On a Monday in September I wrote to myself:

“Grateful I have work where I can drop off Oliver & Annabel to their camp at 9. And then walk to pick them up at 3. And it’s all good. I can still get everything done. I can still do fun side projects, and make it to the gym, and all the stuff I like to do.”

A quarter of small bets

This quarter felt measured. I made a lot of small bets and optimizations. A few examples:

• Waking up at 6 AM instead of 5 AM (and no more snoozing repeatedly)

• Instagram Reels for Good Morning Philly

• Voice mode with ChatGPT

My state of mind was experimentation. If I had an idea, how fast could I execute it (with AI, obviously) and get it out into the world to see whether it was worth pursuing or discarding? That lends itself to trying a lot of different things.

Experimentation is a muscle. It’s a mindset, and it takes time to hone. I’ve been working on it since my Reforge days, and my stunted emotional attachment to people, places, and things gives me an above-average disposition for it. It’s a double-edged sword, though. It’s easy to get caught up in the fun part of work: trying new things. But the only way to make something valuable, or to really enjoy it, is to make consistency your superpower: stick with it for an uncomfortable and unreasonable amount of time.

Here’s what moved this quarter:

Good Morning Philly

Good Morning Philly went from about 2,100 subscribers on July 1 to 3,950 this week. I haven’t missed an issue: 12 this quarter, with a 58% average open rate.

A big question for me all year has been “Is there a there there?” Closing in on 4,000 subscribers after nine months, I think the answer is yes; maybe there is.

I’ve also been thinking about why I’m doing it. Two reasons:

1. Create something valuable and useful for a community my family loves and is so happy to be a part of.

2. The intellectual challenge of building something from scratch. I know I have the skills. Now I have to prove it to myself.

Consulting

Both of my client engagements kept going all quarter. They’re getting more intense, but I’m managing. On July 30 I wrote:

“Time is a constraint because of this phase of life, not because of the jobs.”

Some days it feels like a lot, but not because the work is harder or beyond my grasp. The opposite: I’ve landed in a sweet spot, with one foot in the known and one in the unknown, and I find it challenging and rewarding. What makes it hard is balancing family, other responsibilities, and the side projects I’m so excited about.

Remote Life OS

The Monday remote jobs email for Remote Life OS keeps going, same as always. What’s new is a Thursday issue where I write about what I’m actually doing: how I plan our meals with AI, my monthly money review, and why the work I do keeps compounding.

I’m also moving everything off Kajabi and hosting it myself, starting with my course, Land the Interview, to remove some technical debt and overhead.

Family

Oliver started third grade. He won his first soccer match, and he and Annabel both started piano lessons.

Annabel started kindergarten and turned six (I wrote her a letter). She’s back to rock climbing, too.

Theodore is still in daycare; he’s still a joy, and he takes most of our energy right now. A two-year-old’s emotions, wants, and needs are a lot to manage.

Madeline has proven to be the chill baby, which is exactly what we need. Her grandad suggested three names, and we took the one that means beautiful and calm. She has lived up to it.

The summer was full. We had beach days at Asbury Park. Spent a week at Rehoboth Beach. Dorney Park felt too far one Monday, so we took the kids and my mom to Diggerland instead. We made it to Dorney Park in August anyway. Deborah and Andrew came over from Cork. And Amy and I celebrated 13 years.

What I’m focused on for Q4

• Good Morning Philly: Get to 5,000 subscribers and run a handful of mini experiments along the way: a custom front page, a better subscribe flow, and the YouTube channel. Something to think about for next year: instead of treating this as a side project, do I turn it into a proper media company?

• Work: Keep the clients going strong. Make sure I’m continuing to deliver.

• Writing: Most of this quarter’s optimizing was really getting my processes back on track. I’m writing Good Morning Philly every week, writing for Remote Life OS (including posts on portfolio careers and AI workflows), and I’ve started writing this newsletter again. It took all quarter to get the process in place, but it’s here. Now I just have to keep it up.

• Fiction: I have three fiction projects that have sat on the back burner for over a decade(!), and I’ve started sourcing and researching again. There’s never going to be a good time for this, so I want to bring them forward a little at a time. That way, when I do get a few months to sit down and crank something out, I’ll be ready.

• Family: Halloween. A proper Thanksgiving with all the traditions: football, a movie, karaoke. And at least one week off at Christmas, maybe two.

How did your quarter go? Hit reply and tell me.

This is my sixth quarterly review. Previous reviews: 2022 Q1 · 2022 Q2 · 2022 Q3 · 2024 Q2 · 2026 Q1. I publish them because accountability works better in public.

⭐ Recommendations

🍽️ Eating

🥘 Home Appétit. These save us so much time on school days. You know the 5 pm problem. Everybody’s home, everybody’s hungry, and all you’ve got in the fridge is a bottle of OJ and a bag of shredded cheese. This has been a game changer for us.

📖 Reading

📘 Circe by Madeline Miller. Just finished it, and it was outstanding. I was surprised at how much I liked it. It reminded me how much I loved reading the classics when I was younger, and now I want to go back and reread them.

Annabel turns six on September 17th. I write and publish birthday letters for the kids. Here are Oliver’s, at five and at six, and Theodore’s, and Madeline’s.

“If you could write anything in the garden, what would you write, Annabel?” Amy asked.

You didn’t hesitate.

“All kids deserve to be loved.”

“Why?”

“Because whenever we go to the playground, you check to see if my friends want to come, because you know I like playing with them. And whenever I come home, Daddy makes me yogurt and granola for me, because he knows I like it.”

Some days it’s easy to forget you’re only six. That you already understand love is what you do, not what you say.

Two years ago, in your fourth birthday letter, I wrote: “We don’t have that thing yet, AB, you and I. I think we’ll find it, though.”

I think we’re getting closer. We’re so alike, you and I. We both like our silences and our space away from people. We’re both little black sheep, still figuring out where we belong. Or maybe that’s just me projecting. I do that.

Either way, it can be hard. I think this year it was.

For as long as I can remember, you and Oliver were a pair. There was a whole era where you two were inseparable, as we moved across the world and then meandered our way back. That’s slowly ending, and now we’re figuring out what’s next.

You’ve already had your moments of brilliance. Your first day of kindergarten, for one.

Your mom stayed up the night before making you a banner and setting your teddy bears out on the kitchen table to greet you in the morning. You came down smiling ear to ear, bob cut, book bag strapped across your chest like this was the thing you’d been waiting on your whole life. We stood in a schoolyard, a stream of navy blue and khaki, kids fighting and playing all around us. You headed for the door already chatting with a friend. You waved goodbye. You disappeared without a glance back.

A few days before that, I took you and Theodore to the Please Touch Museum.

You took him under your wing. You walked him through the grocery store and made sure he could pick things out and buy them himself. You brought him into the Alice in Wonderland maze and told him you would keep him safe and show him all the shortcuts.

Six is two steps forward and one step back, my love. It can feel like a maze of its own while you figure out where you fit.

Here’s the one thing you’ll never have to wonder about. You are loved. You’ve got your whole family with you, ready to show you the way whenever you need it.

Happy 6th birthday, my love.

⭐ Recommendations

📺 Watching

🎬 Carolina Caroline. Went in expecting one movie and got a much better one. A Letterboxd review said it best:

“Went in expecting a thrilling, fun and sexy bonnie & clyde style crime thriller and what i got was a deeply profound, irresistibly charming and often emotional character study about the pursuit of happiness.”

🍜 The new Anthony Bourdain movie, Tony. Saw it with my cousins Brian and Brandon; we’ll watch anything Bourdain. I’ve started to re-read Kitchen Confidential. My favorite Bourdain quote, on writing for television:

There is a grim, inevitable and all too predictable trajectory to the passage of a good episode of television. People aren’t as stupid as your minions clearly believe, they don’t need the truth pounded home with meaningless platitudes, or bland generic sum-ups. They’ll get it. …Don’t empower these squirrel-balled nerds by letting them get their way. They will then nibble this show to death like hungry ducks.

🧗 Fall, and then the behind-the-scenes on how they shot it. Just a fun watch; my feet were sweating as I watched it. To work through the direction, they built a tiny scale model of the platform in a backyard first and blocked the entire movie on it, working out how the characters would sit, stand and sleep.

📖 Reading

📕 Sons of Ares, the Red Rising graphic novel, prequel to the series. Great to read it and have visuals of this world.

Almost two years ago, on my first day back from paternity leave, a calendar invite from HR titled “quick sync” landed in my inbox.

You know the rest.

Shortly after that, I decided to try consulting (i.e., working for myself) full-time. Two years feels like just enough time to give an honest evaluation on how it’s all going.

In January, I ran into a parked Tesla outside of a store that sold overpriced cookies in Fishtown. Not a big deal (it was just a fender bender), but I felt terrible.

I called the owner to tell her.

She picked up the phone:

You’re telling me.

By any objective measure, it was a rough start to 2026. There was The Tesla Incident. Our fridge broke. We found water leaking through the stucco on the back of our house, which means we need to replace the entire exterior. We lost Deefer, our dog, in January.

So yeah. Rough quarter.

Underneath all of that, a lot happened.

What happened in Q1

Good Morning Philly newsletter

The biggest thing I built was Good Morning Philly, a free weekly newsletter covering the River Wards (Fishtown, Northern Liberties, Kensington, Port Richmond) that ships every Monday at 6 AM.

Deefer passed away on January 19th, 2026. This is my goodbye letter.

I write and publish birthday letters for the kids. Yes, this includes Deefer Dog. You can read Deefer’s 10th birthday letter here. And here are Oliver’s, Annabel’s, Theodore’s, and Madeline’s recent letters.

Eight months ago, we asked the vet when we’d know it was time. She didn’t hesitate:

I wanted specifics. A date. Confidence levels. Standard deviations. But that was all she gave us.

So I did what any reasonable person would do. I started feeding ChatGPT his entire medical history.

Stage 4 heart murmur. A mass on his adrenal gland invading his vena cava. Seven different pills every day. I logged it all. If the vet couldn’t give me a formula, I’d build one myself.

For eight months, it worked. More good days than bad.

—-

Friday. Amy ran upstairs to get ready. I was trying to get the kids to play Mario Kart. Deefer threw up three times. Then he started throwing up his water. And he kept throwing it up.

This is my friends & family newsletter. You probably signed up after reading one of my articles, a LinkedIn post, or after we met. You’ll get a new letter 1-2x per month.

Madeline Mei Jing Lee was born on November 26th, 2025.

I write and publish birthday letters for the kids. You can read Oliver’s, Annabel’s, Theodore’s, and Deefer’s recent letters.

We went to visit our family friends, Ali and Tommy, with your Mima. They’d just finished remodeling their house.

Ali opened her walk-in closet.

“Tada,” she said. Shoes lined the room floor to ceiling—Manolo Blahnik pumps and Jimmy Choo and Louboutin heels, all on perfect display. I wear Hokas for every occasion, but somewhere The Corrs were playing. It left me breathless.

Later, Tommy took us to the basement, showed us his tool collection. Everything perfectly hung, tools stenciled to the pegboard so you’d know exactly where each one belonged. Everything in its place.

My dream house.

When we left, I asked your Mima: “Did they want kids?”

“Ali did,” she said. “Tommy didn’t. They nearly divorced over it, years ago.”

“Then what?”

She shrugged.

—

Your grandad suggested a few names for you.

We didn’t hesitate. We’ll take the calm one.

Your parents are optimists, Madeline. We wanted to conjure some stillness into your personality. This house runs on chaos—usually after dinner, before bed, the volume rising until someone cries. We were hoping you’d bring some balance.

So far, you’ve held up your end of the bargain. Like you knew we needed it.

You’re also the last one. Which means there’s this tension: we know the most about parenting, but have the least time to do anything about it.

I can’t promise Louboutins or an orderly life. With four of you, I’m not even promising college. You all might flip for it—the winner goes.

But I promise you this: you are born into a family that will show up for you. Everyone is cheering you on. There’s so much love here, Madeline.

It’ll leave you breathless.

This is my friends & family newsletter. You probably signed up after reading one of my articles, a LinkedIn post, or after we met. You’ll get a monthly email.

It was only after Chris died last November that I finally got a reply from an old friend. I’ll call him “Alex”.

Eight years of emailing Alex, with no response. Birthday messages. Life updates. The occasional “thinking of you, man.” I never got anything back.

It took a message about the motorcycle accident to break the radio silence.

It keeps me up sometimes. Because there were times I wasn’t a great friend. There were times (cringey, crawl-into-ball-and-die moments) where I chose convenience over loyalty, where I let him down. And I think maybe I earned the eight-year silent treatment.

But there were good moments too. Times I showed up when it mattered. I want to believe it balances out. I’m not sure it does.

The only move left: look at where you failed, and try to fail less. Look at where you succeeded, and do more of that.

That’s what these reflections are for. Once a year, once a month, every day… the frequency is a detail. But you have to look. Reflection is how you steer instead of drift.

This is a review of my 2025 and a public sharing of my 2026 goals.

At the end, I share why I do this and how I review the year.

To summarize: This helps me look back at what worked, what didn’t, and what I want to focus on in 2026.

My friend Chris passed on November 9, 2024, in a motorcycle accident. He was riding slowly out of a parking lot in Los Angeles. They think he hit something. He fell and died. Last week, I went back to New York for his memorial service.

This is my friends & family newsletter. I publish here for reference and sharing. You can subscribe here.

This month we’ve been visiting family in Cork and Dublin. We built our itinerary around the Taylor Swift Eras Tour that played at the Aviva.

I caught my first hurling match at Croke Park (semi-finals between Cork vs. Limerick), which was a blast.