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.

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?

———

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

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.

———

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.

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.

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 yournextnewsletteridea.com is my next project!

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.

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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.”

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

We Ain’t What We Gonna Be.

A mural of the "I Am a Man" protest that took place in Memphis, TN, during the Civil Rights Movement.

I’ve just finished Jonathan Eig’s biography, “King: A Life.” It’s a remarkable portrait of Martin Luther King, Jr.

I found myself jotting down lines and quotes as I read through the book, but one stuck with me. It comes at a rare quiet moment in what Eig describes as the non-stop travel schedule that was the final dozen years of Dr. King’s life. It comes at a moment when he’s talking to two ordinary Americans, trying to keep their spirits up.

“We ain’t what we want to be, and we ain’t what we gonna be,” he tells them.

King had a vision both simple and radical, one that pushed for huge changes in our society. Those dreams are still unfulfilled today.

And yet, there’s that quote, something he said not in a pulpit or in front of a camera — the promise of better days tomorrow, of change ahead, for each of us, and for a nation.

We go still, onward. We are not yet finished today.

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That’s a photo of the “I Am a Man” mural in Memphis, Tennessee. The mural was created by Marcellous Lovelace with BLK75. The photo was taken by Joshua J. Cotten for Unsplash.