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.
Ask me about my favorite Muppets, and I'll tell you without hesitation: Oscar the Grouch and Cookie Monster. Not Big Bird, despite his gentle wisdom. Not Kermit, despite his earnest leadership. The grouch and the glutton. The cynic and the chaos agent. The two characters who, even at age five, I somehow knew were telling me something important about what it meant to be human.
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've passed on to my own children.
The Grouch's Gift: Permission to Be Real
Oscar the Grouch was revolutionary, though I didn't have the vocabulary for it then. Here was a character who refused to perform happiness. In a world of relentless cheer, Oscar said, essentially, "Some days are garbage days, and that's okay."
He wasn't mean or cruel. He was just... grouchy. Honest about his mood, authentic in his preferences, and completely uninterested in making others comfortable with his state of mind. Oscar taught me that being real was more valuable than being pleasant-a lesson that would prove essential throughout my life.
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 Oscar's perfect counterpart: pure, unfiltered enthusiasm taken to absurd extremes. He didn't just like cookies; he was consumed by them. He made messes. He lost control. He spoke in fractured grammar and sprayed crumbs everywhere, and somehow, this made him more lovable, not less.
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 every Friday for five years, 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. In my willingness to drive cross-country with dogs in a U-Haul, turning a practical move into an adventure. In my decision to volunteer in Faith's computer lab not because I was the most qualified, but because I genuinely loved being there. Cookie Monster showed me that enthusiasm, even when imperfect, creates magic.
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
The art of being lovably flawed became the foundation of my professional life, though I didn't realize it at the time. I built a career as a translator-bridging gaps between different types of people who needed to work together but spoke different languages. My success came not from having all the answers, but from being comfortable admitting when I had questions-and suspecting others did too.
When I started PRSPCT-L it wasn't because I was an expert. It was because I was willing to say, "I don't know everything, but maybe together we can figure it out." That simple acknowledgment of shared uncertainty became one of the field's most valuable resources.
My weekly donut tradition at Caltech exemplifies this approach. Faced with a team drowning in impossible deadlines and technical challenges, I could have brought in motivational speakers or implemented productivity systems. Instead, I brought Foster's Family Donuts every Friday for years. Not because it was strategic, but because it felt right. Because sometimes the most powerful thing you can do is show up with something sweet and say, "I see you."
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 connection.
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.
I hope what you learned from watching me coach Ted's Little League teams, volunteer in your schools, and navigate the various crises and celebrations of family life is 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're 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 or 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.
This is what I hope you carry forward: that being human means being imperfect, and being imperfect can be beautiful. That your flaws, acknowledged and owned, can become sources of connection rather than shame. That showing up as you are-mess, enthusiasm, cynicism, and all-creates deeper relationships than any polished performance ever could.
A Letter to My Children
As I reflect on the decades since those first Sesame Street episodes, I realize that Oscar and Cookie Monster didn't just teach me how to live-they taught me how to love. How to parent. How to build a career and a family and a life worth living.
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.
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 quite 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.
The Inheritance of Authenticity
This is what I hope 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 to 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.
