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.
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.
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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.
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.
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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.
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That’s a photo of me standing over the the final hole at Penha Longa, a golf course in Portugal.
My favorite place to watch the New York City Marathon is on 59th Street and 1st Avenue, right at the moment the runners are coming off the bridge from Queens and turning into Manhattan. When runners turn left on 1st Avenue to head north through the Upper East Side, they’re passing mile 16. They’ve already gone through three boroughs — just two remain.
It’s one thing to watch the pro runners, who even at this point in the race seem to be sprinting through the course, and have no doubt that they’ll reach the finish line. But it’s another to see the regular runners — our neighbors here in New York, or runners who’ve traveled from all over to take part in this race — making that turn. I love to see how people react when they reach that point in the race. They’ve already run 16 miles, a distance I don’t think I’ll ever run in a single day. They’ve been up all day, and they’re obviously tired. But when they see the crowds and hear the cheers, they look reenergized.
I know those runners must have moments of doubt along the way. 26.2 miles is forever, and reaching Manhattan still means they’ve only covered three-fifths of the day’s distance. But I also know that thousands of runners complete the marathon ever year, which means that thousands of ordinary people find the strength to keep moving forward. How do they do it? Maybe it’s because the crowd picks you up, or because they’ve spotted a certain landmark that reminds them how close they are to the finish line. Or maybe it’s something else. Maybe there’s something inside all of us that gives us the courage to keep going.
Sometimes, when I watch runners make that turn at 59th and 1st, it seems like they’re picking up speed, even after 16 miles. How? I’m not sure. But I know that ever year, I watch runners do what seems impossible: Find a little left in the tank to take that next stride.
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I took that photo today, right at the moment runners are about to turn onto 1st Avenue.
Every Sunday, a recurring to-do pops up on my calendar: “Prep for this week’s meetings.” It’s the single most important thing I do all week.
Some weeks — and this is one of them — my week is packed with meetings. I always leave a little gap between calls, but sometimes it’s as short as 15 minutes. There are stretches where I’ll have up to five hours of calls in a row. It can be exhausting, and by the end of the week, I’m often amazed that I can even remember my own name.
That’s why that Sunday prep is so important. For every client, I have a Google Doc with notes from our previous calls for me to review. I go through every meeting and jot down notes for the upcoming call. I also send emails out to my clients, checking in about the agenda for the call. Sometimes, going through my prep takes 20 or 30 minutes. Sometimes, if I’ve got a particularly busy week, it might take two hours.
But it means that when I get to the end of the week, and I’m on hour four of a long stretch of calls, and I only have 15 minutes before the next call, I can open that Google Doc and quickly remind myself of what I need to know. My clients are depending on me, and they expect me to show up ready to talk about their issues. “Sorry, what were we supposed to talk about today?” isn’t an option when someone’s paying for time with me.
Sure, spending a chunk of my Sunday doing prep isn’t always fun. But it always pays off — and it means that I’m always ready to talk, no matter how busy the week might get.
Understanding that you’ll never have all the answers. The only way forward is to have an open mind and keep asking questions.
Whatever you’re working on, remember this: Curious people make the best teammates. Find people who are always curious, and you’ll build a team that builds a great strategy in the long run.
