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’m a big fan of the show “Parks and Recreation.” It’s one of those shows that I loved when it first aired, and have kept watching over the years. It’s fun and silly and always leaves me in a good mood.
I’ve also been listening to the podcast “Parks and Recollection,” where Rob Lowe, an actor from the show, and Alan Yang, a writer from the show, revisit old episodes. On a recent podcast, they brought on Ben Schwartz, a frequent guest star from “Parks,” and got to talking about what it was like to be on set. Every TV show cast talks about how fun it was to work together, but the way Lowe, Schwartz, and Yang described things seemed a little different. What all three kept coming back to was a simple concept: The show worked because the cast and crew got along extraordinarily well. When you make something good with people you like, they said, you get a finished product that’s truly special.
It can be easy to overthink the elements of a great strategy — do you have the right tools, the right amount of funding, the right timing? But sometimes, the best work comes from a simple start: A great team, working together on something they care about. Let the rest come from there.
I spent a few days last week up in Burlington, Vermont, and one day, with temperatures a bit warmer than usual, took a walk down to Burlington’s waterfront park. (It’s called, accurately enough, Waterfront Park.) It’s a beautiful park, with a bike path and a science museum and gorgeous views of Lake Champlain. But the thing that stood out to me most were the swings.
Alongside the water, where you’d expect benches to be, Burlington’s placed these swings, maybe a dozen of them alongside a quarter-mile stretch of waterfront. On a warm day, you can sit there, watching the water slowly move towards shore, as you swing back and forth back towards the water.
A swing instead of a bench isn’t a huge change — at the end of the day, they’re still a place to sit and look at the water — but because I didn’t expect it, I stopped and spent a few extra minutes in that park. It was something different, something unexpected. I found those swings absolutely delightful.
All of us could try to bring the same spirit to our work. Try something small, new, and unexpected. It might lead to the creation of something special.
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That’s a photo I took of the swings in Burlington’s Waterfront Park.
Newsrooms sometimes hire me to produce an audit of their email strategy. They’ll give me logins to their email system and their analytics, and I’ll interview key staffers to understand what they’re doing and where there are opportunities to improve. Then I’ll turn my findings into a slide deck.
When I first produced these audits, the final deck was about 50 slides long. But as I did more of these, and started to identify other areas to cover during an audit, the decks started getting longer. 50 slides became 100, and then kept growing from there. My most recent audit checked in at 206 slides.
As a partner for these newsrooms, my job is always to overdeliver. I want to make sure I give them everything they’re looking to learn — and then some.
But last year, I noticed that when I’d present these longer decks, I wasn’t getting much feedback from the newsrooms. They weren’t asking questions about specific slides or tactics, which seemed odd, since they’d been so curious earlier in the process. What had changed? After I followed up with a few clients, I got my answer: I was overwhelming them with information.
So that became my new challenge: How could I overdeliver without overwhelming?
A few changes really helped. Up front, I started setting clearer expectations for what a client could expect from the audit. I told my teams: This is going to be a lot, and I don’t expect you to do every single thing in here. That freed up the teams to pick and choose what tasks to execute on based on my findings.
I also changed the structure of my presentations. Instead of one big audit reveal at the end, I started coming to my newsrooms with initial findings — a shorter presentation, about 45 minutes long, to talk through the most important topics, and to get feedback about things they wanted to see more of in the audit. That gave them a chance to start thinking through the big themes of the audit before the final deck was presented.
I changed the structure of the deck itself, adding a section at the start with a list of suggested tasks to prioritize. That helped teams understand which tasks were ones to work on right away, and which were ideas to put on the back burner.
I told newsrooms not to invite their entire team to the final audit presentation. Did the sales team really need to sit through 90 minutes of discussion about email deliverability or growth? No, not really. Instead, I started giving the audit presentation to a core group of stakeholders, and then set up smaller presentations to specific teams (sales, product, editorial) so they could focus on the findings most important to them.
And lastly, I started setting up monthly calls to check in with teams after the audit, to talk through their prioritization list, and to help remove any roadblocks in their way.
I’m still searching for other ways to overdeliver without overwhelming. The audit process isn’t perfect, and there are going to be ways to continue to make it even better.
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At top is a slide from an audit presentation to an Inbox Collective client.
If you launch lots of new products or features, several aren’t going to work. You’ll be excited about a big new newsletter launch, and you put it out into the world, and the audience just doesn’t like it. It happens!
The truth is: If you’re not failing, it means you’re probably not trying enough new tests.
When you fail, move on quickly. Don’t double down on your mistakes. Keep testing, keep trying. The more you try, the better the chance that you’ll eventually stumble into something that truly works.
I have a few dozen Inbox Collective clients that I’m working with right now. Some I talk to daily or weekly. Some I talk to once a month or once a quarter. And there are days when I’ll have five or six calls, often stacked back-to-back-to-back. When clients hop on that call, they expect me to be able to pick up exactly where we left off. They pay me too much to be disorganized or unprepared.
When I’m on my call, I’ve got a notebook where I jot down notes and ideas. I find that I stay more focused if I can write things down on paper instead of trying to type up notes as we go.
And at the end of the day, I go through my notebook and type up the notes in a Google Doc designated for every client. If they’re not a client, I create a new Doc for them — often, I’ll find that a casual conversation might lead to something a few months down the road, and having those notes is a hugely valuable tool. I’ll document everything — the date, who was on the call, updates from the team, ideas we discussed, and next steps.
What it means is that over time, I’ve fully documented everything I’ve talked about and done with that client. Some teams have been with me since 2019, and I can’t always remember what we might have tried three years ago. In those cases, it’s great to be able to open up their Google Doc and search for a phrase to figure out if we might have tackled a particular issue already.
If you’re holding regular meetings with a variety of stakeholders, you might want to try the running notes system, too. Set up a doc for every team or individual you meet with, and document your notes from the day. That way, when you need to find notes from a conversation, you’re not searching in your desk for that one notepad that might have your notes, or searching through your inbox hoping to find an email that mentions the topic. You’ll have a document of exactly what you discussed, and when.
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That’s my notebook and a running notes Google Doc, both for WBUR, a client that’s worked with me for nearly three years. At this point, my Doc for them is 44 pages and more than 9,000 words long.
Two days before my bar mitzvah, I did my final rehearsal at the synagogue. I’d spent months working on my Torah portion, practicing in a language I could read but didn’t fully understand. The day of the rehearsal, I screwed up a line — and completely lost it. I started crying, ran to the bathroom, and locked myself inside.
I was 13 years old, and terrified of screwing up in front of all of my family and friends. And since this was the first of the Oshinsky bar mitzvahs, there were going to be several hundred people in attendance. I was scared of looking dumb in front of all of them.
But the rabbi had good advice. He told me: If you screw up a line, it’s OK! Just go back to the beginning of the line, and read it all over again. Nobody will ever notice.
He was absolutely right. Of the several hundred people in attendance, there wasn’t a single one who spoke Hebrew fluently. (Perhaps a few dozen could read Hebrew, but none could’ve translated what I was saying into English.) Which meant that when I did mess up on the day off, I followed the rabbi’s instructions: I went back to the beginning of the line and read it again. Nobody noticed — mostly because nobody else had spent the previous nine months learning and rehearsing a single Torah portion.
I’ve had the same thing happen when giving a big presentation. I’ll have rehearsed and practiced, but then I’ll flub a line or forget to cover a specific slide. My first reaction is often to beat myself up for making a mistake. But the truth is, only I knew how things were supposed to go.
So when it happens, I let the mistake go, and move on. The truth is, the only person who even noticed was me.
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That’s a photo from my bar mitzvah, back in May 2000.
I’m a pretty good skier on a sunny day. When the light is good on the mountain and I can clearly see the next few turns, I ski with a lot of confidence.
But it’s another thing to ski on a wintry day, when the clouds and the mountain seem to merge into one. When the light is flat, seeing the path ahead gets tricky. On those days, I find myself struggling to maintain control — it feels a little like skiing through fog. A bad turn or two and I lose confidence quickly.
So on those days, I try to adopt a mantra: Trust your turns. I’ve been skiing since I was a kid, and I can get down just about anything. (It won’t always be pretty! But I’ll get down.) And when I tell myself, “Trust your turns,” I’m saying: You know the motion — trust your ability to string turns together, even in low light. Ski just like you would on a blue-sky day.
We all want to be able to clearly see the path ahead. But we can’t always see the next turn — or whatever’s around the next corner. And in times of uncertainty, we can’t just stop and wait for things to clear up. Trust the work you’ve already put in, and the processes you have in place.
Trust your turns, and keep going.
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That’s a photo I took on a sunny day at Breckenridge in 2021.
I’m reading Mel Brooks’s autobiography, “All About Me!”, and loved this section about “Young Frankenstein” so much that I’m going to quote it in full. Here’s Mel:
The first cut we put together for a test screening was two hours and twenty-two minutes long. That was pretty long for one of my films. “The Producers” was only eighty-eight minutes. While “Young Frankenstein” ran long, I didn’t want to leave out anything that might possibly catch fire with an audience. I screened it at the Little Theater on the Twentieth Century Fox lot for people who worked on the lot. The theater was packed, and we didn’t get all the laughs we were aiming for. It went well, but not well enough for me. It was just too long.
When the picture was over, I got up in front of the audience and said, “Ladies and gentlemen, you have just seen a two-hour-and-twenty-two minute failure. In less than three weeks from today, I want you back here to see a ninety-five-minute smash hit movie. I want every one of you back!”
Editing was both easy and difficult. Easy because when something was supposed to get a laugh and it didn’t, I simply cut it. Difficult because I was in love with too many moments and had to cut them for the good of the overall film. Sometimes, you have to kill your darlings….
Of course, it was more than three weeks later when I reassembled most of that same audience at the Little Theater. It was actually closer to three months later. But I had a cut that was pretty damn good and wanted to show it. It went like gangbusters! Every single scene in the picture worked. The audience not only laughed their heads off, but there was a palpable feeling of sweet sadness when the picture ended.
I love what Mel describes here: He’s using audience feedback to understand what works and what doesn’t, and then is willing to use that feedback to make his work better — even when it means getting rid of something he’s proud of. Pay attention to what your audience says — they might just make your work better, too.
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.
