Dan Oshinsky | danoshinsky.com

11/20/202211/20/2022

I Am 35 Years Old. This Is What I Believe.

Here we are at a wedding in Colorado. It really is pretty out there!

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.

Overdeliver, but don’t overwhelm.

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!

Whatever you want to do, you can.

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.

11/14/202211/14/2022

Be Proud of the Work You’ve Done.

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.

11/06/202211/06/2022

Don’t Overtinker.

That's my golf swing. I think I'm too hunched over, or maybe my right elbow is too high, or maybe I need to pick a new sport.

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!

11/01/202211/03/2022

What’s Your One Unique Thing?

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.

———

That photo is of the new Chicago SkyClub, and it comes via Delta’s own site.

10/23/202210/23/2022

Be Yourself. (Aggressively So, If Necessary.)

Here's a photo of Jimmy, which was taken back in 2009.

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.

10/15/202210/15/2022

Even The Experts Make Mistakes.

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.)

A few weeks ago, I did something stupid.

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.)

10/10/202210/10/2022

Are You Ready For the Work?

Bob Uecker’s a former baseball player, and longtime radio broadcaster for the Milwaukee Brewers. (You might also remember him as the announcer from the movie “Major League.”) Last week, on the final day of the season, with the Brewers eliminated from postseason contention, Uecker spent the final broadcast of the season telling baseball stories.

Here’s my favorite of his, as explained by Frank Schwab of Yahoo Sports:

Bob Uecker today talking about how he started with the Brewers scouting the Northern League. He didn’t know to have a stopwatch. “I’d cup my hands like I had a stopwatch, then ask the guy next to me, ‘What did you have him at?’ They’d say ‘3.4 seconds.’ I’d say ‘Yeah, me too.'”

It reminded me of something Adrienne Miller described in her book, “In the Land of Men,” about her first day at GQ:

“As [GQ editor David] Granger and I spoke, it became apparent that I did have one thing going for me: I was able to talk about past issues of GQ. Later, he said that I got the job because I was the one person he’d interviewed who’d actually even bothered to open the magazine.”

“ ‘Never underestimate how unprepared most people are,’ he would later observe, correctly.”

Don’t forget your stopwatch. Read the magazine in advance. And if you’re not sure what you need for the first day, ask. Otherwise, you might not be prepared to do the work.

10/02/202210/02/2022

Three Years Ago, He Replied to My Welcome Email. Here’s What Happened Next.

So here’s how a response to a welcome email led to one of the best things I’ve done in my three years of running Inbox Collective.

In October 2019, I get an email from Jan Birkemose, who runs the Danish media website Medietrends. He got my welcome email and wrote back, telling me a little about his business. We start trading notes back and forth. He tells me about these courses he’s running, including a two-day class all about email.

A few months later, Jan invites me to speak as part of that course. It goes well. He invites me back for another session later that year.

And then two more in 2021.

In December 2021, I happen to find myself in Denmark after Mette Will invites me to speak at Email Summit DK. (Thanks again, Mette!) On my last night in town, Jan and I meet in person for the first time. He asks if I’d be interested in hosting an email workshop of my own in Denmark in 2022.

Yes, I most certainly would.

I’d been wanting to do one of these for a while. I’d built up a series of workshop session that I do with individual newsrooms, but I’d never done them with several different orgs in a single room. Only thing had stopped me: Planning the event itself. Booking a space, coordinating with all the different teams, scheduling lunches for a big group — that part seemed intimidating to me.

But Jan had done these sorts of workshops dozens of times already. If I was going to take the leap on something like this, I needed a partner like him.

Fast forward to mid-September. It’s the end of a beautiful fall week in Copenhagen, and we’ve got 20 participants from 16 organizations (who came from four different countries) in the room together. They’ve learned a lot of the past three days (and, thanks to Jan’s planning, been fed every day!), and are telling me about what they’re going to do next.

They’ve got ideas: For surveys to run, and growth tactics they want to implement, and newsletters they want to launch. There’s a lot of excitement in the room, and a lot more work to do, but this group is ready to take it on.

Now that it’s all over, I’m feeling grateful for the opportunity to share what I’ve learned, and grateful for partners like Jan, who believed in this workshop idea and gave me the chance to lead it.

(And thanks for writing back to that welcome email, Jan! It’s amazing to think about the doors that a single email reply can open.)

———

That’s me with the group at the end of the workshop. What a week!

09/25/202209/25/2022

You Don’t Know How Good You’ve Got It.

Here's what the TV quality looked like. Not great!

Two decades ago, I flew British Airways for the first time. I was 13 years old, and it was the greatest flight I’d ever been on.

What made it so great? Two words: Personal TVs. Every seat had its own television, and each TV had a dozen channels. You could flip through and watch any movie or TV show playing on that channel. For a kid like me — especially one who didn’t have cable TV yet — this was heaven.

Tonight, I flew on British Airways for the first time since that flight. And I’m pretty sure it was the same plane I’d flown on 22 years earlier.

What makes me think that? Well, they still had the same TVs — and they still had that same lineup of channels.

In 2022, we’ve come to expect a little more from our in-flight entertainment. We expect there to be dozens, if not hundreds, of on-demand movies and TV shows.

This flight had two channels, showing two movies of their choice, and a picture quality that reminded me of the days of rabbit ears on our set-top box.

Look, I know this is a first-world problem. And it the end, it didn’t really matter at all. Instead of watching a movie, I read a book, did a little work, and took a nap.

But it was a nice reminder of how far things have come in the past few years. The next time I’m flying and I *only* have a few dozen options to choose from, I might be a little more grateful. Sometimes, you need a little reminder to remember how good you’ve got it.

———

That’s a photo of the TV at my seat. The wavy lines aren’t the result of any weird pixelation caused when taking a photo of a screen — that’s just what the screen looked like.

09/17/202212/13/2022

You Can’t Do It All.

Right now, I’ve got a lot on my plate. I’ve got a consulting business, some upcoming workshops, and I’m building out a publication at inboxcollective.com. Any one of these could be its own full-time job — I’m trying to find the right balance to do all three!

And still, I find myself getting excited about new projects.

On my to-do list, I have a big list of “Someday” projects. And true to the word, some days, I get especially excited about them. I’ll start to flesh out ideas for training more newsletter editors, or building out a digital course, or launching a magazine.

But I know I can’t do it all — there are only so many hours in the day, so I have to prioritize. My go-to tactic: I’ll add a note to my to-do list to revisit the idea about a month later. If I’m still excited about the idea after a month, then maybe that’s something I’ll actually start to work on. (Often, a month later, I’m less enthusiastic about it, which confirms that I made the right decision to wait off on that idea.)

It’s not easy to ignore an idea I’m excited about. But I know I’ll have more ideas, and I know I have plenty of work to tackle now. My challenge is staying focused and not letting the shiny new idea distract me from the work I need to do.

———

That’s a screenshot of a recent week on my to-do list. Lots to do — even without new ideas!