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.
This is the 1,000th blog post I’ve published on danoshinsky.com. How’d I get here?
In 2008, I started publishing on this blog, but I got serious about it in spring 2015. I was doing less writing at work, and wanted to make sure I always made time to write.
So every week since, I’ve found something to write. Some are inspired by a conversation I’ve had, or something I’ve read, or something in the news, or something happening at work. When I first started writing, I worried I’d eventually run out of post ideas, but for seven years, I’ve always found something to write about. (There’s always more to say, it turns out.)
Some of these blog posts are good, but many are not. And that’s OK! In a year, if I publish a handful of really good ones, I’m thrilled.
So how do you get to 1,000 posts? You pick a routine, and stick with it.
There’s a lot that’s frustrating about being human, but here’s one thing that’s annoyed me a lot lately: You’re not always at your best.
There are days you show up to do the work, and things feel a little off. It doesn’t matter what the work is — it could be a project, or a big piece of writing, or a day on the golf course. Some days, you show up and know you’re not quite right, even if things felt amazing the last time you showed up to do this work.
It’s hard to accept that your body feels a little different today, that your mind’s in a different place, that your energy’s different than usual. Maybe you know why, or maybe you don’t. But you know, because you know yourself:
Today will be less than perfect.
I like being at my best. I like how confident I feel when I know that I’m doing my best work.
But there’s something to be said for getting through those days when you’re at 70%, when it’s not all there. You make the most of what you can with what you have that day. You find a way.
Accept less-than-perfect for today. Better days will come.
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Naturally, that post was inspired by a morning on the golf course. The day before, I hit the ball so well and felt confident over every shot. The next day, it looked like I’d never hit a golf ball before. It happens.
Every year, we travel to South Florida to visit family. The trips are always a good time, but sometimes, they can feel a little repetitive. We go to the same restaurants, the same beach, the same hotel. We realized a few years ago that we needed to shake things up a little — otherwise, making the trip might start feeling like a checklist of things to do, instead of a true vacation.
So last year, Sally had a brilliant idea: She booked us on a fanboat trip through the Everglades. It was an absolute blast — driving through swampland at high speeds was the highlight of our trip. And afterwards, we agreed: Every year, we’d try something new when we came down to Florida to visit.
This year, that meant a trip to Spring Training to watch baseball, and then an afternoon on a water cruise. Next year, I’m thinking we might rent a speedboat or book a few nights at a fancy new hotel.
Whatever you’re doing — whether it’s going about your day-to-day work or going on a trip to visit family — it can be easy to get stuck in a rut. The easiest way to break out of that is to add something new to the mix. Maybe you change up your commute, or do a pre-work workout to give you a boost. Maybe it means getting away from the office to work out of a different location. Maybe it means shifting your hours, or taking on a new project with different colleagues.
Whatever it is, don’t be afraid to break your routine and try something new. Sometimes, trying something new is exactly what you need to find that spark and help you enjoy things again.
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That’s a photo of us on the fanboat last year. We had a freaking blast on that thing.
When I was 16 years old, I had a news story published in The Boston Globe. I wish I could tell you it was because of hard work or talent, but it wasn’t. I was interning at a news service in Washington, D.C., and one day, thousands of protestors in yellow shirts marched past our office. I asked my boss if I could go outside and ask them a few questions. Turns out they were protesting against the Chinese government — they were from Falun Gong, and one of their members had been detained in China. They’d rallied to try to pressure China into letting him go. The man detained was from Boston. The news service I worked for had a relationship with The Boston Globe. I got some quotes, wrote up the story, and the next day, read my piece in the paper. Right place, right time, right story — that’s how I ended up in The Boston Globe.
When I was 24 years old, I got a job at BuzzFeed. I wish I could tell you it was because I truly believed that BuzzFeed was about to become one of most influential publishers in the world, but it wasn’t. They were launching a section for feature stories, and I’d been doing a lot of that sort of thing with Stry.us. I was curious about what the were doing, so I reached out to chat. I wasn’t the right person for that role, but they invited me to pitch them on a new role within the company. I’d had some success with my newsletter, Tools for Reporters, and thought email might be a good fit there. They agreed. Right place, right time, right background — that’s how I ended up at BuzzFeed.
When I was 32, I left my job at The New Yorker to start Inbox Collective. I wish I could tell you it was because I knew that email was about to become one of the hottest channels in the digital space, but it wasn’t. I’d been working in this space for several years and had learned a lot. I’d launched Not a Newsletter to share some of the things I’d learned. My readers started reaching out to ask if I could consult for them, and at the same time, I started getting invited to travel both in the U.S. and abroad to speak about newsletters. It seemed like a good moment to take the leap. Right place, right time, right strategy — that’s how I started Inbox Collective.
There are so many things that can make or break an opportunity. Do you have the right skills? Do you have the right team? Do you have the right funding?
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.
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.
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.
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.
