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:

“When he has more bad days than good.”

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.

Saturday morning we were at urgent care. Blood work, fluids, anti-nausea meds. They suggested an ultrasound, but MLK weekend made scheduling difficult. I said I’d bring him home and monitor him there, where he’d be comfortable.

I had ChatGPT. I had a plan.

I prepared a triage station in the kitchen. Blue pill bottles lined the countertop. Boiled chicken. Two kinds of broth at the ready.

By noon Sunday he was holding water, but he wouldn’t eat.

That’s okay. Anti-nausea cocktail. Pain meds. Hit him with gabapentin, cerenia, ondansetron.

He was drooling constantly. He’d never been a drooler.

—-

That night he was barely able to rise to his feet. I picked him up, and put him on my lap. We watched The Last of Us. The episode where Bill asks his husband to euthanize him.

“Just give me one more good day,” Bill said.

Fucking HBO.

Deefer’s breathing was shallow, raspy. Then it settled. I picked him back up and brought him back to the kitchen. He took some water. I can still turn this around, I thought.

He had drooled straight through my sweat pants, through my boxers. It was clammy and cold.

—-

Monday morning I came downstairs to our triage station. He was lying in the same spot. I checked the floor and his bed for throw up or piss. Nothing. Good sign. I gave him a rub. Checked his water bowl—he hadn’t touched it.

I went to grab the bowl and slipped on a puddle of urine, hidden in shadow between beige tile and overhead light.

Then I picked him up and realized he was soaked.

I brought him upstairs to the tub. Washed him with the kids’ body wash, then back down to triage.

More pain meds. Nausea meds. Offer water. Offer food.

He kept the meds down. A sip of water. Still refused the food.

I called another emergency vet in New Jersey and scheduled an ultrasound.

—-

“If you are independently wealthy, we could certainly try,” the vet said. “But even if we resolve all of this, there’s still the underlying adrenal gland tumor. His prognosis is not good.”

She paused.

“I’m so sorry.”

She left and I laid him on the couch. I called Amy.

I should have given her more time that morning, before I rushed out the door. A chance to say goodbye in person. She was his person. Hers first, then mine. I wish I had just slowed down.

We FaceTimed so she could say goodbye. Then I called my mom. Then my sister. Then Amy’s mom.

Everyone got their goodbye.

—-

Amy reminded me to take photos and video. So I did.

I pulled his brush from my bag—I’d actually remembered it—and brushed his head, his ears, his belly. The hair came out clumpy from his ears, like loose threads.

I rubbed his paws, his back, felt all the cysts and bumps. Buried my face in his fur. Even old, his fur still smelled like puppy. But there was something else now, too. When he breathed, he smelled cold.

I picked him up, walked to the intercom.

I told them we were ready.

The vet came in with four vials. Milky white first. Then a clear one. Then a bright purple-pink one you could mistake for Calpol. Then one more clear one.

She told me his eyes might stay open the whole time.

They did. They stared at the wall. His heart slowed. The rise and fall of his chest stopped. She put the stethoscope to him and listened for the quiet. We listened together.

Deefer gave one last gasp, a cold breath escaping his mouth.

“He’s gone,” she said.

And so he was. My sweetest boy.

—-

I stayed in the room. Went through the routine one more time, tried to remember how he liked his rubs. His back, his paws, his head. Took one last smell.

Then I buzzed, and a tech came in. He said he was sorry. He took Deefer.

I gathered my things, went to the front desk, paid my bill. It was $1,986.45. We got a $65.40 discount. I didn’t ask why.

I sat in my car. Cried.

When I got home, the kids asked about Deefer.

“Is Deefer dead?”

“Is he not coming home?”

They sat with me for a while.

Then Oliver asked: “Do you want to play Monopoly with me?”

Annabel asked: “Can we get a cat now?”

Life goes on.

—-

That night we went through photos. All the way back. 4,084 days with our boy.

“I wish we could have given him a great meal,” she said. “A burger. A steak.”

I nodded.

“One more good day.”

But most times, you don’t know when to cash in that last good day. You don’t know it’s the last one until it’s gone.

Maybe better that way. Simpler.

Just give the people you love—the ones who love you back—more good days than bad.

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.

“Then they didn’t. Tommy got his way.”

—

Your grandad suggested a few names for you.

美雲 (Mei Wan): beautiful cloud

美怡 (Mei Yee): beautiful and joyful

美靜 (Mei Jing): beautiful and calm

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”.

Oh god, I had not heard, and am so sorry, that’s devastating. Thank you for letting me know…

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.