The Art of Being Lovably Flawed

What Oscar the Grouch and Cookie Monster Taught Me About Building a Life

I am part of the Sesame Street generation, not the nostalgic, "remember when" generation, but the actual first one. I was there for the beginning, sitting cross-legged in front of our wood-grain Zenith television in 1969, watching something that had never existed before: a show that talked to kids like we had brains, that mixed education with pure silliness, and that populated a neighborhood with characters who were unapologetically, authentically themselves.

Oscar the Grouch and Cookie Monster. Those were my guys. Don't get me wrong - Big Bird was sweet and Kermit has great moments. But Oscar? Oscar got it. Some days you just feel grouchy and that's that. And Cookie Monster, the way he'd completely lose his mind over cookies, cracked me up. Still does.

Decades later, as I reflect on the life I've built, the career choices I've made, the way I've tried to parent, the relationships I've formed, I realize how profoundly those fuzzy philosophers shaped my understanding of what it means to show up authentically in the world. More importantly, they taught me lessons I hope I have passed on to my own children.

The Grouch's Gift: Permission to Be Real

I didn't know why I loved Oscar so much back then, but looking back, it makes perfect sense. Every other character on TV was happy all the time - big smiles, cheerful voices, everything's wonderful! Oscar was the only one who said, 'You know what? Today sucks and I'm not pretending otherwise.'

He wasn't a jerk about it. He wasn't trying to ruin anyone else's day. He just sat in his trash can, owned his bad mood, and didn't apologize for it. That was huge for a little kid to see - that you didn't have to be sunshine and rainbows every single day to be okay.

When I found myself translating between temperamental programmers and impatient fundraisers, Oscar's influence was there. When I chose to sit in the political middle seat while others retreated to comfortable extremes, that was Oscar's gift at work, when I admitted to my team that I was struggling after losing my dear friend and colleague Yoko, rather than putting on a professional mask, I was practicing what the grouch had taught me: that authenticity creates deeper connections than any performance ever could.

To my children, I hope you've learned this lesson through watching me navigate both my good days and my difficult ones. When I write about feeling like Charlie Brown most days instead of pretending to be someone more optimistic, that's not pessimism, that's honesty. And honesty, even when it's not pretty, builds trust in ways that false cheer never can.

Cookie Monster's Chaos: The Power of Unfiltered Enthusiasm

Cookie Monster was totally different from Oscar. Oscar sat there being grouchy, and Cookie Monster went gaga over cookies (well, mostly cookies). He'd shove them in his mouth, crumbs flying everywhere, half of the cookies ending up on the floor... 'om nom nom nom.' It was always complete chaos, of course, that's what made it funny. Most characters would eat cookies politely. Cookie Monster attacked them like his life depended on it, and somehow that made him impossible not to love.

Cookie Monster taught me that passion doesn't have to be polite, a lesson that became the foundation for some of my most meaningful choices. When I decided to bring donuts to a struggling database conversion team on Fridays, that wasn't strategic planning. That was Cookie Monster-level enthusiasm for simply showing up and caring about people.

I see his influence in my obsessive Cubs fandom that defies all mathematical logic. I see it in my willingness to drive cross-country with the dogs in a U-Haul, turning a practical move into an adventure. Or volunteering in Faith's computer lab, even though I probably wasn't the best choice, I just really wanted to be there. Cookie Monster taught me that caring too much about something beats not caring at all, even if you make a mess doing it.

Kids, you've seen this in action, whether it was our elaborate Christmas traditions born from last-minute improvisation, or my insistence on keeping score at your baseball games when everyone else was just watching casually. What I hope you learned is that it's better to care too much about the things that matter to you than to care too little about anything at all.

Building a Career on Beautiful Disasters

I built my career primarily as a translator. Not like French to English - more like translating between programmers who think in code and database schemas, and regular people who just wanted the computer to spit out useful information. I got good at taking what the tech guys were saying and explaining it in a way that made sense to everyone else, and vice versa. Turns out there aren't that many people who can do both sides of that conversation.

When I started PRSPCT-L, it wasn't because I was some expert. I just figured if I was confused about something, probably other people were too. That simple acknowledgment of shared uncertainty became one of the field's most valuable resources.

My weekly donut tradition at Caltech exemplifies this approach. My team was getting killed by deadlines and technical problems that seemed impossible to solve. I probably should have taken a more official approach, brought in consultants, reorganized workflows, or whatever managers are supposed to do. Instead, I started bringing donuts from Foster's every Friday. For years. This wasn't some grand strategy; I just thought people needed something good in their week, and donuts seemed like the easiest way to do that.

That tradition worked not despite its simplicity, but because of it. Like Cookie Monster's single-minded pursuit of cookies, the gesture was so genuine, so unfiltered, that it cut through workplace cynicism and created real connections.

Parenting Through Imperfection

These same principles shaped how I tried to raise you. When Faith worried about how Santa would find us in California without a chimney, I didn't have a perfect answer ready. So, we invented Magic Reindeer Feed and Santa's Magic Key traditions born from improvisation and sustained by enthusiasm rather than expertise.

When my attempts to get Kailey to eat everything on her plate led to the notorious episode of hiding sweet potatoes in milk, I learned that being lovably flawed meant acknowledging my mistakes, laughing at them (eventually), and adjusting course. Some of my best parenting moments came not from having all the answers, but from being willing to figure things out together with you.

The St. Nicholas tradition we maintained wasn't about creating perfect memories; it was about showing up consistently, year after year, with both celebration and honest reflection. The "however" paragraph in St. Nick's letter, acknowledging that we all have room to grow, became a family touchstone because it made space for the full spectrum of human experience.

Through watching me coach Ted's Little League teams, volunteering in your schools, and navigating the various crises and celebrations of family life, you've come to realize that parents don't have to be perfect to be good. In fact, the opposite might be true: perfection creates distance, while lovable flaws create connection.

The Wisdom of Messes

What Oscar and Cookie Monster understood and what I've tried to practice throughout my life is that our flaws aren't bugs in the human operating system. They are features. The grouchiness that makes Oscar lovable is the same quality that allows him to cut through false cheer and speak uncomfortable truths. Cookie Monster's chaos creates joy precisely because it's so genuinely enthusiastic.

When I lost my temper on the baseball field, made mistakes in parenting, or had relationships that didn't work out, I wasn't proud of those moments. But they were real. And in that authenticity, followed by genuine apology and growth, I hope you learned something more valuable than you would have from a father who never made mistakes.

Look, I hope you guys figure out what took me way too long to learn: nobody's got it all figured out, and that's actually okay. Your weird quirks and the stuff you're not great at - that's not something to hide. People connect with real, not perfect. Show up as whoever you actually are, even if you're having a bad day or you're obsessing over something stupid. That's way better than pretending to be someone you're not.

Looking back now, I think Oscar and Cookie Monster taught me how to be a decent person. Sounds ridiculous when I say it out loud - two puppet characters on a kids' show. But they showed me it was okay to be grumpy sometimes and to get way too excited about the things you care about. That's pretty much how I've tried to live ever since.

They taught me that authenticity isn't just more honest, it's more effective. More connecting. More human. And maybe, if we're lucky, more fun.

A Letter to My Children

Kailey, Ted, and Faith: you've watched me practice this art your entire lives. You've seen me succeed and fail, show up and stumble, get enthusiastic about things that probably didn't deserve so much enthusiasm. What I hope you've learned is that this is what love looks like in practice, not perfection, but presence. Not having all the answers, but being willing to ask the questions. Not avoiding mistakes, but owning them, learning from them, and moving forward together.

The art of being lovably flawed isn't really about being flawed at all. It's about having the courage to be seen as you are, the wisdom to know that everyone else is just as beautifully imperfect as you are, and the grace to build relationships and a life around that fundamental truth.

I hope that I'm passing on to you not a roadmap to perfection but permission to be gloriously, beautifully, lovably yourselves. To care deeply about the things that matter to you, even when others don't understand. To be grouchy when you need to be grouchy and enthusiastic when something deserves your enthusiasm. To make messes in pursuit of what you love and clean them up with humor and grace.

In a world that increasingly rewards performance over presence, I hope you'll remember what those fuzzy philosophers taught us: that the strongest relationships aren't built on mutual admiration of each other's perfection, but on shared acknowledgment of each other's beautiful imperfections.

Because in the end, the best version of yourself isn't the most polished version, it's the most honest one. And honesty, even when it's messy, even when it makes mistakes, even when it sprays metaphorical cookie crumbs everywhere, is always worth more than the most perfect performance.

Even if it makes a mess.

Especially if it makes a mess.

Why rules matter...

(And Why Arguing About Them Usually Doesn't)

Sometimes the best way to change someone's mind isn't to change it at all.

I've been thinking a lot over the last few months about rules, not the bureaucratic, soul-crushing, DMV-ish kind that make you want to set your employee handbook on fire, but the deeper question of why we need them in the first place. And more importantly, what happens when we try to convince people to follow them by doing exactly the wrong thing?

It started with a conversation I had with a former colleague at Boise State who was frustrated about vaccine hesitancy in our community. Sound familiar? She'd been getting into fights with her family and friends about politics. Big fights. Showing up with printouts from news sites and research studies, she believed that if she could just walk them through the facts, they'd finally get it. Her efforts never worked and actually made everything worse. The harder she tried to convince them, the more they shut down.

"I don't understand it," she confided in me. "The science is clear. Why won't they just listen to reason?"

I thought about the experience Adam Grant wrote about in his 2021 New York Times opinion piece The Science of Reasoning With Unreasonable People, where his stubborn friend, the one who refused to vaccinate his children, no matter how many myths Grant debunked. Grant, an organizational psychologist, eventually realized something profound. When we try to change someone's mind by preaching about why we're right and prosecuting them for being wrong, we often end up strengthening the very beliefs we're trying to change.

The Logic Bully Problem

Here's the thing about being right: it can make you insufferable.

I've been guilty of this myself more times than I care to admit. I do this all the time. Someone says something I think is completely wrong - about COVID, or politics, or even just which way to drive somewhere - and I jump in with all my evidence. I start pulling up articles on my phone, explaining why they're mistaken, basically trying to beat them over the head with facts until they give up.

Turns out that doesn't work. At all. At least not the way we think they do.

When we attack someone's position head-on, we trigger what psychologists call the "psychological immune system." Just like a vaccine inoculates the body against a virus, the act of resistance fortifies the mind against future attempts at influence. We make people more certain of their opinions, not less.

The Motivational Interviewing Alternative

There's a better way, and it comes from an unlikely source: addiction counseling.

Decades ago, psychologists working with substance abuse developed a technique called motivational interviewing. Instead of trying to force people to change, they learned to help people find their own intrinsic motivation to change. The approach is deceptively simple: ask open-ended questions, listen carefully, and hold up a mirror so people can see their own thoughts more clearly.

It's not manipulation, it's genuine curiosity about how someone thinks and what matters to them.

Grant eventually tried this approach with his vaccine-hesitant friend. Instead of asking why he opposed COVID vaccines, Grant asked how he would stop the pandemic. Instead of debating the merits of immunization, he listened for moments when his friend expressed any ambivalence, any "change talk," and gently explored it.

The breakthrough wasn't that his friend suddenly signed up for a shot. It was that he admitted his views could change, that this wasn't a "black-and-white issue." That's not nothing. That's everything.

Why Rules Actually Matter

This connects to something more profound about why we have rules in the first place. Rules aren't just arbitrary constraints imposed by killjoys who hate fun. At their best, they're collective agreements that make cooperation possible.

Think about it: every time you drive through a green light without slowing down, you're trusting that everyone else has agreed to follow the same set of rules. Every time you put money in a bank, use a credit card, or sign a contract, you're relying on systems of regulations that make complex societies function.

But here's the paradox: the more we need people to follow rules, the less effective it becomes to simply tell them to follow rules.

I recently re-learned this the hard way when I tried to convince colleagues at my new employer that a workplace policy they had implemented was overly complicated, burdensome, and failed to follow Financial Accounting Standards Board (FASB) standards. There was one colleague in particular, let's call him Dave, who seemed to take personal offense every time I brought up FASB. At first, I approached it like a prosecutor: "Dave, this is the standard. Here's the logic behind it. We did it this way at my previous employer. End of discussion."

The more I cited FASB and invoked my previous employer's institutional processes, the more creative Dave became in his resistance and explanations. "Well, our auditors approved this approach." "The previous CFO set this up for a reason." "We've been doing it this way for years without problems." "Your old company might have different circumstances." Each response felt like he was building a fortress around the status quo, brick by defensive brick.

I was ready to write Dave off as just another change management "anchor," a DMV-ish cog in the University bureaucracy threatened by the "new guy's" ideas, when a colleague suggested I actually talk with him instead of at him. So I asked Dave for a meeting (in his office, naturally) and instead of lecturing him about past history and compliance, I asked him how the university developed this procedure.

It turned out Dave wasn't anti-FASB or resistant to proper accounting standards at all. The procedure I was critiquing had been his brainchild during a particularly chaotic period when the previous CFO had left suddenly and the auditors were breathing down their necks. He'd cobbled together a solution that worked in the crisis. While he knew it wasn't perfect, it had kept the university compliant during a vulnerable time. When I kept invoking "best practices" from my previous employer, he felt like I was dismissing not just the procedure, but the context that created it and the effort he'd put into keeping things afloat.

Once I understood the history and his actual concerns about changing mid-stream, we could work together on a transition plan. Dave became one of my strongest allies in implementing the new procedures, not because I'd convinced him with FASB citations, but because he felt like his institutional knowledge and past efforts were valued in creating the solution.

The Stag Hunt Principle

Game theorists have a concept called the "Stag Hunt" that explains this beautifully. Imagine a group of hunters who can work together to catch a stag (which feeds everyone) or split off individually to catch rabbits (which will only feed themselves). If everyone cooperates, everyone benefits. But if too many people defect to chase rabbits, the whole system breaks down.

The tragedy isn't that some people are selfish; it's that when trust erodes, even well-meaning people start making choices that undermine the collective good.

Rules work when people buy into them. And people buy into them when they feel heard, understood, and respected, not lectured, shamed, or bulldozed.

This reminds me of something I know intimately as a lifelong Cubs fan: the difference between loyalty born from argument and loyalty born from love.

For decades, people have tried to convince Cubs fans to abandon their team using perfectly logical arguments. "Look at their record!" "They haven't won anything!" "You're wasting your time and money!" The more people told us the Cubs sucked, the more we'd defend them. 'This is our year!' we'd say, every single year, despite all evidence to the contrary.

But nobody becomes a Cubs fan because someone showed them a spreadsheet. You stick with the Cubs because your dad did, or because you love Wrigley, or because misery loves company. It's not a logical decision. It's about tradition, hope, community, and something ineffable that connects us to Wrigley Field, to our fathers and grandfathers, to the beautiful futility of believing that this might be the year.

You can't logic someone into, or out of, being a Cubs fan, and you can't logic someone into following a rule they don't believe in. Both require something deeper than facts; they need trust, connection, and the sense that your perspective matters.

Most diehard Cubs fans don't come from sabermetricians proving (or disproving) the talent of the team. They come from tradition, and more recently, they come from the team finally honoring what we've always believed was possible. Sometimes the best way to change someone's mind is to show them you understand why they think the way they do.

What This Looks Like in Practice

So what does this mean for those of us who care about rules, standards, and collective responsibility?

First, get curious instead of certain. Instead of asking "How can I convince them they're wrong?" try asking "What would have to be true for their position to make sense to them?"

Second, listen for ambivalence. Most people who seem completely rigid actually have some uncertainty lurking beneath the surface. Your job isn't to create that uncertainty; it's to notice it when it emerges and make space for them to explore it.

Third, focus on shared values. Most people want the same stuff you do; they just disagree on how to get there. That parent who won't vaccinate their kid? They're not trying to hurt anyone. They're scared and trying to protect their child, same as you would. The guy who won't wear a mask at work isn't necessarily being selfish - maybe he's worried about looking weak, or maybe he thinks the whole thing is overblown. Start with what you both care about, not where you disagree.

Fourth, resist the prosecutor's impulse. When someone says something you disagree with, your first instinct might be to pounce. Don't. Get curious. Ask them to say more. You might be surprised by what you learn.

The Bigger Picture

None of this means we should abandon our convictions or stop advocating for what we believe is right. It means we should get better at it.

Rules matter; they make civilization possible. But rules without buy-in become DMV-ish bureaucracy at best and authoritarianism at worst. If we want to live in a society where people choose to cooperate rather than being forced to comply, we need to get better at the delicate art of persuasion.

That starts with remembering that the person across from us is a human being with their own fears, hopes, and reasons for believing what they believe. Even when those reasons seem entirely wrong for us.

Especially then.

---

The next time you find yourself wanting to logic-bully someone into agreement, try this instead: take a breath, get curious, and ask them a question you genuinely want to hear the answer to. You might not change their mind. But you might change the conversation. And sometimes, that's precisely where change begins.

"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 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 red staplers and 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.

A few weeks later, I decided to leave my job and try something new. But I'm glad we had that lunch. Watching everyone crack up over terrible movie quotes and argue about whether the special effects were actually good reminded me of why I liked working with these people in the first place.

If you catch yourself making some reference you think everyone will get, maybe don't assume they will. Ask if they've seen it. Better yet, watch it together sometime. You might be surprised by what you learn about each other. 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, 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 before he ever 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.

But the real evil in this movie isn't any person - it's the TPS report. You know, the one with the cover sheet that everyone keeps forgetting, and then eight different managers have to send you emails about it. 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). Those old green-bar computer printouts were ugly as hell, but at least they were honest about it. Now we spend half our time making reports look pretty instead of making sure they actually say something useful. Office Space nailed that - it's not just that there's too much paperwork, it's that none of it has anything to do with getting actual work done. 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. Perhaps because we’ve been them.

Office Space bombed when it first came out, but then everybody started watching it on DVD and quoting it at work. Now you can't say the word 'flair' without someone doing that whole Jennifer Aniston voice thing. The movie came out twenty-five years ago, but I swear I've worked at that exact office. Different company names, but the same awkward meetings and bizarre office traditions that somehow make perfect sense at the time. 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, from his first Little League hit (an RBI triple off Nate Rousey, I still remember Nate cried…), to his first home run the following season. Or about 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, all 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 that he hadn’t plagiarized because I was the one who edited his paper. Unfortunately, I 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. We visited national parks, battlefields, museums, and caught a Cubs game. I’ll always treasure that time. However, what stood out to me 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.