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.

I Worked for Two Years at The New Yorker. This Is What I Believe.

Every year, around Thanksgiving, I write a blog post that I call The Things I Believe. It’s an inventory of the year that was, as I look back on what I’ve learned and the person I am at that moment.

As as I approach my final day at The New Yorker — in September, I start full-time on Inbox Collective — I wanted to look back at two years in this newsroom. It’s been an incredible place to work, and I feel so lucky to have been a part of this team. So as I look back on my time at The New Yorker, this is what I believe:

Whatever it is you do, be the best at it — Whenever someone asks me how to get a job at The New Yorker, I always tell them: This is a place full of the best people in their field. I truly believe we have the best editors, writers, fact checkers, and artists anywhere. My colleagues are so unbelievably good at what they do — I continue to be amazed at how talented this team is. And if your ambition is to work at The New Yorker one day, keep working to be the best in your field. When you are, this place might be ready for you.

Give yourself time to focus — It’s not just that the people who work at The New Yorker are talented. It’s that they’re given the opportunity to focus on their work. It’s not uncommon to hear that a copy editor or a fact checker is going to be working on a particular piece for a few days — or longer — to make sure that the work is done right. Focus breeds excellence.

Make the extra phone call — Before The New Yorker, I’d never worked at an organization that had a dedicated fact-checking team. Our fact checkers check everything — and I do mean everything — that can be checked. Here’s a glimpse into the process, as explained through the experience of actor Daniel Radcliffe, who was once tasked with fact checking a review of a Mexican restaurant. Their attention to detail is remarkable.

Don’t take yourself too seriously — Here’s another secret of The New Yorker: If we just published lengthy profiles about Polish novelists or reported pieces about the future of modern dance, I’m not sure we’d get that many readers. What sets The New Yorker apart is the humor. This is a place that can be silly, goofy, and subversive, and that makes all the difference.

It’s been a joy being a part of this team. I’ll always be a reader — and a fan.

———

That New Yorker cover comes via the excellent @NewYorkerArt Instagram.

When Will Then Be Now?

This is the second in a semi-occasional series of Spaceballs-inspired blog posts.

Lord Dark Helmet: What the hell am I looking at? When does this happen in the movie?
Col. Sandurz: Now. You’re looking at now, sir. Everything that happens now is happening now.
Lord Dark Helmet: What happened to then?
Col. Sandurz: We passed it.
Lord Dark Helmet: When?
Col. Sandurz: Just now. We’re in now now.
Lord Dark Helmet: Go back to then!
Col. Sandurz: When?
Lord Dark Helmet: Now!
Col. Sandurz: Now?
Lord Dark Helmet: Now!
Col. Sandurz: I can’t!
Lord Dark Helmet: Why?
Col. Sandurz: We missed it!
Lord Dark Helmet: When?
Col. Sandurz: Just now!
Lord Dark Helmet: When will then be now?
Col. Sandurz: Soon.

When you’re building something new, it’s hard to be patient. You’ve got a great idea, and you’ve got some momentum, and it feels like you’ve got all the potential in the world. You want to fast forward to the ending — when the work is done, and everyone gets to see your genius idea become something real.

But when it comes to the work, there is no fast-forward button. There are no shortcuts. The work still needs to be done. Networks still need to be built. The team needs to be assembled. Hours need to be put in.

The future you want needs to be made, piece by piece, and day by day. I promise: Then will be now — and sooner then you think. But you’re in now, now. It’s time to start putting in the work.

———

That photo and quote at top comes from Mel Brooks’s classic spoof, Spaceballs.

The Bad Idea Notebook.

I have a lot of ideas — and most of them, frankly, are bad. But having bad ideas is OK — as long as you develop a filter to decide which ideas are worth working on, and which ideas should move to the scrapheap.

I know I’m not along in having bad ideas. I read a story recently about Dr. Seuss, and learned that he was full of bad ideas, too!

In 1939, at the age of thirty-five, Theodor Seuss Geisel was tinkering with an invention that was doomed to failure. Geisel had published a few books under the name Dr. Seuss, but he was hoping that a device he had patented, the Infantograph, would be a money-maker at the techno-utopian New York World’s Fair, which was opening that year. “If you were to marry the person you are with,” the banner that Geisel designed for his pavilion asked, “what would your children look like? Come in and have your INFANTOGRAPH taken!” In the tent, a couple would sit side by side; a double-lensed camera would blend their features together, then plop a composite mug shot atop an image of a baby’s body. “It was a wonderful idea,” Geisel insisted, but, as a feat of engineering, it was more of an evocation of outlandish, off-kilter Seussian machinery than it was a functional prototype. After much fiddling, he scrapped his plans, admitting, “All the babies tended to look like William Randolph Hearst.”

Knowing when to kill your bad ideas is crucial. I run a lot of my ideas through the Shower Test to see if they’re sticky enough. But I’ve also started doing a new thing: Writing my bad ideas down in what I’ve been calling my Bad Idea Notebook.

The Bad Idea Notebook is what it sounds like: a small notebook full of truly terrible ideas. There are ideas for products, for TV shows, and startups in there — all ideas worthy of the scrap heap. Every time I have a quarter-baked idea , it goes into the Bad Idea Notebook.

And sometimes, when I get really excited about an idea, I’ll pop open that notebook and scroll through my list of terrible ideas. It’s a reminder for me: Yes, Dan, you’re excited about this idea right now — but just remember, 70 percent of your ideas are truly terrible. Give it some time, mull over the idea a bit. Think through what it would really take — time, team, money, work — to put this idea into motion.

Often, a few minutes later, having started to think more clearly through things, I’ll realize a few flaws in the idea — and pop open my Bad Idea Notebook to add a new entry. I have lots of ideas, and lots of work already in the mix. The next idea — a better one, often — typically comes around soon enough.

———

That photo comes via Unsplash and AP x 90.

Here, Read This: “Decades after life took them down one path, these women are reinventing themselves.”

The Washington Post profiled eight women who’ve done amazing things in their careers after age 50, and it’s a story absolutely worth reading:

When women turn 50, the world starts to tune them out. Employers see them as less valuable and are more likely to discriminate against them, according to research. Hollywood disproportionately portrays them as unattractive, unfriendly and stupid. Many women describe a sense of invisibility.

But something else happens as women leave their 40s behind. “[For] everyone I know around my age, there’s this major energy shift in being able to ask the question: Well, what do I want now?” writer and cultural critic Heather Havrilesky, 49, told The Washington Post. “Without feeling totally cowed by what you should want, what seems selfish.” The world may tend to forget older women, but they feel freer than ever.

For American women in middle age and later, that might mean returning to ambitions set aside years ago to raise a family or follow a spouse’s career. It might mean finding ambitions they never had before or reaping long-overdue success. “Our culture tells us a story that we’ll lose and lose and lose as we get older,” says Havrilesky. “And it’s not true.”

Read the entire piece here — it’s a great reminder that it’s never too late to chase that big dream.

Outwork and Outnetwork.

A few weeks ago, The Athletic published a piece on Buzz Williams, the new head coach for the Texas A&M men’s basketball team. Buzz used to coach at Virginia Tech, and before that, Marquette. Everywhere he’s gone, his teams have had success — in 11 seasons of coaching at Marquette and Virginia Tech, he’s taken his teams to the NCAA Tournament eight times. So what’s his secret?

The Buzz standard is a no-nonsense, no-excuses approach. He climbed the ladder in coaching by outworking and out-networking everyone. On the back of his calendar is a monthly contact list. There are 58 people in a column labeled personal and 31 apiece for a Texas A&M column and a grassroots/high school basketball column. The people he has contacted are highlighted in yellow. Halfway through May, he had already knocked out 46, 11 and 17, respectively.

Williams is trying to meet daily with a person important to the process at A&M, and similar to a presidency, he believes the first 100 days are critical. Relationships have always mattered most to him — and why he’s successful.

There’s a lot in there to unpack, but the one thing that stood out to me was this phrase: Outwork and outnetwork. So much of the success of a coach like Williams depends on relationships. If you have the relationships in place, a scout or a coach might give you a heads up about an under-the-radar talent. If you’ve established trust with a source, you might be the first to know about a new method for developing players. And a strong network within a college campus might make all the difference when it comes time to getting the funding you need for your team.

Nobody does it alone. It takes hard work — and a network — to help you achieve your goals.

But building that network is simple: Meet people, be kind, and stay in touch. Do those three things, and do it for a long time, and you’ll slowly build the network you need.

Here’s a great example of that, from Phil Knight’s “Shoe Dog,” a wonderful memoir about how Knight built Nike. In it, he tells the story of Jeff Johnson, Nike’s first employee. Johnson, turns out, was a lot like Buzz Williams. Writes Knight:

He worked seven days a week, selling and promoting Blue Ribbon, and when he wasn’t selling, he was beaverishly building up his customer data files.

Each new customer got his or her own index card, and each index card contained that customer’s personal information, shoe size, and shoe preferences. This database enabled Johnson to keep in touch with all his customers, at all times, and to keep them all feeling special. He sent them Christmas cards. He sent them birthday cards. He sent them notes of congratulation after they completed a big race or a marathon. Whenever I got a letter from Johnson I knew it was one of dozens he’d carried down to the mailbox that day. He had hundred and hundreds of customer-correspondents, all along the spectrum of humanity, from high school track stars to octogenarian weekend joggers.

Those relationships, writes Knight, were the key to Nike’s early success. Those early fans told their friends about Nike shoes. They came back as repeat customers. And they gave Nike feedback about the shoes that the company then used to test and improve their product. None of it would have been possible if not for that network — and that wouldn’t have been possible if not for Jeff Johnson and his daily letter writing habit.

I’ll say it again: Meet people, be kind, and stay in touch. Pair hard work with a powerful network, and you never know where it might take you.

———

That photo was taken by Samuel Zeller for Unsplash.

Introducing Inbox Collective, a New Email Consultancy.

In a few weeks, I’m leaving my job as the Director of Newsletters at The New Yorker.

Why would I leave a dream job, you might be wondering?

Well, I’m opening up a little consultancy to help brands with email.

I’ve been working in this space since 2012, when I became the first Newsletter Editor at BuzzFeed. When I first started working in email, it was hard to find anyone in the news space who had expertise in email. Now, most news organizations and brands are investing in it.

But there’s still more work to be done! Ever since I started Not a Newsletter back in January, I’ve been getting notes from readers, telling me about their email goals and aspirations. So many of them have told me that they need help with all parts of their email program — from content strategy to growth, from monetization to deliverability.

And at some point, I realized: The work I’m doing with Not a Newsletter isn’t enough. I can do even more to help this community.

So I’m starting up a consultancy. It’s called Inbox Collective, and it’s here to help news organizations, non-profits, and other brands grow audiences, build relationships, and get results via email.

Interested in working with me? You can read more here.