Tag: keep going

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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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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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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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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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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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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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The Moments Before Launch.

I’m launching a new paid product for my readers this week, and I don’t know how it’ll go. We might sell a lot of the product, and we might not sell much. (We’ll sell something, I hope!)

All I can really control is the process. I’m proud of the work that’s gone into building this product. We’re thinking about this product in a smart way, I think. We’ve asked lots of questions; we’ve reached out to lots of people for feedback. The product itself is pretty darn good.

What I love, though, is this moment right before the product goes out into the world. I’ve worked hard on it and made it better and better. The work that went into it was really good. And even though I worked hard it on, I don’t really know how readers will react until I put it in front of them.

I wish I had more control over what happens next, but I don’t. (The marketing plan is good, but it’s just a plan!) I’ll announce the product this week, and whatever happens, I’ll learn from it. If we sell a lot, if we don’t — I’ll learn more that’ll inform whatever I make next.

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That photo of hot-air balloons flying over Albuquerque comes via Ian Dooley and Unsplash.

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