Author: Dan Oshinsky

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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.

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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.)

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

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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.

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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.

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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.

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

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You’re Going to Make Your Own Choices.

When a reader signs up for Not a Newsletter, they immediately get a welcome email from me, in which I ask two things: Do you have a newsletter, and what’s the biggest challenge you’re facing with it?

Sometimes, the replies will be small and easy to reply to. Struggling with growth? Here are a few slides. Need help with a survey? Here are a few examples.

But other times, the replies involve a weightier topic — writers at major crossroads. I used to send back long responses to these readers, making the argument for why I thought they might want to head in a certain direction. What I discovered is that often, despite a thoughtful and well-sourced reply, they’d go in an entirely different direction.

These readers, I realized, weren’t looking for advice — they just wanted a place to vent.

It didn’t matter if my advice was good or bad. They weren’t looking for advice, and it wasn’t my place to give it.

So I’ve started changing how I reply to those messages. When I think I’ve got one of those emails in my inbox, I try to validate their reply (“That’s such an interesting challenge! I’ve had a few other readers struggle with this — it’s not easy!”) before asking a question or two in reply. I don’t share as many links as I do with other readers. Again, they’re venting, so my job is to listen. The right reply isn’t a solution — it’s a question.

These readers are going to make their own choices. All I can do is listen, ask, and hope that whatever choices they make are the right ones for them.

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That’s the email they reply to when someone signs up for my newsletter, which, by the way, you can do here.

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There’s Always More Work to Do.

the practice courts at the US Open are on right, with more courts on the left. You can see the Grandstand, one of the biggest courts at the facility, on the far left.

So we’re at the US Open last week. We’ve seen some great tennis already, but there’s one star we really want to see: Serena Williams. She’s playing in the night match at Arthur Ashe Stadium, the venue’s biggest court, but we don’t have tickets for the night session. So we do the next best thing: We find out when she’s practicing, and wait on the practice courts for her to arrive.

While we’re waiting, we’re hearing the roars from Ashe, where Coco Gauff, the 12 seed, is playing her second round match. She wins the first set, but trails 5-3 in the second set. The match seems destined for a third set. But then Gauff turns things around. She wins her serve, then breaks her opponent. The match goes to a tiebreak. We hear the roars as Gauff wins the tiebreak, the set, and the match.

And a few minutes later, we hear another round of applause from one end of the practice courts. We look up. It’s not Serena — it’s Gauff, walking out from Ashe directly onto the courts. “Her serve was off today,“ whispers someone behind us. I check the stats: Gauff finished the match with more double faults than aces. Not great.

So there she is, on Practice Court #5, mere minutes after winning a big match on center court, and she’s back out with her coach, working on her serve. For a lot of players, making the third round of a major would be a career highlight. But for Gauff, who made the finals of the US Open last year, there are clearly bigger goals in mind.

It reminded me that even the best in their field have an off day. And what do the greats do after an off day? They get right back to work.

Even when you’re at the top of your game, there’s always more work to do.

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That’s a photo I took of the practice courts, there on the right, at the Billie Jean King National Tennis Center in Queens.

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It’ll Be OK.

That was the view from my cabin porch

I just spent a week up in New England in a cabin, on a lake, in the woods. We didn’t have electricity or internet or cell service. My clients were excited about it: “You deserve a full week off,” they told me. My wife was excited about it: “You’ve earned this!” she said.

I was terrified.

I was terrified of the emails I’d get while I was gone. I was worried that I’d return to find 400 urgent requests that I was a week late on. I was worried that something terrible would happen to a client while I was gone and I wouldn’t be able to help.

And I logged back on yesterday to find… well, about 70 emails that actually required a personal reply. Not a single one was urgent. My website was still functioning. The Google Doc was still live. Nothing broke or went terribly wrong.

And in the week I was gone, I truly got the chance to unplug. I read three books, I swam, I napped, I did a whole lot of nothing.

Today, I’ll reply to all those emails, and tomorrow, I’ll get back to work. But I’m glad I got the chance to unplug.

Turned out that for all my fears, everyone else was right: It was OK to take a week off, and it was worth it.

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That was the view from my cabin. I kept my phone off most of the week, but did turn it on once or twice to take photos.

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The Things You Have to Do to Get There.

There are a few different ways to become a PGA Tour member, but the most direct is by being one of the top players on the Korn Ferry Tour, which is the top minor league circuit for men’s professional golfers. Just making it to the Korn Ferry Tour itself is hard enough — it requires first going through a series of qualifying tournaments, and then life on the Korn Ferry is a grind. While the PGA Tour offers massive checks, the Korn Ferry’s prize money is relatively paltry. (The player who finished in third place in yesterday’s PGA Tour event won $885,000; the prize money for the entire field at last weekend’s Korn Ferry event was $850,000.) But to get to the PGA Tour, you have to go through the Korn Ferry Tour, so those with dreams of playing on the big tour have to go through the minors first.

And yesterday, the PGA Tour announced the 25 golfers who played well enough during this Korn Ferry Tour to qualify for PGA Tour’s upcoming season. I was reading through their bios and found myself amazed by some of their stories.

Among the qualifiers are Paul Haley II, who qualified for the PGA Tour back in 2012 but played poorly in his one season on Tour. He spent a decade bouncing around the minor leagues of golf, but will be back after a strong season on the Korn Ferry. “Maybe if you were younger, you stress out about really small things and when you play bad, it seems like the world is coming to an end,” he told a PGA Tour reporter. “You’re not going to have your best stuff every week. You’re going to miss the cut. You’re going to shoot over par. But just taking that step back and realizing everything is still pretty good.” This time, he’ll aim to stick around on the top circuit in golf.

There’s Ben Griffin, who quit golf and was working as a mortgage loan officer — until his grandfather died, and Griffin decided to give golf one last shot. (A line in his grandpa’s obit: “His motto was ‘Hit them long and straight,’ having loved golf.”) A year later, Ben qualified for the PGA Tour.

There’s Erik Barnes, who had to take a job stocking shelves at a grocery store during the pandemic (base pay: $17/hour) to make ends meet when the Korn Ferry Tour went on hiatus during the early part of the pandemic. He’s 34 years old, but after more than a decade as a pro golfer, he’ll finally make it to the PGA Tour.

And there’s Kevin Roy, who once missed the cut in five straight events, which meant that he went more than a month without collecting a paycheck. Scrolling through Instagram one day, he saw a hat with the words “Have More Fun” and bought it. While other golfers wore hats with sponsor logos on it, he wore his “Have More Fun” hat as he turned his season around and qualified for the Tour. He’s 32 and will be a PGA Tour rookie.

It’s remarkable the things that people will do to achieve their dreams — the sacrifices they’ll make, the work they’ll put in, the challenges they’ll overcome. Even people at the top of their field struggle. But sometimes, reading stories like these reminds me that it’s possible to reach the top of your field — even if it takes a little bit longer than you expected.

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At the top, that’s a video of the 25 Korn Ferry Tour members who officially qualified for next year’s PGA Tour.

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The One Thing I Really Hope People Learn from Not a Newsletter.

Here's a recent screenshot from Not a Newsletter

Not a Newsletter will turn four in January. It started as a weird little side project; now it’s the single most important driver of business for Inbox Collective. Over the years, I’ve written more than 175,000 words for the Google Doc, built an audience of 8,000+ monthly readers, and stretched the Google-Doc-as-publishing format about as far as any one person can.

I can confidently say this: Google Docs aren’t meant for publishing. I get no data from them, they don’t show up in search (even though it’s a Google product!), and they don’t work well on mobile. This format has worked for me, but I wouldn’t recommend it as a publishing platform to anyone else.

But if there’s one lesson I hope people take away from my experience publishing the Google Doc, it’s this: Whenever you can, start small.

The Google Doc was one of the best minimum viable products I’ve ever created. It was small enough for me to quickly prove out the concept and the audience need; it was flexible enough that I could build a half-decent product from Day 1. I didn’t spend a dollar to launch this project, but still could create something that attracted an audience.

I never expected to turn Google Docs into a long-term publishing platform. (That being said, I’m probably stuck with the Google Doc format for as long as I write Not a Newsletter. It’s part of my personal brand now — I’m “the guy with the Google Doc”!) But I hope others learn from the strategy if they’re thinking of launching something new. Start small, start simply, start quickly — and see if you can prove out your concept. If it works, great. Upgrade your tech, invest in the project, and keep it moving forward.

And if not? Move on. There are always going to be other ideas for you to explore.

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That’s a screenshot of a recent Not a Newsletter. If you’re not on the email list, sign up here.

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Go Big.

Paul Simon plays to the crowd at Newport Folk Festival in 2022

One more story from Newport Folk:

We’d been told that at Newport, special guests sometimes show up. And then on Saturday night, Nathaniel Rateliff & The Night Sweats came out and played two Paul Simon songs in a row, and we realized: Paul Simon might be tonight’s surprise guest!

An hour later, after a half-dozen artists had played Simon’s music, Paul himself came out and played five songs with the band.

So we weren’t expecting much on Sunday night. How are you going to top a special guest appearance by Paul Simon? Brandi Carlile was expected to play with some friends. (The set was billed as “Brandi Carlile & Friends,” which made that a fair assumption.) We figured she’d bring out the usual group of indie musicians and colleagues. We didn’t realize one of them would be Joni Mitchell! And that a group of musicians would sit around in a circle and play for — and with — her.

What I loved wasn’t just that Newport brought out two icons. It’s that they found new ways to honor them. They’d clearly asked: How do we pay tribute to these legends? What formats can we try? How do we do something that’s never been done in the history of this festival?

Had a group of musicians played a tribute to Paul Simon, that would’ve been something. Had Brandi Carlile played “Blue” from start to finish, that would’ve been amazing. But instead, they somehow did something even more unexpected.

If you’re going to go big, go big.

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That was my view of the stage for Paul Simon’s set. Paul’s up there if you zoom in far enough.

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