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’ve been helping one of my writers out recently, and they asked a question: Dan, any chance you know how to fix this little WordPress issue that’s been bothering us?
I’ve got this very site on WordPress, and Inbox Collective runs on WordPress, so I know a bit. I told them I couldn’t promise anything, but I’d be happy to give the issue a look.
And then, over the course of the next hour, we managed to fix that issue — plus a handful of other WordPress issues that had been bugging them for a while.
Does it mean I’m suddenly giving up email and going into WordPress design now? Oh, absolutely not. I still barely know anything about this platform.
But I know enough to share and to help — at least sometimes. And on the right day, that might be enough.
I’ve been working with a few newsletter writers who are in a period of transition. For nearly two years, they’d been writing multiple newsletters per week. Now, they’re all trying to figure out what to do next. Should they write more, or less? Should they change the way they monetize?
And my advice, over and over, has been simple: Whatever you do choose to do next, make it work for you.
There isn’t a single way forward here. There is no one-size-fits-all answer.
Which means that the right answer, for now, is the one that works for each of these writers. It’s up to them to figure out what they want to build and how they want to build it. There’s no need to build around someone else’s constraints or rules — they’re free to do what’s best for them.
Maybe that means, as I told one writer, telling their readers that they’d be taking a month off in December so they can get ahead for 2023 and pre-write the first few months of newsletters. “I’m allowed to do that?” they asked me.
You are, I told them, because this is all about making it work for you.
Maybe it means changing up the way they monetize. One writer’s been trying to push forward with a paid subscription, but it isn’t working as well as they hoped. But they do have a fairly large, engaged audience. Advertising might be a better way forward for them.
“Can I just cancel the paid offering and switch businesses models?” they asked me.
You can, I said, because if you’re going to make this work, it first needs to work for you.
What’s the best route forward? Figure out what’s best for you , and work from there.
I keep thinking about this thing I saw a few weeks ago in New York.
I was walking down the sidewalk, and as I looked ahead, I saw something I’d never seen before: A young woman was reading a book while she walked. And this wasn’t some act of passive reading — her face was buried in the book.
It was hard to miss. She almost walked directly into me — I had to slide out of the way to avoid her. (She didn’t seem to notice.)
I know people are busy. I know everyone’s trying to get the most out of their day. But not every activity is one that allows for multi-tasking.
If you truly care about something, you’ve got to make time for it. Maybe that means putting down your phone before bed and picking up a book. Maybe it means blocking out time on your calendar to read. Maybe it means subtracting something — fewer after-work drinks, more reading. Or maybe it means finding ways to responsibility multi-task. (Audiobooks are great for the commute!)
And if you’re walking through New York City, please: Walk responsibly.
I was driving back to New York a few weeks ago. It was one of those days where a 90-minute drive was somehow taking close to three hours. And on the way out of town at the start of the trip, I’d gotten stuck in traffic getting through the tunnel — the same 90-minute drive took nearly four hours.
I was a little sour on New York at that moment. The city can be such a wonderful place to live, but there are parts of it — the traffic is certainly one — that can be so frustrating. Wasting a weekend in traffic made me wonder why I was living here.
I was on a stretch of highway leading through Jersey City and towards the Holland Tunnel. It’s an interesting part of the road — you’re driving among tall buildings, with even taller buildings in downtown New York looming behind.
And then there’s one little window between the buildings where suddenly, you can see the Statue of Liberty emerge. You can’t see the river — just the statue, poking up like a part of the skyline.
It reminded me: Sometimes, you have to go through a lot of everything — work and struggle and crap and things you really don’t want to do — in order to find the stuff that makes it all worthwhile.
The special stuff is out there. You just have to make sure you’re looking for it.
I’m 35 years old, and I’m OK not knowing what happens next.
On a weekly basis, I’m getting asked questions that I don’t have answers to: When will you hire your first employee? When are you going to start a family? Do you think you’ll leave New York? Where would you move?
I don’t know, I don’t know, I don’t know, I don’t know.
There’s a certain pressure to have all the answers. It’s easy to feel like everyone else has it all figured out — why don’t I? But I know that big questions rarely have easy answers.
I do know that I’m tremendously lucky to have the life I have. Every time Sally and I go on a fun trip, or eat a great dinner out, or spend time with friends, or drive home down the FDR at the end of the night, I find myself thinking: Can you believe we get to live in New York City? Can you believe we get to do what we do for work? Can you believe the places we’ve gotten the chance to visit?
I don’t know if I’ll ever have all the answers, but I know this: If this is all there is, this is more than enough.
I don’t know where we’ll be in a year, or if we’ll be able to start a family, or what I might do with my business. Nobody really knows, and I know that it’s OK not to know. I’ll figure out the answers as I go, and I know there will be some surprises along the way. That’s a good thing, I think — a world void of surprises doesn’t seem like much of a world at all.
Who knows what happens next. Here’s to enjoying right now.
Over the past year, there are certain things I’ve come to believe hold true. I know that my beliefs will continue to change. I know that I will change.
But here, at 35, is what I believe:
You don’t have to do everything. You can’t do everything. But whatever you choose to do, it’s enough.
Saying “no” today is the fastest route to saying “yes” tomorrow.
It’s better to be lucky than good, but it’s still pretty important to be good.
Here’s how I’ve been traveling lately: In advance, I’ll ask friends who’ve been to that place for some recommendations. I’ll open Google Maps and star the places they recommend. And then when I get to that place, I start to wander. When I’m hungry, I’ll pull up my map and see if there are any places nearby that I’ve starred. Then I’ll head there. No plans, no reservations — but wherever you end up, it’s probably going to be somewhere great.
Don’t put up the same out-of-office reply every single time you take a few days off. Sit down and actually write something about what you’ll be doing with your time off. You’d be surprised how often a great OOO turns into a conversation starter when you’re back at work.
The right answer starts with a great question.
But also: It doesn’t matter what you ask if you don’t bother to listen.
Oysters on an empty stomach after a red eye is a very, very bad combination.
My definition of “impulsive” has changed as I’ve gotten older. I find myself saying: Did I really just book a trip to the beach a mere 26 days before making the actual trip? Oh, I’m really living on the edge!
Sometimes, a friend is asking for advice, and sometimes, they just want to vent. Know which is which.
Here’s the best way I can explain what I do for work: My job isn’t to have all the answers — it’s to help you ask the right questions.
You know more than you realize. Share what you’ve learned.
And finally: Sometimes, you need a little reminder to remember how good you’ve got it. Because, right now, it’s possible that you’ve got it pretty good.
———
That’s a photo of Sally and I at a wedding in Colorado, on a great night with an amazing view.
A client had a question recently about something I’d worked on at BuzzFeed, so I went back into my email archives to try to find an answer. And what I found, unexpectedly, was this email:
It’s from the end of year 1 of my work at BuzzFeed. It said:
Monday marks 1 year since we really launched the newsletter program here at BuzzFeed. Quick numbers for you:
January 2013 5 newsletters — all automated, with about 20,000 total subscribers Newsletters drove 46,000 clicks to BuzzFeed Newsletters were the 28th biggest referrer of traffic to the site
January 2014 14 newsletters — all hand-curated, with more than 125,000 total subscribers Newsletters drove over 650,000 clicks to BuzzFeed Newsletters are the 8th biggest referrer of traffic to the site
I’ll be honest: I knew I did a lot of work that year — I just didn’t remember how much work!
Looking back, I know I was motivated to prove that newsletters could be a great tool for BuzzFeed, and I remember working long hours to keep the newsletter strategy moving forward. I was making stuff up as I went along, and I didn’t really have many resources at my disposal. I was lucky to have a few wonderful supporters in my corner who helped me stay on track. But even now, looking back at this email — which I wrote — I’m stunned at those results from year 1.
Did I really do that?
I know I can be dismissive of some of the work I’ve done in the past. I know I’m better at this now than I was a decade ago. I don’t always want to talk about the mistakes or lessons I learned along the way.
But I don’t get the chance to build Inbox Collective without that work I put in ten years ago at BuzzFeed. I’m grateful for that work, and I’m proud of it.
As I’ve played more golf over the past year, I’ve realized something: It’s easy to make too many changes.
Every time I check YouTube or Instagram, the algorithm serves me with another video promising a quick fix to my swing. Sure, you’re playing decently, Dan, but what if you adjusted your stance? What if you stood up taller? What if you had more bend in the knee at impact? What if you moved the ball back in your stance? What if you bowed your wrist at the top of the swing? What if you tried a lower follow-through? No, wait, what if you tried a higher follow-through!
And it’s easy for all these thoughts to get in my head and screw everything up. On a normal day, I’m a decent golfer. Not great, not terrible — but the more swing thoughts I have, the worse I play.
When I go to the driving range, sometimes I’ll try to implement a small tweak to my swing, but usually, I’m impatient. If it doesn’t work right away, I’ll drop it, or move on to the next tweak.
But if you keep changing stuff before you have time to see results, how will you know if it’s working?
No matter what it is you’re doing — improving a golf swing, running an A/B test, trying out a new strategy — you have to be willing to be patient. Find things you want to try, and commit to them for a certain length of time. Often, it’s not the tactics that are wrong — it’s just that you didn’t wait long enough to see the results.
———
That’s me, hitting golf balls at Chelsea Piers in New York. Not a bad view for a driving range!
I flew through Chicago a few weeks ago. I flew Delta, like I usually do, even though Chicago O’Hare is a hub for American and United. There aren’t that many flights on Delta out of O’Hare every day, and Delta’s flights have always operated out of some of the oldest gates at the airport.
But when I was there, the Delta staff mentioned something to me: They’d be moving to a brand-new terminal later in the month. That meant new gates, a new check-in area, and a new Delta SkyClub for their frequent fliers.
The SkyClub, in particular, was built with an interesting feature: For flights to New York’s LaGuardia Airport, passengers can board the plane directly from the SkyClub. They don’t need to exit the lounge and go to the gate.
Delta can’t compete with American or United when it comes to the number of flights or the connections they offer at O’Hare. But nobody else at that airport offers the ability for a business traveler to work from the lounge, then walk directly onto the plane. By building something like this, they’re hoping that frequent fliers from Chicago to New York might like the SkyClub enough to permanently change who they fly with.
This got me thinking about the things that make any person or any business stand out. For me, for the past few years, it’s been where I publish — people don’t easily forget the guy with a Google Doc. Many have asked me if I’d ever move Not a Newsletter over to a blog or another format, and the answer’s always been “no.” When you do something that stands out, you lean into it.
You still have to do more than just have a unique thing — if my Google Doc wasn’t very useful, it wouldn’t matter where I publish it. But having a unique thing might help you get noticed amongst the crowd.
I’ve lived in New York City for a decade, so I’ve gotten the chance to see some celebrities on the street. (Apologies to Matthew Broderick for the time I saw you on 21st Street and stared so much that you pretended to check your phone until I walked away. My bad.)
But one of my favorite recurring celebrity sightings was Jimmy McMillan — who you might remember as the Rent Is Too Damn High guy. He lived a block away from me in the East Village, and I regularly walked past him on the street. With such unique facial hair, he was easy to recognize. I often saw him wearing a T-shirt with his logo, which was a drawing of his own facial hair.
Thanks to “Saturday Night Live,” McMillan became a bit of a caricature in popular culture. Most saw him as a one-issue candidate with a memorable look.
But when I think of McMillan, I think of a guy who was unapologetically himself. (All these years later, he’s still pushing the issue of affordable housing forward, and as a New York City resident paying rent, I can’t help but agree with him.) He figured out who he was and what he cared about, and leaned into it.
Remember: It’s easy to blend in with the crowd. It’s easy to be afraid to stand out.
Every time I think about taking that easy route, I think about all those times I saw McMillan out in my old neighborhood, loudly and proudly himself. There’s only one of you; you might as well be whoever you are.
———
That photo of Jimmy was taken back in 2009 by Matt Law, and is used here thanks to a Creative Commons license.
There are three big things that any email sender needs to set up to properly authenticate their emails: SPF, DKIM, and DMARC. These are the three things that an email client like Gmail looks for to make sure that the person or company sending that email really is who they say they are.
And one of my readers pointed out that there was a small issue with part of my authentication settings. Not great — especially for someone who professionally helps out his clients with email authentication!
It was late in the evening, and I’d already had a full day of calls and work. The smart move was to wait until the morning, then make the necessary changes.
Instead, I thought: I do this all the time! I’ve got expertise here — let’s just do it now! So I quickly made some changes, and of course, I made a small mistake.
But when it comes to email authentication, there are no small mistakes — only big ones. And so I woke up the next morning to find out that not only had I made a mistake with my email settings, but now all of my emails were going to spam. I’d taken a bad situation and made things far worse!
A few hours later, the mistake was fixed, but not after quite a bit of panic and a lot of me slamming my head against my desk, asking myself why I’d been too impatient to wait until the morning when I would have been rested and fully ready to take on this task.
I wasn’t happy with myself. But at least I learned a few things — most importantly, the right steps I should follow next time with a client to make sure we get things right.
Everyone makes mistakes — even the experts. You learn from them, you figure out processes to make sure they don’t happen again, and then you move on.
———
That’s what my authentication settings look like now. The big three — SPF, DKIM, and DMARC — are at the bottom. There are only two options: PASS or FAIL. (You can probably figure out which is one you want.)
