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Stay Curious.

Chris Miquel had me on his podcast the other day, and he asked me: There’s so much that the newsletter community is excited (and nervous!) about when it comes to AI — but is there one thing you think we shouldn’t hand over to AI?

And I thought for a moment. Probably seemed like longer on the podcast.

And then I said: Our curiosity.

AI can handle so many things: It can write, edit, create, brainstorm. It can analyze data. It can turn tedious processes into one-click actions.

But I hope that as we integrate AI into our lives, we don’t lose that sense of curiosity. So many of the best things that have happened in the newsletter space — and in the world, of course — have come because of our curiosity.

What happens if I try ______ ? What happens if I experiment with ______ ? What happens if I ask my readers to do ______ ?

Nearly every week, a client asks me something I’ve never been asked before, and that I’ve never seen before, and I say: “I’m not sure, but let’s try it and see what happens.”

These tools are endlessly powerful, but I don’t think they can see the world quite the way we can. Use them — but stay curious.

The curious are the ones who break through.

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Predicting the Future is Hard.

the ESPN article that predicted the future team.

Here’s a little reminder that humans are really, really bad at predicting the medium- to long-term future.

A friend sent me a list of soccer players who might play for the US men’s national team in the 2030 World Cup. It was exciting — look at all these future stars who’ll sure guide the USA to greatness!

And I was a true bummer and sent back ESPN’s predictions from 2022 for the 2026 roster. That list mentioned 31 names for new players who might make the team — players who weren’t on the 2022 squad.

Exactly one 1 out of 31 made the 2026 squad.

And look, that’s soccer. That’s a list that looked at players, all who were playing professional soccer at the time, some for major clubs in Europe, and saying, “Hey, I bet these guys will be even better in four years.” We’re talking about something that should be decently predictable.

And it got 1 out of 31 right.

I’m not trying to pick on the writer from ESPN. (He’s excellent, and a fellow Mizzou grad to boot!) Predicting the future is really, really hard.

It’s a reminder: Don’t get too caught up with what’s happening way down the road. Focus on the immediate future: Next week, next month, next quarter. Keep your eyes on the next steps and you’ve got a better chance to keep moving forward.

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Know What’s Around You.

I’m watching the World Cup today, and there’s a moment in the Argentina-Austria match. Argentina crosses the ball into the box. Thiago Almada is there, inside the box, with a clear chance to shoot on goal, but instead lets the ball pass through to Lionel Messi, who neatly finishes into the back of the net.

And as I’m watching, I’m wondering: How did Almada know that Messi was there?

It took a few replays for me to figure it out.

Just before he entered the box, Almada takes a split-second glance back and sees what’s around him. He’s there, in the image above, on the left. Messi is steps behind him. He doesn’t know yet that the ball is coming to him, but he knows that if it does, he has the choice to shoot or fake out the defender, leaving Messi wide open.

Watch #16 in the middle of the screen. It’s nothing more than a glance.

Some players would have taken the shot right away, not even realizing that their teammate was behind him. Almada, instead, made sure he was seeing the entire field — and by doing so, he set up a history-making goal.

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Have You Considered the Obvious?

Me, teeing off on a par 5. I hit the ball right over the bunker and into the woods — exactly where I was aiming.

I was playing golf over the weekend, and every shot was going straight and to the right. I was so frustrated. I’ve gotten pretty good at figuring out how to diagnose my mistakes and correct them during a round of golf, but I’d never seen this one before. A slice, a hook, hitting the ball fat or thin — I know how to fix any of those, but I couldn’t figure this one out. I tried a bunch of things during the round, but nothing worked. Every shot was a “push”: Straight, and to the right.

Then my buddy sent me a photo of myself after my round. My shoulders were lined up square to the target, but my feet were pointed way right.

I wasn’t pushing the ball to the right — I was hitting it directly where I was aiming.

Sometimes, the obvious fix is right in front of you.

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Figure Out Your Level of Risk.

A pile of white, multi-sided dice.

I had a conversation a few weeks ago with a friend who’s thinking about leaving her job to start her own thing. She asked for my advice, so I gave her something I wish I’d thought more about at the start: When you start a business, you need to figure out your level of risk.

Some people are willing to place big bets on their business. There are plenty of stories out there about people who hired big teams before they had a proven product or put tens of thousands of dollars on a credit card with no clear path to paying off that debt. Some are OK taking on a lot of risk.

I tend to be a bit more risk-adverse. So much of my business is built around coaching calls, where I work with small teams for a low annual fee. If I took on larger projects, I’d make a lot more money, but coaching is far more stable — I start the year knowing how much I’ll be bringing in that year. My coaching clients tend to renew their contracts year after year. Bigger projects, on the other hand, come and go.

Before you start, it really helps to understand how much risk you’re willing to take on. My strategy means that my business has a fairly high floor but a slightly lower ceiling. You might be willing to take bigger swings for a bigger reward — even if it means the chance of failure is a lot higher.

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That photo of dice comes via Zoshua Colah and Unsplash.

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There Is No Scoreboard.

A green scoreboard sits beyond an outfield fence at a baseball stadium.

If you’re an athlete, results are measured in wins and losses. But for the rest of us, there is no scoreboard — no way to clearly measure yourself against others.

Which is a good thing, I’d say. Your success shouldn’t be based on whether you’re doing better or worse compared to someone else. There’s a reason for the expression “run your own race.”

You have to figure out why you do this work. What matters to you? Why does this work have meaning to you? And are you doing work that meets those goals and those expectations?

It’s not about followers or likes or even revenue.

However you get meaning from this work, however you measure up against that — that’s your scoreboard.

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That photo of a scoreboard on a baseball field comes via Unsplash and photographer Dominique Hicks.

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You’ll Figure It Out.

There’s a great story Stephen Colbert told this week about his early days in comedy. Here, I’ll let him take this part:

“I understudied Steve Carell one week at Second City. He was about a year ahead of me at Second City and I had to understudy him, but to do so they said, ‘Well, he plays the euphonium and the baritone horn in the show.’ I said, ‘I don’t know how to play that.’ And they said, ‘You have 6 days. If you don’t do it, Scott Adsit will do it.’ And I said, ‘No, I’ll figure it out.’ So, they wouldn’t rent me one. I had to spend my own money to rent a euphonium and a baritone. Carell wrote out the fingering for it, taught me an embouchure, and I did nothing else for the next 6 days except [learn to play]… I was so obsessed with getting it right because I had to be employed. I needed the job so desperately.”

There are a few things I absolutely love about the story, but it’s that last line that really got me. He was working at Second City, and it was such a competitive place that he couldn’t get passed by. So he was willing to do anything — including learning how to play a horn instrument in six days — to make it work.

And the fun part of the story, of course, is that he figured it out.

It’s a nice lesson: If Stephen Colbert can learn the euphonium in six days, you can figure new things out, too.

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Adapt As You Go.

A Southwest flight taxies in the background as I work on slides at Salt Lake International Airport.

A little win: It’s May 14th, and today’s my first work trip of the entire year.

When I started my business, I traveled a ton for work. In 2019, I gave talks on four continents. It felt like I lived at JFK.

All those talks were really important as I was building the business — they brought in a lot of new clients. But over the years, my priorities changed. The business is stable. I’m booked with client work. And most importantly: I love living where I live and spending time with my family.

I decided last year: If I’m going to get on a plane, it better be for something really good.

Saying no to some other opportunities means I can say yes to the stuff I really want to make time for.

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A Southwest flight taxies in the background as I work on slides at Salt Lake International Airport.

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Opening Up.

Me, on stage, at the very first Newsletter Conference in 2024.

I’m giving the keynote at The Newsletter Conference this Friday — just me, in front of a room of 400 of my peers in New York City. 

I love doing these sorts of talks, and I’ve been lucky to have done a lot of them over the years. One thing I’ve learned, though, is that if I try to memorize the talk, it doesn’t work as well. Some of what happens on stage just has to happen, right there, for the first time. I’m reading the room, figuring out when to try to lighten the mood or when to pause for effect.

But that doesn’t mean I show up without practicing the talk. I always run through the talk multiple times, making sure I know the transitions between sections and giving myself the chance to play with different points of emphasis throughout. I know the material — I just don’t want every word and motion to be choreographed.

But I do always memorize one thing: The first 30 seconds of the talk.

I’ve found that once the talk is underway, I’m going to be fine. But there are always those first few seconds of nervousness, looking out over the crowd and realizing: Holy crap, 400 people have put aside their busy lives to hear my talk. Make it good, Dan!

So that little bit of memorization helps. It gets me through the nervousness and into the meat of the talk. Once I’m in, I know I can take things from there.

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That’s me on stage at the very first edition of The Newsletter Conference in 2024.

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Try On Lots of Hats.

I can’t tell you why, but when I was 18, I decided I wanted to be the kind of guy who wore a Kangol hat.

I wore it for a few months, very much as an experiment. I was a kid trying to figure who I was and how to build a sense of style that felt true to me.

It’s been almost 20 years, so I can say, with absolute confidence now: I was definitely not a Kangol hat kind of guy. But there’s still a little bit of that sense of experimentation in everything I do.

I try on new hats, more figuratively than literally, all the time. What would it look like for me to start a business? To move to a new city? To become a dad?

Lots of what I try to do every year is test out new stuff and see how it feels. Is this for me? Does it feel true to who I am?

I keep trying on new hats, always with the hope that I might find something great. Sometimes, I do. Sometimes, I end up looking back with embarrassment on the things I’ve tried.

You just have to keep trying anyway.

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Yeah, that’s me at 18 in a backwards Kangol hat. You live, you learn.

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