14 Books That Shaped the Way We Think About Newsletters

These stories are presented by InboxArmy, a full-service email and lifecycle marketing agency. Whenever there’s an email project that’s too complicated for me to take on alone, InboxArmy is the team I turn to for help. They’ve got experts to help you build automations, code email templates, and even send campaigns. Their team of email pros can help you get the job done right. Interested in learning more? Schedule a call with them today.

Prefer to listen to this story?

It’s so satisfying when you’re reading something and you come across a passage that you connect to your own work. Maybe you’ve been stuck on an idea for a while, and an inspiring biography or memoir clears away the fog and helps you see the next step. Maybe you’re reading a work of fiction, and the creativity on display inspires you to break the mold with your next piece. Perhaps you Google a footnote and find yourself deep in a wormhole that sets you off on your next passion project.

What’s cool, we’ve found, is that many of the books that have most influenced us and the newsletters we send have little if anything to do with newsletters at all. We weren’t trying to do research or get professional development. And these authors weren’t thinking about newsletters when they wrote — in some cases, they were writing at a time before email even existed. And yet, their writing has helped us better ourselves, our work, and our understanding of our readers.

So today, we wanted to take a step back from the usual email-centric content you see here on Inbox Collective and share a few of the books that have shaped the way we think about our work in the newsletter space. Maybe you’ll find one that helps you better understand and write your own newsletter.

(We’ve linked to Bookshop for each of these books — we like how they support local bookstores, but they also pay us a small commission for every book purchased.)

Amusing Ourselves to Death: Public Discourse in the Age of Show Business — Neil Postman

The first time I read “Amusing Ourselves to Death,” I was puzzled. How could a book written in 1985, before the internet, social media, or email became part of our lives, so accurately describe today’s media landscape?

The answer is that in his polemic, culture critic Postman explains a timeless theory of media. He describes the idea that each technological change alters the way we communicate with our audience. The medium we use shapes our work — it’s up to us to lean into the advantages of that new technology.

To put it another way, you’d talk to your readers differently if you’re writing an idea in a book vs. writing a newsletter vs. speaking on a podcast. 

The unique aspect of email that any newsletter operator needs to understand is that you can broadcast an idea to a wide audience all at once (like with TV or radio) while sharing your unique voice (like on a podcast), but with the ability for a reader to talk back to you (like you’re engaging in a one-on-one conversation). It’s a rare mix, and it’s why the best newsletter operators can leverage that combination of scale, personality, and engagement. They’re leaning into the idea Postman shared — even if email was still years away from becoming part of our lives at the time he wrote it. —Dan

The Country of the Blind: A Memoir at the End of Sight — Andrew Leland

We’ve published several pieces on the importance of accessibility and discussed how many subscribers use screen readers to convert newsletters into spoken language. But before “The Country of the Blind,” a book about how the visually impaired community experiences the world, I’d never truly considered how those users use those screen readers. I assumed that most people listened to text at 1x or 1.5x speed. But as Leland writes, that’s not usually the case:

“Screen readers can also be adjusted to read every letter and punctuation mark aloud, though of course this sort of reading happens rarely — it’s much easier to turn a text up to five hundred words a minute and let it rip. This hyper-speed synthesized speech sounds unintelligible to the untrained ear, like a coked-up C-3PO trying to record an audiobook, but with practice, listeners can comprehend aural reading speeds of more than six hundred words per minute. Most blind people I’ve met crank their screen readers up this fast.”

Understanding that changed the way I think about my writing. I’m not saying I’ll stop using little asides through my pieces — I don’t think anything will break that habit. But if some readers prefer to whip through a newsletter at hyperspeed, it means the writing has to be perfectly clear to be understood at that speed. The better I can edit my work with that reader (or listener) in mind, the more my readers can understand what I’m trying to say. —Dan

Daisy Jones & The Six — Taylor Jenkins Reid

“Daisy Jones & The Six” is a fictional oral history of a rock and roll band akin to Fleetwood Mac, a wonderful read about the highs and lows of building something ambitious. I’ve been lucky to have worked with newsletters at all stages of the process — from the early days, when nobody’s reading, to moments where there are lots of eyeballs on what you’re doing. This quote sums it up nicely — working on a newsletter is, of course, different from being a rock star, but the ups and downs are the same:

Let me tell you the sweet spot for being in rock ’n’ roll. People think it’s when you’re at the top, but no. That’s when you’ve got the pressure and the expectations. What’s good is when everybody thinks you’re headed somewhere fast, when you’re all potential. Potential is pure fuckin’ joy.

That period when everything’s working and everyone’s rooting for you? Pure fuckin’ joy. —Dan

Four Thousand Weeks: Time Management for Mortals — Oliver Burkeman

Most books about productivity tell you how to get through tasks faster so you can take on more tasks. And if you run a newsletter, you probably have a lot of tasks! You’re writing newsletters, you’re replying to readers, you’re coordinating with sponsors, you’re launching new things. Not only does our culture glorify the grind, but there is real value in completing numerous tasks.

But Burkeman’s book isn’t designed to simply help you squeeze more work into the limited time you have. Instead, inspired by a startling fact — a human who lives to the age of 80 only has 4,000 weeks to live — he’s asking bigger questions: Where do you spend your time? Why are you spending your time there? What do you really want to prioritize? What are you going to say “no” to in the years ahead?

As Burkeman writes:

[In] working within the limits of your moment in history, and your finite time and talents, you actually got around to doing — and made life more luminous for the rest of us by doing — whatever magnificent task or weird little thing it was that you came here for. 

Working on a newsletter is probably more “weird little thing” than “magnificent task.” But Burkeman’s book serves as a nice reminder: Any time you get excited about trying something new, it’s worth asking: Is this new thing really worth my time? —Dan

The Good Enough Job: Reclaiming Life from Work — Simone Stolzoff

With a newsletter, it’s tough not to feel like the goalposts keep shifting on you. You’ve gotten your newsletter to 10,000 readers? Bad news: Some other newsletter that covers a similar topic got to 100,000 and got a profile in the New York Times. You’re making $50,000 a year on ad sales? I don’t want to break it to you, but some other newsletter is doing double or triple that. It can be disorienting and discouraging — your big milestone suddenly seems insignificant.

And that’s where “The Good Enough Job” has such a wonderful message. It asks: How much do you really need? What is enough for you? And are you OK with the idea of saying “no” and leaving something — revenue, growth, fame — on the table?

Throughout the book, Stolzoff introduces readers to people who’ve made a conscious choice to say, “This is enough.” It’ll make you consider the idea that maybe what you want isn’t the biggest megaphone or the most money — it’s the confidence to be content with what you have. —Dan

Griffin and Sabine: An Extraordinary Correspondence — Nick Bantock

This illustrated mystery series, published in the early 1990s, really tickled the part of my mind that was stimulated by the anticipation, mystery, and intimacy of person-to-person correspondence. I was in high school when this mystery series came out, the books formatted with real envelopes and letters, exquisitely illustrated, that you could take out and turn over and read as if you were the actual recipient of the letter.

I admit I don’t remember very much about the actual plot of the series (if I recall, it was regarding whether one of them existed or was a figment of the others’ imagination). However, as a youngster who loved writing and receiving letters, these books enforced the feeling I carry to this day that sometimes, the right letter (or email, text, or DM) can provide a dopamine hit of mystery and promise, wit and even romance. Could this missive I’m writing be beautiful and interesting, seductive or illuminating as well? Only one way to find out. —Claire

I Never Thought Of It That Way: How to Have Fearlessly Curious Conversations in Dangerously Divided Times — Mónica Guzmán

I’ll often have an idea that I’m excited about — so excited that I can’t wait to share it with readers. And when I do, I often receive clear feedback: Dan, we don’t like this, or Dan, the way you’re thinking about this is all wrong.

I don’t love being wrong. It’s tempting to be defensive or to fight back. But the better thing, for myself and my readers, is to open myself up to the possibility that someone else might see things differently — and have a great point to make. In “I Never Thought Of It That Way,” Guzmán explores ways to challenge your own assumptions and introduces questions to inspire tough-but-productive conversations. As Guzmán writes:

It can take some guts to set aside your judgment of someone’s opinion to wonder about them. Your intuition, influenced by sorting, othering, and siloing, will want you to howl, fight, or just walk away. It can take some guts, too, to put your opinion into conversation with an opposing one without any armor. What if people get the wrong idea about where you stand?

And what about where you— and they—have been? We get stuck on opinion, too, when we lose sight of the person who holds it—a person who’s arrived at that opinion after walking a path we can’t see.

Which leads us to the most powerful question any of us can ask across a divide:

Where are you coming from?

If you’re going to open yourself up to feedback — and I’ve long suggested that everyone should — then this book can help you collect that feedback more effectively while examining your own biases. —Dan

ReWork — Jason Fried & David Heinemeier Hansson 

Entrepreneur magazine once assigned me a story covering Basecamp’s attitudes toward work (particularly traditional office expectations), so I read the software company founders’ books for research. They had a lot of ideas for working smarter that I felt could be scaled to a company of any size, even a one-person operation like mine. It was a fun, snappy read, and the idea of “selling your byproduct” really resonated with me. Selling your byproduct meant seeing if you can repackage something valuable you may have passively (or not so passively) gained through your process of honing your core product. In my case, that realization led me to self-publish a booklet of freelance pitches I’d successfully sold to clients (self-serving link here!). 

This advice really applies to indie newsletter providers as well — it’s hard to come up with something fresh every week! I’m still learning that I can take a classic old post and brush it off, and readers will feel like they’ve gotten something useful and not just a rerun. I try to experiment with my newsletter’s best asset — my audience — by giving them ways to promote their own businesses and throwing out different deals. (I’ve had success by comping a subscription for readers who donate to my fundraisers.) 

Dan and I have also used this mentality internally — my question for him about what to do next was posed in earnest, and he came up with the idea for us to chronicle our discussion and next steps. Not only did I get some good advice, but we got a good piece out of it that elicited great feedback from the Inbox Collective audience that will probably inspire future pieces.

Recognizing the various ways to get different uses from what you did with your time and energy can be both good business and personally rewarding. —Claire

The Sober Curious Reset: Change the Way You Drink in 100 Days or Less  — Ruby Warrington

At one point during the COVID lockdowns, I received an advanced reader’s copy of this “quit lit” book by Ruby Warrington. After one especially rough night, I decided it was time to expand my occasional month off alcohol and see what 100 days off did for me. Long story short, I haven’t taken an alcoholic drink since I cracked this book about four and a half years ago. 

What does this have to do with newsletters? In her series of challenges to prompt the reader to reconsider their relationship with intoxicants, Warrington addresses the notion of boredom and how many of us turn to substances to avoid having to sit with our own potential banal, unpleasant brains. Warrington asks:

Why are we so anti-boredom? What’s actually wrong with

having nothing to do, and nowhere to go? Does being bored make you a boring person . . . or is it just a sign that you’re clearing out mental space for something new? The truth is that time spent being bored is an essential part of the creative process. Which also makes it an essential part of living a more exciting, fulfilling, and dazzling life.

She then challenges the reader to actively lean into boredom:

In whatever moment you find yourself between meetings, deadlines, errands, and obligations today, instead of reaching for your phone, just sit there and stare into space. DO NOT be tempted to use this time to meditate. Just breathe and enjoy the feeling of nothingness. Consider that in these moments of “being bored” you are clearing internal space for new ideas, new dreams, and new inspiration to drop in.

Despite speaking to audiences of hundreds, even thousands of readers, newsletter writing can be a solitary activity accompanied by highs, plateaus, and lows. As someone who has plenty of mood swings that correlate to my creativity and success, I was reassured and heartened by Warrington’s proposal that boredom is not only natural but an essential part of the process. I’m not defective if I have days where I’m just not feeling it, or wonder what I’m doing, or feel like I don’t have something to say. And to be honest, my readers probably wouldn’t want to hear from someone who doesn’t share that sentiment.

Warrington’s book also includes a challenge to reconsider how you start your mornings, which also changed my life. Instead of waking up and trying to get “ahead” on work, which never seemed to make me feel happier or more accomplished, now in the mornings I take the time to read a novel or magazine, a much kinder and more inspiring way to start my day. —Claire

Sourdough Or, Lois and Her Adventures in the Underground Market — Robin Sloan

“Sourdough” is one of those books where the one-sentence logline doesn’t really do it justice: It’s a work of fiction about an amateur baker and sourdough starter.

It’s also a fantastic, whimsical, weird piece of fiction, and one of the more unique books you’ll ever read. (I’m not the only one who struggled to explain this book. An NPR review explained: “It’s like ‘Fight Club’ meets ‘The Great British Bake Off.’” I don’t think it’s like either, but the point is that it’s hard to explain a 272-page novel all about bread.)

Reading it reminded me of all the times I’ve heard a newsletter pitch for something that just didn’t resonate with me. “Is there really an audience for something like that?” I’d think. And then a year or two later, I might read an interview with the writer — they launched it, and now it’s doing great. Readers love it!

Anyway, give those weird ideas a chance. If the writer is passionate about it, you never know when it might find a home with a bunch of readers who are equally excited about it, too. —Dan

Subtract: The Untapped Science of Less — Leidy Klotz

It’s natural to want to do more. I’ve got a long list of ideas I’d love to try with my newsletter. But the challenge, of course, is time and energy: I run a consulting business and this website, and I’m a dad, and occasionally, I like to grab five minutes alone for myself. (Ten if it’s a good day!)

That’s where Klotz’s book is so instructive. He talks about the mistake that too many people make when it comes to their work and their lives: They add and they add and they add to try to make things better. But we forget about the other side of the equation: Sometimes, we have to subtract. “Subtract” helped me think about the trades I have to make in my life. If I’m going to say “yes” to something new, I need to say “no” to something else so I can make space for that new thing.

But it’s not just about time: it’s also about the newsletters I send. Are there things I can subtract from my email that’ll make it more useful for readers? Do I need that extra sentence in the intro? Do I need the intro at all? By clearing space on the screen for the ideas that matter, I might be able to make those ideas matter more.  —Dan

Surprise: Embrace the Unpredictable and Engineer the Unexpected — Tania Luna and LeeAnn Renninger

In “Surprise,” Luna and Renninger explore the psychology behind surprises. Surprising people is important, they write, because it reminds us “that someone cares deeply about them and believes they are worthy of special attention.” But creating a surprise can be tricky in the newsletter space, since readers often reward routine. The challenge for you as the creator, the authors explain, is striking a balance between routine and unexpected — underpromising and overdelivering on an idea, or sneaking in a little surprise to keep your audience on their toes.

When it comes to launching a new idea, the authors have this advice, which isn’t directed to newsletter operators but feels like it is:

“Observe people’s reactions to your idea. Do they shift uncomfortably or do their eyes light up? Do they change the conversation or pummel you with eager questions? Do you have to explain your idea from scratch or can you compare it to something that already exists (It’s like _______, but different.)? If you’re finding that your idea is too surprising, you have a few options: Iterate some more, find a different audience…, or be patient and wait for the world to catch up to you.”

This is great advice for whatever you launch: a new paid product, a new event, or even a new section of your newsletter. If you can pass the test Luna and Renninger described above, you’ve got an idea that’s going to surprise and delight your audience, who will want to keep supporting you. —Dan

Unsubscribe: How to Kill Email Anxiety, Avoid Distractions, and Get Real Work Done — Jocelyn Glei

I grew up at a time when email was becoming mainstream, so I remember what it was like when a greater percentage of emails actually contained something valuable or interesting compared to requests or dry information, scams, and all the BS that takes up so much space in the average inbox. But as I got more used to pulling the inbox lever to see what treat might be in store for me, I let checking email — oh! Who could this be from? — distract me way too much. This got worse as I got older, acquired portable email devices, and built my career and thus a life that involved even more emails. 

When my second son was a baby, I read Glei’s book, and it helped me get a handle on my inbox. I went from having my email open most of the time and responding to it in real time to assigning a segment of the day to triage and dispatch what I have to. I sometimes still let my inbox run in the background, but I feel less inclined to answer everything right away thanks to Glei’s book. 

It is easier said than done when it comes to not prioritizing email when you are someone who sends emails for work, but I think many people also aspire not to let their technology rule them, and so are supportive when other folks do the same. Notably, Glei clarifies on her site that she no longer considers herself a productivity expert due to burnout. “What we truly need as a society is to be healed from our addiction to productivity,” she writes. “My work has since become about undoing our obsession with doing and advocating for new, heart-centered ways of living, working, and being.” — Claire

Writing Tools: 55 Essential Strategies for Every Writer  — Roy Peter Clark

“Writing Tools” is the book I wish I’d read decades ago. It’s made me think about the choices I make as a writer — the words I use, the ones I cut, the ideas I choose to share. It made me a better writer.

Each chapter in “Writing Tools” offers an idea for how to improve your writing. There’s the practical (“Tool 11: Prefer the simple over the technical”), the creative (“Tool 21: Know when to back off and when to show off”) and the unexpected (“Tool 32: Place gold coins along the path”). Each chapter closes with practical tips to put the chapter’s big idea into action. In a chapter on voice, Clark says:

Read your writing aloud to a friend. As, “Does this sound like me?” Discuss the response.

In a chapter on procrastination, Clark says:

If you are a plodder, it may be worth your time to experiment with some forms of freewriting. If you are stuck, try writing on your current topic for three minutes, as fast as you can. The purpose is not to create a draft, but to build momentum.

And in the chapter on self-editing, Clark suggests:

Flip open to a page of this book at random. Search for clutter. Cut words that do not work.

As I write my newsletter, I try to keep Clark’s voice in my head. I’ll read drafts aloud if the writing feels generic. I’ll do mini-writing sprints to give myself the kickstart I need. I’ll trim the fat from those first drafts.

Anyone can be a good writer. You just need the right tools.  —Dan

Thanks to our sponsor

The stories you’re reading on inboxcollective.com are brought to you by InboxArmy, a full-service email and lifecycle marketing agency. They work with businesses of all sizes to help you write, design, code, and send great email marketing campaigns. When you work with InboxArmy, you’re adding an entire network of email pros to your team — but at a price that works for your business. Interested in learning more? Get in touch here.