I’m Dan Oshinsky, and I run Inbox Collective, an email consultancy. I'm here to share what I've learned about building amazing products and great teams.
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.
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.
Things are busy these days on the work front: Lots of projects, lots of calls, lots of events. My schedule is always busy, and there’s always more work on the horizon, it seems.
So it’s been incredible this week to travel with Sally to Portugal. This was a trip we booked, on a whim, a few months back. Flights were cheap, and hotels were cheap. We booked those, and left the rest entirely unplanned. A few friends sent over recommendations, but truly, until we landed, we didn’t know that much about what we’d do this week.
When we travel, we always like to do a few things: Eat a lot, try a few new things, do something cultural, and try to get some rest. But otherwise, for a trip like this, the goal isn’t to overplan — our work days are full of structure, so a trip like this is the opportunity to about what I’ll call “unstructure”: The opportunity to leave things open-ended, to figure things out day by day.
Does it mean that we might miss out on something essential? Possibly! (Though the staff at the hotel or the taxi driver at the airport will probably point you towards those things anyway.) We’ve found that if you book your hotel and flights, that provides plenty of structure for your vacation. You know where you’ll be and when you’ll be there. Once you’re there, you can ask questions, be curious, explore, and figure out the rest.
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One of the hotels where we stayed had a hike up to a scenic overlook. It was one of those things that wasn’t in any guidebook or even on the hotel’s website — we noticed it on the drive in and asked if there was a path to go check it out. This photo is the view from the top.
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.
In the year or so since I’ve started playing golf again, there have been good rounds (I shot in the mid-80s last week — a fantastic round for me!) and lousy rounds. Sometimes, I’ll feel super confident with a particular part of my game (hitting shots from inside 100 yards, for instance), and then play again a week later and be unable to hit the same shots. This sort of fluctuation with golf, I realize, is normal. It’s a remarkably difficult sport, one that requires a combination of strategy, strength, speed, skill, and luck. Even great golfers can be inconsistent with their play.
A lot of golf is about feel. I’ve played enough now that I have a decent golf swing, one that I can repeat on a regular basis. But some days, the feel for a certain shot isn’t there. Often, I can feel what’s off, and make an adjustment. But sometimes, I’ve got absolutely no idea what might be wrong, and feel tempted to try to fix things on the course.
That’s always a mistake. Trying to make major changes on the course — where you don’t have the freedom for trial and error — usually leads to more frustration.
Practice is where I have the chance to test and learn. On the driving range, I can experiment with different concepts. What happens if I move my hands forward, or the ball further back in my stance? What happens if tee the ball higher up? What if I try a shorter backswing, or a longer follow-through, on short iron shots? Practice is where I can see what works, with the intent of putting those strategies into play on the course.
When I’m playing a round, that’s where I’m expecting to perform the shots that I’ve practiced. Some days, I don’t have a certain shot, and I’m learning how to adjust on the fly. If my driver’s not feeling right that day, I’ll keep it in the bag and use something else off the tee. There’s a part of me that can feel too proud to do that, a part of me that tries to force a shot that isn’t there that day. That’s when I usually find myself hitting my second shot from somewhere deep in the woods.
When you’re doing the work, there are times to practice, and times to perform. Recognizing which is which gives you the chance to focus on what’s most important for that specific moment, and the best chance to succeed that day.
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That’s a photo I took during a round with my dad, a few weeks ago in Nantucket, Massachusetts.
