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.
Two days before my bar mitzvah, I did my final rehearsal at the synagogue. I’d spent months working on my Torah portion, practicing in a language I could read but didn’t fully understand. The day of the rehearsal, I screwed up a line — and completely lost it. I started crying, ran to the bathroom, and locked myself inside.
I was 13 years old, and terrified of screwing up in front of all of my family and friends. And since this was the first of the Oshinsky bar mitzvahs, there were going to be several hundred people in attendance. I was scared of looking dumb in front of all of them.
But the rabbi had good advice. He told me: If you screw up a line, it’s OK! Just go back to the beginning of the line, and read it all over again. Nobody will ever notice.
He was absolutely right. Of the several hundred people in attendance, there wasn’t a single one who spoke Hebrew fluently. (Perhaps a few dozen could read Hebrew, but none could’ve translated what I was saying into English.) Which meant that when I did mess up on the day off, I followed the rabbi’s instructions: I went back to the beginning of the line and read it again. Nobody noticed — mostly because nobody else had spent the previous nine months learning and rehearsing a single Torah portion.
I’ve had the same thing happen when giving a big presentation. I’ll have rehearsed and practiced, but then I’ll flub a line or forget to cover a specific slide. My first reaction is often to beat myself up for making a mistake. But the truth is, only I knew how things were supposed to go.
So when it happens, I let the mistake go, and move on. The truth is, the only person who even noticed was me.
———
That’s a photo from my bar mitzvah, back in May 2000.
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.
———
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.
As we wrap up 2021, and look towards the new year, I wanted to say a few words:
It’s been a strange year — another strange year, I suppose. There have been moments of joy, of celebration, and moments of true alarm. I have no idea what 2022 will bring, but at this point, I wouldn’t bet on “normal.”
This moment in time has been strange for every single one of us.
So here’s my wish for the year ahead: Be kind to the people around you. Be kind to the co-worker, to the person in the supermarket checkout aisle, to the flight attendant, to your friends. This is a time of great stress and confusion, and whatever you’re feeling, the person standing in front of you is probably feeling it, too. Try to be slow to anger, even when things aren’t going your way. A little kindness — a kind word, a gesture, a thank you — might mean the world to them.
Here’s to 2022 — a kinder year, I hope, for all of us.
It’s not all going to go right. You’re going to make mistakes, and you’re going to do things that you wish you could undo.
And when things go wrong, it’s easy to be your own biggest critic. It’s easy to get down on yourself.
But give yourself permission to make mistakes. When things go wrong, try to pick yourself up. Remind yourself that everyone makes mistakes, and that nobody is going to do the right thing every time. Try to cheer yourself on, and push yourself to do better next time — because you know what you’re capable of, and you know that you can show the world how good you can be.
Whatever happened, happened. Now go be your own biggest fan.
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.
———
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.
On Tuesday, I stood on stage in Odense, Denmark, at the 2021 Email Summit, to give a talk in front of a few hundred people. It was the first time I’d been on stage, in front of other people, in 22 months.
There was a moment in time where giving a talk like this didn’t feel all that unusual. I gave a dozen in-person talks in 2019, and had a dozen more planned for 2020. Getting on a plane to a new place — Berlin! Sydney! Montreal! — to talk about email was just something I did.
Since the start of the pandemic, I’ve lost track of the number of talks, webinars, and live interviews I’ve done over Zoom. But I wasn’t sure if — or when — I’d get the chance to do a live talk again.
On Tuesday, I tried to take a moment at the start of my talk to look up at the crowd and remember that feeling I get when I’m presenting. It’s such a privilege to get the chance to share what I’ve learned with others, and while I feel lucky to be able to do so many talks over Zoom, nothing compares to an in-person session.
So I wanted to say thanks to the entire Email Summit team — and to the amazing people I met in Denmark — for giving me that stage, and for the reminder that every opportunity to speak is a true privilege. I don’t know when the next opportunity will come, but I’m grateful to have had this chance in Odense.
I’ve noticed an interesting trend over the past few years of working with newsrooms.
Often, I’ll meet with a team, and we’ll start talking about their daily newsletter product. They’ll tell me they’re determined to launch a daily newsletter that goes out at 6 a.m. I’ll ask why. Is this something their audience has been clamoring for?
And the answer is almost always the same: Our editor in chief or president gets all of their newsletters at 6 a.m., so that’s when we need to send our newsletter, too.
I’ve seen this happen over and over again. The highest-paid person in the room or the loudest voice in the room is the one that gets the most attention. It’s a natural reaction — they’re the boss, so their ideas must be the best ones.
But the hard thing is trying to get the team to dig a bit deeper. Bosses often have great ideas, but sometimes, because they have so much on their plate, they’re also disconnected from what their team knows or what readers want. So I’ll push my teams to ask other questions to make sure they’re taking the right next steps. What are readers telling you? What is your data telling you? What have you learned from previous product launches? And do you have the team to actually send an email at that hour? (After all, to send at 6 a.m. with the latest news probably means someone needs to be up to write and edit the email at 4 or 5 a.m.) Often, these signals point them towards a different outcome.
I’m not saying to ignore your boss entirely. But remember: Just because someone’s got the loudest voice in the room doesn’t mean they’re the only ones worth listening to.
I’m 34 years old, and I know that not everything goes according to plan.
Back in March, Sally and I decided to take a trip up to Vermont to go skiing. We left in the early afternoon, and gave ourselves plenty of time to make it to the hotel in Burlington. We took our time at dinner, and even stopped for an ice cream cone in Massachusetts — we weren’t in much of a rush. In Vermont, I took over driving. Google Maps said we had about 90 minutes to go.
15 minutes in, the snow started coming down — a few flakes at first, and then sheets of it. The winds picked up, and visibility shrunk. I drove with flashers on, at maybe 20 miles per hour, but could barely see in front of the car. We saw an 18-wheeler going south, struggling to keep from sliding off the road. I got off the highway as soon as I could and found a gas station with a big covering to park under. I pulled out the weather app on my phone. A giant storm was passing through Vermont, and it’d be dropping several inches of snow — and bringing high winds along with it — for another three hours.
You learn a lot about a relationship when things get stressful when traveling. I learned early on with Sally that we make a pretty great team on the road. No matter where we are or what the situation is, we’re good at taking a breath, figuring out our options, and making a decision. Life is a series of lefts and rights. Make your choice, and go.
Which is what we started to do at that gas station in middle-of-nowhere Vermont, with temperatures quickly dropping below 0.
Make it to Burlington? Even if the storm did pass through, there was no guarantee that the highway would be passable — and if we did, we might not make it until 3 a.m.
Head back towards the White River Junction, where there were hotels? We could, but the highway was already so slick, and we’d be driving into the worst of the storm.
And then Sally had a third idea: Could we find a way, on back roads, to make it to Montpelier?
Montpelier’s the capital of Vermont, and it’s also the smallest state capital in America. Downtown is just a few blocks, with a handful of cute coffee shops and bookstores and a nice hotel right downtown. Google Maps said if we took the local roads, we were just 60 miles away, and at least we’d be heading in the direction of Burlington. We’d noticed a few cars and trucks passing the gas station, and things seemed a lot less slick on the local roads than they did on the highway.
So we called our original hotel, cancelled our first night, booked a room in Montpelier, and got back on the road.
Other cars had carved a path ahead for us, and I did my best to stay in their tracks. I couldn’t see what was beyond the edges of the road, and tried not to think about what we happen if the car’s wheels went too far to the left or right. I don’t think I went above 35 miles per hour at any point on the drive, but with my flashers on and windshield wipers on high, we slowly moved north, past farmland and over hills and through small towns. “We can do this, we can do this,” Sally kept saying aloud, partly to herself, partly to me. Slowly, our car plowed onward. The trees helped shield us from the worst of the wind and snow. Every 10 miles closer felt like a small victory.
And 90 minutes later, we somehow came over a hill and found ourselves looking at the lights of Montpelier. I cheered, Sally cheered. We pulled over at a gas station, and Sally grabbed a six-pack of Heady Topper, a great local IPA. At the hotel, we discovered that our room had a balcony, so even though it was well below 0 with wind chill, we bundled up, sat outside, and toasted to making things work even when everything went off script. I wasn’t how we’d made it, but we’d made it, and that was worth celebrating.
I think it was my single favorite night of 2021.
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, at 34, is what I believe:
You can’t operate at 110% capacity forever. Do a little less so you can get the most out of what you do.
Launching your own business requires you to get comfortable with being uncomfortable. I got to work with teams this year that I’m absolutely thrilled to call clients, and the revenue from the business is beyond anything I would’ve thought possible. But just because the work is good now doesn’t mean it’ll be like this in a year or two or five. Accepting that things are good now, and might not be this way forever, is part of the job.
You might get nervous doing something you’ve done hundreds of times before. It’s probably not because you’re scared. It might be because you care.
Be generous with how you spend your money, and careful with how you spend your time.
The hardest part about personal growth isn’t the setbacks — it’s the plateaus. Think back to when you first started. You’re a beginner, so improvement is rapid. Every day, every week, every month, you get a little better. It’s exciting! And then: You feel like you hit a wall. Suddenly, you’re not making progress at the same rate. Treading water feels like a step backwards. You get frustrated. You question things. Then you start again, and try to break through. If you’re lucky, you do! You start improving again. But with time, it happens again: Another plateau, and another chance to find yourself and break through.
One day, everything’s going to change anyway — so why not go ahead and do the thing you’ve been wanting to do?
Take time to acknowledge the wins. Even a small win is worthy of celebration.
When you’re visiting a new city, make sure you ask the hotel what time local restaurants close. It might be earlier than you think.
Always book the refundable option when traveling. Sure, you’ll have to spend a few extra bucks now, but when you have to cancel the trip at the last minute and aren’t on the hook for a $500 hotel stay, you’ll be grateful you did.
If you’re traveling with a partner or a group, take a few hours apart to do something solo. You’d be surprised at how much the time alone recharges everyone.
Is New York forever? I have no idea. But it’s all I want for now.
It’s OK to fail. The only mistake you can make is failing to pivot away from your failures.
There’s an element of randomness and luck in every single day. Be grateful when you’re lucky — and when you’re not, be optimistic. Things often even out.
And finally: You don’t have to fill every moment with something. I’m thinking about this moment earlier in the year. It was a Saturday afternoon, and I was running errands in the car, and with traffic, I realized that I’d be out driving for more than two hours. My mind started to go through options. Two hours was a lot of time to do something new. But what should I prioritize? Should I start a new audiobook? A new podcast? Call some friends?
Then I did something I never do: I turned on the radio, rolled down the windows, and let the time pass. Everyone should make time for a few minutes of absolutely nothing.
———
That’s a photo of Sally and I on the chairlift at Stowe, 48 hours after our late-night driving adventure in Vermont. I still can’t believe we made it.
I’m working on my annual “Things I Believe” blog post, and showed Sally the outline the other day. She noticed one bullet point, in which I wrote:
The hardest part about personal growth isn’t the setbacks — it’s the plateaus. Think back to when you first started. You’re a beginner, so improvement is rapid. Every day, every week, every month, you get a little better. It’s exciting! And then: You feel like you hit a wall. Suddenly, you’re not making progress at the same rate. Treading water feels like a step backwards. You get frustrated. You question things. Then you start again, and try to break through. If you’re lucky, you do! You start improving again. But with time, it happens again: Another plateau, and another chance to find yourself and break through.
And she looked at me and said: That’s about your golf game, isn’t it?
I looked down at the ground, and whispered: Yeah, it is.
But the thing is: Inspiration can come from anywhere! Do I wish I’d come up with that thought while walking through the halls of the Met, reading about some obscure painter who’d overcome countless obstacles to finally deliver a masterpiece? Of course! That’s a much, much better story than the truth, which is that I thought of it while double-bogeying on a public golf course in Queens.
But who cares? Sometimes, inspiration strikes while reading a great novel, and sometimes while you’re taking a few minutes to stare out in quiet contemplation at the ocean, and sometimes when you shank a 7-iron into the woods. Wherever it strikes, be grateful it did.
———
That’s a photo of me standing over the the final hole at Penha Longa, a golf course in Portugal.
