Tag: lessons learned

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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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Running on Empty.

a rusty old gas tank in front of a barn in Latvia

This was one of those weeks where it felt like everything happened. I launched a new product. I held a webinar. I talked with 15 different clients. I sent a thousand emails (give or take). I helped a ton of clients with end-of-the-year projects. 

And then Ben got sick, and so did I.

There was a moment on Friday afternoon when I thought about taking on a bit more work. I had a lot more stuff to do. But Ben was down for a nap.

So I took a nap, too.

You can’t operate on empty. You have to make time for yourself. Take a week. Exercise. Cook yourself dinner. Read a book. Go to bed at a reasonable hour.

Do literally anything other than work.

Yes, you’re busy. We all are. But the work isn’t going to be very good if the tank is empty.

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That photo of an old gas tank, left out to rust somewhere in Latvia, was taken by Krišjānis Kazaks and shared via Unplash.

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It’s One Day.

A Denver hockey player fires a puck at the goal.

One of my favorite things to do after one of my teams loses is to check the message boards or comments where fans of that team post.

After a win, fans are always in a good mood. Their team won, the team’s players are heroes. It’s just one win — but hey, this probably means we’re going to win it all!

But after a win, everyone’s on their worst behavior. The quarterback can’t win the big one! The point guard needs to be benched! The pitcher should be cut!

It’s an odd tradition, I admit. Why read the comments after losses? But I like to do it as a reminder: We’re never as good as we are on our best days, and never as bad as we are on our worst days.

And today? It was just one day.

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That photo of a hockey game, featuring Denver University and the University of Minnesota-Duluth, comes via photographer Logan Weaver.

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Keep Betting on Yourself.

15 years ago, I quit my job at a TV station, moved to Biloxi, Mississippi, set up a basic website, and started publishing stories about the five-year anniversary of Hurricane Katrina. I was my own reporter, editor, photographer, publicist, IT team — I did it all. The end result was a fellowship, which led to more reporting in Springfield, Missouri, and then that led to my gig at BuzzFeed.

I bet on myself, and I certainly wouldn’t be where I am today if I don’t make that bet.

But not all bets are big. Inbox Collective was barely a few weeks old when I went to a journalism conference in New Orleans in September 2019. I told my wife that I wanted to host a happy hour for readers of my newsletter. I didn’t have any idea how many people would show up or even if any would show up — but my bet was that if I met some people, something good would come from it.

50 people RSVPed. A few no-showed, a few brought an extra friend. I ended up spending about $400 on drinks. (Thanks to everyone who bought happy hour beers and not full-priced cocktails!)

But most importantly: I landed five clients from that one happy hour.

Anytime I feel stuck, I try to remind myself: Keep betting on yourself. Place small bets, and place big ones. It’s worked before; it may work again.

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I took that photo in 2010 in Pass Christian, Mississippi. It’s of a bust of W. Dayton Robinson, whose $2 million donation helped City Hall expand after Katrina.

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I Don’t Always Have the Answer.

At least once a week, a reader asks me a question, and my reply is: “To be honest: This is one of those questions that’s so far outside my wheelhouse that I’m not sure my advice is worth listening to!”

People are sometimes surprised to hear me say that. I do run an entire business around giving advice for newsletter operators, and I’ve been working in this space for a dozen years.

But the most important thing I’ve learned through my consulting practice is that it’s OK to say, “I don’t know!” No need to pretend I have all the answers.

And if you’re the kind of person asking the question, you should also feel free to ignore my advice entirely! I am frequently wrong, even when I have strong convictions about my answers!

So much of building any newsletter or any business is knowing when to follow and when to find your own way. (And yes, the teams that tend to build the best stuff in the long run do a bit of the former but often more of the latter!)

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I couldn’t quite find the right art for this, so I had to draw something myself using the only art tool I’m qualified to use: MS Paint. (Or, in this case, a free online replica version of MS Paint.)

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