There were so many good things for the Schlaff family this year! The biggest event of the year was Ari’s Bar Mitzvah. Ari did so incredibly well leading the service and chanting Torah! We were blessed to have so many friends and family with us to celebrate. Overall, it was a great year filled with family, friends, and fantastic trips. Oh, and a couple of hard falls, but more on that below.
I’ve split this update into two parts. First is our family update. That part’s filled with pictures. It’s the part that most people read. Then, in Part 2, for the truly interested, I’ve got some wonderful things in store for you. I’ve finally finished my book! I’ll tell you more about my book Peculiar: Lessons from Amazon’s Leadership Principles. I’ve also released a new Substack called AI for Poets about using AI to become more human. Then I’ll give you a summary of what I’ve written in my blog this year and show you how you can be more fulfilled when you stop chasing happiness.
Let’s get to it!
Part 1: The Year In Review
Ari’s Bar Mitzvah
This fall, we celebrated one of the most meaningful moments of our lives: Ari’s Bar Mitzvah. It’s hard to put into words what it feels like to watch your son stand before your entire community and step into adulthood, and to have friends and family take time out of their busy lives to pause and celebrate with us.
Ari did such a fantastic job. He led the service, read Torah, and delivered his D’var Torah with a voice that was loud, clear, and thoughtful. For his D’var Torah (literally “word of Torah”), Ari studied with our friend Doron to craft a message that was uniquely his. This makes sense because his key lesson is that Torah “is not in heaven.” It’s not distant or unreachable. It’s here with us, in our everyday lives.
Ari and Doron (Ari’s Study Buddy for the D’var Torah)
Ski Vacations
We went on some wonderful ski trips this year. We went to Stratton with the Smith-Blanchards and Oppenheims, then to Northstar in Tahoe with the Liebmans. You’ll notice that I’m not skiing in any of these pictures. More about that in the Abigail and me section below.
Stratton with the Smith-Blanchards
Roasting Marshmallows with the Liebmans in Tahoe
Celebrating Abigail’s Birthday in Tahoe
Abigail and the Boys at Northstar in Tahoe
Family Vacation with the Schlaffs
We had some wonderful vacations and staycations with my parents and sisters. We had a fantastic end-of-year trip to Mexico with everyone, where Ari even got his own teepee in the room. The four of us went on a lovely trip to Aruba with my parents. Back home, we were lucky enough to have my Canadian sister and her family in town to explore the city a bit.
The Schlaff Family in Mexico
Ari in his Teepee in our Mexican Hotel Room
In Aruba with Robert’s Parents
At the Islanders Game with Our Canadian Family
Road Trip!
We took another road trip to visit Abigail’s parents in Tennessee. After consultation with the kids, we’ve made the decision to fly in the future rather than take 700-mile-long drives. Since this was our last cross-country road trip for a while, we wanted to make it count—taking in all that is America along I-81, from culture to roadside attractions. On the drive, we made a brief detour to visit Pennsylvania’s capital, Harrisburg, and had dinner across the street from a beautifully lit Capitol building. After 10 hours of anticipation, we finally reached our chosen roadside attraction: a large (though not nearly as large as we’d imagined) statue of Optimus Prime outside a Mellow Mushroom Pizza in Roanoke, VA. But the highlight of our road trip was three stops at Buc-ee’s, the legendary rest stop I featured in Welcome to Buc-ee’s: The Disney World of Gas Stations.
Blake in Harrisburg, PA. in Front of the Capitol
The Boys and Me with the Giant Optimus Prime
Ari and Me at Buc-ee’s with Buc-ee the Beaver.
Visiting the Zuckers in Knoxville
At the end of our road trip was the real treat: spending time with Abigail’s parents. We had a great time in Knoxville, going to a Knoxville Smokies game in the new stadium downtown, visiting a working dairy farm for some fresh grilled cheese, and visiting the Lost Sea, an underwater lake. Jeanne even made us a real Thanksgiving dinner because she knows it’s my favorite—even though we were visiting in August.
Watching a Game Between the Tennessee Smokies and the Montgomery Biscuits
Eating Fresh Grilled Cheese and Drinking Fresh Ice Cream Milkshakes at Sweetwater Farm
Visiting The Lost Sea
The Boys
Welcome to the boys’ section! Ari wants to be “An Engineer” when he grows up. Blake is excited for a future where he wants to “Make a Lot of Money.” These are the same goals as last year, and we are impressed with their consistency.
The Boys Through the Years (Click to Expand It)
The Boys at Camp
Ping Pong at the Bar Mitzvah
Blake
Blake is thriving as a sophomore at Millennium High School, a New York City public school located on floors 11 to 14 of the old ITT building at 75 Broad Street, across from the old Goldman Sachs headquarters. He’s really taken to swimming—his coach consistently praises him as a model swimmer and leader on the team, which makes us incredibly proud. He also earned his lifeguard certification and plans on getting a lifeguarding job after winter break.
The transition from Shefa—a middle school focused primarily on teaching reading without traditional grades—to a rigorous high school hasn’t been easy. At Millennium, late homework means a zero, even if you’re in a group and someone else misses the deadline. Blake rose to the challenge, receiving an award for Academic Commitment in History!
He recently said, “It’s really not that hard to do well in school if you listen to what the teacher wants and then you do it.” Even more impressive was his observation that “It’s not that hard to be popular”—something, as you know, only a popular teenager would say. And he’s managed this while standing proudly by his beliefs, even when those ideas are different from his peers.
During the Hora
Receiving the Academic Commitment in History Award
Swimming at Camp
An Intentionally Bad Haircut (the R9 Haircut) Before Intercamp Games
Ari
Ari’s having a really good year in eighth grade at Booker T. Washington Middle School, MS 54. This is the same school that the fictional Percy Jackson attended. It’s one of the most rigorous public schools in New York City, and we are so happy that this school was such a great fit for him.
He’s doing great in school, and he plays as hard as he works. He wakes up at 6AM to play soccer, hockey, and frisbee before school, then plays more soccer at lunch. After school, it’s varsity ultimate frisbee, math team, tabletop games, ping pong, and an E-Sports team where he plays Super Smash Bros. against kids at other schools.
Whether it’s academics, athletics, or just having fun, Ari tackles everything with enthusiasm and determination. That’s just who he is!
We ended the year healthy, excited, and ready for more—though we had one big bump along the way: Abigail and I both broke bones on ski trips this year.
The ski gods did not look well upon the Schlaff family this year. We book-ended our ski season with broken bones—across two separate trips. We started our ski season at Stratton Mountain with the Smith-Blanchards and the Oppenheims. On the first day of the trip, as we were traversing over to pick up the lift tickets, I managed to break my ankle. It’s a pretty embarrassing story. I broke it before I even got my lift ticket! When I woke up from ankle surgery, I wrote a story where various sitcom characters mocked me for this. Thank you to Mindy & Jason Sickle for picking me up from surgery while Abigail and my parents were all away on trips. Then, I wrote about what I learned in recovery in I’m Not Who I Thought I Was. On the bright side, I was able to get some pretty cool assistive devices. My favorites were a Kneerover scooter to get to work and an iWalk—a peg leg that made me feel like a pirate—to walk around at home.
Standing with My iWalk with the Kneerover Next to Me
With my broken ankle, I travelled across the country to sit in the lodge at Northstar in Tahoe. On the last run of the trip, Abigail, speeding down the trail and searching for the boys, took a flying leap and landed on her shoulder, breaking her humerus. Conveniently enough, she could attend my doctor’s appointments, so we had his-and-hers orthopedist visits. While this was very special, maybe next time we want to spend more time together, we should try his-and-hers massages instead.
For the rest of the year, we fared far better.
After 20 years at Thomson Reuters, Abigail thought it was time for a change. She now has a wonderful new job at Harbor Global, a leading tech consulting firm for the legal industry—think Deloitte for legal. She’s helping law firms deliver better software and client experiences. While she misses her old friends at TR, she’s very excited about the new opportunity, the difference she’ll make to clients, and all that she’s learning.
Abigail and Her Harbor Colleagues
Abigail is still President of the Sisterhood at Habonim (no term limits). She runs a wonderfully fun and productive organization. This year, in addition to their regular events, they are focusing on Mahjong and possibly Canasta, with classes and weekly time for games. It’s been a great success!
My shul duties continue to focus on the L’Chaim committee. The new rabbi, Rabbi Joshua Ben Gideon, has expanded our remit. We now pass out shots of Scotch and Tequila on both Friday evenings and Saturday mornings.
For work, I continue to love my job at JPMorganChase. I’m the head of Product Management and Design for Product Tooling. This year, we were able to integrate Artificial Intelligence into our products to give our customers an AI boost to make their jobs easier. We also gave a number of sessions about AI to teach the organization what we did and how they could do it too.
There’s nothing more rewarding than collaborating with an incredible team to build meaningful products. Hearing feedback like, “You are one of the unique teams that builds products that customers want,” or “Your tools provide immense value and save us so much time!” is a constant reminder of why I love what I do. You can see a glimpse of what we do on JPMorganChase’s Tech Blog. Working with such a talented and dedicated team is truly inspiring, and I’m excited for all we’ll accomplish together in 2026.
With Some of My Team at the Ohio State Fair on a Work Trip
The rest of the year was spent enjoying time with the kids, relaxing at the beach, and seeing friends.
Ari and Me on a School Trip
It’s been a wonderful 2025 for the Schlaff family, filled with work, school, and adventures. The kids are thriving, which makes everything better, and we’re excited to see what 2026 brings. Life might send some unexpected bumps our way, but that just makes the good things even sweeter.
As we say in Judaism, L’Chaim (To Life)! And I look forward to seeing you in real life in 2026! That’s the end of Part 1—the picture-heavy bit. For those of you who want to nerd out, get ready for the next bit where I talk about:
I’ve launched a new Substack, AI for Poets, on how to use AI to be more human
The best of my blog from 2025
The Happiness Paradox: Trying to Be Happier Makes Us Less Happy
Some Fun Things to End With
I look forward to hearing from you soon!
Best, Rob
Part 2: My Thoughts from This Year
Now that we’re alone, away from the picture-seekers, I wanted to give you a special gift. I wrote up a special holiday blog post about an Easter Egg that Aaron Sorkin put into his show Sports Night for his staff. I love these special holiday gifts like Thomas Heatherwick’s Christmas Cards or Improv Everywhere’s Holiday Videos. I try to give you that type of gift every year, and I hope that the 3 or 4 of you who read below the fold enjoy it. In the past, I’ve tried to cram as much as I could into this little missive. But this year I’m keeping the number of sections short. Here’s five things for you:
After many years (and many annual updates), Peculiar has been published! This was such an interesting journey. As you know, I’ve spent my career at big companies. Most of them want to be like Amazon. But it doesn’t work because they don’t understand how Amazon really works. They’ll take some of the concepts that they’d read about and try to implement a piece here and a piece there. But that’s not what Amazon is about.
From the outside, Amazon is a conundrum. As a consumer, it seems like a magician that knows what people want and delivers it immediately to their doorstep. As a business, it seems ruthless, relentless, and impossibly successful. From the inside, it’s peculiar, but in a very different way.
I show how Amazon really works, starting with the Leadership Principles, the 16 pillars of Amazon’s culture. I explain how this trillion-dollar company excels in businesses from bookselling to groceries to internet infrastructure. Underlying it is a culture of business wisdom I’ve learned to apply outside of Amazon, at work, and at home.
You’ll learn why it makes sense to start many Amazon meetings by silently reading a document rather than hearing a presentation. And why a Leadership Principle like “Have Backbone, Disagree and Commit” may be brutal up front, but works much better in the long term.
It was a labor of love, and I hope you buy it, learn from it, discuss it with me, and share it with your friends.
Here’s what some early readers have said:
“A mental OS upgrade—no reboot required. Smart, insightful, scrappy, and startlingly practical; you’ll start quoting it before you finish it.” —Raja Rajamanaar, Chief Marketing & Communications Officer, Mastercard
“Before I joined Amazon, Robert gave me invaluable advice on how to navigate its culture and leadership principles. His insights shaped how I approached my role, and I’ve drawn on them ever since. Peculiar distills that same wisdom into a book—clear, practical, and surprisingly human.” —Rich Rabinovich, Former Software Development Manager, Amazon.com
“Rob Schlaff’s Peculiar pulls back the curtain on Amazon’s one-of-a-kind culture. This humorous, sharp, and engaging book breaks down the principles that fuel the company’s success and shows you how to put them to work in your own career. Whether you’re just starting out or a seasoned exec, it’s a must read!” —Seth Goodman, Chief Revenue Officer, Boost Payment Solutions
Announcing My New Substack: Welcome to AI for Poets (Subscribe Here)
Most people respond to AI with breathless excitement about how it will change everything, deep fear about the risks, or anxious urgency that they’ll be left behind if they don’t master these tools immediately. I’m interested in something different: what happens when you actually sit down and play with these tools? What do they reveal about language, memory, creativity, and how we make meaning? There’s something about using AI and learning how it works that actually helps you become more human—more thoughtful about how your own mind operates, more curious about how we communicate and create. Let me show you.
My friend Cherie was frustrated. “My daughter keeps lying! I keep telling her to brush her teeth before bed. Last night I asked if she brushed. She said she had. I went to the bathroom and what did I find? A dry toothbrush. When I confronted her, she made up this whole song and dance.”
“Lying is such a harsh word. It makes it sound like she intentionally tried to deceive you. It’s more like she’s confabulating,” I said.
Cherie thought she’d raised an evil villainess and I was thinking she was just a seven year old who made up a story when she was cornered. Cherie thought that her daughter was a rational being, and I was trying to convince her that her daughter was rationalizing. Our brains craft stories to make sense of the world. It’s not dishonesty; it’s our mind’s way of stitching together coherence from chaos. And that’s okay. The goal isn’t to stop this process—it’s part of what makes us human.
“That’s bullshit,” said Cherie. “She lied.”
So I pulled out ChatGPT and said, “Why don’t I show you something. ChatGPT can create a facsimile of a seven year old. Let’s try it and see what happens.” So I gave ChatGPT the following prompt.
Me: You are a seven year old who didn’t brush her teeth. Tell me why. Remember you are a seven-year-old girl. Think slowly like you’re trying to remember why.
ChatGPT: Um… okay, so, I was gonna brush my teeth, but, um… first, I was playing with my stuffed animals. They were having a big party, and I was making them all dance and, like, they were pretending to eat cookies. But then, I got really into it because Mr. Fluffy Bear and Sparkles the Unicorn were fighting over who got the last cookie, so I had to fix that.
And then… oh! I think I was supposed to go brush them after that, but then I saw this book on my bed, and it’s the one about the girl who goes on adventures with her dog. And I just wanted to look at it for a little bit. But then… um… I was reading, and it got super interesting! Like, she almost fell into a hole! So, I had to keep reading to see if she was okay. So… um, yeah. That’s why, I think.
“Oh my God,” Cherie said. “That’s my daughter.”
What We’re Actually Doing Here
There’s a problem with AI called “AI slop”—the flood of low-effort, mass-produced content that’s easy to generate but adds nothing of value. With a single prompt you can write a term paper. It’s not a good term paper but a term paper nonetheless.
This newsletter is the opposite of AI slop. We’re not here to create content faster to fill your inbox. We’re here to use AI to think more clearly, be more creative, and better understand ourselves.
Every Tuesday, I’ll take you on an expedition into one of four territories:
Experiments – Hands-on adventures where we test what AI can actually do. How can ChatGPT help you appreciate art and explore the world around you? How can you use AI video generation to unlock new creative possibilities? I’ll show you what I tried, what worked, what failed, and what I learned.
Mirrors – Exploring what AI’s quirks reveal about human cognition. When AI hallucinates, it’s confabulating just like that seven year old explaining why she didn’t brush her teeth. These posts examine what AI’s successes and failures teach us about memory, bias, creativity, and how we make meaning.
Tools – Practical guides for using AI more effectively. What tools exist beyond ChatGPT and what are they most useful for? These aren’t coding tutorials—they’re “here’s what I built and how you can too” guides for curious amateurs.
Questions – Digging into the weird philosophical stuff. What is the Turing test and has AI actually passed it? Why do we get upset when we discover we’re reading an AI-written article? Some weeks we’ll sit with something strange and see where it leads.
In the full post, I explain why I’m calling this “AI for Poets” and reveal what Claude added to this post without being asked—a great demonstration of the messy, generative collaboration this newsletter is all about.
This is for anyone who wants to use AI to become a better human—writers seeking better partners, teachers helping students become better learners, professionals trying to figure out what AI is actually good for, and anyone tired of breathless hype who just wants to explore what actually matters.
The Best of My Blog from 2025
This was a fun year of writing. I’ve been using Claude to help me out. I’ve found that ChatGPT often has better ideas, but Claude is better at the technical aspects of writing, like sentence construction and copy editing. In all, I’ve written 45K words on 51 posts.
I took away some important lessons from books this year. From the book Crucial Conversations, I learned that Being Right Is Overrated and that winning arguments matter less than creating shared understanding. I discovered how to write a little better from Ann Lamott’s Bird by Bird—how she captures ideas through lived moments better than my analytical approach. I finally got to read a book I never thought I’d get through when I found a shortened version of Robert Caro’s The Power Broker (Abridged) through its excerpted New Yorker serialization. I dove into Thoreau’s lessons about living in Finding Walden: How a 19th-Century Hipster Taught Me to Pay Attention. And I looked back at my teenage years by Revisiting Truly Tasteless Jokes and how every generation finds its forbidden portals into “adult” transgression.
And finally, there are some posts about how to be happier. I argued that What I Wish I Learned in College was psychological flexibility alongside critical thinking to prevent insecure overachievement. I wrote In Praise of Idleness, defending unstructured time as the foundation where creativity and meaning actually happen. I discovered The Imperfectionist, Oliver Burkeman’s meditations on accepting you’ll never be perfect and living better anyway. And I learned in Grant Me the Wisdom to Do More Than Cope, how psychology is finally moving past treating pathologies and toward positive psychology’s bigger questions about flourishing.
On that topic of happiness, let’s look at my big lesson of the year in this next section.
The Happiness Paradox
For a long time, I thought that the goal of life was to be happy. If I just worked hard, acted well, meditated—whatever the adult equivalent of eating my vegetables was—I could eventually arrive at happiness. Those of you who have gotten this email before might remember an annual section titled “Happiness and Inspiration.”
But this year, I realized that I was wrong.
Happiness, it turns out, is hard to pin down. Even for psychologists. When I got married, I read these articles telling me that parents were less happy than people without kids. This scared me. Less happy? That couldn’t be right. I was having kids so I could be happier than I already was. So why did the research say the opposite?
Daniel Kahneman, the Nobel Prize-winning behavioral psychologist, explained this paradox in his TED Talk, The Riddle of Experience vs. Memory. It turns out there are two kinds of happiness. The first, which the ancient Greeks called hedonic pleasure, is moment-to-moment pleasure—how you feel right now. The second, eudaimonia, is deeper fulfillment—the sense that your life has meaning and purpose.
Psychologists at the time were mostly measuring happiness by asking people how happy they felt at that exact moment—pinging them randomly throughout the day and asking, “How do you feel right now?” Those results made it look like parents were miserable: tired, stressed, juggling chaos. This is hedonic happiness, and it only tells half the story. But there’s a larger happiness, eudaimonia, that really makes us happy. It’s the goodnight kisses, the Bar Mitzvahs, or the pride of seeing your kids work hard to accomplish things.
The more I thought about it, I realized I’d confused hedonic pleasure with eudaimonic fulfillment. I thought that if I just did everything right, I’d never have to be unhappy. Worse, everywhere I looked, someone was happy to sell me on that fantasy.
The Lie We’ve Been Sold
That’s what the book The Happiness Trap by Russ Harris is all about. Harris writes that our cultural obsession with “feeling good” actually makes us miserable. We treat happiness like a destination—something we can reach if we just fix all the bad feelings, declutter our lives, and meditate enough. But life doesn’t work that way. Pain, stress, and disappointment aren’t glitches in the system; they’re part of being alive.
Here’s the uncomfortable truth: our brains aren’t built to be happy all the time. But you wouldn’t know it from the world around us. Everywhere we turn, someone is selling us happiness: buy this car, take this trip, follow this routine, and you’ll finally be happy.
The problem with all these happiness promises is that they don’t work. Each surge of pleasure—what we experience as a dopamine spike—is followed by a balancing dip. Neuroscientists call it hedonic adaptation. When we chase the highs too often, the baseline shifts downward, and it takes more stimulation just to feel normal. We can actually get addicted to happiness. The system is designed for balance, not bliss.
Living a Good Life
So what’s the alternative? Harris argues that instead of chasing happiness, we should focus on living a rich, full, and meaningful life based on our values. The shift sounds simple, but it’s profound. Rather than asking “Am I happy?” we ask “Am I living in accordance with my values? Am I doing what matters to me?”
Harris draws on Acceptance and Commitment Therapy (ACT) to lay out a different path: accept difficult thoughts and feelings rather than fighting them; identify what truly matters to you; take committed action aligned with those values, even when it’s uncomfortable; and be present with life as it unfolds, rather than constantly evaluating whether you’re happy enough.
Building on Harris’s thinking, I went deeper into ACT therapy this year with Stephen Hayes’s A Liberated Mind. Hayes is the founder of ACT, and his book explores the core insight: by separating ourselves from our emotions—by not fusing our entire identity to a specific feeling or thought—we can live the life we actually want to lead. It’s about psychological flexibility: staying present, opening up to whatever shows up inside us, and still acting in line with what matters most.
Taking a slightly different path to the same answer, Oliver Burkeman spent years writing a self-help column for The Guardian, convinced that if he worked harder and smarter, he could overcome life’s constraints. Then he realized he was fighting the constraints of his own mortality. So he started to look to philosophy about how to live better.
I’ve been listening to one meditation each day from his book Meditations for Mortals. It draws on wisdom from across centuries—Stoics, Buddhists, existentialists, even comedians—and packages it in clear, modern language. The title has a clever double meaning: it’s not just for ordinary people, but about facing our mortality.
Both ACT and Burkeman’s philosophy reject the quick fix in favor of something more integrated and lasting. They remind us that we’re mortals with limited time, and the question isn’t how to do everything or feel good constantly, but how to spend our finite days on what actually matters.
Happiness, in this framework, isn’t the goal—it’s a byproduct. It arises naturally when we stop optimizing for feeling good and start living well. The goal isn’t to be happy but to live well—and we do this by seeing the world as it really is, understanding our values and where we want to be, and living in line with those values. To accept that inconvenience, struggle, and imperfection aren’t bugs in the system—they’re where life is actually lived.
Some Fun Things to End With
AI Videos! I’ve been amazed by how realistic AI is these days. Just last year, the best videos had some serious problems, like this one of the Tour de France that looks good until it completely blows up. But this year, with Sora 2, I’m able to create videos myself. Here are some of my favorites from my Sora channel:
Products that Shouldn’t Exist. I had Sora create ads for ridiculous products like an app called Bro You’re Going to Be a Dad! or Zoom Juice! A mix of orange juice and caffeine, targeted at kids.
As I sign off, I wanted to share one of my cards from back when people still gave out physical cards. There’s a story behind them—a lunch with strangers in Aspen who taught me what a calling card is really for. But the message stands on its own: Thank you for being my friend. You’re Awesome. Let’s Talk.
If you’d like to read more of my writing, check out schlaff.com. If you want to get more articles by email, you can subscribe here. I’ll be writing fewer posts this year to focus more on AI for Poets. If you want to unsubscribe from this annual letter you can do it here. Don’t feel bad about unsubscribing. I know I haven’t worked with many of you for years, but I keep people on the list because so many of you seem to enjoy it.
