I’m Dan Oshinsky, and I run Inbox Collective, an email consultancy. I'm here to share what I've learned about doing great work and building amazing teams.
When a reader signs up for Not a Newsletter, they immediately get a welcome email from me, in which I ask two things: Do you have a newsletter, and what’s the biggest challenge you’re facing with it?
Sometimes, the replies will be small and easy to reply to. Struggling with growth? Here are a few slides. Need help with a survey? Here are a few examples.
But other times, the replies involve a weightier topic — writers at major crossroads. I used to send back long responses to these readers, making the argument for why I thought they might want to head in a certain direction. What I discovered is that often, despite a thoughtful and well-sourced reply, they’d go in an entirely different direction.
These readers, I realized, weren’t looking for advice — they just wanted a place to vent.
It didn’t matter if my advice was good or bad. They weren’t looking for advice, and it wasn’t my place to give it.
So I’ve started changing how I reply to those messages. When I think I’ve got one of those emails in my inbox, I try to validate their reply (“That’s such an interesting challenge! I’ve had a few other readers struggle with this — it’s not easy!”) before asking a question or two in reply. I don’t share as many links as I do with other readers. Again, they’re venting, so my job is to listen. The right reply isn’t a solution — it’s a question.
These readers are going to make their own choices. All I can do is listen, ask, and hope that whatever choices they make are the right ones for them.
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That’s the email they reply to when someone signs up for my newsletter, which, by the way, you can do here.
I just spent a week up in New England in a cabin, on a lake, in the woods. We didn’t have electricity or internet or cell service. My clients were excited about it: “You deserve a full week off,” they told me. My wife was excited about it: “You’ve earned this!” she said.
I was terrified.
I was terrified of the emails I’d get while I was gone. I was worried that I’d return to find 400 urgent requests that I was a week late on. I was worried that something terrible would happen to a client while I was gone and I wouldn’t be able to help.
And I logged back on yesterday to find… well, about 70 emails that actually required a personal reply. Not a single one was urgent. My website was still functioning. The Google Doc was still live. Nothing broke or went terribly wrong.
And in the week I was gone, I truly got the chance to unplug. I read three books, I swam, I napped, I did a whole lot of nothing.
Today, I’ll reply to all those emails, and tomorrow, I’ll get back to work. But I’m glad I got the chance to unplug.
Turned out that for all my fears, everyone else was right: It was OK to take a week off, and it was worth it.
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That was the view from my cabin. I kept my phone off most of the week, but did turn it on once or twice to take photos.
A few months ago, I wrote about living in the moment. “Sometimes,” I wrote, “you’ve got to try something because, honestly, when are you going to get to do it again?”
Sunday was one of those days.
A few months ago, Paul McCartney announced that he was going on tour. One of the dates on a Sunday night in Baltimore. A few childhood friends texted me: Was I in for the show?
Sally and I were — but there was one complication. We’d be coming from a wedding in Connecticut, six states and 300 miles away. It’s a 6-hour drive in normal traffic, but on a summer weekend on I-95, six hours becomes 10 quickly.
We said yes anyway.
Was it a lot of driving? Yes. Did we somehow make it on time? Yes. Were we exhausted by the end of the night? Yes.
Was it worth it to see freaking Paul McCartney play a three-hour, 37-song set? Oh, absolutely.
Sometimes, you have to do something just because you might never get the chance to do it again.
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That’s a photo of Paul on stage in Baltimore. My buddy Ian took the photo. (We had pretty good seats, but Ian had amazing seats.)
When I have conversations with writers in advance of the launch of their newsletter, they often worry about the name of the product. They’ll worry that it’s not clever enough, or that it might be too simple, or that they need to spend more time coming up with the perfect name. (I’m guilty of doing this myself.)
So here’s a story for you, if you’re thinking that the name of your next product launch isn’t quite right:
I was in Sonoma, California, a few weeks ago, walking through their downtown, when I passed a store I’ve seen many times before: Williams-Sonoma. If you’ve bought cookware at any point in your life, there’s a decent chance you thought about buying it from Williams-Sonoma.
I’d never thought much about their name before. But walking past the store, I had that moment. Not an “aha!” moment, but an, “Oh, duh!” moment.
The Sonoma in Williams-Sonoma must mean… they were founded here.
So what about the Williams part? There was a small sign right by the door about Chuck Williams — the man who bought a hardware shop in Sonoma, California, in 1956, and turned it into a store for home cooks.
Chuck Williams. Sonoma, California.
Often, keeping things simple is just the easiest decision — it’s also the right decision.
There’s a lot that’s frustrating about being human, but here’s one thing that’s annoyed me a lot lately: You’re not always at your best.
There are days you show up to do the work, and things feel a little off. It doesn’t matter what the work is — it could be a project, or a big piece of writing, or a day on the golf course. Some days, you show up and know you’re not quite right, even if things felt amazing the last time you showed up to do this work.
It’s hard to accept that your body feels a little different today, that your mind’s in a different place, that your energy’s different than usual. Maybe you know why, or maybe you don’t. But you know, because you know yourself:
Today will be less than perfect.
I like being at my best. I like how confident I feel when I know that I’m doing my best work.
But there’s something to be said for getting through those days when you’re at 70%, when it’s not all there. You make the most of what you can with what you have that day. You find a way.
Accept less-than-perfect for today. Better days will come.
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Naturally, that post was inspired by a morning on the golf course. The day before, I hit the ball so well and felt confident over every shot. The next day, it looked like I’d never hit a golf ball before. It happens.
I was scrolling through LinkedIn last weekend, and in a span of two minutes, saw the same story — same copy, same three images — pop into my feed twice.
The story was about Joshua Bell, one of the most acclaimed violinists of our era. He’ll soon be playing live with orchestras in Portland, Oregon, Stockholm, Sweden, Yerevan, Armenia, and Paris, France — and that’s just in the next four weeks. He performs on a Gibson ex Huberman, crafted by Antonio Stradivari in 1713, a violin twice-stolen and most recently purchased for a reported $3.5 million. And in January 2007, as part of an experiment with The Washington Post, during the morning rush hour at Washington’s L’Enfant Plaza, he performed six classical pieces over the course of 43 minutes, as workers hurried from the Metro station to their offices. The experiment, as the Post’s Gene Weingarten explained, was to answer a simple question: “In a banal setting at an inconvenient time, would beauty transcend?”
Now, you might already know the answer to that question — possibly because you remember the story, which won a Pulitzer Prize, or possibly because you’re smart enough to guess the answer (“no”), but most likely because you’ve seen a version of this story pop into one of your social media feeds over the past 15 years, just as I did over the weekend.
And that version of that story was almost certainly wrong.
Weingarten, the writer of the original piece, tried to set the record straight in a 2014 column. After the piece was published, someone published a summary of the piece to the web. Weingarten found sixteen different errors in it — impressive when you consider that the summary was only 24 sentences long. As he explained:
“This piece — most people’s only direct knowledge of the stunt and its aftermath — was filled with errors significant and trivial, but relentless in their carelessness. I just re-read it, and it is almost incomprehensible how this could have happened, unless the writer read the original piece, forgot about it, and then, months later, tried to summarize it from memory, as though it were not available in original, checkable form just a few clicks away.”
That summary has since been copied and pasted thousands upon thousands of times, and has slowly gathered additional errors as it moves around the web. In the error-filled 2014 version, six people stopped to listen to Bell’s performance, and in total, he made $32. In the 2022 LinkedIn version, of which there are hundreds of posts with identical copy and identical images, four passerbys stopped, Bell made $20, and also, the entire thing took place in New York. (For the record: It took place in Washington, seven stopped, and he made a little more than $32, not including a larger bill dropped in by the one Washingtonian that day who happened to recognize him.)
People share this story for all sorts of reasons. I remember reading it in 2007 as a Ferris Bueller-esque reminder to stop and look around every once in a while. In 2014, Weingarten explained that many religious leaders liked to share the story as proof that beauty is everywhere. On LinkedIn, I saw the story being shared by recruiters as proof that you should look for a new job if your talents aren’t being appreciated at your current company. It’s a great story, and one that can apparently mean just about anything to anyone. It’s what might happen if Hermann Rorschach had written an Aesop’s Fable or two, and asked his patients to interpret that instead of an inkblot.
And I’m sharing this story with you for an entirely different reason. It’s as a warning and a reminder: Be careful about the data you cite when you tell stories like these.
Often, when I’m working with a new client, they’ll mention a tactic they want to try, but then mention a benchmark that’s wildly out of line with reality, and I have to work hard to help them readjust their expectations. A good example: A few years back, there was a story about a local newsletter that used paid acquisition to grow their list. The tactic is just fine — spending money on ads to grow your list is absolutely something certain publishers should try! — but this client kept quoting the cost to acquire an email address, not realizing that the publisher from the story was in a different country, and the amount quoted wasn’t in American dollars. They had the right idea, but somewhere along the way, the data had lost crucial context. (This meant that they were prepared to spend three times what they should have to acquire a single email address.) I’ve seen this sort of mistake happen with large publishers, with individual writers, and every type of newsletter creator in between.
So I’ll say it here again: Be careful about the data you cite when you tell stories like these — it might be wrong, and it might be leading you down the wrong path.
(And if you see someone sharing a story about a New York-based violist who made $20, do yourself a favor and don’t share it.)
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At top, that’s a screenshot of one of the LinkedIn posts. As of this writing, there are over 40 pages of LinkedIn results for the story, all of which are nearly identical. There are even a few in different languages, which appear to have been copied into Google Translate and then copied over from there.
There’s a clip going around with Jon Stewart, who recently sat in on Howard Stern’s show. Stewart’s success in show business is incredible — he won, roughly, a billion Emmys as host of “The Daily Show,” and gave dozens of comedians and writers a huge boost in their careers. Just look at the page of “Daily Show” alums for a moment. It’s a who’s who of current comedy legends.
So Stern wanted to know how Stewart felt about seeing some of the biggest names from his show — comedians like Stephen Colbert, John Oliver, and Samantha Bee — go on to success after leaving “The Daily Show.” Did he ever feel envious of their success?
His answer was so wonderful:
“I never had that sense that someone else’s success was to the detriment of mine. I think it leads to such bitterness when you look at the world as finite and resource-guarded. It leads to such bitterness, and it’s destructive as an emotion. I’ve always felt that everybody’s success expands opportunity.”
I love that quote, and have been thinking about it in relation to the work that I do now. In the newsletter space, it’s easy to look at the success that others are having and think: That should be me! But the truth is: Every time someone launches a great new newsletter, it opens up doors for so many new writers. Those success stories show us all what’s possible with email, what can be done. And when someone succeeds in the industry, it gets so many new writers and creators excited about trying to replicate that success.
There are so many more opportunities in the newsletter space now than there were a decade ago, or even three years ago. Those success stories have expanded opportunities for all of us.
I have a few dozen Inbox Collective clients that I’m working with right now. Some I talk to daily or weekly. Some I talk to once a month or once a quarter. And there are days when I’ll have five or six calls, often stacked back-to-back-to-back. When clients hop on that call, they expect me to be able to pick up exactly where we left off. They pay me too much to be disorganized or unprepared.
When I’m on my call, I’ve got a notebook where I jot down notes and ideas. I find that I stay more focused if I can write things down on paper instead of trying to type up notes as we go.
And at the end of the day, I go through my notebook and type up the notes in a Google Doc designated for every client. If they’re not a client, I create a new Doc for them — often, I’ll find that a casual conversation might lead to something a few months down the road, and having those notes is a hugely valuable tool. I’ll document everything — the date, who was on the call, updates from the team, ideas we discussed, and next steps.
What it means is that over time, I’ve fully documented everything I’ve talked about and done with that client. Some teams have been with me since 2019, and I can’t always remember what we might have tried three years ago. In those cases, it’s great to be able to open up their Google Doc and search for a phrase to figure out if we might have tackled a particular issue already.
If you’re holding regular meetings with a variety of stakeholders, you might want to try the running notes system, too. Set up a doc for every team or individual you meet with, and document your notes from the day. That way, when you need to find notes from a conversation, you’re not searching in your desk for that one notepad that might have your notes, or searching through your inbox hoping to find an email that mentions the topic. You’ll have a document of exactly what you discussed, and when.
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That’s my notebook and a running notes Google Doc, both for WBUR, a client that’s worked with me for nearly three years. At this point, my Doc for them is 44 pages and more than 9,000 words long.
It’s our first night in Lisbon, and we’re hungry. Earlier in the day, we’d passed by a restaurant that looked great — and was busy at lunch, which is usually a good sign — and they’d recommended that if we wanted to come back for dinner, we should either come super early (5:30 p.m.) or late (8:30). We’d come late, but by the time we arrived, they said their dinner service was full for the night.
So we started walking. We passed on Italian food and Mexican food, and weren’t into the steak place on the corner. We stopped at a barbershop that also had a bar inside and got a drink. They recommended a Chinese place up the hill, and so we headed there — only to find that they didn’t serve Chinese food. (Only burgers and cocktails. I still don’t understand why.) We kept walking, and I wasn’t worried about finding a place. I studied abroad in Spain, and restaurants there were always open late, and this was a Friday night, when restaurants are typically open even later. But at about 9:45, restaurants started turning us away. Four or five places told us, “Sorry, we close at 10.” And suddenly, we realized:
We had no idea if we were going to find a place that was open for dinner, we’d walked nearly 10 miles that day up and down Lisbon’s hilly streets, and we were really, really hungry.
So we started getting a little desperate, asking every bar and restaurant we passed — regardless of cuisine — if they were still open for dinner. None were.
I tried to steer us to a local kebab place, since those usually don’t close until 2 or 3 in the morning.
Closed.
We kept walking, and then, finally, on the right, I spotted it: A sushi place with a few people eating outside. We ran in. “Are you still open?” I asked.
“For dinner? Yes, right this way,” the hostess said, and pointed us to a table.
We ordered an excessive amount of food that night — sushi and soups and noodles and beers, as the TV in the corner played ‘00s hits. (I’d never eaten sushi at 11 p.m. while listening to Kanye West’s “Late Registration.” Based on how fast we ate everything they placed in front of us, I think our server thought we’d never eaten before. We ate and laughed and drank and toasted to somehow finding the last restaurant in Lisbon that was still open for dinner.
It was a reminder: Getting lost in a new place can be fun! But maybe next time, we’ll remember to first ask the hotel front desk what time local restaurants close.
With that in mind, here are ten other rules I’ve learned about traveling:
1.) Do something cultural.
2.) Do something active.
3.) Eat a lot.
4.) Try something new.
5.) Meet new people.
6.) Ask locals for recommendations.
7.) Tip well.
8.) If you’re traveling with a friend or a spouse, spend a few hours doing something on your own.
9.) Get enough rest.
And remember: You don’t need to see it all. I love leaving a place thinking, “You know, there’s more to see here! I can’t wait to come back.”
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That’s a photo I took of the view from the Bairro Alto in Lisbon at sunset.
Sports writer Joe Posnanski went on the “Two Writers Slinging Yang” podcast with Jeff Pearlman last week, and he told an amazing story. It’s a story about the time Posnanski, then a young sportswriter covering minor league baseball, had the courage to ask a dumb question of Billy Williams, a Hall of Fame outfielder who was then a minor league baseball coach.
As Posnanski recalls:
So I was sitting next to him, and we were talking a little bit. I don’t even know exactly what pushed me to do this, but I had been dying to know something. I turned to him, and said, “Mr. Williams, can I ask you a question?” And he said, “Yes.” And I said, “What is the difference between a curveball and a slider?”
And as I asked the question — I was probably 19 years old, 20 years old — there were some snickers in the press box, as you might imagine, from people who had overheard. And Billy Williams took my notepad — I had a skinny reporter’s notepad — he took my notepad and took my pen and started to draw the difference between a slider and curveball. And for the next 10 or 15 minutes, he just gave me this masterclass on the difference, how the curveball breaks this way, and the slider breaks this way, but there are different kinds of sliders: This is [Bob] Gibson’s slider, and this is Steve Carlton’s slider, and he would draw that, and this is Tom Seaver’s. He would go through all of that for different players. It was awe inspiring to be getting this lesson about something so basic from one of the best to have ever played the game.
And at the end of it, he said, “And by the way, don’t let these guys get you, the ones that were laughing. They don’t know the difference either.”
It’s a wonderful reminder: There are things that all of don’t know, but might be too afraid to ask. Why? Because simply asking the question might make us feel like we don’t belong in the room.
But it’s OK to ask! Be curious, and be willing to ask the questions you need to ask to get smarter. Often, you’ll find that others are more than willing to share what they’ve learned. You just have to be willing to ask the right question first, even if it feels a little foolish.
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That’s a photo I took of then-University of Missouri pitcher Ryan Clubb. I have no idea what pitch he was throwing in this photo.
