The Sunday Digest: Newsletter Advice, and Our First Crossword

Happy Sunday!

Charli D’Amelio may have 100 million TikTok followers, but we’ve got 7,000 words for you to read today. An hour of audio content, too—and if you’re looking for something a little more interactive, don’t go just yet.

That’s right—it’s the first installment of the Everything Crossword, kicking off with a Thanksgiving edition. Scroll down for that and so much more, including our favorite writing from the Bundle and everywhere else this weekend.

We’re also remembering Tony Hsieh today—some of you reading this may be doing the same. Nothing speaks louder about his importance to our community than the outpouring of memories from people he touched personally over the course of his career. On that note, we’ve collected some of the wonderful personal stories people have been sharing about him this weekend below. Rest in peace, Tony.

What We Published

The lowdown on this week’s output, including 4 articles and 2 podcasts.

🦠 Julie Eberfeld is Listening

by Sherrell Dorsey in Free Radicals

To executive-turned-diversity consultant Eberfeld, diversity isn’t just a problem for HR—it warrants a strategic approach. If leaders and companies “want the best talent, they have to embrace diversity and inclusive leadership, full stop,” she tells Sherrell Dorsey in this enlightening and important conversation.

Read it (3,241 words)

💝 News Roundup #10: Snap launches its own version of Creator Fund & rare interview with OnlyFans CEO

in Means of Creation

This week’s roundup of passion economy news—complete with Li Jin and Nathan Baschez takes, as always—covers the future of OnlyFans, the membership trend sweeping creator platforms, and much more.

Read it 🔒 (2,107 words)

🔮 Three Shorts: Snap, Apple, Vox

by Nathan Baschez in Divinations

Our new Divinations series unpacks strategy in as few bullet points as possible. In the latest installment, Nathan looks at Snap’s new TikTok-esque Spotlight feature, the lowered developer fee in the App Store, and talent shakeups at Vox. Read on for “why Vox Media seems to be caught between a rock (NYT) and a hard place (Substack).”

Read it 🔒 (1,124 words)

🗣 Episode Six: The Omniscient Writer 🎧 

on The Long Conversation with Rachel Jepsen

This week on our podcast dedicated to the craft of writing, Dan, Adam, and Taylor Majewski each told host Rachel Jepsen about ten jobs they might have had in another life. Based off a writing exercise one listener wrote us was “absolutely incredible,” the ensuing conversation covered alternate realities and why we do personal writing with an audience in mind.

Listen (34 min)

🕊 Why Ask Jerry

by Andy Sparks in Ask Jerry

“One thing that’s drawn me to Jerry’s career are the ways in which he makes me feel seen,” writes Andy Sparks of coach and “radical self-inquiry” leader Jerry Colonna. In this conversation, Jerry reveals the motivation behind Andy and his new series: “making the people asking the questions feel like they’ve actually been heard.”

Read it (471 words)

💞 #46 - Is Substack Really Milquetoast? 🎧 

on Talk Therapy with Dan Shipper and Nathan Baschez 

Digging into a recent article claiming that Substack is becoming homogeneous, Dan and Nathan pushed back on the notion that independent newsletter writers have to choose between quality and frequency.

Listen (17 min)

What We’re Reading

Advice for Newsletter-ers

This week has brought more coverage of the Substack Boom, but novelist Robin Sloan also dropped some newsletter-ing wisdom, inspired by Patrick Tanguay’s Sentiers newsletter:

“A personal email newsletter ought to be divided into seasons, just like a TV show.”

It’s a clear, quick piece—and it indulges a few counterarguments against organizing your newsletter as such, so it’s worth a read no matter your which side you fall on.

More Good Writing

What’s Going On


Puzzle Time

When he’s not busy dissecting strategy, Nathan is coming for Will Shortz’s crown. You’ll have to click over to play it, but head back here to let us know what your finishing time is.

Tweets of the Week

We still want you to write for us!

Are you sitting on the next great piece of practitioner-focused business writing? Last week, we announced the Everything Fellowship, an open contest for $1,000, and your essay published here. 

We’re still accepting pitches, so submit yours (along with a writing sample) at the link below. The submissions we’ve already received have been exciting, diverse, and have covered new ground. We’d love it if you added yours to the mix. If you have any questions, send them to [email protected].

Winner’s Circle

Last week, we announced the first winner of our Survey Raffle—and now we’ve got another. Congrats to Sara R. from Santa Clara, CA, and thanks for leaving us some useful feedback! Here’s what Sara chose, if you’d like to read along:

An Invitation to Everything

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@MattWeatherall over 1 year ago


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