You Always Have More in the Tank.

runners coming off the 59th Street Bridge, about to make the turn onto 1st Avenue during the 2021 New York City Marathon

My favorite place to watch the New York City Marathon is on 59th Street and 1st Avenue, right at the moment the runners are coming off the bridge from Queens and turning into Manhattan. When runners turn left on 1st Avenue to head north through the Upper East Side, they’re passing mile 16. They’ve already gone through three boroughs — just two remain.

It’s one thing to watch the pro runners, who even at this point in the race seem to be sprinting through the course, and have no doubt that they’ll reach the finish line. But it’s another to see the regular runners — our neighbors here in New York, or runners who’ve traveled from all over to take part in this race — making that turn. I love to see how people react when they reach that point in the race. They’ve already run 16 miles, a distance I don’t think I’ll ever run in a single day. They’ve been up all day, and they’re obviously tired. But when they see the crowds and hear the cheers, they look reenergized.

I know those runners must have moments of doubt along the way. 26.2 miles is forever, and reaching Manhattan still means they’ve only covered three-fifths of the day’s distance. But I also know that thousands of runners complete the marathon ever year, which means that thousands of ordinary people find the strength to keep moving forward. How do they do it? Maybe it’s because the crowd picks you up, or because they’ve spotted a certain landmark that reminds them how close they are to the finish line. Or maybe it’s something else. Maybe there’s something inside all of us that gives us the courage to keep going.

Sometimes, when I watch runners make that turn at 59th and 1st, it seems like they’re picking up speed, even after 16 miles. How? I’m not sure. But I know that ever year, I watch runners do what seems impossible: Find a little left in the tank to take that next stride.

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I took that photo today, right at the moment runners are about to turn onto 1st Avenue.

Optimize for Curiosity.

a magnifying glass shows a path forward in the forest

When you’re building a new strategy, you’ve got choices on what to optimize for: Growth, engagement, or revenue.

Or you can make another choice: To optimize solely for curiosity.

What might that mean?

Recognizing that a good test starts with a great question — so you need to ask as many questions as you can.

Finding a team that’s able to step back from the little details to ask, “I know this is a bit different, but what would happen if we tried this?”

Being humble enough to avoid doubling down on a good idea that didn’t quite work.

Keeping yourself open to new possibilities, even if they don’t seem obvious at first.

Understanding that you’ll never have all the answers. The only way forward is to have an open mind and keep asking questions.

Whatever you’re working on, remember this: Curious people make the best teammates. Find people who are always curious, and you’ll build a team that builds a great strategy in the long run.

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That photo of a magnifying glass comes via Steven Wright and Unsplash.

The Power of Small, Weekly Habits.

a screenshot of one folder of newsletter examples

A year ago, I realized that clients were asking me, over and over again, for examples of certain things:

Dan, do you have any examples of great pop-ups to convert readers from our website to our newsletter?

Have you seen any good examples of promotions on Instagram?

Do you have any examples you can share of amazing welcome emails?

So I started compiling examples into a big Google Drive file, and shared it with clients. But then I made another choice: I added a weekly note to my calendar to keep adding to the Drive. I created a folder on my laptop where I could store examples that I’d noticed over the course of the week, and then, every Friday, I’d upload them to Drive.

Sometimes I only have an example or two to upload on Friday, and sometimes, I’ll have dozens. But over the course of a year, I’ve uploaded hundreds of examples that I can refer clients to. It’s not an exaggeration to say that this one project has changed the way I work with clients. It’s one thing for me to be tell them about the concept, but it’s another to be able to show them a handful of great examples from their peers.

And had I decided to, say, update the file every month or every quarter, I’m not sure I would’ve stuck with it. (It took a lot of work to upload that first, giant batch of examples!) Instead, by focusing on a small, weekly habit, it feels so much more manageable — and the long-term result has been so much more than I ever could’ve expected.

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That’s a screenshot of the pop-ups folder. There are now more than 30 examples of pop-ups I love that I can share with clients.

Still Not Dead.

Willie Nelson on stage in Saratoga Springs

I saw Willie Nelson perform on Sunday, and here’s something I didn’t realize about Willie until he walked out on stage: He’s 88 years old.

88! And still performing live, currently on a 14-stop tour over two months in 10 states!

Now, at that age, nobody’s expecting Willie Nelson to go out and play a marathon set. But I was impressed by the way Willie still found a way to put on a great show:

• He limited the set list to an hour — he’s played about 11 songs per night on the 2021 tour so far, instead of what had been 17 song sets pre-pandemic, per data on Setlist.fm.

• He loaded the lineup with not one but three openers, stretching what would be a normal concert into a six-hour-long festival.

• He toured with his son, J. Micah Nelson, and let him take lead on a few songs. (Willie’s kids can really play, so fans didn’t mind Willie taking a step out of the spotlight for a few minutes.)

• He didn’t waste much time with banter, saying a few words between songs — or just moving right into the next number.

All in all, it meant a set with a lot of hits and very little filler. I’m sure Willie would love to have the energy of a younger artist, able to go out and play for 2+ hours as a headliner. But he’s 88, and he’s got some limitations — and he still found a way to make it work.

As Willie sang that night: He’s still not dead, and still on the road. Impressive stuff.

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That’s a photo I took of Willie and his band on September 12, 2021, in Saratoga Springs, New York.

Finding the Energy (On the Days When You Just Don’t Have It).

Denis Shapovalov pumps his fist after winning a point during his first-round match

I went to the U.S. Open yesterday to watch some first-round tennis matches. If you’ve never been to the U.S. Open, you should really try to go if you can — even if you’re not a tennis fan. The Billie Jean King National Tennis Center is an absolutely spectacular place to spend a late-summer day. Sure, you can go to one of the big courts to see big names — Arthur Ashe Stadium seats nearly 24,000, and it’s where you’ll find stars like Novak Djokovic and Naomi Osaka — or you can check out one of the outer courts, where you’ll catch top 100 players playing for just a few hundred fans. (Yesterday, I watched a matchup of two top 75 talents from the second row. Pretty cool.)

But one of the highlights of the day was watching Denis Shapovalov, the tenth-ranked player in the world. He played at Louis Armstrong, the second-largest stadium on the grounds, in the middle of a Tuesday afternoon. His was the third match on that court that day, and many of the fans who’d come for earlier matches had drifted out to other courts. Shapovalov played a stadium that was less than a third full.

Still, Shapovalov’s a star in the tennis world, and a player who could absolutely make the finals in Queens this week. To win the U.S. Open requires a player to win seven matches, and the men’s matches can last up to five rounds (and can sometimes go as long as four or five hours). Shapovalov couldn’t afford to let his match go long. He needed to dispatch his opponent (Federico Delbonis, the 47th-ranked player in the world) as quickly as possible.

Shapovalov did just that, winning in straight sets (and in less than two hours). But what I found fascinating was the way Shapovalov stayed engaged at every moment in the match. In front a sparse crowd that seemed more interested in checking their phones than watching the match, it would’ve been easy for Shapovalov to lose focus. But without the crowd keep him engaged, Shapovalov found his own ways to bring the energy. After every point he won, he gave a little fist pump. After big shots, he looked over at his box, nodding to them and letting them know that he was locked in. After breaking serve or winning a set, he’d let out a little scream, or a “Let’s go!” A few times, he gestured to the crowd to make noise.

This was the sort of match — against a talented and experienced opponent — where Shapovalov could’ve lost focus for a bit and let the match stretch into a fourth or fifth set. But he simply refused to let himself disengage. He was both player and hype man, never letting his attention drift, even when the crowd’s energy dropped.

I spent the subway ride home thinking about ways to try something similar with my own work. It’s easy for my energy to slip, especially at the end of a long day of calls. Maybe I need to find ways to take small breaks: A walk around the block to reset, or even a few jumping jacks in the ten minutes between calls. Maybe I need to start keeping a gratitude journal, so I can use those few minutes to jot down thoughts about the good that’s come from that day.

But seeing Shapovalov play, I was reminded that to be at the top of my game, I have to find ways to maintain that focus throughout the day — especially when the energy isn’t naturally there.

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I took that photo of a Shapovalov fist pump during yesterday’s match.

Saying “No” Isn’t Easy.

That photo of a beautiful stop sign in Portugal comes via Kristaps Grundsteins and Unsplash.

I’ve written before about the importance of saying “no,” about how you have to be careful what you choose to work on, and why turning down work is often the right move.

But the truth is: I’m still not very good at saying “no.”

It’s hard to turn down work — especially when it involves projects I’m excited about. It’s hard to turn down revenue for the business. It’s hard to say “no” to people I’d love to work with.

I know that saying “no” is often the right move for me. But it’s still hard to do.

Right now, I’m reading “Eat a Peach,” the memoir from chef David Chang, and he talks often about the pressure of working as a chef — one whose success opened up all sorts of exciting new opportunities for him: Opening new restaurants, writing books, even TV. He writes that at times, he felt like he needed to hit rock bottom before he would be willing to change the way he worked.

“The paradox for the workaholic,” he writes, “is that rock bottom is the top of whatever profession they’re in.”

That line’s stuck with me the past few days. I’m not a celebrity chef, but I’ve been lucky to have had some success — and to have gotten a little publicity — the past few years. I’ve gotten all sorts of interesting new opportunities as my business has grown.

And I’m starting to understand what Chang might have experienced himself. I love to do this work, and if I could say “yes” to every potential client, I would. 

But that’s not an option.

So I need to keep getting better at saying “no.” I need to do it for my family, for my friends, for my business, for my industry — and for myself. Saying “no” is what I need to do make sure I’m prepared to say “yes” to the right opportunities going forward.

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That photo of a beautiful stop sign in Portugal comes via Kristaps Grundsteins and Unsplash.

It Never Gets Easier.

skiier going off the jump

There’s this lie that we tell ourselves when things are complicated and hard: “Once I get through this stretch, things are going to get easier.”

I’ve told myself this more times than I can count. Dan, if you can just finish this task… if you can just get through this month… if you can just take care of this deadline — it’s going to get easier from there.

But that’s not really how this works.

It’s OK that things can be hard. Things can be hard because you’re trying to learn new skills or taking on new challenges. Things can be hard because you’re in a new role or a new job. Things can be hard because you’re pushing yourself to get better. Things can be hard because life gets in the way — you’ve got more responsibility or more people to care for than you did when you were younger.

Every so often, I have to remind myself: Things are never going to be quite as easy as they are right now. Work — and life — tends to get more complex over time.

But you’re going to find a way to push through and keep doing the work. You’ve done it before, and you’ll do it again in the months and years to come. Things never get easier, but you’re also getting smarter and savvier, and building the team to help you take on these challenges. You’ll be able to take on tomorrow’s obstacles as they come.

So enjoy this moment, right now. Yes, things seem overwhelming some days. But these challenges and obstacles will beget new ones. One day, you’ll look back on these moments and tell yourself: What I would give to merely have those types of problems today.

It’s not getting easier, but that’s OK. You’ll be able to take these challenges head on anyway.

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That photo of a skiier going off a jump comes via Unsplash and Maarten Duineveld.

Share As Much As You Can.

When I was getting started with Inbox Collective, I made a conscious decision: I wanted to help as many people as I could, which meant I needed to share a lot.

Not a Newsletter remained free — even as others built large, paying-subscriber-only lists — because I knew that keeping it free and open would allow me to help newsrooms, non-profits, and individuals who couldn’t afford to pay.

I launched new resources for readers to download and use, like my list of growth ideas, because I knew it would help them take the next steps with their newsletters.

I gave away time every month for 1-on-1 calls, so I could dig in with my readers and really help them figure out specific challenges.

And I’ll admit: I was worried at times about this! Was I giving away too much? Would people think, “Well, I guess he’s shared everything he knows! No need to listen to this guy anymore!”

But the results are clear: By giving away a lot, it’s brought even more people into the Not a Newsletter audience: New readers, and, yes, many new clients. By sharing tools, resources, and strategies, it’s attracted a larger audience for me to help — whether they’re working with Inbox Collective or not. (And many clients tell me: We’ve learned so much from you already, so we’re excited to hire you and learn even more!)

The ultimate metric of success, for me, isn’t revenue — it’s impact. So I’ll keep sharing, as often as I can, as much as I can. I know there’s more I can do to help.

Lefts and Rights.

I took this photo, in October 2018, of the view of New York, looking north from 1 World Trade Center after a thunderstorm.

I just finished “The Only Plane in the Sky: An Oral History of 9/11,” by Garrett M. Graff. It’s a remarkable book — a book that had me gasping, in tears, and often at a loss for words.

In it are hundreds of stories of the day — stories, of course, told by the survivors of September 11th, 2001. So many of the stories are ones where a single decision may have saved a life: The chef who stopped in to get his glasses adjusted before heading up to his floor; the salesman who was told that his tie didn’t match his shirt, so he headed back to his desk to get a new one; the woman who was fired from her job on the afternoon of September 10th; the dad, who took the ferry to the office, and lived, while his son, who took the train, did not.

Stephen Blihar, an officer with the NYPD, described thinking back upon the day like this: “It was a day of lefts and rights.”

I can’t stop thinking about that phrase: A day of lefts and rights. There are so many choices we make — in a day, in a career, in a lifetime. We agonize over the big choices, when often the small ones — go left, or go right? — are the ones with the most impact. We make the best choices we have, with the best information we have, but who knows what will come of all of it?

Anyway, read the book.  I can’t recommend it enough.

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I took that photo, in October 2018, of the view of New York, looking north from 1 World Trade Center after a thunderstorm.

See If It Works. Then Build It Yourself.

When I’m working with a team on a project, one of the first questions I’ll ask is: How do we start as quickly as possible?

Let’s say we’re working on a new design for an email. Instead of hiring someone to do coding — on a concept that may or may not work! — I’ll use an email builder that allows us to build an email that’s pretty close to what we want. Will it be exactly what we want? No, probably not. But we’ll get 80% of what we want in 20% of the time.

Once we’ve got that built, we can test it out, see how it goes, and make additional tweaks and changes. Maybe we’ve got a winning concept, and if that’s the case, that’s when we’ll go to the designers to get it to 100%. Maybe we don’t, and we’ve got to keep testing. The good news is, we won’t have wasted valuable resources on a concept that didn’t work.

There are so many tools out there that allow you to test and iterate quickly. Instead of building your own stuff, or wasting time on ideas that might not work, utilize those tools, and see if you can get something live that allows you to collect feedback, learn, and move forward.

First, just see if it works. You can always keep building from there.

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That photo of a construction site comes via Unsplash and Shivendu Shukla.