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.
I was on a call with a client a few weeks ago, and they told me they wanted to build the best possible email strategy in 2024.
“That’s great,” I told them. “But I don’t want you to be thinking about what’s best. I want you to be thinking about what’s next.”
Thinking “best” can lead to magical thinking, to dreaming of blue sky situations where you’ve got all the budget and resources you need. It can lead to planning for a day that may not come.
Instead, take a look at what you’re doing right now and ask yourself: What’s the next thing we can do to make our newsletter strategy better?
It might be a small step, and that’s OK. Some of the best newsletters out there were built thanks to a lot of small steps forward.
The next step may not be perfect. It may just be… what’s next.
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I took that photo, more than 15 years ago, while walking the Camino de Santiago in Spain.
I read Andrew Leland’s new book, “The Country of the Blind,” this week. It’s a memoir about a writer who has been slowly losing his sight over the previous decades, and he uses the book to better understand life as a blind person in the United States. It’s a fascinating read, and a reminder of just how much sight shapes the way I think about the world. (Even in trying to write that last sentence, the first three phrases that came to mind — “a glimpse into Leland’s life,” “an illuminating read,” “an eye-opening experience” — all reflect a bias towards sight.)
One chapter towards the end of the book truly struck me. Leland visits the Colorado Center for the Blind, a place where members of the blind community stay for months as they learn new skills, from woodworking to cooking to navigating the outside world. Leland meets a younger student at the Center, Ahmed, who offers some advice about how to get around as a blind person:
The single most important skill for blind travel, Ahmed later told me, is that “you have to be willing to get lost, and be confident in your ability to figure it out.” In the early days of his blindness, he once took three hours to traverse a route that would have taken him five minutes with a sighted guide. Eventually he got better at navigating Washington, DC, learning the direction of traffic, the patterns of certain stoplights, the way the sound of another person’s footsteps changes as they begin descending a set of stairs. In Colorado, he learned to use cardinal directions, and can now often figure out which way he’s facing from the feeling of the sun on his face. But, he added, “it’s not like once you leave [the Colorado Center for the Blind], you’ll never get lost again.” … Getting lost is not always comfortable, or pleasant, but it is an organic and fundamental part of the human experience. The more one is able to accept it, rather than fight it, the more skillful one becomes in one’s travels.
Later in the chapter, Leland describes the experience of Ahmed and two other students heading to a local store. As Leland writes, not only do Ahmed and his classmates make it to their destination safely, but Ahmed is so comfortable on the walk that he does some it while walking backwards!
Anyway, I’ll be thinking about this line for the rest of the day: “You have to be willing to get lost, and be confident in your ability to figure it out.”
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That photo of a darkened staircase comes via Unsplash and photographer Carolina Pimenta.
I was rewatching “Pulp Fiction” on a flight the other day. My favorite chapter of that movie is the scene with Winston Wolf, the fixer. Vincent Vega and Jules Winfield get themselves into hot water, and The Wolf gets them out of it.
And I was struck by a thought, rewatching it, that a lot of people think that my job at Inbox Collective is basically that of The Wolf.
Some teams come to me thinking that I’ve got all the answers or magic fixes. I often do not.
What do I actually do? A good advisor isn’t there to have all the answers. My job is to help you ask the right questions — and figure out how to find the answers together.
I’ll admit, it’d be fun to be The Wolf, to be able to come in, survey the situation, and identify a quick fix.
But my job, if I do it well, is to do more than fix the glaring short-term issues. I’m here to help teams build the right strategy in the long term.
All of that starts, not by having all the answers, but by figuring out the right questions.
I found myself jotting down lines and quotes as I read through the book, but one stuck with me. It comes at a rare quiet moment in what Eig describes as the non-stop travel schedule that was the final dozen years of Dr. King’s life. It comes at a moment when he’s talking to two ordinary Americans, trying to keep their spirits up.
“We ain’t what we want to be, and we ain’t what we gonna be,” he tells them.
King had a vision both simple and radical, one that pushed for huge changes in our society. Those dreams are still unfulfilled today.
And yet, there’s that quote, something he said not in a pulpit or in front of a camera — the promise of better days tomorrow, of change ahead, for each of us, and for a nation.
We go still, onward. We are not yet finished today.
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That’s a photo of the “I Am a Man” mural in Memphis, Tennessee. The mural was created by Marcellous Lovelace with BLK75. The photo was taken by Joshua J. Cotten for Unsplash.
We took the week off last week to go to Guadeloupe, a small island in the French part of the Caribbean. There are a lot of reasons I love Guadeloupe — this is my second trip there — but what I especially love is how disconnected I can be there.
Most of the tourists in Guadeloupe are from France or Quebec, which means you’re not hearing people talk about the news or politics. The TV channels aren’t American TV channels, so you’re not watching much TV. I put my phone on Airplane Mode when I land, so I’m not constantly hearing the ping of texts and emails. And the internet connection at the hotels isn’t great — which ordinarily would be an issue, but it means that on a vacation like this, I’m generally not looking at my phone as often I would.
All of which meant that I got to take a true week off, save for two brief windows when I actually responded to emails just to make sure I didn’t come back to hundreds of unread messages. Otherwise, I spent the week enjoying the beach, reading, and unwinding.
There are trips when I’ll spend some time working and take calls, but there’s something special about those weeks when I truly get to unplug. Weirdly, it can be hard to take time away — it’s so tempting to grab the phone and try to stay connected to what’s happening! — but it’s also so necessary to actually take the time off.
And if you’re going to take time off, you should mean it. Go read a book. Do nothing for a while. You deserve it.
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That’s a photo I took at the beach on Guadeloupe one afternoon.
In the spring of 2019, I was starting to think about leaving the New Yorker to start Inbox Collective. But I was still nervous about it. Was it the right time to leave? Was I ready to take on the responsibility of building a new business?
And that’s around the time a recruiter reached out to ask about a job.
It was a good job with a big title at a major news organization, making more money than I’d ever made it my life. I wasn’t looking for another job, but I interviewed anyway. It was the kind of offer I had to at least consider. I wasn’t sure what to expect.
Within 20 minutes of the first interview, I knew what I wanted to do next.
I wasn’t excited about the idea of taking another job. I still loved my job at the New Yorker.
But more than anything else, I felt excited about the idea of starting my own consulting business — well, equal parts excited and nervous. Whenever I feel nervous, that’s usually a good thing. It’s a signal that I really care about something.
So I started to ask myself: Why, exactly, am I still doing the same old thing if I’m ready for what’s next?
By the end of the month, I told my bosses that I was leaving to start Inbox Collective.
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That’s a photo of me talking to a group of newsrooms in Sydney in fall 2019, a few months after starting Inbox Collective.
Last night, I went to the Cotton Bowl in Arlington, Texas, to see my Missouri Tigers play Ohio State. Through the first 40 minutes or so, there wasn’t a lot to get excited about. Ohio State led 3-0 at halftime. Missouri could barely move the ball on offense. There were a lot of Missouri fans near us who were angry, distraught, or dismayed. (Many were all three.)
And then, in the final 20 minutes, everything flipped. Missouri scored a touchdown, then scored another, then forced a fumble to put the game away. Final score: 14-3, Missouri.
My analysis of the game looked a lot different after 60 minutes of football instead of just 40 minutes.
It’s a reminder for me, whether you’re watching football or working on a new project, that there’s a tendency to decide that things are over a little too soon. I know I’ve been guilty of declaring that something won’t work — even if I don’t have the data I really need to make that decision.
Often, the right move is it let everything play out. Once you have all the data, then you can look at what happened, break down the numbers, and decide what to do next.
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That’s the photo I took of the post-game celebration at the Cotton Bowl.
For the past decade, I’ve lived just a few blocks away from the United Nations. And yet, until this week, I’d never actually been inside.
If you’re visiting New York, the UN is worth a visit. It’s tough to visit the UN and not feel a little bit optimistic about the future of the world. Diplomacy is never easy, and yes, we’ve got massive global challenges ahead of us, but it’s amazing to visit a place where all the countries of the world have come together to try to solve big problems. World hunger, nuclear disarmament, climate change — the world gathers here, at a campus on 1st Avenue, to try to find the answers.
I was familiar with a lot of the places we saw on the tour. I’d seen the big Assembly Hall on the news. I’d seen photos of delegates sitting around the table of the Security Council Chamber. But there were a few rooms I’d never seen.
One was the chamber for the Economic and Social Council. The room was designed in 1952 from Swedish architect Svem Markelius.
It’s a beautiful room, featuring wood from Swedish forests. But there’s one particularly unique feature of the room: The ceiling is unfinished.
That’s on purpose, our tour guide informed us. It’s a subtle reminder: The ceiling is unfinished because the work of the UN will always be unfinished. There will always be more to do.
Here’s to whatever work and whatever challenges lie in the year ahead.
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I took that photo of the Economic and Social Council chamber on a visit to the UN.
If you’ve spent any time with me in New York, I’ve probably taken you to Breads Bakery.
Breads opened a decade ago, and as you’d guess by the name, they make fantastic breads: Ornate challahs, delicious croissants, and amazing black and white cookies. But the showstopper at Breads is the chocolate babka, layered with Nutella and dark chocolate. Bring one home, throw it in the microwave for 15 seconds, and you’ve got something close to perfection.
There are other babkas in New York. Some are quite good. But Breads exists on a different level. It’s the kind of babka that’s worth a 30-minute trip, each way, just to get your hands on it.
Not everything is worth the money or the time. I think about that a lot with the stuff I’m working on. It can be tough to know what tools to use or which projects to prioritize. With whatever you’re working on, it helps to have people in your corner who can tell you when something’s worth the trouble. But when you hear from folks that something is worth it, you always make time for it.
(And if you’re at Breads, the chocolate rugelach is great, too.)
It’s easy this time of the year to get caught up in everything. There’s so much to do before the end of the year — last-minute projects, those to-dos you promised you’d handle before Dec. 31 — and you and your colleagues are probably going on vacation soon. The clock seems to tick faster and faster this time of year.
When you’ve got so much going on, it’s OK to take a beat to pause, reset, and refocus on the handful of things that actually need to get done. So often, we get caught up worrying about all the things we have to do instead of actually doing stuff.
Just take a minute for yourself to slow things down and reset. You’ll get the important stuff done; it’ll be OK.
