Author: Dan Oshinsky

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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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How I Named Inbox Collective.

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

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 stry.com 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 domainr.com, 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 (“Inboxx.com”) 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:

Collective.

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.

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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.

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

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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.

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That photo comes via Unsplash and Estée Janssens.

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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.

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That photo comes via Islam Hassan for Unsplash.

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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?

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

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