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 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.
Understanding that you’ll never have all the answers. The only way forward is to have an open mind and keep asking questions.
Whatever you’re working on, remember this: Curious people make the best teammates. Find people who are always curious, and you’ll build a team that builds a great strategy in the long run.
A year ago, I realized that clients were asking me, over and over again, for examples of certain things:
Dan, do you have any examples of great pop-ups to convert readers from our website to our newsletter?
Have you seen any good examples of promotions on Instagram?
Do you have any examples you can share of amazing welcome emails?
So I started compiling examples into a big Google Drive file, and shared it with clients. But then I made another choice: I added a weekly note to my calendar to keep adding to the Drive. I created a folder on my laptop where I could store examples that I’d noticed over the course of the week, and then, every Friday, I’d upload them to Drive.
Sometimes I only have an example or two to upload on Friday, and sometimes, I’ll have dozens. But over the course of a year, I’ve uploaded hundreds of examples that I can refer clients to. It’s not an exaggeration to say that this one project has changed the way I work with clients. It’s one thing for me to be tell them about the concept, but it’s another to be able to show them a handful of great examples from their peers.
And had I decided to, say, update the file every month or every quarter, I’m not sure I would’ve stuck with it. (It took a lot of work to upload that first, giant batch of examples!) Instead, by focusing on a small, weekly habit, it feels so much more manageable — and the long-term result has been so much more than I ever could’ve expected.
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That’s a screenshot of the pop-ups folder. There are now more than 30 examples of pop-ups I love that I can share with clients.
But the truth is: I’m still not very good at saying “no.”
It’s hard to turn down work — especially when it involves projects I’m excited about. It’s hard to turn down revenue for the business. It’s hard to say “no” to people I’d love to work with.
I know that saying “no” is often the right move for me. But it’s still hard to do.
Right now, I’m reading “Eat a Peach,” the memoir from chef David Chang, and he talks often about the pressure of working as a chef — one whose success opened up all sorts of exciting new opportunities for him: Opening new restaurants, writing books, even TV. He writes that at times, he felt like he needed to hit rock bottom before he would be willing to change the way he worked.
“The paradox for the workaholic,” he writes, “is that rock bottom is the top of whatever profession they’re in.”
That line’s stuck with me the past few days. I’m not a celebrity chef, but I’ve been lucky to have had some success — and to have gotten a little publicity — the past few years. I’ve gotten all sorts of interesting new opportunities as my business has grown.
And I’m starting to understand what Chang might have experienced himself. I love to do this work, and if I could say “yes” to every potential client, I would.
But that’s not an option.
So I need to keep getting better at saying “no.” I need to do it for my family, for my friends, for my business, for my industry — and for myself. Saying “no” is what I need to do make sure I’m prepared to say “yes” to the right opportunities going forward.
A former BuzzFeed colleague of mine just left a job there for a new role, and we had lunch the other day. She asked me if she should know anything about working at a new job — a real job, where there isn’t a test kitchen and where staff writers don’t wear JNCO jeans as a fashion experiment.
“They’re going to think you have magic beans,” I told her.
She looked at me funny. (And I don’t blame her.) I went on.
“When you leave BuzzFeed for a new company, they’re going to unusually curious about what you’ve learned at BuzzFeed. They might think you know some sort of deep secret of the internet — that someone on the BuzzFeed team, on your first day, gave you the cheat code to unlock all that internet traffic that BuzzFeed gets every day. And they’ll be a little disappointed when they find out that there isn’t a secret to BuzzFeed at all.”
I paused for a second.
“There wasn’t any big secret to BuzzFeed — just a set of lessons that helped us build a platform that readers loved. Remember those lessons: Test out weird ideas. Be willing to look stupid, and be willing to move on when things don’t work. When you get the chance, hire smart, curious people who listen to one another. Make sure you have the tools you need to test out your ideas. Make sure you know what you’re measuring when you do the work.”
She nodded along.
“Just show up and do the work every day,” I reminded her. “I’ll take your work ethic and the lessons you learned from BuzzFeed over a bag of magic beans any day.”
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That’s a photo of a giant LOL sign that hung at the entrance to the BuzzFeed office on 21st Street in New York.
I’m on vacation this week, out west visiting my family. I’m doing the stuff you do out here: Spending time at the pool, reading, taking afternoon naps, firing up the grill.
But I’m also working, pretty much every weekday morning, for a few hours.
This isn’t supposed to be some sort of treatise on the importance of hustle, some #nodaysoff mission statement. I’m a unique case: I’m in my 30s, I don’t have kids, and I run a one-person business — one I’ve built to serve a lot of small clients (instead of a few big ones). What I’ve done in the past is the traditional vacation: Shut down the laptop, turn on the out-of-office reply, and then return a week or two later to dive back in.
But with Inbox Collective, I’ve discovered that if I shut down everything for a week or two, here’s what happens:
1.) I return to a million unanswered emails (since there’s no one else clients can redirect their questions to).
2.) The week before vacation and the week after vacation are absolutely stacked with meetings, as clients try to squeeze in time before I leave.
The last time I took a week off, I spend the entire week stressed out about how much work I had the next week. I seemed miserable the entire trip.
So I’m making adjustments. On recent trips, I’ve tried to carve out a little time in the morning — about 2-3 hours — to reply to emails and take calls. I’ve blocked off every afternoon for myself, and I’ve turned on my out-of-office reply so people know I’m not going to write back right away. And it’s working: My inbox is manageable, my schedule when I return from vacation is fairly normal, and once the clock hits about 11 a.m., I shut down the laptop and head out do to something fun.
It seems a little odd to still do some work on my time off. But if this is what I need to do to make sure I actually enjoy the time off — to work 10-15 hours a week, even on vacation — then it’s a trade-off I’m willing to make.
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That’s a photo of me, on one of my afternoons off, on the golf course. A beautiful day, but a pretty terrible lie for that particular shot.
There’s this lie that we tell ourselves when things are complicated and hard: “Once I get through this stretch, things are going to get easier.”
I’ve told myself this more times than I can count. Dan, if you can just finish this task… if you can just get through this month… if you can just take care of this deadline — it’s going to get easier from there.
But that’s not really how this works.
It’s OK that things can be hard. Things can be hard because you’re trying to learn new skills or taking on new challenges. Things can be hard because you’re in a new role or a new job. Things can be hard because you’re pushing yourself to get better. Things can be hard because life gets in the way — you’ve got more responsibility or more people to care for than you did when you were younger.
Every so often, I have to remind myself: Things are never going to be quite as easy as they are right now. Work — and life — tends to get more complex over time.
But you’re going to find a way to push through and keep doing the work. You’ve done it before, and you’ll do it again in the months and years to come. Things never get easier, but you’re also getting smarter and savvier, and building the team to help you take on these challenges. You’ll be able to take on tomorrow’s obstacles as they come.
So enjoy this moment, right now. Yes, things seem overwhelming some days. But these challenges and obstacles will beget new ones. One day, you’ll look back on these moments and tell yourself: What I would give to merely have those types of problems today.
It’s not getting easier, but that’s OK. You’ll be able to take these challenges head on anyway.
A few weeks at the PGA Championship, I watched as Garrick Higgo — a 22-year-old South African — teed off on Sunday at 7:40 a.m. That’s what happens when you’re eleven shots over par, as Higgo was after three rounds. (For the non-golfers out there: The pros typically shoot several shots under par.) He’d had a tough tournament, and I was mostly watching because, well, it was something to do while eating breakfast on a Sunday. I watched Higgo for a little while, and it was clear that he could play — it just hadn’t been his week. He hit several shots close to the flag, and seemed to play freely without the pressure of having to worry about winning the tournament. The announcers mentioned that Gary Player, a retired South African golfer and winner of nine major championships, was a mentor of his. (Not bad when your mentor’s in the Hall of Fame.) That Sunday was Higgo’s best round of the entire event: He shot a 69, good for three shots under par. The PGA Championship was his first-ever PGA Tour event.
I remember watching and thinking: Here’s a pro golfer — he’d never played on the PGA Tour, but he’d won several events in Europe — who clearly could play. In his previous four pro events, he’d finished in the top ten all four times, and won two of them. But even a pro sometimes can’t seem to find his swing.
Anyone can have a bad day, or a bad weekend, even if you work hard and have all the talent in the world. As a friend from the midwest once put it, folksily: “One day chicken, next day feathers.” Bad days happen.
Still, you keep moving forward. The PGA Championship was Higgo’s first-ever PGA Tour event. But I imagine Gary Player told him after the tournament: Pick up your head, kid. If you do the work, and keep competing, you never know when you’ll break through.
Turns out he didn’t have to wait long. A month ago, in his first PGA Tour event, he finished in 64th place, fourteen shots behind the champion. Today, in his second PGA Tour event, Higgo won the whole thing — and the $1.3 million grand prize that came with it.
I suppose there’s another fowl-friendly quote that my midwestern friend would’ve used for an occasion like this: Winner winner, chicken dinner.
The New Yorker did an interview with John Swartzwelder, one of the most prolific writers in the history of “The Simpsons,” and a man who is legendary for his privacy. (The New Yorker described him as “reclusive, mysterious, almost mythical.”) The interview’s fascinating and funny, but I particularly enjoyed this part:
How much time and attention did you spend on these scripts? Another “Simpsons” writer once compared your scripts to finely tuned machines—if the wrong person mucked with them, the whole thing could blow up.
All of my time and all of my attention. It’s the only way I know how to write, darn it. But I do have a trick that makes things easier for me. Since writing is very hard and rewriting is comparatively easy and rather fun, I always write my scripts all the way through as fast as I can, the first day, if possible, putting in crap jokes and pattern dialogue—“Homer, I don’t want you to do that.” “Then I won’t do it.” Then the next day, when I get up, the script’s been written. It’s lousy, but it’s a script. The hard part is done. It’s like a crappy little elf has snuck into my office and badly done all my work for me, and then left with a tip of his crappy hat. All I have to do from that point on is fix it. So I’ve taken a very hard job, writing, and turned it into an easy one, rewriting, overnight. I advise all writers to do their scripts and other writing this way. And be sure to send me a small royalty every time you do it.
That’s interesting. So create an imperfect world and then improve it?
That’s the way I do it.
I absolutely love this idea. And the most interesting thing for me is, it’s actually the second time I’ve heard this idea this month!
The other time? On the podcast “Two Writers Slinging Yang,” as shared by award-winning food writer Alan Richman. He told host Jeff Pearlman:
I would sit down with my notes in front of me and whatever’s in my head, and I would write a first draft, and I would make sure it was much longer than the story was going to be. I would write maybe three or four thousand words, just off the top of my head, just spewing it out and typing it, and I knew that was not going to be the story. But that gets everything out of my head. By doing that, I would say, “Oh, this is important.” I would start to see what I had in my head and what would make the story… I always wrote a first draft as fast as I could until I got everything out of my head and on paper. And then I would write the second draft, and that’s when I’d start to write.
Someone once said all writing is re-writing, and that’s what I believe in. I re-write and re-write.
Here are two very different writers: A comedy writer, and a writer of long food feature stories for GQ. But they both know their strengths — they’re good at re-writing! — and have built their creative process around that strength. When you’re a writer, you’re judged on your output, not your process. Who cares how you get there? All that matters is that you get there.
Whatever it is you do, play to your strengths. Figure out what you like doing most, and see if there’s a way to build your process around that.
Last week, a friend was giving a presentation for work, and asked if she could include a slide with a few email tips she’d learned from me. At the top of the slide was an explanation of who I was.
“Here’s some advice from Dan Oshinsky,” she’d written, ”newsletter guru.”
I cringed.
The truth is, I’m not a guru, or an expert, or any of the other titles that people throw around. I’ve seen a lot in my time in this space, and shared a lot with others. But the thing I like most about my job isn’t that I get to share what I’ve learned with my clients.
It’s that I get to keep learning.
Often, as I get to work with a client, we’ll realize that there are things they want to try that I don’t have the answers for. And to me, that’s the most exciting part of the job — the chance to learn something completely new!
So we’ll start asking a few questions. We’ll dig into the issue. I might even reach out to others who’ve tried something similar, just to get their perspective.
And then we’ll start to test and learn. We’ll keep asking questions until we get some answers — even if they’re not the answers we expected.
I know that I don’t have all the answers. But I have a lot of the questions to help me figure out how to get the answers that me and my clients need.
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That’s a photo of me giving a talk at an event in Sydney in 2019.
