Tag: lessons learned

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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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Embrace the Imperfection.

Brandi stands center stage underneath the spotlight, behind her red lights and her face projected on a giant screen inside a red ring.

There are days when I’m really excited about the future of AI, and days when I get a little scared about the possibility that AI’s going to take over everything.

But on Tuesday, I went into Salt Lake to see Brandi Carlile play. She did this thing in the middle of the show where she asked the crowd for requests. I thought they might have been plants, but no: She’s been doing it at every show.

And seeing something like that — the crowd screaming out their favorite songs; the artists trying to figure out, in real time, what guitars they needed to play and what key the song was in — was such an amazing thing. I loved seeing Brandi try to pick out a fan in a crowd of thousands, hoping that she actually remembered the song this fan wanted her to sing. I loved the band talking through, on a hot mic, how they wanted to handle these songs acoustic — who’d play what part, how they’d play the intro or the ending.

AI can be a bit of a know-it-all. Ask it for the idea chicken dish or a strategy to sell widgets, and it’ll spit out an answer in seconds. It’s often right, too.

But there’s something special — something so human — about seeing something happen in real time. Watching Brandi and her band on stage reminded me that some of my favorite moments are the ones that aren’t quite perfect. They’re messy, they’re unexpected, they sometimes go wrong.

I don’t think AI will ever be able to make moments like that.

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I took that photo from way in the upper deck at Delta Center.

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You Can Make Time For It — If You Want To.

Ben hikes through a shady section of a dirt hiking trail in Utah.

A funny thing I’ve noticed lately: I’ll be chatting with a friend and mention something that I was able to make time for — going skiing, spending time with the kiddo, reading books. And they’ll say, “Oh, I wish I had time for something like that!”

But when you probe a little deeper, you find that they often do have the time. We’ve all met people who are willing to wake up at 6 so they can squeeze in a workout before work, but who can’t seem to find the time to cook dinner.

And I get it: We’re all busy, and there’s never enough time for everything. But if there’s something you really value, there’s often a way to make space for it.

For me, one of those things is getting outside. I was feeling a little sluggish the other day, and I had a break between calls. I sat down, ate some lunch, and watched crappy TV on the couch for an hour. Weirdly, lying down on the couch didn’t particularly help with that sluggishness!

And as I went downstairs to go on my calls, I found myself asking: Why didn’t I get outside for a 20-minute walk to clear my head?

Yes, I’m busy. No, I don’t have time for everything. And no, I don’t need to fill every minute of the day with something.

But I have 20 minutes for a walk. I have time to read before bed. I can move things around so I can do the stuff I want.

I do have the the time if I want it.

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That’s a photo I took last summer of the kiddo and I on a little hike together here in the mountains.

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