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.
Anytime he sees a ceiling fan, and our new home has a few of them, he pauses to admire it. I keep thinking that he’ll grow tired of them — It’s just a ceiling fan, I want to tell him! They cost $127 at Home Depot! — but he never does. He watches them spin with awe.
There’s something special about watching him appreciate a new thing. He’s only 1, and there are so many new things he hasn’t experienced yet. So when he sees something new, he takes his time with it. He watches it, he admires it, he considers it. He takes pleasure in experiencing new stuff.
I’m not saying you should take 20 seconds to pause in awe every time you see a ceiling fan. But we could all use a little reminder to shift our perspective. I’ve tried to take a page from my son’s book and take a moment to appreciate anything new in my world, even if it’s something small.
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That photo of a bedroom — white bedspread, two bedside lamps, a bit of light coming in off the far wall, and a brown ceiling fan — comes via Lotus Design N Print and Unsplash.
On a call today, a client asked me an interesting question. “A few people unsubscribe every time we send an email,” they said. “Is that normal, or is that something that happens just to us?”
The good news, I told them, is that it happens to everyone. I used to write a newsletter called This Week in Cats, which had a 60%+ open rate — at a time in which being above 40% was rare — and we saw unsubscribes every week. (I still have no idea what those readers thought they were getting into.) If that newsletter lost readers every week, then every newsletter will lose readers.
But the bigger thing: I’m glad they had the courage to ask the question. Building something new can be a lonely business. It takes guts to be willing to ask: Is this normal? Or am I going through something that nobody else goes through?
Be brave enough to ask. You might find that what you’re going through is a lot more common than you think.
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That’s a photo of an early edition of This Week in Cats, featuring that week’s cat of the week — a cat, with a white belly and brown and black striped fur, sitting upright and looking surprisingly sad.
We moved this month from New York City to Park City, Utah. It’s gorgeous here — I’m writing this as the sun sets, and I’m watching it set from my living room window.
On a daily basis, I see people biking and running on the trail that runs near our backyard. I see people with kayaks strapped to their roofs and people with hiking backpacks heading out for a big hike.
These first few weeks here, for me, have been filled not with outdoorsy trips but with other stuff — with calls, with emails, with lots and lots of unpacking.
So Sally and I have had this recurring conversation: If we’re going to live in a place this wonderful, we need to take advantage of it. I don’t know if we’ll be here for a year or forever, but I need to treat it like we’re only here for a short period of time — that way, I’ll have the urgency to take advantage of this place and do all the stuff I should be doing in a city like this.
I could work from anywhere, but I’ve chosen to live here. And if I’m not going to make time to enjoy this place, what exactly am I doing here?
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I took that photo on a morning walk with my son here in Park City. It was sunny and bright — basically a perfect morning to walk along one of the city’s many trails.
Jon Stewart did this great interview the other day with Matthew Belloni on “The Town” podcast, and this part really stuck with me:
Jon Stewart: Post-mortem is the gift to the gods in terms of improving content and really anything.
Matthew Belloni: So Tuesday morning, it’s, “What did we do right? What did we do wrong? Did this land? Did this not?”
Jon Stewart: It‘s Monday night, and it has to be an agnostic process. It’s not a blame process. It’s always a constructive, like, “How do you feel that worked out?” You always have to be self-examining, reflective of the process, little things, because it’s the only thing that keeps you on top of it.
It’s a lesson I think more of us could apply to our work.
Running an end-of-the-year campaign? Make sure you put time on the calendar the week after the campaign ends to review everything and document lessons for next time.
Launching a new newsletter? Set up check-ins on the calendar every few months to make sure you’re meeting your goals and want to continue investing in that newsletter.
Building a new business? Make sure you hold quarterly reviews to track what’s what working, what isn’t, and what you want to do next.
It’s not enough to put the work out into the world. You also have to make space to review, reflect, and iterate.
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That photo of Jon Stewart accepting a Peabody Award on stage in 2005 — he’s in a black suit with a dark tie and is behind a podium with a gold replica of the award — comes via the Peabody Awards and a Creative Commons license.
I moved to New York at 24. My move-in day was the day of SantaCon. I was young enough to find it kind of charming. (It was not, it is not.) My first apartment had ceilings so low that I couldn’t lift my hands all the way above my head. I didn’t care. I was excited to be here, but I figured I might live here a year or two, then move onto the next thing.
I had no clue what I was getting myself into.
I didn’t know that BuzzFeed would become what it was in the mid-2010s — a rocket ship where I’d get to learn from some of the smartest people on the internet. I didn’t know that I’d get the chance to work at The New Yorker and be a small part of an incredible team guiding that publication onto its next chapter. I didn’t know that newsletters — this weird little corner of the internet that no one seemed to really care about! — would be my calling card. I didn’t know I’d get the chance to start Inbox Collective and work with so many amazing teams around the world.
I didn’t know that I’d live here long enough to go, “Yeah, I remember when that Duane Reade used to be a pretty great indie music venue!” I didn’t know that I’d develop such strong feelings about specific bagel places and pizza shops. (I made sure to get one last everything at Ess-a-Bagel and make one last trip to Spumoni Gardens!) I didn’t know that those only-in-New-York moments happen to everyone if you live here long enough. (Meeting Clyde Frazier, while he was wearing a Dalmatian-print suit, at the tailor! Seeing a show in Central Park and having Jackson Browne show up as a surprise guest! Accidentally scaring Matthew Broderick when I walked past him on 21st St!)
And I certainly didn’t know about all the lifelong friends I’d meet in New York. I didn’t know I’d meet my incredible wife here. I didn’t know I’d start a family here. I didn’t know I’d get to watch my son grow up here.
I hope I’m leaving New York a better person — more adventurous, more curious, more kind — than I was when I showed up.
What an incredible gift and joy it’s been to be a small part of such a wonderful place. New York has been so good to me.
I’m excited for what’s next, but I’m going to miss this place.
Thanks for everything, New York.
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At top: Me in early 2013, before I discovered the importance of hair product, in front of the yellow BuzzFeed “WIN” wall in the lobby of the 21st Street BuzzFeed office.
At bottom: Me in May 2024, on a bright stage at The Newsletter Conference in New York City, interviewing a few fellow newsletter operators (Stephanie Talmadge, Louis Nicholls, and Chenell Basilio) about newsletter growth strategy.
Before my son was born, I wondered how long it would take before I asked a truly stupid question.
Other friends had told me their stories about asking that first dumb question. One friend confessed that they called the pediatrician’s emergency line the first night home from the hospital because their child was crying. “Yeah, they’ll do that,” the pediatrician chuckled, and hung up. Another told me that they misinterpreted the doctor’s instructions before leaving the hospital. They called the pediatrician the day after they got home, reporting back that they child had pooped three times when the doctor had told them to make sure their newborn pooped once. “We meant at least once, not only once!” the pediatrician laughed. Every new parent, it seemed, asked something stupid.
I was a new dad who’d never changed a diaper before. The only thing I knew for certain was that I knew nothing. I knew I was going to ask something dumb — eventually, at least.
It took me 45 seconds.
Ben was born, and the doctors called me over to a little scale where they were weighing Ben. I looked down at his tiny feet. They were black.
I hadn’t remembered reading anything about black feet in any of the parenting books.
So I asked them: Are his feet supposed to be black? Is that normal?
That’s when they held up a piece of paper with his tiny footprint on it. They’d pressed his feet in black ink to make the footprint.
It was the first of what would be many, many stupid questions.
But getting that first one out of the way really did help! With a baby, new stuff happens all the time, and I quickly became unafraid to ask, even when I knew the answer was going to be something obvious. I didn’t have to preface questions with, “I know this might be a dumb question, but….” I just asked.
I constantly remind myself: There’s so much I don’t know, and there’s no reason to pretend like I know everything.
Even when it feels like it might be a stupid question, I now just ask.
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That photo at top is of me the night we got home from the hospital. I’d changed about five diapers at that point. I didn’t have my technique down, but hey, I got better.
He’ll be peacefully asleep when, suddenly, something jolts him awake. The pacifier’s long since fallen out, but he can’t find it to soothe himself back to sleep.
So instead of searching for the pacifier or trying to suck his thumb, he does the funny thing: He sits upright and cries.
He’s so tired that he barely sit upright. And yet, he sits, waiting for me or my wife to come in and fix things. (Fixing things usually entails finding the pacifier, putting it back in his mouth, and then helping him lay down.)
I wish I could explain to him that things are OK. I wish I could explain how he could solve the problem without needing our help.
He’s still a bit young to understand that. But one day, I’m looking forward to being able to explain to him that he’s got everything he needs to handle the situation himself — and then watching him handle it with ease. I know he can do it.
We sometimes need to make a change with the work we do. The question is: How big a change do you need to make?
Sometimes, you just need to make a shift. The change is small — you’re refocusing on something new, but it’s within the normal scope of what you’d do already.
Sometimes, you need to pivot. You’re making a big change — taking your skills and applying them to something outside your current orbit. The skills and the work might look similar, but you’re doing it in a different space.
And sometimes, you need to sunset things. You’ve done the work, you’ve learned the skills, but you’re ready for something brand new. You’re ready to shut down what you’re doing and move into a brand new field.
For my work, for instance, a shift would be changing my focus from working with newsrooms to working exclusively with non-profits. A pivot would be moving from newsletter consulting to building an agency to help newsletters grow. And to sunset would mean shutting down Inbox Collective to focus on something new.
None of these match where I’m at right now, but maybe they will be in the future. When it comes time to make a change, the big question remains: Shift, pivot, or sunset?
A few years ago, I was working on a project with the team at Poynter. They had a landing page for their newsletters, but it wasn’t very good. There weren’t any details about any of their newsletters — what they were, who wrote them, when they’d show up in your inbox. As a result, the page wasn’t driving many sign-ups.
I showed them a bunch of options for how we could make things better. We all agreed on a new template — but it was going to take a long time for us to build out that ideal page. Instead of waiting until that page was done, we decided we’d first take a small step in the right direction.
That next step was to update the existing page with more details about the newsletters. It wasn’t perfect, but it was an improvement over what they had.
And then, a few weeks later, the Poynter team launched the final version of the page, which had a brand-new design, more details about each newsletter, and the ability to easily sign up for multiple newsletters at once.
I tell my teams often: Direction is more important than speed. Everyone wants to make big leaps forward — but sometimes, the right move is to take small steps in the right direction.
Every year, I spend a few days with friends who also have their own solo businesses. The offsite, as I’ve come to know it, started with just one friend. It’s grown to a group of four — each of us with our own unique perspective on how to build a great business.
Last night, I gave a presentation to the group, where I walked through a few ideas for the future of Inbox Collective. Some were small ideas that I wanted suggestions about; one was a major moonshot for the business, something that would radically change the course of the business. I wasn’t sure if I was ready to do something so big, something that might take Inbox Collective from a one-person operation into a pretty sizable business. But I wanted to know what they thought.
And I loved that the group had a unified response to that last idea: We love the idea as a business — but we’re not sure we love it for you.
It’s exactly what I’d been thinking, so to hear three friends immediately come to the same conclusion was heartening. Their hesitancy gave me confidence that I was already on the right track. Some ideas, even if they’re interesting, are worth saying “no” to.
Today, one of my friends here on the offsite tried to offer an apology. “I hope we weren’t too harsh about that last idea,” he said. I waved him off. I told him: I presented the idea because I wanted to know what you three honestly thought about it, and the fact that you all were so skeptical of the idea — and skeptical because you felt it didn’t line up with my current priorities and needs — told me everything I needed to know.
I wanted the feedback, good or bad. I’m glad I’ve got a group in my corner who can point me away from the ideas that don’t make sense for me.
