Categories
Home Page

Welcome to My Site!

About Me

I’m a devoted husband and father to an awesome family. For work, I’m a currently an Executive Director at JP Morgan Chase focusing on Product Tooling. I’m a Product Manager who looks at the goals of the business and uses technology to deliver those business and customer goals. In the past, I’ve driven transformational change at Citi, AIG, and Amazon Web Services. For more information about what I do at work, please visit my LinkedIn profile.

My Writing

If you’re new here, check out my blog highlights. Also, take a look at my library.

My Blog

I collect stories. There are so many amazing things happening every day. I need to spend some time writing them down before they slip away. Some of these ideas are so powerful that they hit me like a bolt of lightning. It’s my job to capture that lighting and put it in a bottle to share it with you. I want to capture that feeling that Archimedes had when he had an insight sitting in the bathtub screamed “Eureka!” and ran naked down the street. I know that I’ll rarely if ever make it there, but that won’t keep me from trying!

Here’s some of my latest posts:

And here are some of my posts about AI and ChatGPT:

Blog Highlights

Here are some highlights from 2024

One of my favorite topics for the last few years is writing about AI. I explored it from a number of different perspectives:

ChatGPT has helped me quickly turn ideas into complete blog posts and respond in real-time to things I’ve encountered. This year, it made it easier to explore a range of interesting topics like:

With ChatGPT, I learned to capture the small, wonderful moments of my life in writing. It’s like catching a lightning bug in a jar—preserving fleeting beauty to reflect on later. I was able to write about appreciating the sunrise, visiting a classic movie theatre owned by Netflix, and how to turn a nighttime drive into a light show.

Finally, I spent some time writing about self-improvement. Some of my favorite pieces were about the importance of asking for help and practicing self-control. Surprisingly, I even learned a valuable lesson about communication from AI—it’s programmed to respond with honesty, helpfulness, and harmlessness, qualities we humans could aspire to as well.

My Virtual Library

I wanted a place to put all the stuff I think is awesome. Growing up, I always wanted to have a great library in my house. I remembered the excitement when I learned that I could buy the entire collection of The New Yorker in bound volumes and put them in my house. I’d imagined that I would collect great encyclopedias from the past to peruse whenever I pleased. They would live in mahogany bookcases that looked like they’d belonged to JP Morgan. Then I realized that a New York City apartment doesn’t have the space for a physical library. So I did the next best thing. I’ve created a virtual library that includes lots of the things I enjoy, like my favorite books, words, and humor. You can check it out on the menu at the top of the page.

Categories
Life Lessons Technology

Can Something Be Too Convenient?

Can something be too convenient? That’s a question I’ve been grappling with for years.

You see, I’m a product manager. My entire job is built on making things more convenient for customers. In tech speak, we call it “removing friction.”

That’s the Silicon Valley playbook: find pain, remove friction, scale up, cash out. Mobile payments eliminate the pain of carrying cash. Delivery apps eliminate the pain of calling for takeout—no more language barriers, no more phone tag, no more getting your address wrong. Dating apps eliminate the pain of rejection. And in each case, you make the system smoother, faster, cheaper. The user wins. The investor wins. Everyone wins.

Until something breaks.

Friction and Resilience

A few weeks ago, Amazon Web Services’ main data center in Northern Virginia—US-EAST-1—went down. For hours, the internet itself seemed to wobble. Ben Thompson at Stratechery pointed out that this wasn’t just a glitch; it was a parable.

In theory, the internet was built to be resilient—decentralized, redundant, and nearly indestructible. But over time, everyone put their data in the same place: the cheapest, easiest region. The system that was supposed to be distributed became dangerously centralized.

As Thompson wrote, “the true price being paid for global efficiency is [lower] resiliency.”

The smoother we make things, the more brittle they become. And the more dependent we are on a single, frictionless path, the more catastrophic it is when that path fails.

That’s not just an engineering story—it’s a human one too.

What Convenience Does to Us

I’ve watched this pattern play out in my own life. The more convenient things become, the less I can tolerate even the smallest frustration. Waiting in line feels intolerable. A phone call that requires me to deal with another person—especially when I’m frustrated and want to just get something done—feels like a huge imposition.

People are inherently inconvenient. They misunderstand me. They have different goals than I do. They make mistakes. That’s what makes them people rather than machines.

What we call inconvenience is often just engagement with the world. Dealing with the tiny annoyances of everyday life—lines, neighbors, phone calls, mistakes—builds the muscles of empathy and flexibility. These little failures and frustrations are what keep us human.

If you smooth out every human interaction, you risk smoothing out what makes life worth living.

You can see it in dating.

Faith Hill’s piece in The Atlantic describes how fewer teenagers are getting into relationships. Many say love feels “too risky” or “too much work.” They prefer “situationships”—connections without commitment, emotions without vulnerability. It’s the frictionless version of romance.

But that friction—the awkward silences, the heartbreak, the vulnerability—is what makes connection real.

We’ve come to see friction as failure. Waiting, misunderstanding, uncertainty—all feel like bugs to be fixed. But these “bugs” are what teach us how to adapt.

The beauty of life is that everyone you meet lives in a slightly different context. Every interaction forces you to adjust your own. It’s inconvenient, but this is what living is all about.

Addiction to Convenience

In his audio series Inconvenient Truth, Oliver Burkeman makes an observation that stuck with me:

“It’s like we’re constantly trying to outrun any difficulties in our lives. Yet, the smoother we make things, the worse the remaining difficulties feel. No matter how quick and easy things get, you never stop being inconvenienced. It’s just that your standard of inconvenience shifts along with technology and the new reality. The goalposts keep moving, and maybe there’s a societal delusion that we can outrun our instinct for inconvenience.”

Oliver Burkeman, Inconvenient Truth

That’s the heart of it. We’re addicted to convenience—not because it makes us happier, but because it feeds the illusion that we can finally escape frustration.

And companies know this. Amazon has built an entire business model around the fact that customers always want more. As Jeff Bezos puts it, customers are “beautifully, wonderfully dissatisfied” even when they’re happy—which means there’s always another pain point to solve, another bit of friction to remove.

Addiction always starts as a solution. It works at first—it makes life easier, smoother, more efficient. But over time, it hollows us out. The less friction we experience, the less resilient we become. Waiting in line, calling a restaurant, talking to a stranger—these once-normal parts of life now feel intolerable. We’ve built a world that promises we’ll never have to feel discomfort again.

We don’t call this addiction because it looks like progress. We call it “innovation.” But the underlying pattern is the same: every shortcut erodes a bit of our tolerance for reality.

It’s tricky because that’s what I’ve been trained to do at work. But I’ve realized that just because I have access to all of these tools of convenience, that doesn’t mean I need to use them all.

The Magic Dial

If convenience is an addiction, how do we break ourselves of it? The best answer, of course, is to consult a psychologist. But I’ve been reading psychologist David Burns a lot over the last few months, and he offers a framework that’s helped me think about this differently.

Burns is one of the founders of Cognitive Behavioral Therapy, and one of his most important tools is what he calls “the magic button.”

Here’s how it works: Burns asks patients to imagine he has a magic button. If they press it, their problem disappears completely. A person with social anxiety would never feel anxious around people again. Someone with perfectionism would stop caring about mistakes entirely.

At first, almost everyone wants to press the button.

Then he asks them to think about it more carefully. If you press the button and your social anxiety disappears, you might also stop caring about how you come across to others. You could become insensitive, oblivious to social cues. Your anxiety, while painful, is also trying to protect you—it’s what makes you considerate, what helps you read the room.

The very thing that causes pain also carries something valuable inside it: care, conscience, awareness.

What people really want, Burns says, isn’t a magic button. It’s a magic dial. They want to turn their anxiety down from an 80% to a 10%—not eliminate it entirely.

At work and in life, we’re thinking too much about magic buttons, when what we really need are magic dials.

I don’t want to eliminate all inconvenience from my relationships. I want enough friction to stay engaged, to stay flexible, to keep building those muscles of empathy. I want to be inconvenienced by my kids when they interrupt my work, because that interruption reminds me they’re real and present and need me.

The beauty of being alive is this constant reworking of context, this endless recombination of perspectives. It’s messy and inefficient and sometimes exhausting. But it’s also what makes connection possible. It’s what makes love possible. It’s what makes us more than just nodes in a perfectly optimized network.

Life is inconvenient because people are inherently inconvenient. Everyone you meet lives in a slightly different context—different assumptions, different experiences, different ways of seeing the world. Every interaction requires me to adjust, to translate, to meet someone where they are.

That’s not a bug. That’s the whole point.

Categories
Life Lessons Uncategorized

I’m Not Who I Thought I Was

For most of my life, I carried around a fixed idea of who I was: Smart. Impulsive. A little weird. “This is just who I am,” I’d tell myself, as if it was literally set in my genes. But this year, after reading some great books on psychology and working with a life coach, I’ve learned to start letting go of that story of a fixed me.

Nothing made me realize how unstable the concept of “I” really is quite like breaking my ankle. There’s nothing that represents “me” more than my body, and I had this revelation lying on an operating table watching a doctor prepare to cut open my leg and screw a metal plate into my ankle. This wasn’t a doctor wrapping my arm in a cast—this was hardcore carpentry on my body.

When I woke up in my cast and started moving through the city, I realized how interconnected the world was and how reliant I was on it. I’d always thought of myself as independent, self-contained. Now I saw how much I depended on everything around me.

I thought people would be annoyed by me. But it was actually the opposite. People went out of their way to help—holding doors, offering to carry things, scanning for ways to make my life easier.

Then there were the products. I was delighted to find that companies made devices exactly for my condition. If I needed to get to work on the subway, I could use a Knee Rover, scooting along by pushing with my good leg. If I needed to do the dishes, I could strap on the iWALK and feel like a modern-day peg-legged pirate.

But each of these devices made me far more aware of the world around me. I started noticing things differently: where the stairs were, where the scooter couldn’t go. On the Knee Rover, I learned about sidewalk slopes—not just forward and backward, but left and right. Suddenly, the infrastructure of the world—the parts we usually ignore—became visible.

What I’ve come to realize is that the world isn’t made up of individual people so much as the interconnections between them. The Buddhist teacher Thich Nhat Hanh calls it “interbeing”—the idea that we don’t just exist, we “inter-are.” Remove the surgeon, the Knee Rover, the helpful strangers, the sloped sidewalks, and there’s no “me” to speak of.

The philosopher Martin Buber wrote something similar: that we become real, become someone, not in isolation but in genuine encounter with others. Every person who held a door, every designer who thought about accessibility, every stranger who made eye contact and asked if I needed help—they weren’t just helping me navigate the world. They were part of what made me me in that moment.

Categories
Design Fun Stuff

Welcome to Buc-ee’s: The Disney World of Gas Stations

Welcome to Buc-ee’s, the world’s most magical gas station—a place where travelers from every corner of this great country find comfort, refreshment, and a moment of cheer along their journey. Here, the spirit of the open road lives on—in the laughter of families, the sparkle of spotless tile, and the scent of freshly carved hot brisket and homemade fudge. It’s dedicated to wanderers and wayfarers who believe that even the briefest stop can be touched by joy.

We visited our first Buc-ee’s on our summer trip to Knoxville on I-81 to see my Abigai’s parents. We pulled into the Mount Crawford location, Virginia’s first Buc-ee’s. The first thing we noticed was its sheer size. This place is massive—120 gas pumps and 74,000 square feet of retail space, making it one of the largest convenience stores in the world. Despite over 600 parking spots, finding a space still took a minute. It was packed.

When we opened the door, we were hit with a low roar—the sound of hundreds of people crammed into the store. It felt like arriving at Magic Kingdom for rope drop, except this was 1 PM on an average Sunday. And the smell: sticky-sweet Texas BBQ sauce hanging in the air, promised something far better than typical gas station fare.

After hours in the car, we made a beeline for the bathrooms. Even with the crowds, there was no line. The bathrooms are enormous, with 50+ individual stalls. They’re legendary for their cleanliness, winning Cintas’s “America’s Best Public Restroom” award. As founder Arch “Beaver” Aplin said, “You can build it out of gold…but if you don’t clean it, at the end of the day, you end up with dirty gold.”

Then there’s the food. I like to call it rest stop gourmet. We grabbed soft, melt-in-your-mouth brisket sandwiches. We also picked up homemade fudge and a few bags of beef jerky (from two dozen varieties) from the jerky wall, plus Buc-ee’s signature snack: Beaver Nuggets, caramel-covered puffed corn.

But Buc-ee’s is so much more than the food and bathrooms. The brand is half the magic. Long before you see the store, Buc-ee’s billboards appear miles out—each one mixing dad humor with road-trip poetry: “Top Two Reasons to Stop at Buc-ee’s: #1 and #2” or “You Can Hold It… 262 Miles More!” By the time you pull off the highway, you already feel like part of the club.

Inside, that cartoon beaver grins from every shelf, turning ordinary merchandise into part of the experience. My teenage son bought a Buc-ee’s onesie to wear for Halloween—part joke, part personal brand building. That’s the power of Buc-ee’s: they’ve made a gas station mascot cool enough that a teenager will willingly wear it as a costume.

The Buc-ee’s Onesie

The souvenir shop rivals any tourist destination—like Cracker Barrel on steroids, selling Buc-ee’s branded and Texas-themed merchandise. We picked up tote bags and even a Buc-ee’s outdoor sofa. We wanted to continue the Buc-ee’s experience even after we went home.

But where did this magical place called Buc-ee’s come from? Founded in 1982 by Arch “Beaver” Aplin III (his nickname stemming from childhood and a quirky toothpaste-cartoon beaver mascot) and partner Don Wasek, Buc-ee’s began as a simple convenience store and gas station in Lake Jackson, Texas, with a goal of providing “clean, friendly, in-stock” service that would stand out. In 2003, it opened its first true “super-travel center” in Luling, Texas. By 2012, it had erected a 68,000-square-foot store in New Braunfels, widely deemed “the world’s largest convenience store” at the time.

After dominating Texas for decades, Buc-ee’s began expanding beyond its home state around 2018–19, starting with Alabama, then Florida, Georgia, and Tennessee.

Even with all of this brand equity, Buc-ee’s doesn’t have its own online store. That doesn’t mean you can’t buy Buc-ee’s merch online, though. In true Texas-sized entrepreneurial fashion, one fan, Chris Koerner, saw the gap and filled it. When he realized there was no way to order Beaver Nuggets or a Buc-ee’s hoodie from home, he loaded six shopping carts with every Buc-ee’s branded product he could find—650 items in all—and built an unofficial resale site called Texas Snax. Today, his company ships everything from jerky to plush beavers across the country, doing hundreds of thousands of dollars in sales each month. Buc-ee’s, for its part, doesn’t object—as long as he makes it clear that he’s independent from the company.

What Buc-ee’s understands—and what so many businesses miss—is that people don’t just want a transaction. They want an experience, even in the most unlikely places. Especially in unlikely places. In the middle of a long highway stretch, when you’re tired and restless, Buc-ee’s transforms a mundane pit stop into something worth talking about, worth remembering, worth taking home. That’s not just good business. That’s magic.

Note: The New York Times wrote a nice piece on Buc-ee’s earlier in the summer Buc-ee’s, a Pit Stop to Refuel Cars, Stomachs and Souls, Spreads Beyond Texas.

Categories
Judaism Life Lessons

The Best Birthday Ever: Ari’s Bar Mitzvah

A few weeks ago, we celebrated Ari’s bar mitzvah. Words can’t really capture the feelings I have about it. Watching my son become an adult, surrounded by family and friends—there’s nothing like it. Yes, we had a fun party. But a bar mitzvah is more than that. It’s a spiritual life event.

This transformation—from ordinary celebration to sacred moment—is the heart of Jewish practice. As Harold Kushner says in To Life!: “Everything in God’s world can be holy if you realize its potential holiness. Everything we do can be transformed into a Sinai experience, an encounter with the sacred. The goal of Judaism is not to teach us how to escape from the profane world to the cleansing presence of God, but to teach us how to bring God into the world, how to take the ordinary and make it holy.”

Ari’s Moment to Shine

First of all, I need to give Ari all the credit in the world. He stood in front of everyone—family, friends, our entire community—and led the service, read Torah, and delivered his d’var Torah with a voice that was loud, clear, and thoughtful. This was his moment, and he owned it.

For his d’var Torah, he worked with our friend Doron. They studied together for many sessions as Ari figured out what he wanted to say. Doron pushed him, as his study partner, to dig deep and find his own meaning. His Torah portion, Nitzavim, was almost impossibly perfect for the occasion. “You are all standing today,” it begins—and there was Ari, literally standing before us, taking responsibility for his own Jewish life. He taught us that the Torah “is not in heaven”—it’s not distant or unreachable, reserved for angels or scholars. It’s here with us, in our mouths and in our hearts, in the way we walk, think, and act.

He illustrated this lesson with his own observation. At Camp Ramah, he noticed that the song during the Torah procession was much faster than at Habonim. At first, he thought it was just a different tradition. Then he realized: at Habonim, you walk all the way around the shul, so you need a longer song. At camp, with a smaller space, the song had to be faster—like how the Jeopardy music is exactly 30 seconds because contestants have 30 seconds to answer.

He owned this whole line of thought—taking the general lesson that we need to adapt Judaism to our context and making it his own, all within the framework of Jewish tradition. He was proud of his thinking, and everyone was impressed. The Cantor even cried. This is the kind of thinking of an adult.

Over the past few years, I’ve watched Ari take responsibility for this work. He studied hard for his Torah portion, showing up week after week to prepare. He volunteered for his mitzvah project, packing care packages and writing cards for American soldiers overseas through an organization honoring Stu Wolfer, a Jewish American soldier killed in Iraq who worked with my wife. As Ari pointed out, real tzedakah costs something—it comes from the prime hours of your day, not just leftover time or money.

Ari’s best moment happened at an unlikely point. The Rabbi made a joke during the service. It was kind of an awkward joke, as he’s a new Rabbi and didn’t know the community that well. In fact, this was his first large event. He said, “I’m going to tell you a secret. You became a bar mitzvah when you turned 13.” Ari, genuinely surprised, did this very physical double-take—hands to his head, “Oh my God, you’ve blown my brain!” The whole crowd cracked up. That humor, that ease in front of everyone, helping the Rabbi co-lead the congregation—it was pure Ari.

The Power of Ritual

What does it mean for a 13-year-old to become a man? He still can’t drink, vote, or drive. But rituals serve a purpose—they take ordinary events and make it holy.

I used to scoff at the idea of birthday parties: “Why celebrate? It’s just another day.” But I’ve realized that a birthday is an opportunity—it’s a vessel, an opportunity you fill with meaning. It becomes a moment for people to focus their energy on you, to make it special.

A bar mitzvah is a birthday party on steroids. It’s one of the few times in life when friends and family will fly across the country to mark an occasion.

When God comes to your party, something shifts. What was merely fun becomes a simcha—joy with purpose. It’s about sanctifying life itself. Everyone came not just to have a good time, but to witness an important milestone: Ari’s sacred transition from boy to man in Jewish tradition.

The Gift of Presence

In addition to having God’s presence, we also had the presence of all the people who came to celebrate. Those who traveled from out of town, those who participated in the service, and even those who simply woke up on a Saturday morning, rolled out of bed, and came to shul.

This collective energy is what fuels a simcha. As William James wrote, “My experience is what I agree to attend to.” Each person who shows up is making a choice about where to direct their time and attention—and that choice matters.

The pandemic taught me just how much. Suddenly it became easy to “attend” a bar mitzvah or funeral virtually. You could drop in on an event without changing out of pajama pants, maybe playing Angry Birds when things got boring. No travel required, no time lost, no real inconvenience.

But something essential was missing. These virtual gatherings felt hollow, and it wasn’t just the technology’s fault. What makes occasions like these special isn’t the logistics or even the food—it’s that people feed them with something vital: their time.

This is when I finally understood something I’d always dismissed as a cop-out. In the days of the Temple, we gave animal sacrifices. Today, we’re told, the sacrifice we bring is our time. I used to think this was just a convenient excuse for the absence of ritual offerings. But now it makes perfect sense.

Time is the most valuable thing we have. We each have limited time on earth, and how we spend it defines our lives. When people gather to celebrate together, that collective sacrifice creates something sacred. As William James also wrote, “The greatest use of a life is to spend it on something that will outlast it.”

To really create a wonderful simcha, everyone must give part of their life to it—their presence, their energy, their attention. Each person becomes a contributor to something larger than themselves, breathing life into the celebration until it becomes truly alive with shared joy and purpose.

I went into Ari’s bar mitzvah expecting to feel proud, but I experienced so much more. When my friends and family give their time—the most precious thing they have—to sanctify a moment in Ari’s life, something shifts. I’m not just throwing a party. I’m participating in something ancient and sacred, bringing God into the world one shared moment at a time. No wonder words felt inadequate.

Categories
Life Lessons Meditation

The Imperfectionist

I have a secret: I’m not perfect. I’ve stopped trying to be. Why am I telling you this? Isn’t a blog post supposed to help you become a little more perfect? Not this one. This is about giving up the constant struggle for perfection, and in doing so, leading a better life.

The Imperfectionist is the title of Oliver Burkeman’s blog. These essays are compiled into his book Meditations for Mortals, which I thoroughly enjoyed. The title sounds simple, but it has a very British double meaning. I originally thought the word “mortals” was referring to ordinary people, but it also refers to the finitude of life.

I’d been searching for a book of daily meditations—something that could set my day off on the right note. This one has truths I’d always sensed but couldn’t name. I’ve read the whole thing back to front 3 or 4 times this year, for 10 minutes each day while my tea steeps and the house is still silent.

Before this, he wrote columns for The Guardian about productivity, convinced that if he just found the right system, he’d finally get everything done. But each trick only bred more tasks—the emptier his inbox, the faster it refilled. Doing more didn’t bring calm; it just changed the game of whack-a-mole. Eventually he saw that the goal wasn’t to finish his infinite list but to change the way he thought about it. His solution: treat your to-do list like a river, not a bucket—something that flows endlessly past you, from which you can dip a few meaningful things, and let the rest drift on by.

The book draws on wisdom from across centuries—Stoics, Buddhists, existentialists, and even comedians—and packages it all in clear, modern language. It answers many of the key questions of life like:

  • What should I do with my life? Carl Jung says: discover your life task—the thing your deeper self is already moving toward. You don’t choose it; you uncover it. The work isn’t to decide what to become, but to listen closely enough to become what you already are.
  • How do I keep from feeling overwhelmed? Create a done list. Instead of staring at what’s unfinished, notice what you’ve already done. It’s as simple as not deleting the items on your to-do list once they’re completed.
  • What if my life could’ve turned out better? Maybe it could have—but then it wouldn’t have been yours. Simone de Beauvoir marveled that out of hundreds of millions of chances, one sperm met one egg and became her. Change even a tiny detail, and you disappear.1
  • What should I do when I feel completely lost? As comedian Mitch Hedberg put it: “If you find yourself lost in the woods, fuck it, build a house.”

Burkeman even has BBC radio shows exploring these ideas further. I particularly enjoyed An Inconvenient Truth,2 where he argues that convenience culture is a bit of a fraud. Companies try to convince us we need their products to remove life’s inconveniences. He uses the example of a hypothetical baby care app that raises your child without any hassle. Would anyone actually want that? Of course not—because inconvenience is where life is lived.

Each morning, as my tea steeps, I still listen to one meditation and let it settle. I still make mistakes—I get frustrated, I leave tasks undone, I make mistakes. But now I see those things differently. They’re not failures. They’re just life as a mortal.

Note: Much of Burkeman’s work is available for free on Spotify and/or the BBC.

Footnotes

  1. This one is from Burkeman’s book 4000 weeks. ↩︎
  2. Note that you have to listen to these from the bottom up because the most recent episodes are on top. ↩︎
Categories
Articles Books / Audiobooks

Robert Caro’s The Power Broker (Abridged)

The First Article in The Power Broker Excerpt

To me, reading The Power Broker by Robert Caro always seemed like an intellectual bullying move. There are some of us that can’t get through a 1344-page book, no matter how hard we try. It’s just not going to happen. Even the audiobook clocks in at 66 hours long.

On the other hand, it sounds like an awesome book. Barack Obama and Conan O’Brien call it their favorite book. One of my favorite podcasts, 99% Invisible, even ran a book club on The Power Broker, using it to unpack how power quietly shapes cities. Guests included The Good Place creator Michael Schur, former U.S. Transportation Secretary Pete Buttigieg, and even Caro himself. The New Yorker even published a satire piece on this phenomenon.

I’d resigned myself that I was never going to get to it. But then I discovered that the book was serialized into a series of articles in The New Yorker. These articles appeared in the issues in the summer of 1974. True to form, this was one of the longest serializations, broken up into 4 pieces for a total of 79,000 words—the length of a substantial book:1

  • “The Best Bill‑Drafter in Albany”, July 14, 1974
  • “If the End Doesn’t Justify the Means, What Does?”, July 21, 1974
  • III: “How Robert Moses Got Things Done”, August 4, 1974
  • IV: “Point of No Return”, August 11, 1974

Reading these articles, I realized that Robert Moses didn’t just shape New York—he built it. Every time I drive around the city, I find myself asking: How did all these roads get here? I understand the Manhattan grid of the early 1800s, but what about the highways, bridges, and parkways? None of them have changed in my lifetime, yet most were built only after the automobile arrived around 1900. The answer, it turns out, is Robert Moses. As Caro says in the introduction:

Standing out from the map’s delicate tracery of gridirons representing streets are heavy lines, lines girdling the city or slashing across its expanses. These lines denote the major roads on which automobiles and trucks move, roads whose very location, moreover, does as much as any single factor to determine where and how a city’s people live and work. With a single exception, the East River Drive, Robert Moses built every one of those roads. He built the Major Deegan Expressway, the Van Wyck Expressway, the Sheridan Expressway and the Bruckner Expressway. He built the Gowanus Expressway, the Prospect Expressway, the Whitestone Expressway, the Clearview Expressway, and the Throgs Neck Expressway. He built the Cross-Bronx Expressway, the Brooklyn-Queens Expressway, the Nassau Expressway, the Staten Island Expressway and the Long Island Expressway. He built the Harlem River Drive and the West Side Highway.

Only one borough of New York City—the Bronx—is on the mainland of the United States, and bridges link the island boroughs that form metropolis. Since 1931, seven such bridges were built, immense structures some of them anchored by towers as tall as seventy-story buildings, supported by cables made up of enough wire to drop a noose around the earth. Those bridges are the Triborough,[*] the Verrazano, the Throgs Neck, the Marine, the Henry Hudson, the Cross Bay and the Bronx-Whitestone. Robert Moses built every one of those bridges.

Scattered throughout New York stand clusters of tall apartment houses built under urban renewal programs and bearing color, splashed on terraces and finials, that in the twentieth-century American cityscape marks them as luxury dwellings. Alongside some of these clusters stand college lecture halls and dormitories. Alongside one stand five immense dingy white expanses of travertine that are Lincoln Center, the world’s most famous, costly and imposing cultural complex.

Caro, Robert A. The Power Broker: Robert Moses and the Fall of New York.

This doesn’t even mention the 148,000 apartments and 600+ playgrounds. That’s why this cartoon, from this summer, is still so relevant:

New Yorker Cartoon, Emily Berstein, July 28, 2025

Caro spent seven years researching The Power Broker. Remember, this is a man who has only written two major works in his life—the other being his still-unfinished, multi-volume authoritative biography of Lyndon B. Johnson. Caro was such a relentless researcher that Robert Moses stopped speaking to him after Caro began asking pointed questions that challenged Moses’s official narrative.

Caro carefully unfolds the history of these projects. One of my favorites is how suburban Long Island exists largely because Robert Moses wanted to get New Yorkers to the beach. In the 1920s, when he was Parks Commissioner, Moses envisioned a vast network of beaches and parks—Jones Beach, Sunken Meadow, Hither Hills—that would offer working-class city residents a democratic escape from the sweltering, crowded tenements of New York. But the problem wasn’t just building the beaches—it was getting people to them. So Moses didn’t just build parks; he built the parkways to reach them. With meticulous strategy, he secured funding, dodged political opposition, and used obscure legal provisions to seize and rezone land for long, scenic highways like the Southern State, Northern State, and Wantagh Parkway. These roads weren’t just infrastructure—they were invitations.

Once the highways were built, people flooded out of the city in their cars, and where they stopped for recreation, they eventually stayed to live. The desire to reach the beaches started a new pattern of suburban growth. Moses didn’t just give New Yorkers access to sand and surf; he redrew the map of where people could imagine their lives unfolding. What began as a public amenity strategy became the foundation for postwar suburban expansion—sprawling communities along the corridors that led to the coast.

It’s written with the pace and drama of a novel, but at heart it’s a tragedy. Caro structures The Power Broker like the story of a fallen hero—someone who begins as an idealist and ends as a cautionary tale. In the early chapters, Moses is a sympathetic character: a brilliant reformer who wants to clean up the graft and inefficiency of Tammany Hall, a man who genuinely believes parks and public works can ennoble a city. But as his power grows, so does his arrogance. The same moral certainty that fueled his reforms hardens into something darker.

Caro captures this transformation as a novelist would. The idealist who once built Jones Beach so ordinary New Yorkers could see the ocean becomes the autocrat who lowers the parkway bridges so buses—and thus poor and Black families—can’t reach it. The planner who once dreamed of playgrounds for children ends up bulldozing their neighborhoods to make way for expressways. By the time he’s slicing the Cross Bronx through the heart of working-class communities, he’s stopped seeing citizens at all—only obstacles.

The only problem with the book is that it’s too powerful—and for decades, it’s been almost the only story we have about Moses. Written in the spirit of the 1960s and ’70s Jane Jacobs movement, it reflects a moment when the tide had turned against Moses’s brand of top-down modernism. By then, expressways had become symbols of destruction, not progress, and the neighborhood voices Moses once ignored were finally being heard. Caro channels that spirit, using Moses as both subject and warning: the man who thought he was saving New York by remaking it in concrete and steel was, in Jacobs’s eyes, dismantling the very fabric of the living city.

The book uses Moses as the embodiment of an entire era—making moses into a villain. Caro channels all the arrogance, blindness, and hubris of mid-century modernism into a single man, as if Moses alone poured the concrete and cleared the neighborhoods. But Moses wasn’t acting in a vacuum—he was the product of a culture that worshiped progress, trusted technocrats, and believed problems could be solved by building something big. By personalizing that system, Caro gives us a gripping story, but also a convenient scapegoat. The real story isn’t just about Robert Moses; it’s about everything going on at that time.

And there’s a larger problem: there’s really only one major book about him—and it’s a 1,344-page tome. While the book offers different sides of Moses, there’s only one theory of the case, and it’s from Caro. His Moses—the brilliant tyrant who built New York and broke it in the same breath—became the definitive version. Over time, that version hardened into truth.

When The Power Broker came out in 1974, New York was falling apart—graffiti on the subways, crime in the headlines, garbage piling up on the sidewalks. The city that had once believed it could build its way into the future was now on the verge of bankruptcy. Caro’s book didn’t just tell the story of Robert Moses; it told the story of a whole generation. It gave shape to what people were already feeling—that the modern world, with all its glass towers and expressways, had failed them. The Power Broker offered them an explanation.

So even reading the entire book doesn’t give you the whole story. Paul Goldberger, the architecture critic for the New Yorker, adds some crucial context. Goldberger reminds us that Moses wasn’t some rogue genius operating outside his era—he was his era. Every major American city in the mid-century was tearing itself apart in the name of progress, trading subways for expressways and neighborhoods for parking lots. Moses just did it bigger, faster, and more visibly than anyone else. To say he single-handedly ruined New York is to miss the deeper truth: that he was the clearest expression of what America believed at the time—that the future could be engineered. Goldberger writes that “Moses didn’t bring down New York, and he didn’t single-handedly sell its soul to the automobile. Indeed, New York probably comes closer to having a workable balance between cars and mass transit than any other city in the country.”2

I’m so glad that I finally got to read The Power Broker, in its abridged form. It is a phenomenal book, full of history, drama and intrigue. But the book needs to be read in context. The book’s subtitle, “Robert Moses and the Fall of New York,” doesn’t really ring true 50 years later. We wouldn’t have the Triborough Bridge or the Long Island Expressway. We wouldn’t have Long Island as we know it today.

For me it’s personal. Moses bulldozed working-class neighborhoods to build Lincoln Center, which jumpstarted the redevelopment of the Upper West Side—the theaters, restaurants, and brownstones that define it today. As part of that transformation, he built our apartment building in Lincoln Towers. I owe my home, my kids’ elementary school down the block, and the neighborhood I love to Robert Moses.

Footnotes

  1. I was able to download the PDFs from the New Yorker digital archive from the New York Public Library. ↩︎
  2. Paul Goldberger, “Eminent Dominion: Rethinking the Legacy of Robert Moses,” The New Yorker, February 5, 2007. ↩︎
Categories
Human Behavior Life Lessons

Happy All the Time?

One of my wife’s favorite books from growing up was Happy All the Time by Laurie Colwin. It stands proudly on our bookshelf like a little totem to childhood optimism—a promise that somewhere out there, happiness could be a permanent state if you just figured out how to arrange your life correctly.

For a very long time, I believed that too. I even had a section on my website called “Happiness and Inspiration.” I thought that if I read enough, optimized enough, meditated enough—whatever the adult equivalent of eating my vegetables was—I could eventually arrive at happiness.

But this year, I realized I was chasing the wrong goal.

Continue reading “Happy All the Time?”
Categories
Judaism Meditation

A Mindful Yom Kippur

Over the past year, I’ve been practicing mindfulness. I’d meditate for fifteen minutes a day, sitting quietly, watching my thoughts drift by. I was also working on my psychological flexibility, separating my thoughts from my emotions. At first, it felt like exercise for the brain: uncomfortable, sometimes boring, but strangely strengthening. Over time, though, I noticed something deeper.

I really saw the benefits of this on Yom Kippur. I realized how closely these practices mirror the essence of the holiday. In many ways, Yom Kippur is a 25-hour meditation—an invitation to step away from food, distractions, and earthly concerns, and instead focus on prayer, presence, and who we are in relation to God.

Continue reading “A Mindful Yom Kippur”
Categories
Books / Audiobooks Media

Revisiting Truly Tasteless Jokes

The First Book of the Series

Why does my son watch these horrible Instagram influencers who spew misogyny, racism, and hate? There’s Andrew Tate, arrested on human trafficking charges. And Dan Bilzerian, who literally threw a porn star off a roof. I want to yell that my generation was different, that we were better, that we never fell for such garbage.

But then I remembered Truly Tasteless Jokes.

I was thirteen when someone passed me the book on that long bus ride from camp to Hershey Park, and I knew I was holding something special. It was a secret portal into adult humor—the kind of stuff that would get you grounded just for knowing it existed. This was the 1980s, that lawless time before warning labels. No gatekeepers, no protection—just forbidden fruit waiting to corrupt curious kids like me.

We’d huddle around our contraband. If you were there, you remember the jokes. If not, they’re too tasteless and horrible for me to print here. We’d memorize them and trade them like baseball cards, each one more shocking than the last.

It was taboo. It was like looking at dirty magazines, but somehow more accessible because they were just books in the bookstore. Just an aisle away from the Nancy Drew books. What I didn’t understand then was that this wasn’t just some random collection of offensive humor—it was a cultural earthquake.

A Cultural Phenomenon

Truly Tasteless Jokes wasn’t just an offensive book series. It was a legitimate cultural phenomenon. At one point, Blanche Knott had four books on the New York Times bestseller list simultaneously—the first time that ever happened.

The books were so popular that more respectable authors and publishers complained that the New York Times bestseller list was being defiled. This led to the creation of the “Advice, How-to and Miscellaneous” category on the bestseller list.

Looking back, Truly Tasteless Jokes was a product of its cultural moment. The 1980s were Reagan’s America—a deliberate rejection of the political correctness of the 1960s and 70s. As cultural critic Luc Sante observed, they were “a sigh of release, a sign that we weren’t living in the politically correct Sixties and Seventies anymore, and could behave like pigs if we wanted to.”

It was the original anti-PC phenomenon, a middle finger to civil rights progress and social consciousness. The jokes weren’t just offensive—they were intentionally, aggressively offensive. They were a backlash.

The Woman Behind Blanche Knott

The author on the cover was listed as Blanche Knott. I’d always thought this was a female pen name for a male syndicate who wrote the books—like Franklin W. Dixon was to the Hardy Boys. But the books, including dozens of sequels, had a single author—the improbably named Ashton Applewhite..1

Applewhite was an underpaid assistant editor at St. Martin’s Press, earning just $8,500 a year while writing book jacket copy. Between assignments, she collected offensive jokes on cocktail napkins and “While You Were Out” slips, stuffing them into her desk drawer. Her original title was her favorite joke: What’s the Difference Between Garbage and a Girl from New Jersey? The punchline: garbage gets picked up.

When the manuscript first made the rounds, one editor at Penguin said, “If we published this, the little bird would have to hide its head under its wing in shame.” A woman at another publisher told the agent, “We can’t publish this here. I’m not even sure we can Xerox this!”

But Ballantine did publish it. And America spoke—loudly, to the tune of millions of copies. It sparked copycats and even a VHS tape. The tape is fairly lackluster; however, it does include early clips of Andrew “Dice” Clay, who perfectly captured the spirit of the jokes in the book.

The Reckoning

There are different ways to look at the legacy of Truly Tasteless Jokes. The documentary Tasteless featured comedians defending the book and comedy in general, even when it sometimes hurt people, positioning it as a fight against cancel culture, with performers arguing that humor serves as a necessary release valve for society’s tensions.

Contrast that with the Decoder Ring podcast, where the host insisted on highlighting how awful the book was and demanded that Applewhite apologize for writing it—which she eventually did. While the impulse is understandable—these jokes are horrible—there was something deeply counterproductive about the whole exercise. The host was so focused on moral purity, so determined to distance herself from the content, that she completely missed the point.

That kind of heavy-handed liberal righteousness, that desperate need to prove you’re on the right side, that reflexive “you can’t talk about that” energy—that’s exactly what caused this phenomenon to emerge in the first place.

Going Forward

Here’s the thing about teenagers and offensive content: they’re going to find it. Whether it’s Truly Tasteless Jokes in the 1980s or Andrew Tate on Instagram today, kids are drawn to transgression. They want their forbidden portals into adult humor and adult rebellion.

The question isn’t how to eliminate that impulse—it’s how to channel it constructively. When we create an environment where certain thoughts and jokes are so forbidden that they can’t even be discussed, we don’t make them go away. We just make them more powerful.

We need to resist the urge to sort everything into neat moral categories—good or evil, acceptable or unacceptable, worthy of cancellation or worthy of praise. Real people are messy. Real growth happens in the gray areas. When we demand that everyone meet some impossible standard of moral purity, when we insist that past mistakes define present character, we’re not creating a better world. We’re creating a world where we’re terrified of authenticity, and growth becomes impossible.

Footnotes

  1. Applewhite tells her story in Being Blanche, a 2011 Harper’s Magazine piece that’s worth tracking down. The article is paywalled, but most libraries provide digital access to Harper’s archives—and it’s an incredible read that reveals the woman behind the phenomenon. ↩︎

Categories
ChatGPT Human Behavior

From Sapiens to Silicon: The Evolution of Storytelling Species

I think I’m the most special person on earth—part of the most special species on Earth. Not because of my job or my talents or anything I’ve accomplished, but because I’m human. And if you’re reading this, you probably think you’re the most special person on earth too—for the exact same reason.

But what really makes humans special? According to Yuval Harari’s Sapiens, it’s not tool use—crows can bend wires into hooks. It’s not language—whales sing and bees dance. It’s not even raw intelligence. What sets us apart is that we can believe in things that don’t exist, and then build entire civilizations on top of them.

Seventy thousand years ago, we were evolutionary middle-managers. Not the strongest, not the fastest, not even the smartest animals around. We were just… adequate. Then something extraordinary happened—what Harari calls the “Cognitive Revolution.” We learned to tell stories and, more importantly, to believe them together.

Evolution’s Bug Becomes a Feature

What gave humans the ability to tell these stories? Bigger brains. The kind that could handle abstract thinking, symbolic reasoning, complex language. But at some point, our brains got so large they created a problem evolution had never faced: they literally wouldn’t fit through the birth canal.

We had to be born early, before our brains could fully develop. Human babies arrive half-finished, completely helpless, but infinitely programmable. A gazelle can run within hours of birth. Human babies can barely hold up their own heads.

This seemingly terrible design—a brain that devours 20% of our energy and takes decades to mature—became our species’ superpower. It’s what lets a caveman’s descendant become a medieval peasant’s descendant who becomes a modern computer programmer, all without changing a single gene. Same hardware, completely different software.

The Invisible Infrastructure of Civilization

Walk around any city and you’ll see the infrastructure: roads, power lines, water mains. But the real infrastructure—the stuff that actually holds it all together—is invisible. It’s made of stories.

Consider Apple Inc. You can’t touch Apple—it’s not a physical thing. It’s a legal fiction, a story we’ve agreed to tell about ownership and corporate structure. Yet this imaginary entity employs 150,000 people and moves more money daily than some countries see in a year. The story of “Apple” has become functionally real through collective agreement.

Nations work the same way. The border between New York and New Jersey exists nowhere in nature—it’s a line we’ve drawn on maps and in our minds. But people organize their entire lives around it, pay taxes because of it, even fight wars over similar invisible lines.

Human rights might be our most beautiful fiction. There’s nothing in the laws of physics that says humans deserve dignity or freedom. But we’ve collectively decided to believe in these concepts, and that belief has toppled governments and reshaped the world.

Silicon Storytellers

Now we’re trying something unprecedented: we’re teaching machines to tell stories.

Instead of neurons firing in skulls, it’s synthetic neurons firing across vast server farms. Instead of culture gradually shaping a child’s mind, we’re using training data to shape artificial minds in mere months.

And what emerges is not just smarter calculators or faster search engines. We’re building storytellers. Systems that can spin up convincing worlds, simulate human voices, and generate fictions that ripple outward into real consequences.

These aren’t tools in the old sense — hammers and plows that rest when we put them down. They’re more like co-authors we’ve set loose: storytellers who never sleep, never age, never forget.

Reprogramming Ourselves

It’s unsettling to realize that the truths at the center of our lives—money, nations, even identities—can be mirrored so easily by AI. But that realization also gives us enormous power.

First, it reminds us that the stories we tell about ourselves are just as flexible. I am the kind of person who always fails at math. I can’t change careers this late in life. These aren’t biological limits; they’re personal fictions. And like any fiction, they can be rewritten. Psychologists call this psychological flexibility—the ability to observe our internal narratives as constructs rather than absolute truths, and to consciously choose whether they still serve us.

Second, it shows us how much our attention really matters. Every belief system runs on attention—from religions to social media platforms to the voice in your head that won’t shut up at 3 AM. You can see this most clearly online: your feed isn’t some neutral window on reality. It’s shaped by what you click, what you linger on, what you reward with your time.

This principle extends everywhere. You don’t need to track every market swing or breaking news alert. You can choose where to invest your mental bandwidth. That story that you “should be” doing something else, feeling bad that you’re not more productive? You don’t need to listen to it.

Here’s the thing: attention is a finite resource. Shift how you spend it, and you’re not just curating your information diet—you’re curating your reality.