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.


That video comes via Fried Egg Golf.

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.


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

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.

Be Something to Someone.

The Pitchfork homepage in late February 2009.

The team at Slate put together a great oral history of Pitchfork, the music site that ran from 1996 until 2024, and there was a line in there from Chris Kaskie, Pitchfork’s former president and co-owner, that really stuck with me.

“We are not trying to be everything to everybody,” he said. “We’re trying to be something to someone.”

It’s something a lot more of us could take to heart. Whatever it is you do, your work doesn’t have to matter to everyone — just to someone.


At top, a screenshot of the Pitchfork homepage on a random February in 2009.

Should You Work on That Idea?

Using Domainr, I can see if a domain name is available

Here’s a little trick I use to decide if I actually want to work on a project:

Let’s say I’ve got an idea, and I get really excited about it. I buy a domain for the website for the project, and start jotting down notes. I’m convinced that this is my next big idea!

The next step’s been a game changer for me: I go and add a note to my to-do list — one month in the future. I remind myself to revisit the idea then.

And then I do nothing — at least for 30 days.

Often, a month later, I look at the idea and go: Why was I so excited about this? That’s not a bad thing, I think — I’ve just saved myself a bunch of time and effort on an idea I wasn’t all that excited about!

But if I’m still excited about the idea a month later, that’s how I know it’s worth the investment, and that’s when I actually start to work on it.


I like to use Domainr to come up with domain names. But I don’t think is my next project!

Learning How to Work Weekends With a Kid.

A sharpened pencil sits on top of a blank spiral notebook.

Weekends are different now as a new dad. Before my son was born, I’d often spend a little time on the weekend doing some work. That might mean a little time on a Saturday morning doing some writing, and then time on Sunday evening prepping for the week ahead. If I had the time, I might cross a few other things off my to-do list.

But this year, the routine’s had to change. What I realized is that on a weekend with a baby, I might be able to carve out two or three hours for work. But in that window, I’d probably only get one or two things done.

At first, getting so little done on a weekend felt like failure. I’d find myself feeling stressed on a Sunday night about how little I’d accomplished.

What I needed was a shift in mindset. Getting 1-2 things done on a weekend isn’t a failure — I’ve got a kid now! I’ve got other responsibilities!

If I get 1-2 things done, that’s a very good day.

That shift has made all the difference. If I get a few hours to take care of work, I’ll look at my to-do list and figure out what the priority task (or two) is. That’s all I’m working on that weekend. If I get through those tasks faster than expected, I don’t go back to the to-do list for additional tasks. I leave everything else for Monday morning.

Getting those 1-2 things done is more than enough.

Everything else in my life has shifted since becoming a dad — it makes sense that the way I work on weekends needed to, too.


That photo of a blank notepad and pencil comes via Kelly Sikkema and Unsplash.

Every New Experience Can Be a Learning Experience.

a rainbow of colors on a bookshelf

I’m lucky to have a job where I learn new things every day.

Every new client brings me questions I haven’t had to answer before. Every new project introduces challenges I’ve never dealt with before. Every new year brings opportunities I’ve never had before.

And that’s just what happens at work. When I come home, being a new dad means I learn all sorts of new stuff every day — sometimes, a few new things a day. (Sometimes, that new stuff involves learning ways to not get peed on.)

You try, you do, you screw up, you learn. I’m not going to say I get smarter every day — I’m still working on that part! — but every new experience is a learning experience. You just have to be willing to see it that way.


That photo of a bookshelf comes via Jason Leung and Unsplash.

Find What Works For You.

I talked with a group of publishers a few weeks ago, and they told me they’d just come back from a conference where a speaker told them that the right number of links to include in email was 15. They wanted to know: Did I agree?

And I told them what I know to be true: There is no “right” strategy for email.

There is no right topic.

There is no right format.

There is no right number of links.

There is no right number of emails to send per week.

It’s up to you to figure out what works for you and your audience.


That’s my first BuzzFeed newsletter. It had just five links. We tested it — and figured out that we could add a lot more!

Your Imperfect Next Step.

I was on a call with a client a few weeks ago, and they told me they wanted to build the best possible email strategy in 2024.

“That’s great,” I told them. “But I don’t want you to be thinking about what’s best. I want you to be thinking about what’s next.”

Thinking “best” can lead to magical thinking, to dreaming of blue sky situations where you’ve got all the budget and resources you need. It can lead to planning for a day that may not come.

Instead, take a look at what you’re doing right now and ask yourself: What’s the next thing we can do to make our newsletter strategy better?

It might be a small step, and that’s OK. Some of the best newsletters out there were built thanks to a lot of small steps forward.

The next step may not be perfect. It may just be… what’s next.


I took that photo, more than 15 years ago, while walking the Camino de Santiago in Spain.

Be Willing to Get Lost.

A splash of white light on an otherwise darkened staircase.

I read Andrew Leland’s new book, “The Country of the Blind,” this week. It’s a memoir about a writer who has been slowly losing his sight over the previous decades, and he uses the book to better understand life as a blind person in the United States. It’s a fascinating read, and a reminder of just how much sight shapes the way I think about the world. (Even in trying to write that last sentence, the first three phrases that came to mind — “a glimpse into Leland’s life,” “an illuminating read,” “an eye-opening experience” — all reflect a bias towards sight.)

One chapter towards the end of the book truly struck me. Leland visits the Colorado Center for the Blind, a place where members of the blind community stay for months as they learn new skills, from woodworking to cooking to navigating the outside world. Leland meets a younger student at the Center, Ahmed, who offers some advice about how to get around as a blind person:

The single most important skill for blind travel, Ahmed later told me, is that “you have to be willing to get lost, and be confident in your ability to figure it out.” In the early days of his blindness, he once took three hours to traverse a route that would have taken him five minutes with a sighted guide. Eventually he got better at navigating Washington, DC, learning the direction of traffic, the patterns of certain stoplights, the way the sound of another person’s footsteps changes as they begin descending a set of stairs. In Colorado, he learned to use cardinal directions, and can now often figure out which way he’s facing from the feeling of the sun on his face. But, he added, “it’s not like once you leave [the Colorado Center for the Blind], you’ll never get lost again.” … Getting lost is not always comfortable, or pleasant, but it is an organic and fundamental part of the human experience. The more one is able to accept it, rather than fight it, the more skillful one becomes in one’s travels.

Later in the chapter, Leland describes the experience of Ahmed and two other students heading to a local store. As Leland writes, not only do Ahmed and his classmates make it to their destination safely, but Ahmed is so comfortable on the walk that he does some it while walking backwards!

Anyway, I’ll be thinking about this line for the rest of the day: “You have to be willing to get lost, and be confident in your ability to figure it out.”


That photo of a darkened staircase comes via Unsplash and photographer Carolina Pimenta.