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 have all sorts of to-do lists. I’ve got a list of ideas — “somedays,” I call them — that I want to try. I’ve got notes written down on yellow legal pads and in various Google Docs. I know I won’t act on many of these ideas.
I never worry about running out of ideas, but I know that sometimes, I forget about a really good idea. So it’s helpful to keep coming back to these lists to look through things. What am I still excited about? What could I work on as part of another project? Often, I find a chestnut in one of these docs — but I have to make sure to make time to review and give each of the ideas some thought. I don’t want to let anything slip through the cracks.
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That photo of a small notepad and wooden pencil on top of a wood table, was taken by Michaela St for Unsplash.
My son has this funny habit. We’ll take him upstairs to the hallway in front of his room. There will be a few doors open: One to his room, one to the guest bathroom, and one to the guest bedroom. Ben will start to crawl towards one room — but then pause, and spin towards another, and the pause, and spin towards a third. Sometimes, he’ll spin in a circle, for an entire minute or two, unsure what room to crawl towards. There are just too many choices!
And I get it! I often do this myself. I’ll have one too many choices, and instead of just making a choice, I spin my wheels and end up going nowhere.
But the next time I find myself doing that, I’ll try to think about Ben moving in circles. When he does, I try to give him a little pat on the butt to nudge him forward. It doesn’t really matter what choice he makes — he just needs to make one. I need to remember to do the same.
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That photo is from Joel Fulgencio for Unsplash, and it’s of a series of blue walls, with holes cut in the middle, that are in Hong Kong on top of a parking garage. It reminds me a little of when you’re standing between two mirrors, and the reflections seem to go on forever.
My son had an important doctor’s appointment today in Salt Lake City. It was an appointment with a specialist who’s tough to get time with. We booked the appointment a few months ago.
And today, I showed up to the appointment — and found out I was two hours late. We’d put the wrong time on the calendar, and the next available appointment isn’t for a few more months.
I wanted to scream, cry, and crawl under a rock. (Ideally, all three at the same time.)
But anytime something like this happens, I try to figure out a plan to make sure it doesn’t happen again.
So for big appointments like this, I’m putting a few new rules in place. I’ll double-check the appointment time against texts or emails the doctor’s office might send. If they don’t send that, I’ll call the office directly to confirm the time. And you better believe that for something like this that requires a drive, I’ll be checking Google Maps the night before to make sure I get to the appointment on time.
Mistakes happen, and that’s OK. But if you do make a mistake, figure out the processes you can put in place to prevent them — as best you can — going forward.
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That’s a photo of the sunset over the hospital down in Salt Lake, with the mountains in the background. Honestly, it might have the prettiest view of any hospital I’ve ever seen.
I bought this piece of art today at the Farmer’s Market downtown. It’s a big piece of wood, probably about five feet long, and on it is a carving of the mountains here in Utah. This week, I’ll hang it behind my desk.
But the memorable thing for me wasn’t the purchase of the art — it was walking it to the car.
Now, you’d think that a guy my height (I’m about 6’4’’) carrying a five-foot-long piece of wood might get noticed while walking down the street. I’m hard to miss! And yet: In that short walk, I cannot tell you how many people nearly walked directly into me.
Look, I’m as guilty as any of being distracted by my phone. But today was a nice reminder: The stuff directly in front of you might be pretty important. (Walking into me or that piece of art would’ve been a less-than-fun experience for someone.) It’s easy to miss things happening in our world, but we shouldn’t be missing the obvious stuff that’s literally right in front of our faces.
So look up every once in a while — hopefully to pay attention to what’s happening in your world, but at the very least, because you might be about to walk into a tall guy carrying a big piece of art.
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I don’t have a photo of the art, but here’s a photo that Olivia Hutcherson took for Unsplash of downtown Park City in 2018 at the Farmer’s Market, with small white booths lining the street and red flowers in the foreground.
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.