"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.

The Transparency Tightrope: Leading with Clarity Without Losing Focus

In today’s workplace, “transparency” has become a buzzword—often invoked with the best of intentions, but not always with a shared understanding. As senior managers, we’re frequently asked to walk a fine line: be open, be honest, be accessible—but also, deliver results, protect strategic priorities, and maintain momentum.

But what happens when transparency is interpreted as “tell me everything, all the time”?

This is the tension many leaders face. The desire for openness can sometimes morph into a culture of over-disclosure, where colleagues expect to be looped into every decision, every nuance, every draft. And while inclusivity is vital, so is clarity of purpose.

Here’s how I think about navigating this balance:

1. Define What Transparency Is—and Isn’t

Not long ago, a few team members expressed frustration that they hadn’t been informed about a personnel change until after the action had been finalized. Their concern was rooted in a genuine desire to feel included and informed. But it also revealed a common misconception: that transparency means real-time access to every decision as it unfolds.

I reflected on that moment a lot. The truth is, there are times when we simply can’t share everything—especially when it involves sensitive personnel matters. Transparency doesn’t mean violating confidentiality or prematurely disclosing decisions that are still in motion. It means sharing what we can, when we can, with honesty and context.

This tension is often amplified by generational expectations. For example, younger colleagues—raised in an era of open-source collaboration and instant updates—may expect a level of visibility that feels excessive to more seasoned professionals who were trained to compartmentalize information until it’s fully baked. Neither perspective is wrong—but they do require calibration.

Transparency, in this sense, is not about omniscience—it’s about trust. It’s about ensuring that when we do communicate, it’s with clarity, purpose, and respect for all involved.

2. Anchor Communication in Purpose

When we communicate, we should ask: What does this person need to know to do their job well? Not: What do I know that I haven’t shared yet? This shift keeps transparency aligned with action.

I remember a time when we rolled out a new reporting tool. A Gen Z analyst asked why they hadn’t been included in the early planning meetings. Meanwhile, a Gen X team lead said, “Just tell me when it’s live.” Same project, different expectations. We realized we needed to clarify not just what we were doing, but why certain people were involved at different stages.

Purpose-driven communication helped us bridge that gap. We didn’t need to loop everyone into every meeting—we just needed to explain the roadmap and how each role fit into it.

3. Use Transparency to Build Trust, Not Noise

Trust grows when people feel informed, not overwhelmed. That means being honest about challenges, clear about direction, and intentional about what’s shared. Oversharing can dilute focus and create confusion.

This is especially important in multigenerational teams. Millennials may interpret silence as secrecy, while Boomers may see constant updates as a distraction. The goal is to build a rhythm of communication that respects both preferences.

A few years ago, we tried a “radical transparency” experiment by opening up all project dashboards to the entire department. Within weeks, we were fielding questions about line items that had nothing to do with most people’s work. It created anxiety, not alignment.

We learned that transparency without context is just noise. Now, we focus on curating what’s shared—providing the right level of detail for the right audience. That’s what builds trust.

4. Create Channels, Not Floodgates

Structured updates, regular check-ins, and accessible documentation can satisfy the need for visibility without turning every conversation into a town hall. Transparency thrives in systems, not in spontaneity alone.

During a cross-generational team project, we noticed that our younger staff preferred real-time updates in Teams, while others wanted a weekly summary email. We ended up creating a shared OneNote with key decisions and action items, updated weekly, and linked in both formats.

It wasn’t flashy, but it worked. Everyone had access to the same information, in the way they preferred to consume it. That’s the kind of channel-building that supports sustainable transparency.

And those systems should be flexible enough to meet people where they are. A Gen Z team member might prefer a shared dashboard or real-time doc, while a Gen X colleague might appreciate a weekly digest. The medium matters as much as the message.

5. Model the Balance

As leaders, we set the tone. When we’re thoughtful about what we share—and when—we teach others to do the same. We show that transparency is a tool, not a trap.

I once had a direct report who was hesitant to hold back information, fearing it would be seen as secretive. We talked about the difference between being transparent and being indiscriminate. I shared how I decide what to communicate: Is it actionable? Is it timely? Is it respectful of others?

That conversation helped them find their own balance—and it reminded me that modeling transparency isn’t just about what we say. It’s about how we think.

In the end, transparency isn’t about knowing everything. It’s about knowing enough to move forward together—with empathy, intention, and respect for the diverse ways our colleagues process information.

The Parapet Moment: Leadership, Courage, and the Duty to Stand

159 years later, reflecting on the Battle of Fort Stevens and the leadership lessons we still need

I have an Abraham Lincoln related photograph—not unlike the one I've shared before of my children at Gettysburg—that captures the VI Army Corps Monument, a commemorative stone and marker at Fort Stevens in Washington, D.C. The earthworks at the fort are modest now, hemmed in by suburban streets and the ordinary rhythm of modern life. But standing there, you can almost feel the weight of what happened on this sweltering July day in 1864, when Lincoln became the only sitting president to face enemy fire.

VI Army Corps Monument

Today marks 159 years since that remarkable moment, and I've been thinking about it more than usual—particularly as we approach the 160th anniversary next year and head into another presidential election season. The story of Fort Stevens isn't just about bullets and bravery—it's about leadership under pressure, the courage to stand when others might flee, and the delicate balance between personal risk and public duty. In a political climate where leadership often feels performative rather than principled, Lincoln's example on that parapet feels both distant and urgently needed.

When Leaders Must Stand

On July 12, 1864, Abraham Lincoln stood on the parapet of Fort Stevens, five miles north of the White House, watching Confederate forces under General Jubal Early probe the defenses of the nation's capital. The stakes could hardly have been higher. Early's raid represented a last-ditch Confederate attempt to disrupt Union supply lines, weaken Northern morale, and potentially capture Washington itself.

When a Confederate sharpshooter's bullet struck an officer standing near the president, those around Lincoln urged him to take cover. Whether it was General Horatio Wright who politely asked him to withdraw, or a young Oliver Wendell Holmes Jr. who allegedly shouted "Get down, you damn fool!", the message was clear: the president's life was in immediate danger.

But Lincoln had come to Fort Stevens for a reason. As historian Charles Bracelen Flood observed, "It became a remarkable scene: the commander-in-chief at the head of his marching soldiers and a great crowd of civilians, all headed out of the city along a wooded road toward the thunderclaps of cannon fire." Lincoln understood that leadership sometimes requires physical presence—that showing up, even at personal risk, sends a message no speech can convey.

This wasn't recklessness. It was calculated courage. Lincoln knew that his presence at Fort Stevens would inspire the soldiers defending the capital and reassure a frightened civilian population. As one of his closest confidantes, Orville Browning, later recorded, "The President is in very good feather this evening. He seems not in the least concerned about the safety of Washington." Lincoln's calm in the face of danger became a source of strength for others.

As we head into 2024—an election year that promises to test our democratic institutions once again—Lincoln's example feels particularly instructive. In an era when political leadership too often means retreating to safe spaces, echo chambers, and carefully managed appearances, the image of a president willing to share genuine risk with those he leads offers a stark contrast.

The Moral Turning Point

What happened at Fort Stevens went beyond military tactics. Union Colonel John McElroy later called it "the Moral Turning Point of the War," arguing that the successful defense of the capital restored Northern confidence in multiple ways: economically, politically, and spiritually.

The battle inspired Americans' confidence in the Union economy—the value of government-backed currency rose from 35 cents to 48 cents after the victory. More importantly, it demonstrated that the Union could protect its most sacred symbols and institutions. As McElroy explained, "The soldiers of the North, while fighting for the preservation of the Union, always had on their hearts the capital of their country, and they fought that the government might live."

The defense of Fort Stevens represented something larger than military victory—it was a defense of democratic governance itself. Lincoln's willingness to share in the danger, to stand with his soldiers rather than retreat to safety, embodied the kind of leadership that democracy requires: present, accountable, and willing to bear the consequences of collective decisions.

The Forgotten Hero

But perhaps the most compelling lesson from Fort Stevens comes from someone who received no official recognition that day. Elizabeth Thomas, a free Black woman whose property was requisitioned by the Union Army for the fort's construction, not only lost her home and livelihood but may have saved Lincoln's life.

According to historical accounts, when Thomas saw Lincoln standing exposed on the parapet, she "yelled to the soldiers standing near him, 'My God, make that fool get down off that hill and come in here.'" Her quick thinking and fearless advocacy—shouting at the President of the United States to take cover—exemplifies the kind of active citizenship that democracy depends upon.

Years earlier, when Union soldiers had demolished her home to build the fort, a "tall, slender man dressed in black" had consoled her with the words, "It is hard, but you shall reap a great reward." That man was Lincoln himself. The "great reward" may indeed have been the opportunity to save his life—and with it, the future of the nation.

Thomas's story reminds us that citizenship isn't just about voting or holding office—it's about the willingness to speak truth to power, even when that power towers above you. Her courage that day was no less significant than Lincoln's decision to stand on the parapet in the first place.

Leadership Lessons for Today

The Battle of Fort Stevens offers three enduring lessons about leadership and citizenship that feel particularly relevant as we face our own civic challenges:

• First, presence matters. Lincoln could have monitored the battle from the safety of the White House, receiving reports and issuing orders from a distance. Instead, he chose to be where the work was being done—sharing the risk, demonstrating commitment, and inspiring others through his example.
• Second, moral courage is contagious. Lincoln's willingness to stand firm in the face of danger gave strength to others. When leaders demonstrate genuine courage, it creates permission for others to act courageously as well.
• Third, democracy thrives on unlikely heroes. The most important voice at Fort Stevens that day may not have belonged to the president or his generals, but to a Black woman who had already sacrificed her home and still found the courage to protect the man who embodied the Union cause.

Standing on Our Own Parapets

We may not face Confederate sharpshooters, but as we approach both the 160th anniversary of Fort Stevens and the 2024 presidential election, we face our own version of Early's raid—challenges to democratic norms, institutions under pressure, and a citizenry that sometimes seems more interested in retreating to safety than standing firm for shared principles. The question isn't whether we'll face moments that test our civic courage, but whether we'll be ready when they come.

The lesson of Fort Stevens isn't that leaders should seek out unnecessary danger, but that they should be willing to share in the risks that democracy entails. That means showing up for difficult conversations, defending unpopular but necessary truths, and remaining present even when it would be easier to retreat to the safety of like-minded communities. As we evaluate candidates and platforms in the coming election cycle, perhaps we should ask not just what they promise to do, but whether they demonstrate the kind of leadership that shows up when it matters most.

And for the rest of us—those who may never hold high office but whose voices matter just as much—Elizabeth Thomas stands as a powerful reminder that speaking up isn't just a right; it's a responsibility. Democracy doesn't preserve itself. It requires ordinary people doing extraordinary things: running for school board, speaking at town halls, volunteering for campaigns, or simply refusing to stay silent when they see something that threatens the common good.

The Unfinished Work Continues

Today, Fort Stevens remains a humble earthwork that once hosted the only moment in U.S. history in which a sitting president faced direct and purposeful gunfire from an enemy. It's a quiet place now, visited more by joggers than pilgrims. But as we mark the 159th anniversary of that July day and look ahead to next year's milestone and the choices that await us in 2024, the lessons it offers about leadership, courage, and active citizenship remain as relevant as ever.

Lincoln's decision to stand on that parapet—and Elizabeth Thomas's decision to yell at him to get down—remind us that democracy isn't a spectator sport. It requires leaders willing to share in the dangers they ask others to face, and citizens willing to speak truth even to the most powerful among us. As we approach an election that will test these principles once again, we might do well to ask ourselves: Are we prepared to stand on our own parapets when the moment demands it?

The parapet moment comes for all of us eventually—that moment when we must choose between safety and service, between retreating and standing firm. When it comes, may we find the courage that Lincoln and Thomas showed on that July day in 1864: the courage to stand where we're needed, to speak when silence would be safer, and to remember that the work of democracy is never finished—it just passes from one generation to the next, one choice at a time.

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The lessons of Fort Stevens remind us that courage isn't the absence of fear—it's the willingness to act in spite of it. As we mark 159 years since that remarkable day and prepare for both the 160th anniversary and another presidential election, we need more leaders willing to stand on the parapet and more citizens brave enough to tell them when they're making dangerous mistakes. The republic they defended that day in 1864 still depends on both.