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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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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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Give Yourself Time to Think.

A white flag is visible in the distance, as are the mountains of Park City, as I stand over a yellow ball in the fairway.

I played my first round of golf of the season today, and I did the thing I always like to do early in the season: Instead of taking a golf cart, I walked.

There’s the exercise component of it — walking the course, particularly up here in the mountains, requires real effort. (Today’s round: 5.5 miles of walking, and the equivalent of 22 floors of elevation change.)

But there’s another reason: It gives me time to think.

When I drive a cart, I’m always rushing on to the next shot. But when I walk, I’ve got time to consider what just happened. I think about adjustments I need to make, and go through the next shot. Before I even get over the ball, I’ve already talked myself through what I need to do.

I try to do the same thing with my work, too. Sometimes, it feels like I’m in such a rush from one call to the next, one from project to another. I don’t even give myself time to think.

And that’s where it helps to block off a few hours on the calendar to take a step back. Whenever the weather cooperates, I try to get outside for a little walk by myself, or get on the phone to talk with a friend about what I’m going through. And I love doing quarterly reviews to evaluate what’s working and what isn’t.

You can’t just rush onto the next thing. You need to give yourself time to think.

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I took that photo on the back nine at Mountain Dell Golf Course, in Salt Lake City. On the long walk up that hill, I had a realization about my swing — and played the final seven holes just four shots over par. (For me, that’s about as good as it gets!)

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Are You Still Curious?

I’ve been running Inbox Collective for almost eight years. Before that, I spent seven years in email roles at the New Yorker and BuzzFeed. Spending 15 combined years in a single space — certainly one as niche as email — is an awfully long time.

A friend asked me the other day: Do I think I’ll work in this space forever?

I told them: I’ll keep doing this as long as I stay curious about it.

Something I love about my job is that I keep learning new things. Clients challenge me every week with questions I don’t know the answer to. I still love finding the right answers.

But I imagine that one day, the curiosity won’t be there. (It would be easy to get complacent and lean on answers that worked a decade ago — even if they don’t work anymore.) And when that happens, that’ll be the sign that it’s time to move on.

Until then, as long as I stay curious, I’m excited to keep working in a space I really love.

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That’s a photo of me taken back in 2017 at an email conference in Brisbane, Australia. Tough to believe that I’ve worked nearly a decade in this space since that photo was taken!

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Get a New Game Plan.

A person draws a series of wireframes using a pen and paper.

The kiddo’s been going through some sleep issues lately. It’s been tough — for him, of course, but also for us. We usually put him down around 7 or 7:30, and then we get some time at the end of the day for ourselves: To read, to watch something on TV, to clean up, to make lunches for the next day. A few hours to reset really matters.

But with the sleep issues, it’s been harder. Instead of a quick bedtime, it’s been stretched to a period of sometimes a couple of hours at the end of the night. I find myself getting mad at him for not going down, even though I know it’s not his fault.

So we’re asking for help and hiring a sleep consultant to help us figure out what to do.

The hard part with a situation like this is: I have no game plan right now. We’ve long had a great routine at bedtime, but it’s not working anymore. We need someone to help us put together a new strategy.

When I have a game plan, I feel empowered. Every night isn’t perfect, but I know how and why things work. All of us, from time to time, need a new structure to get everything back on track.

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That photo of a person drawing a wireframe comes via Kelly Sikkema and Unsplash.

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You Still Have to Put in the Work.

I have been doing the consulting thing since 2019. I have done more calls, more audits, more interviews, than I ever could have imagined. Sometimes, I think that I’ve done so much of this work that I’ve seen it all — that there’s nothing left to learn.

Every time I start to think that, I stumble onto a new problem, a new challenge, or a new opportunity, and I realize I don’t know how to do this just yet. No matter how far I go with Inbox Collective, there is always more work to put in, new things to learn, and lots to be curious about.

Sometimes, people ask me if I think I’ll do this job forever. I doubt it. One day, I’m sure I’ll find that I’m not interested anymore in putting in that work, asking that extra question, or trying to learn that new thing. That’ll be the sign that it’s time.

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That photo of three men washing windows in Singapore comes via a photographer named Victor and Unsplash. It doesn’t have much to do with this post. I just liked the photo.

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