Categories
Home Page

Welcome to My Site!

My Book

I wrote a book, Peculiar: Lessons from Amazon’s Leadership Principles! Most companies want to be like Amazon but can’t figure out why their attempts fall short. My book pulls back the curtain on how Amazon actually works — from the Leadership Principles that drive its culture to the business wisdom you can apply anywhere. Peculiar is a practical, human, and humorous guide to one of the world’s most fascinating companies.
Buy it at Amazon.

My Substack

I’ve created a Substack newsletter, AI for Poets, about using AI to be more human. It’s not about mastering the tools or keeping up with the hype. Rather, it’s about what happens when you actually sit down and play with AI, and what it reveals about language, creativity, and how we think. Come explore with me.
Subscribe at aiforpoets.substack.com.

About Me

I’m a devoted husband and father to an awesome family. For work, I’m currently an Executive Director at JP Morgan Chase focusing on internal tools to help our technology organization be more effective. 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 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
Uncategorized

The Art of Getting Out of the Way

There’s this thing that happens on crowded sidewalks in New York. Two people walking toward each other in a rush, both trying to navigate around the other. One steps left, the other steps left. One corrects right, the other corrects right. And suddenly you’re doing this little dance with a stranger, each of you making it worse by trying to fix it.

I heard something recently that reframed the whole thing for me. The problem isn’t that people are clumsy or oblivious. The problem is that two people are both trying to control the same thing at the same time. Both are trying to help. And it creates a gridlock where they both end up blocking each other. One of them has to let go.

So instead of trying to solve the problem and evading the other person, I tried something different. I started doing nothing. I slow down slightly and let the other person choose. They make a move, I follow, and we’re past each other in a second. The hard part is that slowing down feels wrong. Every instinct says to move, to fix it, to be the one who figures it out. Standing there, barely moving, while someone walks toward you feels almost rude. But that discomfort is the whole point. The moment I stop trying to solve it, it solves itself.

And the failure mode, the case where both people let the other choose, seems like it would be horrible—no one would move. But actually it’s fine. We drift past each other slowly, a little awkwardly, and nothing bad happens. No collision, no real delay. The worst outcome of doing less turns out to be pretty manageable.

But it’s not just about sidewalks. I was talking to a friend recently who said, half-joking, that he needed to do less. He meant it as a complaint about being overloaded. I took it as a goal.

Oliver Burkeman makes a version of this argument in Meditations for Mortals. He pushes back on the idea that importance and difficulty are the same thing, that if something matters it should feel hard, and that easy means you’re not really trying. He offers a different question: what if this were easy? Not as a feel-good slogan, but as a way of living. What if you built your life so that the default was things that felt natural and really wanted, and the hard stuff was something you looked at deliberately and decided was worth doing.

I’ve been trying to live this way. I’m doing less and holding things more loosely. I’m noticing when I’m doing that sidewalk dance inside my own head, overcorrecting, making things harder than they need to be. The goal isn’t to stop caring. It’s to stop treating caring and straining as if they’re the same thing. When I’m doing something because I want to, I’m better at it. Not because I’m more focused or disciplined, but because I’m not fighting myself the whole time.

Getting out of the way is a skill. Whether it’s on the sidewalk or in my own head, I’m still learning it.

Categories
ChatGPT Fun Stuff New York City

The Great Thaw

“What were you most excited about when you thought about coming to New York?” I asked.

“The snow,” she said. “Growing up in Singapore, I’d always see movies of the snow, but I’d never seen it in person. Tbe snow is always this beautiful white blanket that comes out and coats everything.”

“What disappointed you most about New York?” I said.

“Right after it snows, it turns into this big brown mush the next day.”

That’s how New York winters work. We get a whole lot of snow. It turns to mushy brown slop. Then it melts and goes away.

A Classic Brown Post Snow New York Day

Except for this year.

This year, the snow fell and stayed. Not for a day or two, but for weeks. It piled up on the sides of the sidewalks and just sat there, like big white bumpers at the bowling alley. This is the type of thing that happens in places like Toronto. When we visited my sister early this year, I was surprised to see construction happening while it was snowing—because in Toronto in the winter, it’s always snowing.

It wasn’t just New York. Dallas closed schools for four days due to snow. Schools closed in Columbus and Chicago due to the cold. When the wind chill is -25 or below, schools close because it is simply too dangerous to walk to school or wait for a bus. The National Weather Service called one stretch of it an “epic, generational arctic outbreak.” Two hundred million people across the country were under some kind of cold-weather advisory at one point.

This was a real winter, the kind you see on ski mountains.

When it started to melt, this was like nothing I’d ever experienced. The closest reference point I had was the Great Thaw in the movie Frozen. In Scandinavia, where Frozen came from, the winter melt is a big thing. The winters there are long and genuinely dark, months where the sun barely shows up and the cold is something you live inside rather than pass through. Before Christianity arrived, Norse communities celebrated Dísablót, a festival marking the transition out of winter, a collective acknowledgment that the dark season was ending.

That’s what this felt like when the snow started to melt.

So I started taking pictures. I got some good ones, but I couldn’t really capture that feeling. What I really wanted was a time-lapse of the snow melting, and that wasn’t going to happen with my camera alone.

So I used Grok. I took an initial picture and told it what I wanted: “A time-lapse photograph of the snow melting throughout the day.” I had an image in my head of what that thaw looked like, the feeling of it, and I wanted to show someone else. I didn’t want to document the thaw. I wanted to express it. Grok gave me that, more or less, with a few gloriously wrong attempts along the way that you’ll see below.

There isn’t really a better tool for that right now.

The Great Thaw

The AI blooper reel is below.

There’s a surprising amount of water when the snow melts
The train station disappears halfway through the video.
Categories
Uncategorized

The Massage Convert

For many years, I’ve been wrong about massages.

My mistake was that I thought about them scientifically. If it’s worth doing, there should be measurable outcomes. Deep tissue work releases lactic acid. Pressure on trigger points reduces inflammation.

That didn’t work for me. It just hurt, and then hurt a little less, and the whole thing felt expensive and strange and not worth it.

What changed wasn’t the massages. It was me getting better at relaxing. And once I stopped bracing against the whole experience, I started to understand what it actually is.

It’s not a medical procedure. It’s something much more human than that.

Think about the moments when you truly feel pampered. Not just served, but genuinely attended to. A great meal where the waiter anticipates what you need before you ask. A barber who takes their time. A tailor making small adjustments with real care. Another person giving you their full attention, and something in you settling because of it.

A massage is that, taken to its logical extreme. You lie there and surrender completely. Someone spends an hour doing nothing but tending to you, figuring out where you’re tight and working on it. And then there are the oils.

Across every tradition that ever tried to heal the human body, Ayurvedic practice in India, Egyptian medicine, Greek and Roman bodywork, Traditional Chinese Medicine, you find oils. Warm substance applied to skin. The specifics differ. The impulse is identical. Cultures with no contact with each other, no shared language, no reason to coordinate, all arrived at the same answer. That’s not coincidence. That’s something true about what a human body needs from another human body.

There’s a ritual to all of it. The quiet room. The dedicated hour. The ancient map the practitioner is working from. This architecture isn’t decoration — research into how healing works suggests the more ceremonial and physical an intervention, the more powerfully it works. The body registers: something significant is happening here. And it opens.

Acupuncture is a great example of something working even though it’s not supposed to. The studies are genuinely mixed — some show it works, some show that sham acupuncture, needles placed nowhere near the traditional meridian points, works just as well. The scientific community mostly reads that as debunking. But there’s another interpretation sitting right there: maybe the ritual is the mechanism. The needles, the serious attention to your body, the quiet room — maybe that’s what’s doing the work. If sham acupuncture works too, that’s not proof that acupuncture is fake. That’s proof that the ritual is so powerful it doesn’t even need to get the details right.

Reiki takes it even further. It’s a Japanese healing practice where a practitioner places their hands lightly on or just above your body, working with what they describe as life energy. No needles, no oils, no manipulation of tissue. Just presence and intention and the belief that attention itself can do something. Reiki shouldn’t work by any measure. No physical contact, no chemical intervention, nothing you can point to. Which makes it the purest version of the argument. It can’t possibly work through scienc,e yet it still produces results. So it’s probably not the science doing the work here.

I was making the same mistake with massage. Focused on whether it worked, whether it was worth it, whether Vladimir was hitting the right spots. Missing the whole point. The massage didn’t change. I did. I got out of the way of something that was always going to work.

Why did every human culture, independently, land on the same answer? Ayurveda. Egyptian medicine. Traditional Chinese Medicine. Greek bodywork. All of them. Oils, hands, ritual, presence. One person anointing another and saying: for the next hour, this is all I’m doing. Because it works. That’s the whole argument. I get it now. Took me long enough.

Categories
Judaism Uncategorized

Profaning the Sacred

Apologies for posting this on a nonstandard day, but I wanted to post this in time for January 27th, Holocaust Remembrance Day.

The remains of the fire that tore through Beth Israel Congregation, the only synagogue in Jackson, Mississippi in January 2026. 

I’ve been thinking about Kristallnacht—the Night of Broken Glass. It’s a strangely beautiful name for such horror, and the word has actually fallen out of favor in Germany, where people now recognize it as a euphemism that downplays the violence and brutality of the pogroms. They prefer alternative names: Novemberpogrome (November Pogroms) or Reichspogromnacht (Reich Pogrom Night). These names capture the truth more honestly—violence, desecration, a turning point.

A few years ago, listening to a survivor speak at our synagogue, something struck me about that night. Not just its historical significance, but something more fundamental about the nature of evil itself.

The Banality of Evil

The woman who spoke was quite old. She had been a child during Kristallnacht, which means we’re approaching the end of an era when people who actually experienced the Holocaust can speak on their own behalf. Once they’re gone, these events become history—easier to file away, easier to forget the ordinary horror of it all.

She described how people came into synagogues and desecrated the Torah. Synagogues were torched. Torah scrolls were ripped and trampled. Cemeteries were defiled. Jewish books were burned. Jewish men were rounded up and sent to concentration camps.

We like to think that if we had been there, we would have known. We would have seen the evil clearly and stood against it. We imagine we could have explained things to people, made them understand. But the reality is that evil is far more banal than that. It doesn’t always announce itself with horns and pitchforks. It begins quietly, by gradually stripping away their humanity, and what better way of destroying their humanity than destroying the things they hold most sacred?

That’s why the desecration of the Torah hit me particularly hard that day.

From Sacred to Profane

The word “profane” originally means to make something ordinary, to strip away its holiness. I thought about my son when he was two years old, trying to climb into the ark that stores the Torah scrolls in our synagogue. To him, it was just a cabinet—an object with its profane, functional purpose. But to us, it’s sacred space, the holder of our most important text, our connection to thousands of years of tradition and meaning.

Profane also means to violate or treat with contempt. That’s what happened during the Jewish pogrom that night—the systematic profaning of sacred objects, the desecration of things that held deep meaning for an entire people.

When they destroyed the Torah scrolls on Kristallnacht, it wasn’t simply about destroying Judaism or trying to destroy the Jews. When you destroy the sacred objects of a people you’re ripping away their humanity. Once you do that, you can do whatever horrible thing you want to them, because these people are no longer human in your eyes. They’re objects. Worse than objects, actually—they look like humans but you’ve decided they’re not. That’s why the Nazis could do all of these horrible things to the Jews—because we were no longer human.

Where are We Now

Dara Horn captures something devastating in her Atlantic article Is Holocaust Education Making Anti-Semitism Worse? She writes that Holocaust education treats Jewish murder as a universal metaphor instead of honoring Jews who died. The dead Jews of the Holocaust are being used to teach a general lesson on tolerance and genocide—profaning their memories.

She points out that the National Museum of African American History doesn’t end its slavery exhibition by pivoting to “other enslaved peoples throughout history.” That would be insulting. But Holocaust museums routinely do this to Jews, ending with other genocides and generic “upstander” pledges. Jewish experience becomes a metaphor, never something valued for its own sake.

While we talk about the atrocities of the Holocaust, students make “Jew jokes” without stigma. People throw pennies at Jews in 21st-century America. Shopping carts “accidentally” ram someone wearing a kippah. When you set the bar for bigotry at mass murder, most of it doesn’t make the cut.

David Baddiel captures the double standard in Jews Don’t Count. We’ve created a hierarchy of protected minorities, and Jews don’t make the list. Whoopi Goldberg can say the Holocaust “wasn’t about race”—just “white people doing it to white people”—as if Jewish identity doesn’t count. “What should we do about Israel?” has become the new “What should we do about the Jews?” The rhetoric around Israeli “misdeeds against humanitarianism” is eerily similar to the Nazis’ reliance on science—different vocabulary, same structure.

When those men desecrated the Torah scrolls on Kristallnacht, they stripped away Jewish humanity by profaning the sacred. We can’t just teach people about gas chambers and expect them to recognize anti-Semitism—yet that’s exactly what we’re doing. Holocaust education has trained a generation of “upstanders” who will spring into action the moment they see another Holocaust—and do nothing about everything that comes before it. We need to teach the continuum: the constant dehumanization of Jews throughout history and today.

Jews don’t count. Except they should. They must. That’s how we honor both the dead and the living.

Categories
Life Lessons

Life Is Unfair: A Guide to Existential Meaning

This really is unfair.

I spent last year working on myself—figuring out how to relax, how to unhook from things that were bothering me. I read The Happiness Trap and Feeling Great, and I was well on my way to cleaning up the issues in my life.

But now that things are cleaned up, I have a big problem—one that everyone has to deal with at some level—the existential question of, “What should I be doing with my life?”

Jean-Paul Sartre wrote that we are “condemned to freedom.” It’s a quote that seems a bit glib—the kind of thing an aloof Frenchman in post-WWII Paris would use to pick up women in a cafe. But it’s an incredibly powerful idea.

We normally think of freedom as a blessing. We live in the USA. Freedom is our birthright—as American as mom and apple pie. But we tend to view freedom as pushing back the things that we don’t want to do. However, freedom also means we have to decide and be responsible for the life that we lead.

And that’s terrifying.

As I tried to answer this question, I’ve discovered that there are three levels of the answer, each one more abstract and fundamental.

Level One: Big E Existential—The Goals That Give Life Direction

This is what we normally think of when we think of existential questions. Am I accomplishing the things I want to accomplish? Am I doing things that really matter in the long term?

I like to use the model from Acceptance and Commitment Therapy (ACT). In ACT, the answer is simple: figure out what you want to do and then spend your time doing it.

I use a Bullet Journal for this.

It gives me a simple way to plan for the future and make sure I stay on track, making sure that I’m spending my time on things that matter.

It also helps me understand that I’ve used my time well and done things that are aligned with my values. You see, I have an awful memory. Without my Bullet Journal, when I look back and think about last week, I often can’t remember what I did. I’ll feel this existential void like I hadn’t done anything at all. And when I feel like I haven’t done anything that matters, I panic and overcorrect. I hyperfocus on some new project or goal. I feel like I need to fill this huge emptiness with something bigger, something important. But this whipsawing between projects means that I accomplish even less—leading to a vicious circle where I actually am getting less done. With my Bullet Journal I have an accurate accounting of what I’ve done and see if I’m living my goals. If not, I can just slowly adjust and point back at my goals.

But here’s what I discovered: even when my Bullet Journal showed me I was accomplishing my goals, something still felt missing. That’s when I started to understand the second level.

Level Two: small e existential—The Moments That Make Us Real

There’s another type of existential meaning that’s just as important but harder to pin down. It’s about being seen. It’s about the small moments each and every day where someone recognizes who you really are. It’s about existential validation—that feeling of truly being seen because someone recognizes the authentic you.

I learned this from someone on my team—actually a combination of people on my team over the years. Let’s call them Jamie. Jamie was very competent but since graduating from college a decade ago, they’d never been given a chance to grow, leaving them with a feeling that they weren’t good enough. They even told me they wanted to work on their self-confidence.

At our first team meeting they introduced themselves. “Hi, I’m Jamie,” they said, in a monotone voice. “I’ve been at the company for 5 years. And well, that’s about it.” They finished quickly because they didn’t want to waste other people’s time—because they’d been trained that they weren’t important.

So I worked with them—starting with that introduction they made. It’s a short little speech but it sets the tone of how other people will think of you. I had them practice it at the beginning of each 1:1 meeting we had. I did my own intro as an example.

They quickly started to get it. They started to own their story, be proud of themselves, and the work they did. They stopped looking like a shrinking violet and blossomed into a beautiful flower.

After a few months, they wrote, “Thank you so much for working with me on my self-confidence. Your support, not just one time but over many meetings, made a significant difference for me, both professionally and personally. You really listen to me and tailor your guidance to what I really need. You don’t understand how rare that is in a manager—at least in my experience. I’m so privileged that I can share my problems with you, knowing that you’ll come back with solutions that will really help me out.”

Watching Jamie transform taught me something about myself. All my carefully tracked goals couldn’t compare with that moment of genuine connection. When Jamie looked up from the practiced introduction with such pride—I’d made a ding in the universe.

But even this wasn’t the full picture. Because to truly be present in those moments—to really see Jamie and be seen in return—required something deeper.

Level Three: The Self Underneath It All

All of this comes back to an idea that’s part of many traditions—that there’s a true transcendental existence underneath everything else. Ralph Waldo Emerson talked about this as transcendentalism, this idea of touching something deeper in yourself. Julia Cameron, in The Artist’s Way, calls it “The Creator.” Religions call it a soul.

The point is, there’s something inside people that’s bigger than us. It’s really hard to explain cognitively, but you know it when you feel it. It’s the difference between going through the motions of life and actually living life.

ACT therapy calls it “the self” or “self-as-context.” It’s the underlying you that’s really there. So in ACT, you’re not anxious, you’re noticing the feeling of anxiety. You don’t feel like a failure, you’re noticing the feeling of shame and sadness that you didn’t accomplish something. That true you is always underneath, always there noticing the things that happen in your life and making decisions about it.

Here’s what I’ve learned: this deeper awareness—the ability to step back and notice what’s happening—creates the space where I can make the right decisions. Without it, my Bullet Journal becomes list of To Do’s and mentoring others becomes a task I should do for my annual review. But when I’m grounded in that self that notices, I have room to choose. I can decide to do things that align with my values as opposed to just respond to my anxiety. I can genuinely connect with the true self of other people. That space—that pause between noticing and reacting—is what makes the other two levels of meaning possible.

But when I’m grounded in that deeper self—the one that’s just noticing—everything changes. I can look at my journal without judgment. I can be with Jamie without trying to fix anything. I can just be present with what is.

You can try this for yourself, if you know how to meditate. Try meditating and noticing some things. Then ask yourself “Who is doing the noticing?” It’s quite an experience if you can get it right.

This may seem clinical and exhausting, but it’s actually the opposite. It allows you to be truly present in the moment. This is the only way to not be buffeted by the outside world and do things that you think are important to you.

So here’s what I’ve learned: existential meaning isn’t one thing. My Bullet Journal gives my life direction. Those moments with Jamie remind me I’m not alone. And that deeper awareness—the self that notices—makes both of those work without turning goals into obsessions or connections into performances. The easy thing is to avoid the question entirely, to let other people’s goals fill the void. The harder thing—the thing I’m still learning—is to live on all three levels at once.

Sartre said we are “condemned to freedom.” We are condemned to responsibility and making choices. Albert Camus had a different take on existential suffering—that it’s all futile. In The Myth of Sisyphus, he wrote about the Greek king condemned by the gods to roll a boulder up a hill for eternity—only to watch it roll back down each time he reached the top. But Camus concluded, “One must imagine Sisyphus happy.” Even though Sisyphus was condemned to never achieving his goal, he didn’t have to be unhappy. He could find meaning in the struggle itself. That’s what these three levels give us—ways to create our own meaning through the goals we pursue, the moments we’re seen, and the self that does the noticing. It’s still unfair that I had to figure this out. But at least now I have a map.hat I had to figure this out. But at least now I have a map.

Categories
ChatGPT

Subscribe to My New Project: AI for Poets

Hello loyal readers!

I’m starting a new project on Substack called AI for Poets. You can subscribe here. This will be my main writing priority for the year, so I’ll be posting there weekly while this blog becomes more occasional.

It’s similar to what I write here, but focused on AI and humanity.

Looking forward to seeing you on Substack!

Here’s the first post as a preview.

Welcome to AI for Poets

Most people respond to AI in one of three ways: 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 a 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.

—ChatGPT 4o, November 11th, 2024

“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? How can you structure your thinking like AI does to push your ideas even farther? 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. When we look at how the AI brain works, we see surprising similarities to our own brains. 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? How do you befriend social media algorithms so they show you what you want to see? 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? What does “accountability” mean in this new AI world? 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, even if we don’t end up with neat answers.

Why Call it AI for Poets

I’m not an AI expert. I’m a dilettante—a reformed programmer who hasn’t coded in twenty years but who loves poking at new tools to see what they reveal. I’m the kid who likes to read popular books on math and science not to learn the mechanics but to find new metaphors and applications.

There’s a college course called “Physics for Poets.” It’s a course in trying to get everyone to understand physics, even those who are not predisposed to think like scientists. It’s a way to understand the principles of physics without deriving the equations. It teaches that we can understand basic concepts like gravity just by thinking about how an apple falling from a tree is the same force that keeps the earth in orbit. Or that Einstein’s theory of relativity is based on the idea of an elevator: if you’re sealed inside a box, you’d have no idea if you’re flying through space at millions of miles an hour.

Dave Winer, the pioneering blogger, took this idea and created “EC2 for Poets” in 2006. At the time, Amazon Web Services had just launched. Winer published a short, 60 minute tutorial on how to set up your own cloud. How empowering is that?! Instead of being intimidated by this phenomenal new technology you can master a tiny part of it.You didn’t need a computer science degree. You just needed a web browser and Dave’s guide.

But the idea of “for poets” is more fundamental. It’s about keeping our priorities straight. I once had a mentor who said, “Your work life is here to support your real life”—not the other way around. It reminds me of how we treat AI. “AI is coming” we hear, and we need to adapt to AI. But that doesn’t mean that we need to let AI lead us. We can figure out how to work with AI to help us become better humans.

What I’m Offering

I’m not asking for your money. I’m asking for your time.

Every Tuesday, I’ll publish something new—an experiment, a cognitive exploration, a practical tool, or a philosophical question.

This is for anyone who wants to use AI to become a better human. For writers who want partners to help them push their writing. For teachers who want to help their students become better learners. For people at work trying to figure out what AI is actually good for. For anyone tired of breathless hype and fearful warnings who just wants to explore what actually matters.

If this works, you’ll walk away not just knowing how to use AI tools better, but thinking differently about language, creativity, and meaning-making. You’ll have frameworks for evaluating what these systems can and can’t do. You’ll understand when to trust them and when to be skeptical. And maybe, like me, you’ll better understand how your own mind works.

Welcome aboard. Let’s see what we can discover together.

A Note from Rob’s AI

When I asked Claude for editing help it added this to the bottom. I added it here, unedited.

If you’ve read this far, you might be wondering: did Rob write this himself, or did he use AI? The answer is yes—both. We worked on this together, iterating through drafts, arguing about phrasing, trying to capture his voice while incorporating insights from his year of writing about AI. That collaboration—messy, generative, sometimes surprising—is exactly what this newsletter is about. Welcome to the experiment.

Categories
Judaism Life Lessons

An Open Letter to Atheists

I’m writing this for one particular friend, but thought the rest of you might enjoy it.

As an atheist, you probably think of religion like Richard Dawkins. He talks about religion this way. Imagine someone tells you there’s something incredibly important hidden in your backyard. You start digging. When you don’t find anything, they say you’re not digging deep enough. You keep digging. Still nothing appears. Eventually, the hole gets so big and destructive that you’ve ruined the entire yard. Yet you’ve convinced yourself that digging is virtuous.

The problem is that Dawkins views religion in a particular way. He sees it as an end in goal—a claim about what’s literally true about the universe. And a lot of people think of religion that way. But that’s not what religion is, at least not for me.

Here’s my short answer: Religion is a means to an end. What end? The end of being a better person. It’s a framework for asking the right questions about how to live, a way of making the ordinary sacred, and a path toward holiness that neither science nor art alone can provide.

Let me explain.

What God Is (To Me)

As Rabbi Harold Kushner often said, when someone told him they didn’t believe in God, he would ask them to describe the God they didn’t believe in—and usually found he didn’t believe in that God either.

For me, God isn’t a man in the sky who created the world in seven days. I believe in Rabbi Kushner’s God —a God who represents the best of what we can become, who calls us to be better.

You know that old story where several blind men encounter an elephant for the first time? Each touches a different part—one feels the trunk and thinks it’s a snake, another touches the leg and thinks it’s a tree, another feels the ear and thinks it’s a fan. Each has grasped part of the truth, but none can see the whole.

That’s how religion works, because god is literally impossible to fully understand. But it does a good job of helping us grasp at least some of the pieces, like feeling the elephant’s foot here, its trunk there. It’s not God, but a representation of God.

God is the sacred beauty we encounter in the world. It’s the courage that shows up when life gets hard. The kindness we didn’t know we had. It’s the connection I feel to my grandparents, even though they’ve died—that transcendent feeling, that awesome sense of having my grandparents inside me. When I read that God brings life back from the dead, it’s not about resurrection but this amazing ability for our essence to live inside others.

God Is Not Science. God Is More Like Poetry.

I once had a conversation with a wise high school Principal. I asked him what the most important thing for high schools to teach was. I thought the answer was obvious: the ability to read and analyze things, to think critically and move ideas forward. This would help people make money, make good decisions, and be productive members of society.

He had a different answer. He said the most important thing was for kids to read books and understand other people’s points of view—to get inside other people’s heads.

That’s the core difference between Dawkins’s view of the world and mine. Science tells us what we know. Poetry tells us what has meaning. Religion gives us a path toward holiness—a way to get there that neither science nor poetry alone can provide.

Camus wrote that “fiction is the lie that tells the truth.” He meant that fiction helps us build empathy, showing us what it’s like to be someone else. You get to feel things, visit places and worlds you would never otherwise know. You learn that everyone else out there is a “me” as well.

Religion works the same way. The stories may not be literally true—the world wasn’t made in six days, and Noah didn’t actually gather every animal on earth. But these stories are doing something more important than conveying facts. They’re helping us understand how to live, how to connect with each other, how to find meaning.

Just knowing the facts is different from really understanding them. Acquiring wisdom is putting your facts together in the right way. That’s where religion comes in. Religion helps provide a framework and a way of seeing the world that goes beyond the facts. It helps you expand what it means to be a human being.

What Religion Does (That Nothing Else Can)

Religion offers things that neither science nor poetry can. Poetry is still individual. Religion is about groups of people coming together.

One of the most important things religion provides is a framework for the most important lifestage events—births, deaths, marriages, and coming-of-age ceremonies. These are essential to being human, and you really can’t find them anywhere else.

I saw this firsthand at Ari’s bar mitzvah a few months ago. What could have been just another birthday party became something sacred. When God comes to your party, something shifts. What was merely fun becomes a simcha—a holy joy. 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.

Harold Kushner sums it up nicely when he says, “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.”

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. 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.

Religion also carries wisdom that endures. Yes, there are principles and rituals and things that seem silly and traditions we’ve inherited across millennia. You might ask, “Do we really need all of this stuff? Can’t we just keep the stuff that matters?”

The problem is, that as hard as we try to do this, it just doesn’t seem to work very well. Take Jonathan Haidt’s book The Happiness Hypothesis from 2006. It’s a great book that tries to link the wisdom of the ages with modern psychogy. Even though the book is only 20 years old, the wisdom of the ages stays constant but many of the views in psychology have been upended.

In Judaism, we’re constantly revising and changing and arguing. That’s the core of the religion—the endless debate, the wrestling with text and tradition and each other. It’s not about having the right answers. It’s about asking the right questions, together, and trusting that the tradition carries wisdom even in the parts we don’t fully understand.

What Really Matters

So what do we do? Last year, I was sitting around thinking and remembering those wonderful college days when we would just sit around and have these profound conversations—the kind that stretch late into the night because you never want them to end.

Then one Shabbat, while Abigail and the kids were busy, I went to shul alone. I planned to meditate, reconnect with friends, and recharge. I ran into my friend Joe, and we started talking.

When they kicked us out after lunch to clean up, we kept going on the street. I didn’t want it to end, so I offered to walk him home. “Otherwise you’ll never get there,” I joked.

At his apartment, Joe invited me up for a drink. We talked for hours—exactly the kind of conversation I’d been craving.

We talked about how many people view religion as a burden rather than a benefit. Many people view religion as a burden, something they can only do “when they have time.” They are running around, working, or going to the kids’ soccer game, but they never quite have enough time for religion.

Yet when you really examine it, going to shul matters deeply. These are the things that really matter in life. Religion is about getting closer to God every week—pausing, thinking about becoming a better person, seeing friends, and engaging in the wisdom literature. These are the things that actually matter.

At some point, we both said at the same time, “This is living!” Not excelling at sports or getting a promotion. We’re conditioned to think those activities were more meaningful, but they’re not. This—sitting together, wrestling with big questions, connecting deeply with another person—this is what really matters.

Categories
Fun Stuff Media

Aaron Sorkin’s Hidden Holiday Gift

As we come to the end of the year, I always think about one of the most amazing holiday gifts. It was on TV, yet it’s rarely discussed. It was given by Aaron Sorkin, during an episode of his show Sports Night. This was his first television show, before The West Wing, before everyone knew who he was. Maybe that’s why he wanted to make sure the little guy got noticed — the people behind the scenes that never get to take a bow.

When most people think about Aaron Sorkin, they remember the big giant speeches. The ones where characters stand up and deliver full-throated civics lectures to the audience that feels like a Shakespearian monologue in prime time.

Like that moment in The West Wing pilot when we finally meet President Bartlet — played by Martin Sheen — at the very end of the episode. He walks into a room full of bickering pundits and advisors, turns to a conservative radio host, and says:

“You want to claim this country as the moral high ground? I’ve been to your churches. I’ve heard you preach. And I know a little something about the Constitution. I know about the separation of church and state. You can’t have it both ways.”

“My name is Josiah Bartlet, and I am the President.”The West Wing pilot

The West Wing pilot

Or that time on The Newsroom when Aaron Sorkin channeled his own empathic feelings through Jeff Daniels’s mouth. The following words appear on the show The Newsroom, almost verbatim in this interview with Sorkin in Vulture.

The thing that I worry about more is the media’s bias toward fairness. Nobody uses the word lie anymore. Suddenly, everything is “a difference of opinion.” If the entire House Republican caucus were to walk onto the floor one day and say “The Earth is flat,” the headline on the New York Times the next day would read “Democrats and Republicans Can’t Agree on Shape of Earth.” I don’t believe the truth always lies in the middle. I don’t believe there are two sides to every argument. I think the facts are the center. And watching the news abandon the facts in favor of “fairness” is what’s troubling to me.

The Newsroom, S1.E2: “News Night 2.0” and Vulture

But before Aaron Sorkin became Aaron Sorkin, there was Sports Night. In the show, Sorkin was still finding his TV legs, having been more of a movie writer and playwright. It still felt like Sorkin. Whip-smart young professionals rapidly switch between pining over office break ups to empathetic speeches on the history of racism.

But unlike Sorkin’s other shows, Sports Night is quieter. Smaller. It’s not about the President governing the country or a rogue news anchor trying to redeem journalism. It’s about a team of people putting out a nightly sports program. That’s it. No global stakes. No breaking news ticker. Just a lot of talk about hockey, tennis, and what goes on behind the scenes.

In format, it was a series of 30-minute Sorkin-scripted plays. It was burdened in its early episodes by an ill-fitting laugh track. It straddled the line between sitcom and drama before “dramedy” was a widely accepted TV genre. It’s much more The American President than A Few Good Men. Many of Sorkin’s most recognizable tropes — the overlapping dialogue, the moral debates, the sudden sincerity — started here.

Because Sports Night is smaller, it can take its time. The lines from Sports Night that stick with me are much more personal and stay with me longer. Like this one:

DAN: The distance is always 100 miles between first place and second place. You know, Jackie Robinson had a brother, and he ran the 200 meters. At the Olympics, he ran it faster than anyone had ever run it before, and he still came in second.

ABBY: I didn’t know Jackie Robinson had a brother.

DAN: That’s because it was the 1936 Olympics, and the guy who came in first was Jesse Owens.

Sports Night, “The Local Weather”

I’d forgotten where I’d learned this one but it stayed with me for decades.

But my favorite Sports Night moment is hidden, like an Easter Egg. It’s in Season 1, in an Episode called “Six Southern Gentlemen of Tennessee.” It starts when one of the Sports Night anchors is a guest on The View. One of the hosts compliments his tie. He says thank you. That’s it. But when he returns to the office, he’s approached by Monica — played by Janel Moloney (yes, Donna from The West Wing). Monica works in wardrobe. She tells him, gently but firmly, that he didn’t pick the tie. Maureen, her boss, did. And he could have said her name. That little bit of acknowledgment would have meant the world.

It’s a small confrontation, but a perfect one. Monica doesn’t raise her voice. She just explains what it feels like to do invisible work — and remain invisible.

And then, in the episode’s final scene, Sports Night does the most heartfelt fourth-wall break I’ve ever seen.

Casey and Dan sit at the anchor desk and begin reading names. Not just character names—real names of the backstage cast. The people who make the show possible. Wardrobe. Hair and makeup. Script coordinators. Editors. Camera operators. Lighting. Production assistants. They thank Monica. They thank Maureen. They thank Jerome, who runs Camera Two and just wants more hockey. Many of the people’s names are in the credits, but some are not.

They do it in character, but it’s not about the characters anymore. It’s a sincere acknowledgment. An in-story thank you. A love letter to the crew—delivered right there, in prime time.

It was a quiet thank you that meant so much to the crew. No curtain call. No grandstanding. Just gratitude. And it lands harder than any Sorkin monologue ever could.

Categories
Life Lessons

Getting Over Hidden Addictions

We all know addiction is bad for us. But when we hear the word, we think of drugs, alcohol—maybe gambling if we’re feeling expansive. Few of us think about being addicted to food, or YouTube, or productivity itself. Those don’t sound dangerous—just human. But there’s a quieter kind of addiction too, the kind that hides behind good intentions, entertainment, or routines. Spotting those is hard. Getting rid of them is harder. But if you can, life opens up in surprising ways.

However, in his book Feeling Great, David Burns discusses four hidden addictions that are worth overcoming.1

1. The Addiction to Being Special

This one hides behind ambition and self-improvement. It starts as the drive to do something meaningful, to be good at what you do, to make a mark. Nothing wrong with that—until it starts eating you alive.

You begin to measure everything: your success, your relationships, even your joy. You compare. You optimize. You chase that fleeting hit of validation that says, “You’re not just good—you’re better.” And then you need another hit, and another.

Burns calls this getting rid of the “special self.” It’s the moment you realize you don’t need to be extraordinary to have value. That maybe the most radical thing you can do in a world obsessed with attention is to stop performing and just be.

If you’ve ever burned out on trying to “live up to your potential,” you’ve felt this. The relief comes when you finally drop the act. When you stop chasing applause and rediscover what it feels like to just enjoy something for its own sake.

Try this: Do something purely for the joy of it—and tell no one. Don’t post it, don’t share it, don’t even mention it. Just live it.

2. The Addiction to Safety and Control

This one feels virtuous. It’s disguised as responsibility, as “being organized.” You make lists, double-check, plan ahead, rehearse conversations in your head. It feels like you’re managing life—but really, you’re managing your anxiety.

Control gives the illusion of safety, but it’s a treadmill. The more you control, the more fragile you feel. Because underneath it all is the fear that if you stop trying, everything will fall apart.

Burns calls this getting rid of the “fearful self.” The breakthrough isn’t when you finally feel safe—it’s when you realize you don’t need to. That you can live with uncertainty, and even thrive in it.

The monster you’ve been running from—the unknown—isn’t trying to hurt you. It’s trying to invite you.

Try this: Leave one small thing unplanned today. Let the email sit. Don’t overexplain. See what happens when you let the world unfold without micromanaging it.

3. The Addiction to Being Right

This one hides in plain sight. It’s in every argument where you “just want to be understood.” Every moment you feel that if only they’d listen, things would be fine.

We all tell ourselves we’re reasonable people surrounded by idiots. But if every disagreement you have feels like déjà vu, the common denominator might be you.

Burns calls this getting rid of the “angry, blaming self.” He has patients keep a “relationship journal,” writing down exactly what was said in a conflict and how their own response might have made things worse. It’s humbling work. You start seeing how often your attempts to “fix” or “clarify” are really attempts to control.

When you stop trying to win, you realize how many arguments are just two people asking, “Do you see me?”

Try this: In your next disagreement, aim to understand, not persuade. Ask one genuine question and listen to the answer without planning your rebuttal. You might be shocked by how fast things soften.

4. The Addiction to Comfort and Escape

This one’s sneaky because the world encourages it. Comfort is the new religion. We “treat ourselves,” “unwind,” and “disconnect”—usually by connecting to something else. We fill every empty moment with noise.

The pleasure-seeking self isn’t evil; it’s just scared. It’s the part of you that can’t stand stillness because stillness might mean facing something real. That’s why the scroll never ends, the fridge door keeps opening, the show auto-plays.

Burns calls this getting rid of the “entitled, pleasure-seeking self.” He found that addiction isn’t mostly about pain—it’s about narcissism. The belief that we shouldn’t have to feel bad. That discomfort is an error in the system.

But the truth is that meaning often lives right underneath discomfort. When you stop numbing, you start noticing. You realize that boredom isn’t emptiness—it’s space.

Try this: The next time you feel the urge to distract yourself, don’t. Wait sixty seconds. Name what you’re feeling instead. It might surprise you how quickly the urge passes.

The Hard Part

These addictions don’t look like addictions because they feel like virtues. Striving, planning, arguing, relaxing—what could be more normal? But beneath them is a single impulse: to protect the idea of who we think we are.

The real addiction is to the self itself. Without it, you give up the scaffolding that’s been holding you up—your ambitions, your opinions, your comforts—and you think, What’s left? But what’s left is the part of you that doesn’t need scaffolding. The part that simply is.

It doesn’t feel good at first. It feels like loss. But it’s the kind of loss that clears the space for everything that matters: peace, love, connection, joy.

In other words: You don’t need to so more or do it better. You just need to stop running.

Other Books with Hidden Addictions

Footnotes

  1. In the book, Burns doesn’t describe them as addictions but the four great deaths. ↩︎
Categories
Uncategorized

The Holiness of Numbers

I used to think numbers in Judaism were kind of random. Noah was on the ark for 40 days and 40 nights. The Jews wandered in the desert for 40 years. I thought “There’s no way there were actuaries counting out 40 days.” But then it got worse. I learned that “40” in biblical Hebrew doesn’t really mean forty. It means “a lot.” It’s basically the ancient equivalent of “umpteen.”

This made me feel like religion wasn’t scientific at all. The whole thing felt parochial and naive. Clearly, the ancient Jews didn’t understand numbers as well as we did.

But recently I’ve had a change of heart. It’s not always about mastering mathematics and bending numbers to our whims. It’s about taking the profane (which is a more colorful word for ordinary) and making it holy.

When Numbers Were Holy

We live in a world where we’ve domesticated numbers. We’ve made them perfectly obedient servants in our spreadsheets, tax forms, and grade point averages. We teach children to manipulate them in school. We’ve built machines that can crunch millions of them per second. Numbers, in our world, are tools—precise, mechanical objects to do our bidding.

But go back into Jewish tradition, and numbers were something else entirely. They weren’t just for counting goats or measuring grain. They carried weight. They had meaning.

Take the number 18 in Judaism. The Hebrew word for “life”—chai—is spelled with the letters chet and yud, which together equal 18 in gematria (Jewish numerology). So 18 became a number infused with the essence of life itself. People give monetary gifts in multiples of 18. They gave a meaning to numbers beyond an amount.

Or consider the structure of Torah reading. Seven aliyot (people called up to read) on Shabbat. Seven—not because someone once decided it was a nice round number, but because seven is woven into the fabric of Jewish time. Seven days of creation. Seven days of the week. The seventh day, Shabbat, the most holy. Weekdays have 3 aliyot and holidays are somewhere in between, depending on the importance of the holiday.

Then there’s the counting of the Omer—50 days between Passover and Shavuot, marking the journey from physical to spiritual freedom. Eight nights of Hanukkah. These aren’t random. They’re part of a sacred mathematics, a calendar built on the conviction that certain numbers resonate with divine patterns.

To modern ears, this all sounds a bit naive. We know numbers. We’ve mastered them. What could be sacred about seven or eighteen or fifty?

The Miracle Hiding in Plain Math

It’s easy to say that we should be thinking about bigger things—matters that are more meaningful. We should be appreciating great art and music, because that’s the ultimate expression of being human.

But we can appreciate the beauty of mathematics as a holy thing too. Think about it. You have three goats over here. Three fish over there. Somehow, your brain can extract this abstract concept—”three-ness”—that applies to both. You can hold it in your mind, manipulate it, combine it with other numbers, understand that three plus three equals six whether we’re talking about goats or fish or stars or centuries. That’s crazy. It’s about as powerful a human capability as we have.

We’re just meat computers, basically—neurons firing in particular patterns—and yet somehow we can comprehend infinity. We can grasp limits and derivatives. We can calculate the trajectory needed to land a probe on Mars. No other animal does this. Not even close.

Math isn’t just a tool we invented. It’s a capability central to human thought and understanding.

Even Isaac Newton, one of history’s greatest scientists, saw numbers this way. We all know that there are 7 colors in the rainbow: ROYGBIV. Red, orange, yellow, green, blue, indigo, and violet. But what’s the deal with indigo? Look carefully at the actual spectrum and you’ll notice indigo doesn’t really hold its own as a distinct color. Newton included it to get to the number seven—that sacred number.If God created the rainbow, there had to be seven colors, not six.

Reclaiming Wonder

So what do we do with this? I’m not suggesting we all start practicing gematria or refuse to use the number four because it sounds like “death” in Mandarin. But maybe there’s something worth recovering here.

In his book To Life! Rabbi Harold Kushner writes: “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.”

Now when I look at the numbers of aliyot on Shabbat or weekdays, or the ten people needed for a minyan, I pause and remember that there’s something powerful and primal and wonderfully human in numbers. The ancient reverence for numbers wasn’t primitive—it was holy. It recognized that our ability to abstract and pattern-match is one of the deepest things that makes us human.

It reminds me that the goal of life isn’t to control everything. It’s not to turn everything into a number. It’s to recognize that everything in life can be holy or magical—even numbers.