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Thanks for Everything, New York.

I moved to New York at 24. My move-in day was the day of SantaCon. I was young enough to find it kind of charming. (It was not, it is not.) My first apartment had ceilings so low that I couldn’t lift my hands all the way above my head. I didn’t care. I was excited to be here, but I figured I might live here a year or two, then move onto the next thing.

I had no clue what I was getting myself into.

I didn’t know that BuzzFeed would become what it was in the mid-2010s — a rocket ship where I’d get to learn from some of the smartest people on the internet. I didn’t know that I’d get the chance to work at The New Yorker and be a small part of an incredible team guiding that publication onto its next chapter. I didn’t know that newsletters — this weird little corner of the internet that no one seemed to really care about! — would be my calling card. I didn’t know I’d get the chance to start Inbox Collective and work with so many amazing teams around the world.

I didn’t know that I’d live here long enough to go, “Yeah, I remember when that Duane Reade used to be a pretty great indie music venue!” I didn’t know that I’d develop such strong feelings about specific bagel places and pizza shops. (I made sure to get one last everything at Ess-a-Bagel and make one last trip to Spumoni Gardens!) I didn’t know that those only-in-New-York moments happen to everyone if you live here long enough. (Meeting Clyde Frazier, while he was wearing a Dalmatian-print suit, at the tailor! Seeing a show in Central Park and having Jackson Browne show up as a surprise guest! Accidentally scaring Matthew Broderick when I walked past him on 21st St!)

And I certainly didn’t know about all the lifelong friends I’d meet in New York. I didn’t know I’d meet my incredible wife here. I didn’t know I’d start a family here. I didn’t know I’d get to watch my son grow up here.

I hope I’m leaving New York a better person — more adventurous, more curious, more kind — than I was when I showed up.

What an incredible gift and joy it’s been to be a small part of such a wonderful place. New York has been so good to me.

I’m excited for what’s next, but I’m going to miss this place.

Thanks for everything, New York.


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At top: Me in early 2013, before I discovered the importance of hair product, in front of the yellow BuzzFeed “WIN” wall in the lobby of the 21st Street BuzzFeed office.

At bottom: Me in May 2024, on a bright stage at The Newsletter Conference in New York City, interviewing a few fellow newsletter operators (Stephanie Talmadge, Louis Nicholls, and Chenell Basilio) about newsletter growth strategy.

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Just Ask The Question.

Before my son was born, I wondered how long it would take before I asked a truly stupid question.

Other friends had told me their stories about asking that first dumb question. One friend confessed that they called the pediatrician’s emergency line the first night home from the hospital because their child was crying. “Yeah, they’ll do that,” the pediatrician chuckled, and hung up. Another told me that they misinterpreted the doctor’s instructions before leaving the hospital. They called the pediatrician the day after they got home, reporting back that they child had pooped three times when the doctor had told them to make sure their newborn pooped once. “We meant at least once, not only once!” the pediatrician laughed. Every new parent, it seemed, asked something stupid.

I was a new dad who’d never changed a diaper before. The only thing I knew for certain was that I knew nothing. I knew I was going to ask something dumb — eventually, at least. 

It took me 45 seconds.

Ben was born, and the doctors called me over to a little scale where they were weighing Ben. I looked down at his tiny feet. They were black.

I hadn’t remembered reading anything about black feet in any of the parenting books.

So I asked them: Are his feet supposed to be black? Is that normal?

That’s when they held up a piece of paper with his tiny footprint on it. They’d pressed his feet in black ink to make the footprint.

It was the first of what would be many, many stupid questions.

But getting that first one out of the way really did help! With a baby, new stuff happens all the time, and I quickly became unafraid to ask, even when I knew the answer was going to be something obvious. I didn’t have to preface questions with, “I know this might be a dumb question, but….” I just asked.

I constantly remind myself: There’s so much I don’t know, and there’s no reason to pretend like I know everything.

Even when it feels like it might be a stupid question, I now just ask.

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That photo at top is of me the night we got home from the hospital. I’d changed about five diapers at that point. I didn’t have my technique down, but hey, I got better.

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You Can Handle It.

An impeccably clean baby's room, with a white crib, tall green plant, and a "Dream Big" neon sign on the wall, which seems like it would probably scare a baby. Oh, and there's a blanket over the crib — whoever took this photo probably isn't aware that that’s a safety hazard for such a small child.

My son sometimes does this funny thing at night.

He’ll be peacefully asleep when, suddenly, something jolts him awake. The pacifier’s long since fallen out, but he can’t find it to soothe himself back to sleep.

So instead of searching for the pacifier or trying to suck his thumb, he does the funny thing: He sits upright and cries.

He’s so tired that he barely sit upright. And yet, he sits, waiting for me or my wife to come in and fix things. (Fixing things usually entails finding the pacifier, putting it back in his mouth, and then helping him lay down.)

I wish I could explain to him that things are OK. I wish I could explain how he could solve the problem without needing our help.

He’s still a bit young to understand that. But one day, I’m looking forward to being able to explain to him that he’s got everything he needs to handle the situation himself — and then watching him handle it with ease. I know he can do it.

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That photo of a baby’s room — one that’s far too clean to be my baby’s room — was taken by Collov Home Design for Unsplash.

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Shift, Pivot, or Sunset?

The sun sets behind clouds as trees glow in the foreground.

We sometimes need to make a change with the work we do. The question is: How big a change do you need to make?

Sometimes, you just need to make a shift. The change is small — you’re refocusing on something new, but it’s within the normal scope of what you’d do already.

Sometimes, you need to pivot. You’re making a big change — taking your skills and applying them to something outside your current orbit. The skills and the work might look similar, but you’re doing it in a different space.

And sometimes, you need to sunset things. You’ve done the work, you’ve learned the skills, but you’re ready for something brand new. You’re ready to shut down what you’re doing and move into a brand new field.

For my work, for instance, a shift would be changing my focus from working with newsrooms to working exclusively with non-profits. A pivot would be moving from newsletter consulting to building an agency to help newsletters grow. And to sunset would mean shutting down Inbox Collective to focus on something new.

None of these match where I’m at right now, but maybe they will be in the future. When it comes time to make a change, the big question remains: Shift, pivot, or sunset?

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That’s a photo of a sunset, taken by Dawid Zawiła for Unsplash.

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Keep Making It Better.

A few years ago, I was working on a project with the team at Poynter. They had a landing page for their newsletters, but it wasn’t very good. There weren’t any details about any of their newsletters — what they were, who wrote them, when they’d show up in your inbox. As a result, the page wasn’t driving many sign-ups.

I showed them a bunch of options for how we could make things better. We all agreed on a new template — but it was going to take a long time for us to build out that ideal page. Instead of waiting until that page was done, we decided we’d first take a small step in the right direction.

That next step was to update the existing page with more details about the newsletters. It wasn’t perfect, but it was an improvement over what they had.

And then, a few weeks later, the Poynter team launched the final version of the page, which had a brand-new design, more details about each newsletter, and the ability to easily sign up for multiple newsletters at once.

I tell my teams often: Direction is more important than speed. Everyone wants to make big leaps forward — but sometimes, the right move is to take small steps in the right direction.

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Those are screenshots of the Poynter newsletter page. Thanks to the Internet Archive’s Wayback Machine for the screenshots of earlier versions of the page.

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Ask For Advice. Be Willing to Listen to the Answers — Good or Bad.

Every year, I spend a few days with friends who also have their own solo businesses. The offsite, as I’ve come to know it, started with just one friend. It’s grown to a group of four — each of us with our own unique perspective on how to build a great business.

Last night, I gave a presentation to the group, where I walked through a few ideas for the future of Inbox Collective. Some were small ideas that I wanted suggestions about; one was a major moonshot for the business, something that would radically change the course of the business. I wasn’t sure if I was ready to do something so big, something that might take Inbox Collective from a one-person operation into a pretty sizable business. But I wanted to know what they thought.

And I loved that the group had a unified response to that last idea: We love the idea as a business — but we’re not sure we love it for you.

It’s exactly what I’d been thinking, so to hear three friends immediately come to the same conclusion was heartening. Their hesitancy gave me confidence that I was already on the right track. Some ideas, even if they’re interesting, are worth saying “no” to.

Today, one of my friends here on the offsite tried to offer an apology. “I hope we weren’t too harsh about that last idea,” he said. I waved him off. I told him: I presented the idea because I wanted to know what you three honestly thought about it, and the fact that you all were so skeptical of the idea — and skeptical because you felt it didn’t line up with my current priorities and needs — told me everything I needed to know.

I wanted the feedback, good or bad. I’m glad I’ve got a group in my corner who can point me away from the ideas that don’t make sense for me.

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That’s a slide from my presentation to the group.

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A Little Impact is Enough.

A green and black butterfly flaps its wings on a green leaf.

We visited South Florida this week, and while we were there, we stopped by this place called Butterfly World. I was so pleasantly thrilled by what we found: A small series of gardens featuring thousands of butterflies and hundreds of birds. (One butterfly even landed on Sally’s hat and walked around with us for a while.)

So I started reading a bit more about Butterfly World’s founding. It’s a sweet story: An retired electrical engineer named Ronald Boender had a passion for raising butterflies at his home, and then kept chasing that passion. Raising butterflies led to meetings with people who had butterfly farms, which led to the creation of Butterfly World.

No one’s going to claim that Butterfly World is changing the world. But not everything needs to be a world-changer. Sometimes, it’s enough to make just a little impact, wherever you are. And Butterfly World was just that: A beautiful series of gardens, and a sanctuary to some beautiful creatures.

Here’s to the impact that Ronald Boender had in South Florida.

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I took that photo at Butterfly World on April 19, 2024.

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Give Yourself a Constraint.

I’ve never played Talking Stick Golf Club, in Arizona, but I’m fascinated by one of the golf holes on their course. The hole, no. 2 on their O’odham Course, measures 500+ yards, and at first glance, the hole appears to be unusually straightforward. The hole is flat and straight, with just two bunkers near the green. It looks more like a driving range than a golf hole.

The catch is that there’s a fence on the left side of the hole, and any shot that goes left of the fence is out of bounds. Hit it over the fence, and you’ll take a penalty stroke. It’s possible to play well to the right to avoid the fence — but eventually, as you get closer to the green, you’ll have to hit a shot with out of bounds lurking behind. The hole has one interesting feature — you can’t go left — but that constraint makes this a fascinating hole to play.

It’s a great reminder that simple constraints can be powerful. When you’re planning a new project, sometimes it helps to give yourself some limitations. Maybe you’re operating on a limited budget or a limited timeframe. Or maybe you’re intentionally giving yourself a restriction to see how it impacts creativity. I remember seeing a songwriter once who told me that he played a game on tour: He’d give everyone on the tour bus a song title, and they’d all have a day to write a song with that title. The song could be in any style and about any topic — as long as it had that title. There’s still room for creativity, but you do have to write with that restriction in mind.

I don’t think constraints are a bad thing. I know I can get a bit carried away when I’m dreaming up a new project. Sometimes, a rule or two can be what I need to focus on the elements that matter most.

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That video comes via Fried Egg Golf.

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New Magic in Old Material.

Colin Hay plays guitar in front of a crowd at New York's City Winery.

I went to see Colin Hay, the former frontman for Men at Work, perform this week. He was great, as I’d hoped, but what really wowed me was watching him create new variations on old songs. Five decades of playing songs meant that he could improvise in the moment, taking one song and intertwining it into the next. He seemed to find new magic in old material.

And it was a reminder for me of how important it is to keep making adjustments. There are certain talks I’ve given over and over again, but I’m always trying to find ways to tweak things to keep it fresh. The core message is the same, but the delivery keeps changing.

You could play the same hits the same way, I suppose, but there’s something to be said for the performer who finds ways to keep things feeling new.

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I took that photo of Colin Hay performing at City Winery in New York on Monday, April 1.

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Try It. Then Figure Out What You Want to Keep.

A few years ago, I saw Adam Sandler perform live. He was recording what would become his first comedy special in decades, and honestly, I wasn’t sure what I was in for.

What I was in for, it turned out, was something both funny and unpolished.

Sandler’s set, which he’d trim down to about 70 minutes for TV, ran nearly two hours. He performed original songs and some stand-up material. Some bits worked; others didn’t. The cameras rolled the whole time.

What I discovered later was that this was Sandler’s creative process. He does the same thing with movies: He records lots of takes, lots of different ways, and then figures out which is the funniest once he gets to the editing bay. The goal when he’s recording is to capture all sorts of options — he’ll figure out what works later on.

That’s not a bad way to approach your work. Some things become hits, and others flop. You don’t really know which is which when you’re making it. You can’t always see around corners.

So instead of hoping that your first idea will be the right one, try doing a bit more than you expect. Leave yourself some alternatives. If something doesn’t work, that’s OK. You’ll have a Plan B already waiting for you.

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