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The Only Time Is Now.

The truth is, I almost didn’t leave The New Yorker when I did.

I knew that I wanted to start Inbox Collective. I knew there was a market for my services. I knew that I had an opportunity to help the journalism world.

But I wasn’t sure if the timing was right.

Sally was in nursing school. She was 18 months in, with a year of classes left. She’d graduate in Spring 2020. And my thought was simple: Sally still had a few semesters of tuition left to pay, we were a one-income household, and if Inbox Collective didn’t work, we’d be a no-income household. Leaving my job to start a consultancy was a gamble, and the safe move was to wait until Sally had graduated and gotten a job — sometime in the summer of 2020.

But Sally convinced me to take the leap anyway. She reminded me that I had momentum and a clear opportunity. There was something else, too, something we talked about a lot at the time: The window for me do this was open, and we weren’t sure how long it would stay open. There was risk in leaving my job to start something new, but also risk if I waited too long and the window closed.

Now looking back, if I’d waited, I don’t think I’d ever have left to start Inbox Collective. Taking the leap to start a business is tough enough during good times, but during a recession and a pandemic? There’s no way.

It’s a reminder that when you’ve got something you’re excited about, and something you feel ready to take on, the only time to try it is now. If you wait, the window might close, and you might miss out on that opportunity forever.

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That’s a photo of me giving a talk in Sydney last year — one of many pretty amazing experiences that I couldn’t have had without taking the leap.

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Be Willing to Let Things Go.

When I think back on my time at BuzzFeed, there was a lot that made us successful. We hired a talented, diverse group of creators. We invested in learning and development programs so staff could continue to grow in their roles. We built strong product and data teams to provide the resources so we could try things that no other media company could do.

But we also were willing to let a lot of things go.

There’s a long list of BuzzFeed projects that launched — some to significant fanfare — that didn’t work.

There aren’t many who still remember projects like BuzzFeed University (a program to encourage advertisers to build their own sponsored content), Fre.sh (a dashboard tracking the biggest stories on the internet), or Star.me (a social network that allowed you remix content). We launched these, and quickly realized that they weren’t working.

Sometimes, BuzzFeed launched projects that flopped — but showed a few signs of promise. Often, someone on staff would latch onto those projects and try to figure out how to take what had worked and turn it into something new.

But with certain projects, we knew early on that there wasn’t an audience for the thing we’d built. So instead of compounding our error and continuing to funnel resources and staff into a failure, we let it go, and moved on to whatever was next. There was always another idea that was worth trying.

No one wants to see a project fail. But it happens. Anytime you launch something new, make sure you know in advance how you’ll measure success for this new thing — if you do that, you’ll be able to see clearly when a project works, and when it doesn’t.

When it doesn’t, you may have to let it go. If there isn’t an audience or a need for the project, no amount of tinkering or investing is going to help. Better to quickly move on to the next idea than to lose more time trying to fix what doesn’t work.

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That’s a screenshot of the BuzzFeed Fre.sh homepage on October 23, 2013. As you can tell from the list of stories here: It wasn’t nearly as useful to readers as we hoped it would be.

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Be Silly.

Carl Reiner died this week. He was 98.

When I think of Carl, I think of his friendship and partnership with Mel Brooks — in particular, their work on the “2000 Year Old Man.” I remember listening to those records as a kid and being amazed at how funny they were. It was just two comedians having a conversation, but those records always made me laugh. (“How many children do you have?” “I have over 42,000 children. And not one comes to visit me.”)

What amazed me most was how silly they were. I think the “2000 Year Old Man” was the first time I realized that adults were allowed to be silly. Until then, I thought that was something only kids could be. I still tend to gravitate towards people who are silly — silly people have such amazing energy, and bring a sense of joy and wonder to everything they do.

The more I watched from Carl — from “The Dick Van Dyke Show” to “The Jerk” — the more I saw that silliness and playfulness in everything he did. As I’ve thought about him this week, it’s the quality I keep coming back to.

Thanks for the laughs, Carl. And thanks for teaching me to be a little bit silly every day.

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Something To Look Forward To.

By the end of January, I had my calendar for the entire year pretty much set.

I knew where I was going to give talks this year, and had the flights planned out. I knew which weddings I’d be going to. I had some vacation days penciled in.

Then Covid-19 hit here in the U.S., and all of that changed.

I used to have a nice balance of remote work and in-person work. Now, like everyone else, my work’s shifted entirely online. I’m not sure when I’ll fly next or when I’ll travel again for work.

And that’s OK! I’m lucky to be the position that I’m in. Inbox Collective is doing well, and I’ve got my hands full with work. I feel incredibly grateful for the opportunities that I have.

Still, I’m realizing how much I miss being able to look forward to the next thing: The next trip, the next birthday party, the next night out. Zoom is such a useful app, but it’s not the same as being there with friends or clients.

Here’s the closest thing I’ve found to life before Covid-19: This past weekend, my wife and I decided to get out of town for a few days. We rented a car and drove upstate. We didn’t do much — we ate, we drank, and we saw a few friends from a distance — but just knowing that we had something like that on the calendar lifted both of our moods for an entire week.

Going forward, I’m going to try to keep putting something on the calendar to look forward to. It could be small (setting aside some time to meet a friend in the park) or big (a road trip somewhere). I’m not going back to the pace I had a year ago, and that’s alright by me. Just knowing that something’s coming up is enough to keep me moving forward.

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That’s a screenshot of Flighty, the app I use to track my travel. That’s what my travel schedule looked like from March through June. (Obviously, it all changed.)

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I Hope You’ll Join Me in Supporting The Marshall Project.

I’ve been thinking a lot about the platform I have, and how I can use it to help. Then I had an idea for a way to do just that — to help newsrooms and nonprofits send better emails, and to raise a bunch of money for an amazing cause. In the first 24 hours, we raised more than $1,000 for The Marshall Project.

So here’s how you can help and get access to a resource to help you grow your email lists, too.

I’ve created a new guide with 25 great ways to grow your email list. I hope you grab these slides, get your colleagues together on Zoom, and talk through them. I think you’re going to find a few new ideas worth trying.

To get access, all you have to do is first make a donation to The Marshall Project, a non-profit newsroom that covers criminal justice. I can’t imagine a more important moment for this kind of reporting. You’ll be supporting an amazing cause.

If you donate $10 or more, I’ll send you the slides. In July, I’ll donate 100% of all contributions to The Marshall Project. (And if you’d rather donate to them directly, you can do so here. Forward me the confirmation email and I’ll send you the slides.)

You can donate at this link.

We’ve already raised more than $1,000 from 100 different donors. I hope you’ll join us all in giving to The Marshall Project.

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You Smug Assholes.

At The New Yorker, we had an inbox where readers could write to us with questions, comments, or concerns, and I made it my mission to check that inbox every weekday. Some days, it took me five minutes to go through and reply to all the emails. Sometimes, it took me an hour. But I always made time to reply.

Why? The New Yorker couldn’t exist without its readers. Revenue from readers — subscription revenue, plus revenue from events like The New Yorker Festival — is what allows that newsroom to keep publishing. So the thought was simple: Readers are what allow us to do our jobs, so we should always be making time for them.

I’ll never forget an email I got in 2019. The subject line read, simply: “You smug assholes.”

I replied to just about every email in that inbox, and many of those conversations were tough ones. Just from the subject line, I knew a little about what I was getting into with this particular email.

The reader had a few issues: They were upset with the magazine’s politics, they were having trouble with their subscription, and they had a few questions about our editorial process.

Over the course of a few emails, I answered their questions one by one, and checked in with certain editors so I could offer an informed reply to certain topics. I helped troubleshoot their subscription issues. And slowly, the tone of the conversation began to change. I tried to do my best to listen and to ask. I tried to do my best to help.

And by the end of our thread, this reader wrote back to tell me: “Thank you so much for your help. I love The New Yorker, and can’t wait to be a subscriber for years to come.”

Over the course of a few emails, we went from “You smug assholes” to “a subscriber for life.”

It’s a reminder for me, especially now: Don’t be afraid to have a difficult conversation. Listen to the people around you, and make sure you’re opening up channels to hear from all sorts of voices. Make time to listen, learn, and ask. You never know where those conversations might lead.

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That photo at top, titled “Day 52/366: 2/21/12 – New Yorkers”, by memsphere, is licensed under CC BY-NC-SA 2.0

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The One Thing I Truly Believe.

Every Thanksgiving, I write a blog post called “The Things I Believe.” And in it, I write the same thing: “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, this year, is what I believe.”

I think being willing to change your beliefs is an amazing thing. It signals that you’re listening and learning. It says that you’re willing to grow as a person.

I know that in my life, I’ll continue to change and grow. But there’s one thing that I truly believe, one thing I don’t believe will ever change, and I think it explains a lot about who am I am and why I make the decisions that I make:

I believe that life is about the people you surround yourself with — the people you care about, the people you love, the people you stand up for. I believe that nothing is more important those relationships.

It’s not about money, or fame, or accolades. It’s about people.

It’s why I try to make things that are open to as many people as possible. It’s why I block out time every month for new conversations. It’s why I share what I’m learning with the people around me. It’s why I make time for birthday cards, anniversary texts, and regular catch-ups.

I’m not perfect at this. I know I can do more to build new and stronger relationships, and I know I need to more.

But this is what I believe: These relationships matter. Putting others first is what this life is all about.

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That photo of one of Pittsburgh’s many bridges was taken by Willie Fineberg.

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Keep Moving.

There is so much we need to accomplish. It can feel overwhelming at times to look at the to-do list and see what still needs to be done. The tasks ahead can feel endless.

But the work doesn’t happen all once. Change happens incrementally. You point yourself in the right direction and slowly start moving there, step by step. It’s only through persistence and time that you’re able to move things forward.

The most important thing is to keep making progress. You won’t always go as fast as you want, and you won’t always get where you’re going as quickly as you want. Even when you reach that destination, you may find that things have shifted — there may be new goals and new milestones ahead. Good.

Keep pushing forward.

Keep trying to make things a little better every single day.

Keep moving.

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That photo comes via Zac Ong and Unsplash.

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Make the Right Choice for Right Now.

clock on 5th Avenue

No one knows what happens next. We don’t know what things will look like in two weeks, two months, or two years. We don’t know if we’ll be working in offices again, traveling to conferences, or even sitting down at the table with loved ones. Sure, you can make a prediction about the future — but your prediction is little better than a guess.

What we’re living through is going to change us. As novelist Arundhati Roy wrote in April:

Historically, pandemics have forced humans to break with the past and imagine their world anew. This one is no different. It is a portal, a gateway between one world and the next.

So how should you approach making a tough choice about an uncertain future? Try to think through two big questions:

What do you know right now? — Do your research. Read a lot. Talk with people you trust, and listen to what they have to say. Try to collect all the information you can about the situation.

What do you believe right now? — Trust your instincts. Think about what you need at this moment. Put all the options on the table, and make the best choice you can with the information you have.

You may not end up making the perfect choice in the long run. Again: To make the perfect choice for whatever’s next, you’re going to need to get a little bit lucky. But you do have the power to look at the current situation, ask the questions you need to ask, think through the options in front of you, and make the right choice for right now. 

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That photo of a clock on Fifth Avenue comes via Unsplash and photographer Trevor Bobyk.

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A Thought on My 33rd Birthday.

I turn 33 today. A year ago, I was just thinking about leaving The New Yorker. I didn’t know that in the year ahead, I’d get to work with clients across the country and across the world. I didn’t know how much this business would grow. (I’m not sure I even realized that I was building a business!) I didn’t know that I’d have the chance to give talks to teams on four continents. I didn’t realize how familiar I’d get with Zoom. I didn’t know I’d get to spend so much with Sally in such wonderful places: Rio, Salt Lake, Surf City. I didn’t know how much I would learn.

I don’t know what 33 will bring. This year’s been unexpected, eye-opening, and full of opportunity. I hope I get to do it all again, and more, in the year ahead.

Onward.

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