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.
College athletics are in flux right now. Teams are changing conferences (Rutgers vs. UCLA and Oklahoma vs. Kentucky will soon be in-conference matchups), and Name, Image, and Likeness rules mean that some athletes are now (legally) collecting checks from sponsors. Greg Sankey, commissioner of the Southeastern Conference, addressed all these changes this week at the conference’s annual media days for football. “It’s never going to be the same,” he said, “but it doesn’t have to be the way that it is”
The same could be said for many businesses. It’s certainly the case for the news world, where I come from. Are we going back to the days when local newspapers employed hundreds of journalists? Probably not. But it’s up to us to build something new moving forward. Just this week, I’ve talked with local news outlets investing in solutions journalism, digital outlets building out new models for revenue sharing with writers, and individual writers who are building an entire business through their own newsletters or podcasts.
Everything changes, and that’s OK. We can fight it, or we can accept it and try to figure out how to build the best possible future for ourselves. The choice is ours.
A few weeks ago, I had what might seem like the flight experience from hell.
We were flying to San Francisco for a wedding. The flight was at 7 a.m., which meant getting up well before 5 to get to the airport. Even if the flight had gone perfectly, the early wake up meant that I was going to be a little grumpy.
But from the start, everything that day went a little screwy. There was a ton of traffic getting to the airport. The trip from the parking lot to the terminal took forever. We got to check-in exactly one minute late, which meant that we couldn’t check one of our bags, and had to try to sneak a giant bag through security. Our flight had mechanical issues, so we had to make an emergency landing in DC. We got stuck there for 9 hours. The delay took so long, Delta had to fly in a new crew from several different cities just to staff the flight. We didn’t get to San Francisco until nearly midnight — 12 hours after our expected arrival.
And yet, as I think back on that day, all I can think of are the people who helped us along the way.
There was the Delta agent at check-in at JFK, who calmly talked us through what to do even though we were late for check-in.
There was the pilot, who kept us updated about everything happening with the plane.
There was the crew in DC, who ordered pizza for hungry passengers and delivered news, good or bad, whenever they had it.
There was the employee at the airport lounge in DC, who kindly let us bring in a friend from the flight, even though we were only allowed two guests.
There was the TSA agent at Dulles, who let us back through security after we stepped out (unwisely, we later realized) to get some air, even though he had every right to tell us, “Sorry, you have a boarding pass for a different airport. You can’t enter.”
There was the friend on the flight who texted us to come back to the gate after we’d started to seriously consider leaving and staying the night in DC.
There was the crew — based in four different cities — who volunteered to fly to DC to make sure we got to California.
There were a half-dozen different times when the day could have absolutely gone wrong. Instead, at every key moment, we found people willing to help us, even on a day when nothing seemed to go right.
It’s easy to be pessimistic. It’s easy to feel like the world’s fighting against you.
But look around. You might find a few kind people, going well out of their way to help — even on those tough days.
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That’s a photo I took from the runway at Dulles International Airport. That day, I saw the sun rise and the sun set from my seat in coach — on the same plane.
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.
Passover starts later this week, and there’s a song we’ll sing during the Passover service, which is known as a seder. The song is called “Dayenu,” which translates to, “It would have been enough.”
We sing that if God had merely found a way for the Israelites to exit Egypt, it would have been enough.
And if God had merely supplied the Israelites with food, it would have been enough.
And had God had merely brought us the Torah, it would’ve been enough.
And so on, and so on.
The idea is that even one of these acts would have been enough. (But in the telling of the story, God provides all of these things, and more.)
The song is one of gratitude, and it’s one I remind myself of whenever I think about the life that I have or the business I’ve built. Do I want more? Sure. I know there’s a lot more out there. But I look at what I have — an amazing family, wonderful friends, and a great job — and have to be grateful.
I’d like more — but this is already more than enough.
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That photo of matzah, a staple of Passover, was taken by Flickr user ohadby, and is used here thanks to a Creative Commons license.
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.
There’s a bagel place on my corner here in New York, and I’ve been going there for years. It’s a great spot with really good bagels, but there’s something that’s always bugged me about it.
On a weekday, this bagel place has about five employees behind the counter taking orders. On weekends, they might have eight or nine. And they always operate the same way: One of the employees takes your order, and then slices your bagel, and then makes your order, and then walks over the cash register, where he then takes off his gloves, and then throws them away, and then rings up your order, and then bags your bagels, and then puts back on a new set of gloves, and then, finally, walks back to the front of the line to take another order.
I know, it’s a bagel place — no one’s expecting them to operate with maximum efficiency. But the one thing that surprises me is that in all the years I’ve been going there, they’ve never added one thing to the line: A cashier. Adding a single dedicated cashier to the operation would speed up the entire operation. The cash register is always a chokepoint on their line — sometimes, it takes longer to ring up a customer than it does to make a bagel. Instead of being back at the start of the line serving another customer, the staff is waiting at the cash register for their turn to collect payment. Maybe that doesn’t seem like a big deal, but every time I go in on a weekend, I see a handful of people who pop in, realize that the line’s too long, and decide to go elsewhere. If the line moved even a bit faster, many of them might wait around to buy.
Every time I go to this bagel shop, I think about what it’s like to manage a team. So much of being a good manager is freeing your team up to do their job. Sometimes, that means taking on responsibility for stuff that isn’t glamorous or exciting, or finding strategies to streamline the process so your team can do the work it needs to. Or it means paying attention to the obstacles in your team’s way, and looking for solutions to remove those hurdles.
Until you stop and really pay attention to what’s happening, you might not notice the little things — like how spending the money to hire a new cashier might actually make your business more money.
I spent a few days last week up in Burlington, Vermont, and one day, with temperatures a bit warmer than usual, took a walk down to Burlington’s waterfront park. (It’s called, accurately enough, Waterfront Park.) It’s a beautiful park, with a bike path and a science museum and gorgeous views of Lake Champlain. But the thing that stood out to me most were the swings.
Alongside the water, where you’d expect benches to be, Burlington’s placed these swings, maybe a dozen of them alongside a quarter-mile stretch of waterfront. On a warm day, you can sit there, watching the water slowly move towards shore, as you swing back and forth back towards the water.
A swing instead of a bench isn’t a huge change — at the end of the day, they’re still a place to sit and look at the water — but because I didn’t expect it, I stopped and spent a few extra minutes in that park. It was something different, something unexpected. I found those swings absolutely delightful.
All of us could try to bring the same spirit to our work. Try something small, new, and unexpected. It might lead to the creation of something special.
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That’s a photo I took of the swings in Burlington’s Waterfront Park.
I’m a pretty good skier on a sunny day. When the light is good on the mountain and I can clearly see the next few turns, I ski with a lot of confidence.
But it’s another thing to ski on a wintry day, when the clouds and the mountain seem to merge into one. When the light is flat, seeing the path ahead gets tricky. On those days, I find myself struggling to maintain control — it feels a little like skiing through fog. A bad turn or two and I lose confidence quickly.
So on those days, I try to adopt a mantra: Trust your turns. I’ve been skiing since I was a kid, and I can get down just about anything. (It won’t always be pretty! But I’ll get down.) And when I tell myself, “Trust your turns,” I’m saying: You know the motion — trust your ability to string turns together, even in low light. Ski just like you would on a blue-sky day.
We all want to be able to clearly see the path ahead. But we can’t always see the next turn — or whatever’s around the next corner. And in times of uncertainty, we can’t just stop and wait for things to clear up. Trust the work you’ve already put in, and the processes you have in place.
Trust your turns, and keep going.
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That’s a photo I took on a sunny day at Breckenridge in 2021.
I’m reading Mel Brooks’s autobiography, “All About Me!”, and loved this section about “Young Frankenstein” so much that I’m going to quote it in full. Here’s Mel:
The first cut we put together for a test screening was two hours and twenty-two minutes long. That was pretty long for one of my films. “The Producers” was only eighty-eight minutes. While “Young Frankenstein” ran long, I didn’t want to leave out anything that might possibly catch fire with an audience. I screened it at the Little Theater on the Twentieth Century Fox lot for people who worked on the lot. The theater was packed, and we didn’t get all the laughs we were aiming for. It went well, but not well enough for me. It was just too long.
When the picture was over, I got up in front of the audience and said, “Ladies and gentlemen, you have just seen a two-hour-and-twenty-two minute failure. In less than three weeks from today, I want you back here to see a ninety-five-minute smash hit movie. I want every one of you back!”
Editing was both easy and difficult. Easy because when something was supposed to get a laugh and it didn’t, I simply cut it. Difficult because I was in love with too many moments and had to cut them for the good of the overall film. Sometimes, you have to kill your darlings….
Of course, it was more than three weeks later when I reassembled most of that same audience at the Little Theater. It was actually closer to three months later. But I had a cut that was pretty damn good and wanted to show it. It went like gangbusters! Every single scene in the picture worked. The audience not only laughed their heads off, but there was a palpable feeling of sweet sadness when the picture ended.
I love what Mel describes here: He’s using audience feedback to understand what works and what doesn’t, and then is willing to use that feedback to make his work better — even when it means getting rid of something he’s proud of. Pay attention to what your audience says — they might just make your work better, too.
I just finished “Subtract,” a fascinating book by Leidy Klotz about what humans do when given the chance to improve a situation. He writes that our first impulse is almost always to add something — to take what’s already there and add more to it in order to improve whatever it is. But he suggests that we often forget about another option: Removing elements to better the situation. If we can get to a point where we start thinking about both options, “add and subtract,” Klotz writes, we might discover opportunities that would otherwise be ignored.
Just after finishing the book, I spent a few days in Denmark, and over and over, saw examples of Klotz’s concept in action.
In hotel showers in the U.S., I often get frustrated when water leaks out onto the bathroom floor. But at our hotel in Copenhagen, the hotel had thought of an ingenious solution: Instead of adding some sort of barrier to keep the water in, they’d built the shower floor on a slight angle, to keep the water flowing more easily back towards the drain. In all the showers I took there, the water never leaked out onto the floor.
Or take their beautiful subway system, built in the early 2000s. In New York, lines often form at the entry point to the subway as travelers swipe their cards to enter the station. In Copenhagen, they’d removed those barriers entirely — and replaced them with a handful of check-in points, spread out all across the station, where people could tap their subway card before getting on the train. Even when the stations were busy, I never saw the same chokepoints that I do here in the U.S., since there was no one spot where lines could form.
Once I started noticing the ways the Danes had thought “add and subtract,” I couldn’t stop seeing them around town. Every subway station had added an underground room where someone could park their bicycle, which meant that they didn’t have to carve out space on street level for bike parking. At restaurants, people always paid at the exit, which meant that servers didn’t have to waste time running credit cards back and forth to the table, and could instead of focus on getting food and drink to customers.
Or how about this: On regional trains in other parts of the world, trying to find an elegant solution to allow passengers to move between train cars, an engineer might add a sensor that automatically opens the door whenever someone gets close to the door. But there’s a weakness of that approach: Often, someone’s standing close to the door not because they want to move to another car, but because the train is full, and lots of people are forced to stand. In that case, the door might constantly be opening and and closing — which is both annoying for passengers and lets in cold air during the winter.
But in Denmark, engineers found a simple solution. They kept that sensor, which is just above the door — but it only opens the door when someone waves their hand horizontally just in front of the door. It’s an unusual motion that someone would only do on purpose, which meant that on the crowded trains we rode on, the doors only opened when someone actually wanted to move to the next car.
I loved seeing the way the Danes had clearly considered all sorts of options — ways to add elements, like bicycle parking, when necessary, and ways to remove elements, like unnecessary bathroom features, when it made more sense. They’d thought “add and subtract” — and built amazingly functional spaces as a result.
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That’s a photo of the doors on the regional train. Two people are standing right next to it, but because no one’s waving their hands horizontally underneath the sensor, the door remains closed.
