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. 


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

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.


How I Named Inbox Collective.

When I was 23 years old, I decided to launch my first news organization. I decided to call it

It was a news organization dedicated to telling untold stories in undercovered places — areas that folks in the news business now refer to as “news deserts.” I thought the name was clever. I’d pronounce it “Story.” I liked the .us, too — it implied that these were both American stories (“U.S.”) and our stories (“us”). It felt like an inclusive gesture.

It turned out that nobody could pronounce the name (“st-RYE” is how most said it) or tried to type in to their browser (which I didn’t own). I decided from then on that whenever I launched a project, it needed to be:

1.) Something people could easily pronounce and remember.
2.) A dot-com address.

It was a year ago this month that I decided I was going to leave The New Yorker to start a consulting business. On a long flight for work, I spent a few hours trying to come up with a name for my consultancy.

I started with names that seemed to have a mission attached to them, and a tagline to go with each:

3 A.M. Strategies — A consultancy for those who wake up in the middle of the night worrying, “Do I have a plan? Who do I call to fix this?”

Duct Tape Industries — When things are broken, we’ll figure out how to stick it all back together.

Zig Zig Zag — When others zig, we’ll zag. Let’s try things that no one else is trying.

But none of those actually reflected email, which is my core focus. So I pulled up, a search engine for available URLs, and started typing in phrases that had a connection to email.

“Inbox Outbox” was already taken. “Unread Media” (a reference to the number of unread emails in your inbox) was available, but seemed a little off. (Was I really a media company?) I thought about misspellings (“”) before remembering my “You have to be able to spell it” rule. I jotted down “Send Now Strategies,” which was available, and seemed like a decent option.

I kept going. My flight was showing “You’ve Got Mail” — a rare movie that features email prominently — and I put it on, trying to find something from there to use. I came up with two — “Lone Reed” and “Fox and Sons” — but they were both way too obscure. I didn’t want to spend the first five minutes of every call with a prospective client reminding them of a tiny detail from a two-decades-old movie.

But “Fox and Sons” — the name of the Tom Hanks-owned bookstore — got me thinking about how to pair names together. I tried my initials first: “DCO & Company.” I wanted something tied more to email than to me, especially if I decided to grow the company beyond just a single-person operation.

“What about Inbox and Company?”, I thought. I wrote it down — it was a contender.

Then I thought about other business-like suffixes, and tried to pair those with email related words.

• Company
• Ironworks
• Strategies
• Foundry

I considered a few permutations (“Inbox Ironworks,” “The FWD Foundry,” “bcc Strategies”). And then I tried another ending:


As in: a collective of offerings — Not a Newsletter, a consulting business, webinars, talks — to help businesses send better email.

I started typing in ideas to Domainr to see what was available. Email Collective was taken. FWD Collective was taken.

Inbox Collective was available. It fit everything I was looking for: It was clearly about email, it was easy to remember and to spell, and it was a dot-com address.

I sat on the name for a few days, saying it over and over in my head. A few days later, it still seemed right.

I bought it as soon as I got home.

Do It Again. Make It a Little Better.

A few weeks ago, we tried making pizza at home for the first time. It wasn’t even close to being from scratch — the pizza dough was purchased at the local market, and the tomato sauce was from the jar — but we broke out the pizza stone and a bunch of toppings and gave it a go. The result? Not bad!

But there was room for improvement. The cheese was nice and bubbly, but the crust was a little soft on the bottom.

So we decided to try again, really trying to get the crust right. This time, we rolled out the dough a little thinner, and put it on the pizza stone for about seven minutes before adding on the toppings and cheese. An improvement — but still not perfect!

So we started asking around to friends who do this: What’s your secret? How do you get the crust right?

And one friend suggested: Have you tried putting the stone in the oven in advance for 30 minutes first to get it nice and hot, and then adding the pizza to it?

We’d never thought about that before.

So we’re going to keep trying. Every time we make this thing, we’re trying to make it a little better. A small tweak here, a slight adjustment there. It’s never going to be perfect, but we’re going to keep working to do better.

It could be pizza, it could be your work. Just keep working to make things a little better, bit by bit, until you get it right.


That’s a photo of our first pizza — not bad for a first attempt!

One Week at a Time.

Something I’ve noticed in my conversations this month: Lots of organizations are trying to craft a long-term plan. 

It’s how we’re used to thinking about the future. You’ll sit down with your team and say: Here’s what we’re going to achieve this quarter. Here are our goals for the year ahead.

But no one knows what will happen next. We’re all making this up as we go along — so trying to craft long-term plans is a little foolish. You’re making a plan for a future that may not exist.

It’s hard to do, but if you can, focus more on the immediate future. For instance, I’ve been telling teams with newsletters: Right now, your daily email is focused on the crisis in your community — deaths, illnesses, the situation at hospitals. But next week, it might need to shift, as the crisis goes from a medical one to an economic one. In a few months, if the virus comes back in your community, you might need to pivot again. My best advice: Be willing to adjust the products on a week-to-week basis to make sure you’re serving your readers as best you can at that moment.

It’s hard for us to shift to a short-term mindset. It’s not our default position. But the organizations that think about today, tomorrow, and this week are the ones that will move nimbly and build things that truly help their audience when it’s needed most — now.


That photo comes via Unsplash and Estée Janssens.

Finding Some Sort of Normal.

It isn’t easy finding a sense of normal these days. Staying at home day after day, everything seems to blend together. I know we’re not alone in this. Even Vox created an article titled, simply, “What day is it today?” All of us are having trouble making sense of time during this crisis.

So Sally and I have started to institute one small tradition: A long Sunday walk. We take the same route every Sunday, walking for 90 minutes or so down to the water. It’s simple, but it’s a way for us to mark the time clearly. If we’re on that walk, it means the week is about to begin, and we’ll talk a little about what’s to come in the days ahead.

We’re still trying to find other milestones for the week to help us mark the time. It does help us feel just a bit more normal, here in this moment. We don’t know when all of this will end, but until then, we’ll have our walks to remind ourselves of the week that was and the week ahead.


That photo comes via Islam Hassan for Unsplash.

Lessons Learned vs. Lessons Observed.

I was reading an interview with Gerald Parker, a leading pandemic expert who worked in the Bush administration on the nation’s pandemic strategy plan. It’s a fascinating interview in which Parker talks about the lengths that previous administrations went to prepare the country for a pandemic like this, and I found this exchange particularly striking:

We’ve had lessons observed over and over: SARS, the 2009 pandemic, Ebola, Zika, and so forth. I say “lessons observed” very purposefully. That’s different from “lessons learned.”

We’ve observed things, but we haven’t really turned them into lessons learned.

Yes, Parker’s saying, we’ve seen pandemics before, and yes, we know what happened. But in this case, we didn’t learn from them — because had we done so, we would have made changes to prevent something like this from happening again.

On a note far less serious note than pandemics: I’ve had countless conversations over the years that fit this exact phenomenon. Someone will tell me, “We know that we should do this, and we’ve seen others succeed by taking this step… but we just haven’t done it yet.” Even though they know it’s a best practice, or a necessary next step, they still haven’t been able to do so.

Now’s a good time for all of us to revisit the things we’ve observed. If there’s something you believe can help — or know will help — why haven’t you taken the step to actually learn the lesson and implement the changes you need?


That photo of an observation point comes via Unsplash and Matt LaVasseur.

We’re All Making This Up As We Go Along.

a road into the fog

One of the great not-so-secrets of life is this: All of us are making things up as we go along.

Every time you meet an expert or a leader in a space, you have to remember: They don’t know what’s going to happen next. Maybe they’re unusually smart and can see what’s coming around the corner, but they don’t have a crystal ball. They’re figuring things out as they go, making adjustments, and trying to do the right thing with the information they have.

Right now, during this crisis, we’re seeing that play out in real time. None of us know how long this crisis will last, or what the long-term effects of this crisis will be, which means that it’s impossible to accurately plan for the future. We’re all trying to make plans for the unknown.

You do still have some control, though. Think about taking these two next steps:

1.) Identify a long-term mission — Understand how you hope to serve your audience in the years to come. The tactics and strategies you implement to deliver on that mission may (and almost certainly will) change, but know what that big picture goal is for you and your team.

2.) Think in terms of weeks, not months or years — This crisis is moving so quickly that trying to plan even a few months out seems unwise. Focus on the immediate future. What are the things you can do today, tomorrow, and this week to help your audience through the crisis? People will remember how you treated them and the things you did to help them at a moment like this.

Here’s what that looks like at Inbox Collective: My mission is to help news organizations and non-profits build an audience and a sustainable future for themselves. In the short-term, that means putting most of my paid consulting on hold so I can release new resources to help my readers improve their email programs, take part in webinars and calls to discuss strategy, and offer free 1-on-1 coaching calls to help these organizations brainstorm next steps. It’s what I can do right now to continue to build towards that long-term mission.

We’re all making this up as we go along, and there are no clear answers here. But if you have the long-term mission and the short-term next steps, hopefully you can navigate clear of this crisis. 


That photo of a road leading into the fog comes via Katie Moum and Unsplash.

Planting the Seeds for Whatever’s Next.

plants growing

In the past 24 hours, I stumbled upon two very similar quotes from two very different people.

The first: I was reading a New York Times essay by Christoph Niemann about a trip to Eastern Europe, and he quoted former Estonian President Lennart Meri, who in 1992, just a year after his country was granted independence from Russia, famously said: “Our situation is shit, but this is the fertilizer for our future.”

The second: J.B. Smoove of “Curb Your Enthusiasm,” went on a podcast recently to talk about his comedy career, and he said, “I like to plant seeds. I’m a seed planter. Whether that tree grows a week, a month, a year, five years, ten years from now, at some point, it’s going to grow. It’s just a matter of how fast it’s gonna grow.”

None of us really knows what things will look like a few weeks or a months down the road. We don’t know if we’re headed for a recession, a depression, a global change in the way we do business — or if this all just a blip.

But what I do know is that this is a moment for us to plant seeds. In the next few weeks, I’m going to launch a few small projects — some on my own, some with partners in the news space — to try to be helpful. I’m not focused on driving revenue with these projects. The goal is just to help, in the way I can be helpful, at a time of need.

Long term, my hope is that the help I give and the relationships I build now will lead to interesting things down the road — whenever and whatever that might be.

As the former President of Estonia and a guy on HBO both wisely noted: Now’s the moment to plant the seeds for whatever’s next.


That photo of plants growing comes via Unsplash and photographer Markus Spiske.

It Happens When It Happens.

My mother used to have this expression: “Hurry up and wait.” I remember when we used to go to the beach, and there was this one part of the trip that required us to get on a ferry. The ferry captain would announce that we’d be docking in 20 minutes, and people would rush to the exits, even though they weren’t going to be able to get off the boat for another 20 minutes. Mom always laughed at the idea of rushing to get to the exits before you could exit. We’d sit on the top deck of the boat instead, enjoying the final minutes of the ride into the dock. “Everyone else is just hurrying up to wait,” she’d tell us.

Right now, at this moment, we’re all dealing with the COVID-19 pandemic. We’re calling airlines to ask for refunds on upcoming travel. We’re on hold with the doctor’s office. We’re waiting to check out at — or just to get in to — the grocery store.

We’re all going through this together, and not nearly as quickly as we want. The whole world, it seems, is in hurry up and wait mode.

These next few weeks — and months, if we’re being honest with ourselves — things aren’t going to be normal. Our lives are being disrupted, and things are going to change.

What I’m trying to remind myself is: Things will get moving again, and life will go on, even though we’re not entirely sure when. Things will happen when they happen.

In the meantime: Be kind to one another, and be patient with one another. These are stressful times. The least we can do is show kindness and patience in this moment.