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 Stry.us, 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.

Make Time for the Work.

When you become a boss or a manager, you have to learn how to deal with meeting creep — that phenomenon when meetings take over your calendar, with barely enough time to take a breath between them. You’ve got check-ins and calls and workshops and presentations. Every hour between 9 and 5 is booked.

And the question becomes: When do you actually do the work?

There are a few strategies I’ve tried over the years that have helped lessen the burden of meetings on my calendar:

1) Make your meetings better — Make sure everyone has an agenda for the meeting up front. When the meeting starts, recap the topics that need to be discussed, and see if anyone has anything else they need to discuss. Close the meeting with clear next steps. And by all means, try to finish on time!

2) Turn some meetings into drop-bys or emails — There are a number of meetings that could be solved by taking 5-10 minutes to drop by a coworker’s desk to talk things out. And there are far too many meetings that could have been a quick question solved over email. Know when you need to call a meeting (to build consensus, to decide on next steps as a team, to check in with a team member, etc.) and when you can save time.

3) Make time on your calendar for actual work — That might mean blocking out 90 minutes a few times a week on your calendar to sit down and do real work. It’s tough to get anything done when you’re only getting five minutes between meetings to try to take on a project. If your day’s overrun with meetings, block some time off so that others can’t take over your entire calendar.

Another idea: Save certain types of meetings — 1-on-1s, for instance — for certain days of the week. So many employees take days off on Mondays and Fridays throughout the year — meaning that any Monday/Friday check-ins end up getting frequently rescheduled — that maybe you want to move all of your 1-on-1s for mid-week, and save Monday and Friday for full work days.


That photo of an office building comes via Dylan Nolte for Unsplash.

Don’t Overthink It.

This morning, I had an idea for a friend, but I wasn’t sure how to tell them. I started thinking about how I’d present the idea to them. In my head, I started writing the email to them — how I’d say hi, maybe share a story or two from the weekend, then get into the idea, couch the idea with a few different caveats just in case they didn’t like it, and then close with a “lemme know!” kind of thing at the end. I spent the better part of breakfast thinking about that email, writing and rewriting it in my head.

I can overthink things sometimes, and this was one case. It was a simple idea, not all that controversial. It didn’t need a whole email. In fact, I realized, it didn’t need an email at all — a text would do the trick.

So that got me out of the rut. I picked up my phone, and fired off the text. Two sentences, and it was done. If my friend wants to follow up, they can. If they want to talk about it on the phone, they can. But I spent 20 minutes this morning overthinking an email I didn’t even send, and then 20 seconds sending a text instead. I wish I could have those other 19 minutes and 40 seconds back.

Send the email, send the text, make the decision — and move on. You’re too busy to waste time overthinking something as small as this.


When you search “overthinkingon Unsplash, that photo by Nathan Dumlao pops up.

The Power of a Warm Welcome.

Inbox Collective’s been going for a few weeks now, and I’m working with several different clients. But those clients are coming from an unusual source — not, as many suspect, from cold calling, networking, or even SEO.

They’re coming because of my Google Doc — and more specifically, because of my welcome email.

Back in January, I launched Not a Newsletter, the Google Doc where I share advice about sending better email. With it, I also created an email alert for readers to find out when the next edition would go live. A little while later, I migrated everything over from TinyLetter to Campaign Monitor so I could set up an automated welcome series. Every reader who signs up for my newsletter now gets this message in their inbox:

The next edition of Not a Newsletter won’t be out until next month. But in the meantime, I want to know more about you. I actually mean that: I want to know who you are, and why you’re so interested in sending better emails!

Hit reply to this email (I’m at dan@inboxcollective.com), and tell me:

1.) Do you have a personal newsletter, or work on newsletters as part of your job?

2.) What’s the biggest challenge you’re facing with your newsletter(s)?

Let me know, and I’ll do my best to make Not a Newsletter the best resource it can be for you.

The secret of the email world is that welcome emails open at incredibly high rates — often multiple times higher than a normal email. (77% of readers open my welcome email.) And when you get a chance like that to make a first impression, you better take it. If the inbox is a living room, the welcome series is a host inviting you in, taking your coat, and getting you comfortable in your new surroundings.

So with my welcome series, I’m getting right to the point: By asking readers to reply to the newsletter to tell me what they’re struggling with, I’m starting a conversation about their email needs. (I’m not selling them anything or pitching them on Inbox Collective — just asking a question to get the conversation going!) I reply to every single one of these emails. (Even if I can’t do much to help, it never hurts to offer someone a friendly hello.) Sometimes, I can help them right away — with a link or a tip to push them in the right direction. Sometimes, I can hop on the call to talk about the issue in greater detail. And in a few cases, those conversations can actual lead to work for Inbox Collective.

Soon, I’ll go further with the welcome series: Adding additional emails detailing resources readers can use, and next steps on how they can work with me. The welcome series is an opportunity — and it’s one that anyone who works in email should be taking advantage of.


That welcome mat photo comes via Jon Tyson and Unsplash.

Here, Read This: “Gone in 3.9 seconds.”

I got the question for the hundredth time the other day: Why would you leave The New Yorker now?

And what I keep saying: Right now, I have an opportunity to help a larger community — news organizations, non-profits, brands — with email. The moment exists right now for me to help, and I don’t know how long this moment will last. So if I want to help, I need to do it right now.

I was thinking of that while reading the story of JamesOn Curry, a former basketball player whose NBA career lasted all of 3.9 seconds. He was a high school star, a college star, and dominated the NBA’s minor leagues, but his actual NBA career never took off. His is a Moonlight Graham story — the athlete who made it the big leagues, but never got more than that one chance. It’s a reminder: Enjoy the moment. You never know when that might be the only one.

Read Curry’s story, “Gone in 3.9 seconds,” here on ESPN.com.

Give Yourself Time.

Today is my last day at The New Yorker — and tomorrow, Sally and I will get on a plane, go to a beach, and do a whole lot of nothing for a few days.

If you’re switching jobs, that time off between work is invaluable. Once you get into the new job, those first few months will be intense. You’ll be meeting people, getting up to speed, and going through the montage scene. It’s going to be a lot — and if you don’t give yourself time to recharge, you might burn out.

So do yourself a favor: If you’re leaving for a new job, ask your new boss for time off — two weeks, minimum. (They’ll want you to start right away. Don’t be afraid to push back.) Give yourself the freedom to go travel somewhere nice for a few days — the kind of vacation you might not get to take once your new job starts. Get away from email, get away from work, and just enjoy yourself. Give yourself the time to read, to travel, to relax, to do as little as you please. Don’t hop into the next thing until you’ve taken that time for you.


That photo was taken the last time I took some time off and went to the beach for a whole lot of nothing.