Tag: lessons learned

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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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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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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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Be Willing to Prove It.

The Jim Bridger billboard, as seen roadside in Salt Lake City.

A few months ago, I started noticing billboards around town with a photo of a guy who looked kind of like Davy Crockett and a message: “Jim Bridger discovered the Great Salt Lake.“ I didn’t think much of it.

But I kept seeing them — you can’t drive five minutes in town without seeing a billboard with Jim Bridger’s face on it.

So then I got curious: Who was spending all this money to promote an explorer who died almost 150 years ago?

Turns out: It’s actually an experiment in proving that advertising works.

There’s a company, Reagan Outdoor Advertising, that owns all these billboards. They had a challenge: How do you prove the ROI, or return on investment, on a billboard to an advertiser?

So they came up with their own experiment.

They told the Salt Lake Tribune that they surveyed locals about Jim Bridger before the billboards went up, and they’ll do so after the campaign is over. Then they’ll have data to share, showing that locals went from knowing nothing about Bridger before to knowing at least a little bit about him after. A lot of locals are going to say, “Yeah, isn’t he the guy who discovered the Great Salt Lake?“

And then they’ll make the pitch to local businesses: If these billboards could have that kind of impact about a previously-anonymous 19th century explorer, then they could surely have similar impact for a modern brand.

It’s a great reminder: If you’re going to make the claim, you need the data and the story to prove it first. And if you don’t have the data, well: You might need to get creative to dig it up.

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I took that photo of the Jim Bridger billboard in Salt Lake. It’s the same billboard everywhere — same copy, same yellow background, same drawing of Bridger.

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Little Stuff Matters, Too.

My son loves going to Costco, and for a funny reason: He loves the checkout process.

At Costco, you get your receipt from the cashier and then hand it to an employee at the exit. They look at the items on the receipt and then cross-reference it with what’s in your cart.

But when you’ve got a toddler with you, the Costco employee will also turn the receipt over, draw a smiley face on the back, and hand it to your child.

My son absolutely loves the smiley face drawings. When we go to other grocery stores, he always wants to know: “Can they draw a happy face for me?”

When it comes to serving your audience, it’s not always about the big things. The little things matter, too.

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I took that photo on a recent trip to Costco.

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Make It As Hard As You Want To.

I was driving home last weekend, through Emigration Canyon. On a weekend, there are tons of cyclists and runners on that road — people literally biking and running up a mountain. It’s impressive to see.

But then I saw something I’d never seen before: Two men, on unicycles, riding up the mountain.

Going up that road — it involves more than 1,000 feet of elevation change — is hard enough on a bike or on two feet. But on a unicycle?

And so I got home and went to YouTube, and there were all sorts of videos of people doing even more incredible things on unicycles there. They’re doing on two wheels what I wouldn’t dare do on one.

It was a reminder for me: You get to decide what challenges you take on. And with those challenges, you get to decide if you want to do things on easy mode or hard mode.

What’s right for someone else isn’t what right for you.

(And heck, I know mountain unicycling isn’t right for me!)

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