodore and Taylor

The Bride & Groom

Tonight, we come together to celebrate a truly special occasion—the love and commitment of two remarkable people: my son Ted, and his beautiful fiancée, Taylor. As we gather for this rehearsal dinner, I’m overwhelmed with joy and gratitude.

I’m deeply thankful to the Kewleys for raising such a wonderful daughter, and for the warmth and kindness with which they’ve welcomed Ted into their family—as if he were their own. I’m also grateful to Ted’s mom, Amy, for helping raise a young man who has become not only compassionate and full of integrity, but someone capable of loving with his whole heart. And I’m thankful to all of you—family and friends—for being here to honor and support Ted and Taylor, not just tonight or tomorrow, but throughout the beautiful life they’ll build together.

From the moment Ted introduced Taylor to our family, it was clear she was someone special. Her warmth, grace, kindness, and unshakable patience have brightened our lives in ways we never imagined.

As a proud parent, I could tell you countless stories of watching Ted on the baseball field—like his first Little League hit (an RBI triple off Nate Rousey—I still remember Nate cried…), his first home run the next season, or his no-hitter in high school followed by a championship-clinching homer at Arcadia. Later, I watched him pitch the final innings of his college career at LMU during the WCC tournament—moments that filled me with pride.

And there are stories off the field, too. Like the time Amy and I were summoned to the principal’s office in sixth grade—his teacher had accused him of plagiarism. I was indignant—I knew he didn’t plagiarize because I was the one who edited the paper. Unfortunately, I’d used a word that wasn’t yet in his vocabulary. Lesson learned—for both of us!

When Ted decided to move to the East Coast, we spent a memorable week driving across the country—visiting national parks, battlefields, museums, and catching a Cubs game. I’ll always treasure that time. But what stood out most was how eager he was to get to the destination—because Taylor was waiting.

Through all of life’s highs and lows, I was never concerned about Ted finding his way. But that didn’t stop me from worrying all the same. He came to New York without a job or a clear plan—but with Taylor in his heart. That’s when I realized she wasn’t just his girlfriend; she was something more.

Later, when they visited me in California over Father’s Day weekend, I had the chance to really get to know Taylor. Ted, in his infinite wisdom, decided to take one of his groomsmen, Max, to the U.S. Open at Torrey Pines… on Father’s Day. He brought me back a button that read, “My son went to the U.S. Open on Father’s Day and all I got was this button…” But the truth is, he gave me something even better: time with Taylor. And in that time, I saw firsthand what a thoughtful, genuine, and extraordinary young woman she is—and how lucky Ted is to have found someone so special.

As I look at Ted and Taylor together, I’m reminded of love’s power to transform our lives. Their story is a testament to what it means to find not only a partner, but a soulmate—a confidante, a best friend.

Tomorrow, you’ll exchange vows and begin the incredible journey of marriage. As you do, remember to savor each moment, stand beside each other through life’s inevitable ups and downs, and never lose sight of the magic that brought you together. May your love deepen with each passing day, and may you always find comfort, strength, and joy in each other’s arms.

So tonight, let’s celebrate the love that Ted and Taylor share, and the light they bring to all of us. Let’s raise a glass to the beautiful journey ahead.

To Ted and Taylor—may your marriage be filled with laughter, joy, and endless adventure. May you build a life rich in love, understanding, and shared dreams.

Please join me in a toast:

Here’s to a lifetime of happiness, to love that never fades, and to the beginning of forever.

Cheers!

Three Things, One Ending

They say that in the end, only three things matter: how much you loved, how gently you lived, and how gracefully you let go of things not meant for you.

Normally, I'd roll my eyes at something like that — probably scroll past it on social media while muttering something cynical under my breath about inspirational fonts. But this time, it landed differently. Maybe because I’m sitting in the aftermath of another love story that didn't end with a bang, but with the soft unraveling of two people who genuinely tried.

We did love each other. That part, at least, is still true. Somewhere along the way, we carved out a space for each other — one that felt safe and light-filled, even if the world outside was chaotic. There were real moments of joy, partnership, laughter, and a quiet sense of “we’re in this together.” And I believed in it — in her, in us.

But somewhere in the middle of making space, we forgot to keep communicating.

I let the pressure get to me. Work was wild, unpredictable — the kind of stress that shows up in your jaw and your blood pressure and your dreams. And with her between jobs, I felt like I needed to carry it all — to be strong, to figure out a way to financially support both of us without adding to her burden.

So I stayed quiet.

I thought strength meant silence. That not telling her how hard it was would somehow protect her. I see now that it didn’t protect either of us. Instead, it just widened the distance. Turned connection into assumption, love into guesswork.

And she was carrying her own weight — heavy and invisible. Her frustration built like steam behind a closed door. The more stressed she got, the more it seemed like everything set her off: the kids, the dogs, the state of the world, and sometimes me. Instead of talking to me, she started talking at me. Or past me. Or not at all.

When things were hard, she began to compare me to her ex — expecting that I would let her down in the same ways, bracing for betrayals I hadn’t committed. And I couldn’t convince her otherwise. I didn’t always know how to show up in those moments. Sometimes I got defensive. Sometimes I just shut down. Sometimes I honestly didn’t know what I’d done wrong — only that I’d disappointed her, again.

So no, we didn’t end because we stopped loving each other.

We ended because we stopped talking.

And that brings me back to that third thing: letting go.

I’m not good at it. I hold on to words said in anger and texts left unanswered. I replay conversations looking for the moment I could’ve done it differently. But I’m trying to be better. To forgive her. To forgive me.

Letting go, I’m learning, doesn’t mean pretending it didn’t matter. It means accepting that it did — and still choosing to release the version of the future I once held so tightly.

So yes, I loved her. And yes, I tried to live gently beside her. And now, I’m trying to let go — not because the love wasn’t real, but because grace demands it. Because if only three things really do matter in the end, then I want to get this one right.

Even if it takes me a little while.