No Regrets.

Here’s a story I’ve seen a few times now: A friend takes a job at a great company. It’s a huge, well-deserved role for them. Everyone agrees: They’ll do big things there.

And then a year or two later, that friend steps away from the role. From the outside, it seemed to be a good fit in terms of responsibility, opportunity, and salary. But the day-to-day of it was a different story. They weren’t learning or growing, or felt unhappy in their role. They decided to leave.

But when I’ve asked these friends afterwards if they regretted the decision to take the job in the first place, they’ve almost always told me: No, definitely not. Again, it’s the same story: These are people who did their homework before taking the job. They talked to people at the company, and asked as many questions as they could. The job didn’t work out, but it was OK: They’d still made the right decision at the time. And I’ve seen stories like theirs countless times — stories of people who made a decision that didn’t work out, but who still don’t regret the choice they made.

I’m thinking back to something I wrote back in 2011, in my annual “The Things I Believe” post. I wrote: 

Try not to regret bad decisions. Just make the best decisions you can with the best information you have.

Eight years later, that still holds true. You don’t always have control over what happens after you make the decision — but you have total control over the decision itself. Do your research, talk to people you trust, and make the best decision you can. Even if the choice doesn’t work out as well as you’d hoped, I’ve found that as long as you made the right decision for the moment, you’ll walk away with no regrets.


That illustration comes via Katerina Limpitsouni and unDraw.

I Am 32 Years Old. This Is What I Believe.

I am 32 years old, and I’ve taken the leap. Twelve months ago, I was at The New Yorker — a dream job at a dream organization — and focused on the work ahead of me. Nine months ago, I started giving regular talks about how news organizations could get more out of email, and realized that I could help those newsrooms in a more hands-on way — you know, in the future. Six months ago, I started thinking that maybe that work could happen sooner, possibly as soon as mid-2020. Three months ago, I left The New Yorker and launched a consultancy to start the work immediately.

This year moved fast.

What changed? I started asking more questions of my colleagues in other newsrooms, and really listening to what they were telling me. I heard over and over again: We need help growing our audience and turning them into subscribers or supporters, and we want to learn from the work you’ve done at BuzzFeed and The New Yorker. I realized that my moment to help was right now, and that if I wanted to serve this community, the work couldn’t wait.

So I made the leap. I’m thankful for everyone who had my back: The friends and family who offered support (and free legal aid!), the colleagues who helped me figure out how to approach consulting work, and the readers who reached out to work with me (and told their networks to do the same). This consultancy is just me, but it also feels like the biggest team I’ve ever been apart of. I feel incredibly, incredibly lucky.

This year, I’ve given talks on four continents in front of more than 100 news organizations. I’ve written more than 35,000 words about email for newsrooms and non-profits, and had nearly 3,000 readers in more than 50 countries sign up to be alerted every time I write. I’ve launched a consultancy, signed more than 20 clients, and helped launch dozens of email products.

It’s been the single most transformative year of my life, and the work’s only just begun. I don’t know what the future holds, but I’m pretty sure I can see just around the corner — and what’s coming next is exciting and terrifying all at once. I can’t wait.

Above all, I’m thankful for Sally. A year ago, the idea of leaving my job to start my own business — while she was still in school! — would have been unthinkable. But it was Sally who gave me the green light to do this. She kept telling me: “You can’t wait. You have to do this now.” I’m remarkably lucky to be married to someone so supportive, and so selfless. Doing this work meant that I would be busier than ever before, and traveling more than ever — and yet, she’s been my biggest champion. I wouldn’t have, couldn’t have done this without her. Every day, I try to do work that makes her proud.

Over the past year, there are certain things I’ve come to believe hold true. I know that my beliefs will continue to change. I know that I will change.

But here, at 32, is what I believe:

God bless Google Docs.

I tend to oscillate between “This is going to work!!!” and “Holy shit, what am I doing???” on a weekly basis. I’m scared and excited, but never bored, and always thrilled to be doing this work. That’s how I know I’m in the right place.

Nobody has everything they want. Life is about making the most of whatever you have.

Just be honest with people. If you screw up, if you don’t have the answer, if you’ve got something that needs to be known: Be open, be transparent, and be direct. It’s the best way.

Doing the right thing is usually the right thing.

Be confident but not arrogant. There’s a line there. Don’t cross it.

Keep making things better. I gave this one talk six different times this year — but every time, I learned something new, and then made the next one a little better. Just because the work is finished doesn’t mean the work is done.

Life is unexpected. One minute you’re waiting in the Brisbane airport, thinking about the giant presentation you need to put together on the flight home. The next, you’re freaking out because your water bottle leaked in your backpack and your laptop’s dead and the presentation’s in 36 hours and you’re completely, totally fucked. The next, you’re wondering why there can’t be an Apple Store inside the airport. The next, you’re walking through duty free and realizing: They sell MacBooks here — tax free! The next, you’re boarding your flight, passport in one hand, the brand new laptop you bought 20 minutes ago booting up and restoring all your files from the cloud so you can finish that presentation on the plane.

Like I said: Life is unexpected, but also pretty amazing if you’re ready for it.

New rule for traveling: Water bottles always stay outside your backpack.

Whatever it is you do, be the best at it. I’ll always be thankful to The New Yorker for teaching me that.

Less isn’t always more — but it’s enough.

When you start traveling regularly, you’ll realize that the four greatest words in the English language are: “Sir, we’ve upgraded you.”

Listen. Learn. Work. Repeat.

Right now, everything is potential — and potential is pure fucking joy.

Privilege is a tailwind, and I’ve had a strong wind at my back all these years. I know I’m lucky, and want to do the most I can with this opportunity for as long as I can.

And lastly: You don’t have to have all the answers when you start. Keep trying new things, and keep learning along the way. You’ll get there.

Give More Away.

I’ve had conversations with friends in the consulting world who’ve told me: Don’t give too much away for free. If you do, your clients might not need you anymore.

And I think exactly the opposite is true.

I’ve made Not a Newsletter — 11 editions so far, totaling more than 36,000 words — free and open to anyone. I’ve shared documentation on how to set up dashboards in Google Analytics, calculators to help with subject lines, and guides to building newsletters and Courses — all for free. I’ve done interviews, shared lessons, and given as much away as I can.

The hope is this: In the long run, by being generous with my community, they’ll be generous back. They’ll share these resources with their colleagues. They’ll recommend my services to their friends. They might even hire me to work with them.

My bet is that they’ll say: Look at all that Dan’s done for us already. Shouldn’t we hire him and see what else he can do for us?

And here’s the thing: Even if every member of my newsletter list wanted to hire me, I couldn’t say yes to all of them. So by giving so much away, I have the opportunity to help as many members of this community as I can.

It’s worked for me in 2019, and I hope to do even more of it in 2020. I’m not sure if it’s the best way to build my business — but I know it’s the right thing to do, and doing the right thing is usually the right thing.


That photo of a gift comes via Ekaterina Shevchenko for Unsplash.

Try It Yourself.

There are things I’ve learned over time, stuff that’s worked for me. When I’m giving a talk about email, I’ll mention some of these best practices. But it’s always followed with a caveat:

Don’t take my word for it.

Try it yourself.

If you read a case study that says a green subscribe button converts readers best, you should try it yourself! If you hear that the optimal time to send a newsletter is Tuesday at 1 p.m., you should try it yourself! If you attend a talk where the speaker tells you the perfect welcome series should be a week long or a month long or a year long, you should try it yourself!

What worked for one person or one company might not work for another. Don’t blindly follow advice. Test something out and see what you learn. You won’t know what’s best for you until you try it yourself.


That very generic stock footage at the top comes via David Travis and Unsplash.

Don’t Get Stuck on Repeat.

I first heard of ghost repeaters through a songwriter I love, Jeffrey Foucault, who has a song — and an album — called “Ghost Repeater.” As Foucault explained in the liner notes:

“Ghost Repeaters are empty radio stations scattered around the country to re-broadcast demographically tailored playlists, endless echoes of American market culture, from thousands of miles away.”

I remember my days at BuzzFeed when we’d try a new idea — quizzes, video, email — and then dozens of copycats would spring up, seemingly overnight. I remember being at The New Yorker, seeing other sites realize that our subscription strategy was working, and then watching other news organizations across the country try to copy it. Some of these places put their own spin on things, but many were just ghost repeaters — copying even the tiniest details and formats.

Original ideas are hard to come by. When I look around the media landscape and beyond, I see a lot of the same ideas, repeated over and over again.

But the thing is, what works for one place might not work for you. When I give talks about my work at BuzzFeed and The New Yorker, I always say: My team had success with these sorts of ideas, products, and tests. But don’t take my word for it. Try it yourself. See what works best for you.

And one more thing: Focus on your unique audience — who are they, and what do they need that only you can serve? Focus on delivering value for them every day. Focus on being the best version of you — with whatever it is you do best.

Write It Down. Remember Who You Are — And Who You Were.

It’s been almost a decade since I started keeping a journal.

I’d never thought of myself as a journal kind of guy, but there was this online journaling tool that came out of Y Combinator, called OhLife. It launched right around the time I moved to Biloxi to work on, and it seemed like an interesting way to document my days on the Gulf Coast. Every day, they’d send me an email that said, “How did your day go?”, and I’d write back. It became a habit at first, and then a ritual. A day couldn’t end without me writing down a few thoughts.

As I wrote more entries, OhLife would write back to me and say, “Remember this? One year ago you wrote…”, and include an entry from a year ago on that day. There were moments in 2013 when I was in New York, working at BuzzFeed, and reading about things that had happened in Mississippi — all of which made me wonder: Had all that happened in just the past year?

In 2014, OhLife shut down, but I kept journaling. My current setup is simple: I’ve got an email that lands in my inbox every day at around 6pm. I reply to it, and the reply gets added to a doc with all of my previous entries. Every once in a while, I’ll open up my doc and search for a random date, just to see what I wrote on that day. As I write every year in my Things I Believe post: “I know that my beliefs will continue to change. I know that I will change.” And every time I look back on my notes from a particular day, I’m reminded of just how true that is.

I didn’t realize that the simple act of journaling would mean so much to me. It’s a moment for reflection in my day, and an opportunity to document my progress (or, in those early years, the lack thereof). I think it’s one of the most valuable things I do every day.

And if you want to get started with journaling, there are apps that make it easy. There’s even one of this list that allows you to send everything via email!

Give it a try. Over time, you might be surprised to reflect upon the person you were back then — and the person you’ve become today.


That photo comes via Hannah Olinger for Unsplash.

Celebrate the Little Victories.

My Washington Nationals are — and I can’t believe I’m typing this — heading to the World Series. They’re a remarkable story. On the morning of May 24, the Nationals were 19-31, with just a 22.2% chance of making the playoffs, according to FanGraphs. You can see what happened next, in the playoff probability chart above. They turned the season around, going from 12 games under .500 to finishing 24 games above .500. On Tuesday, they’ll begin a series vs. the Houston Astros for the championship.

How’d they do it? A lot’s been made of the chemistry on the team, or the positive attitude of manager Davey Martinez. But here’s another wonderful anecdote from MASN reporter Byron Kerr:

There is a long hallway between the coaches’ and manager’s offices and the training area next to the Nationals clubhouse on field level at Nats Park. Along this wall is a collection of baseballs positioned on a long single shelf that runs down the hallway. Each ball represents a win the Nats enjoyed so far in 2019.

Written on each baseball are the names of one or more players who, in the estimation of manager Davey Martinez, were the most valuable in each of those victories.

And as Martinez later mentioned in the piece:

Martinez’s players would come by during the season and pick up each ball and reminisce about that particular victory during their turnaround run.

“Every now and then, I see guys just going in there, staring at each ball and dates,” Martinez said. “And what we’ve done and how we did it. I could tell that they really appreciate it. You hear them say, ‘Oh, man, I remember this. Strasburg was dealing this day.’ Or, ‘(Gerardo) Parra. Grand slam this day in L.A.!’ They all talk about it and remember it. It’s pretty cool to hear ‘em call each others’ names out, knowing they all participated at some point.”

A baseball season’s 162 games long. Opening Day was nearly seven months ago. There are so many games, and it’s easy to forget about all the little moments that led to this one big opportunity. But I love the idea of the wall of baseballs. Every day, the players walk by that shelf and think about those daily achievements — the wins and the contributions that got them there. They’re a public reminder of the work that’s been done over the course of a season.

There are so many ways to bring an idea like this to your office:

      • Have an award that’s given out weekly/monthly to an outstanding teammate (and give out a physical trophy or prize that can sit on their desk)
      • Shout out a big achievement in an email to the larger team
      • Hold a regular all-hands meeting to celebrate team victories
      • Make a public space in your office to highlight teammates who’ve done great work
      • Stop by a colleague’s desk to privately say thank you for their effort

However you do it, celebrate those little wins. When your colleagues make a difference, make sure they know how much you appreciate it. You never know what a difference it might make.


That graph at top is off the Nationals’s playoff odds throughout the season, as charted by FanGraphs.

Be Flexible on the Details.

There’s an excellent profile of Jeff Bezos and Amazon in this week’s New Yorker, by Charles Duhigg, and the whole thing is worth reading. One paragraph in particular stood out to me:

Most firms have a mission statement that even the C.E.O. has trouble remembering. Amazon employees, Freed discovered, studied the Leadership Principles like Talmudic texts. During his first few years, he occasionally pulled colleagues, and even Bezos, aside to ask questions. What, for example, does “leaders are right a lot” really mean? Bezos explained, “If you have a really good idea, stick to it, but be flexible on how you get there. Be stubborn on your vision but flexible on the details.” Executives at other companies tended to lay out definitive plans. But Bezos urged his people to be adaptable. “People who are right a lot change their mind,” he once said. “They have the same data set that they had at the beginning, but they wake up, and they re-analyze things all the time, and they come to a new conclusion, and then they change their mind.”

Being stubborn on the vision but flexible on the details is such a good way to approach work at an office. The big picture matters — have a sense of where you want to go, and what you want to deliver. But those little details? The tools you use, the timeline for a project, all of the minutiae — those can always change. Don’t get tied up by the little things. Be flexible, and let your team drive the details.


That’s a photo of an Amazon Kindle at top. It was taken by Amanda Jones for Unsplash.

Here, Read This: “Draw the Owl.”

I love this post from Daniel Zarick, a former product manager at Twilio, about the strategy at his old company. The focus was always on starting quickly and figuring things out as you go. Or as they put it: “Draw the owl.”

Start figuring it out. Put some of the pieces together. When you truly get stuck, ask for pointed advice. Stuff like “What sort of salary should I be asking for at my experience for this type of job?” and “Do you think X marketing strategy is good for this type of product?”

Nobody else can lay out all the steps for you, because nobody else has been you or is in your situation.

You’ve just got to draw the owl.

Read the whole post here.

Less is Enough.

You’ve heard the expression, “Less is more.” I don’t believe that to be true.

I think less is enough.

I believe that, yes, you should sketch out those big plans. You should think about the best-case scenario. You should lay out the roadmap — the work you want to do in six months, in twelve months, and beyond.

But you should also be willing to start soon. Remember: Direction is more important than speed. The goals you want to achieve are ambitious, and they’re going to take time. You’re not going to be able to move as fast as you want to go.

But you can start. It won’t be everything you want, but take the first step anyway. Start moving in the right direction.

Less isn’t everything you want — but it’s enough to start.


That photo by Jamie Templeton was published on Unsplash.