Author: Dan Oshinsky

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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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Everything Changes, and That’s OK. (Part II)

That's a photo I took of The Linda Lindas on stage at Newport Folk on July 24, 2022

57 years ago today, Bob Dylan went electric at the Newport Folk Festival. Reports say the crowd shouted and booed at Dylan — “Like a Rolling Stone” had been released only days earlier, and the crowd at Newport Folk wasn’t prepared for an artist suddenly heading in a new direction.

Yesterday, I went to Newport Folk, and saw an all-girl teenage punk rock band, The Linda Lindas, absolutely rock the festival. Newport Folk is more than folk now — there are acoustic acts, and bluegrass, and country, and even rap. Watching The Linda Lindas reminded me of how much even established brands like Newport Folk can change. The festival that was once synonymous with Dylan and Joan Baez and James Taylor is now the kind of place where a teenage rock quartet can show up and command a stage for an hour. I’d bet that there were more than a handful of people at the festival yesterday who had parents or grandparents at that Dylan show in 1965, and yesterday, those in attendance roared for a band that wouldn’t have fit in fifty years ago at that festival.

It’s OK that Newport’s changed. It’s OK that one of the original American music festivals can now host Joni Mitchell and The Roots on the same stage in the same afternoon. The spirit and mission of Newport remain the same, but the sounds coming off those stages are as different as ever.

And not everything changes. At one point during yesterday’s show, one member of the The Linda Linda, guitarist Lucia de la Garza, pointed towards a voter registration tent just off stage. “Us kids can’t vote,” she said, “but you can!” Their sound didn’t sound like anything from the original version of Newport Folk, but at the moment, if you closed your eyes, their message sounded a lot to me like Newport in 1959.

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That’s a photo I took of The Linda Lindas on stage at Newport Folk. They’re amazing. If they come to your city, go see them!

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Everything Changes, and That’s OK.

people at work on a construction site

College athletics are in flux right now. Teams are changing conferences (Rutgers vs. UCLA and Oklahoma vs. Kentucky will soon be in-conference matchups), and Name, Image, and Likeness rules mean that some athletes are now (legally) collecting checks from sponsors. Greg Sankey, commissioner of the Southeastern Conference, addressed all these changes this week at the conference’s annual media days for football. “It’s never going to be the same,” he said, “but it doesn’t have to be the way that it is”

The same could be said for many businesses. It’s certainly the case for the news world, where I come from. Are we going back to the days when local newspapers employed hundreds of journalists? Probably not. But it’s up to us to build something new moving forward. Just this week, I’ve talked with local news outlets investing in solutions journalism, digital outlets building out new models for revenue sharing with writers, and individual writers who are building an entire business through their own newsletters or podcasts.

Everything changes, and that’s OK. We can fight it, or we can accept it and try to figure out how to build the best possible future for ourselves. The choice is ours.

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That photo of a construction site comes via Shivendu Shukla and Unsplash.

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Introducing… Inbox Collective’s New Website.

That's what the new website looks like

One of the great lessons from BuzzFeed was to launch stuff quickly. Put it out there in the world, try to build an audience, and then decide what to do next. The simpler and faster, the better!

It’s why when I launched a website for Inbox Collective in 2019, it wasn’t a website — it was a set of Google Slides. Put it out there, see what happens, then figure out what’s next. If you have enough to start, then start.

Over the past three years, what’s happened is that the business has grown and grown. And it’s become obvious to me that I didn’t just need a better website to explain how I consult with brands. I needed a place to share more stories to further serve the email community.

So here we are: Inbox Collective is officially a real website. We’ll be publishing a few times per month, with case studies, how-tos, feature stories, and more. You can check it all out here.

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