The making of a newsletter
There's the ideal, and then there's the reality. Plus: four reader giveaways!
Your Five-Year Plan is a newsletter about embracing life’s profound uncertainty.
Maybe your own plans went up in flames; maybe you’re considering a big, scary leap. This is your trusty companion while you’re writing the next life chapter.
Welcome to the conversation—and to the adventure that unfolds when your plans go sideways. This is letter #45. ✨
🎁 Four gifts for four lucky subscribers
April marks this newsletter’s first anniversary. In honor of that milestone, I’m writing about creativity this month—and giving away an armful of books to subscribers! As a generous bonus, the author of one these books is offering you an extra treat.
If you’re living through change, or considering making one, chances are you could benefit from the wisdom offered in one of the following books:
🚀 Life Is in the Transitions: Mastering Change at Any Age, by
. This book right-sized my understanding of how much change is “normal” during our lifetimes, and made me feel like part of a big community—rather than someone going through transition alone. Want an empowering narrative about change backed by lots of data and stories? This is the pick for you.⛰️ Adventures in Opting Out: A Field Guide to Leading an Intentional Life, by
. Reading this book feels like sitting down for coffee with a warm, wise, encouraging friend, which is exactly what you need when you’re making a radical shift. Thinking about embarking on an uncharted path—or just starting along one? This is the pick for you.💰 Money and Love: An Intelligent Roadmap for Life’s Biggest Decisions, by Myra Strober and
. Money and love are the source of life’s most high-stakes decisions. Too often, though, we’re making these decisions on a wing and a prayer. Making a tough call about your finances or relationships—one that could benefit from a bit more structure? This is the pick for you.
Enter the book giveaway
It’s open to all US-based subscribers of this newsletter! Just drop a comment that includes the book emoji (🚀 for Bruce’s book, ⛰️ for Cait’s book, or 💰 for Myra and Abby’s book) that fits your situation.
On May 1, I’ll pick one winner per book at random.
Plus: a course giveaway, courtesy of author Abby Davisson
Abby is teaching a live, virtual, cohort-based course starting April 26. It’s called Make Big Life Decisions with More Ease and Less Angst (I mean…yes, please).
For anyone considering a choice that feels scary, daunting, or exciting—maybe a career pivot, a move, investing in a relationship or leaving one—Abby will help you break down a complex decision into manageable pieces. You'll walk away with an action plan customized to your specific situation and constraints.
Abby has generously offered a free spot in her course to a reader who could benefit. To be entered into a drawing for the spot, apply using this link by April 19 and mention "Your Five-Year Plan" in the question that asks "How did you hear about this course?" The winner will be notified by April 22.
Even if you don’t win, all readers can enter code PLAN100 for $100 off the course price. (Reach Abby at abby@abbydavisson.com with any questions.)
On to today’s letter!
When we see the finished product of someone’s else’s creative work, it’s easy to romanticize what led there.
We know that a final draft is usually the result of a first and second one; still, our sanitized vision of the drafting process usually isn’t the full or accurate picture. Because that, of course, would include some combination of procrastination, existential despair, and—depending on the week—a primal scream or two.
That’s why I loved
’s paywalled-but-worth-it photo essay that walks readers through her own Sunday letter process: it’s refreshing, hilarious, and utterly relatable in its messiness.Over the last year, I’ve aspired to many newsletter-writing best practices, only to find that my reality strays wildly from these ideals. Whether or not you’re working on a creative project, you’re well aware of this ideal-versus-reality dynamic, too.
Recently, a friend casually mentioned having rented her own office space. Immediately, I conjured a vision that included a lofty ceiling, bay windows, and afternoon Nespresso breaks. The reality: an office perched above the local hardware store, recently abandoned by a guy named Keith who’d left all his sweaty cycling gear behind.
Still, once the gear got the boot, it was an enormous upgrade from the home bathroom closet where she used to call clients while hiding from her two small children. (In her words, “Thank God for Zoom backgrounds.”)
In honor of the messy reality we all share, here’s how the newsletter sausage gets made…in an ideal world, and in the real world.
Content calendar 🆚 vibes and intrusive thoughts
In an ideal world, my content calendar would tell me what to write for the next four weeks. In reality, I listen to gut feelings.
On the first Monday of each month, my Google calendar brightly reminds me to “Plan content calendar!” for the next few weeks. This ping, brought about by my well-intentioned past self, always makes me feel a little bit worse, though I ignore it anyway.
Then, I remember
’s missive Best Practices are Boring, which has become a touchstone for how I think about writing. In it, she opines (before sharing a delightfully unhinged Instagram Story from January Jones):I want to get newsletters that come in at completely random days and times, focusing on topics that the author clearly is battling intrusive thoughts about. I want to get a newsletter that’s a pure rant about Cinnamon Toast Crunch. I want to open an email and read something with energy, something with verve, something with the strong voice of the writer coming through.
I can’t say that I live up to the letter of this advice; I tend to stay “on-topic” and I currently publish (most) Fridays.
But I’m obsessed with the spirit of her message: to choose fiery over lukewarm, and to never apologize for flubbing a publishing cadence that almost nobody keeps track of. Far better to wait until you’re “battling intrusive thoughts” about a subject, then hit send.
When I’ve run out of intrusive thoughts, I consult the long list of potential topics I keep handy, and consult my gut: does anything feel urgent? If so, is it consistent with whatever ✨vibes✨ I’m feeling that week?
If not, I skip publishing—and use that time to see a movie, read a book, or visit a new bakery instead. Turns out, rest is often the key to inviting better vibes and a fresh batch of intrusive thoughts!
Consistent idea flow 🆚 idea feast and famine
In an ideal world, I’d receive a consistent drip of newsletter ideas, courtesy of the muse. In reality, I experience generative periods followed by long fallow stretches.
When my mom was in hospice care, I was stressed and exhausted. Still, the love, warmth, connection, and teamwork that defined that moment made it creatively generative. One sleepless night, I started a Google Doc to fill with future essay topics—even though my writing practice was dormant—and filled five pages in fifteen minutes.
Later, during the depths of my grief, it felt like I’d never have a good idea again.
Over the last year, that pattern has repeated itself many times over. Because I can’t predict when the next idea will arrive, I’ve developed a habit of writing everything down, so I can access those fleeting thoughts when I need them.
An organized idea capture system 🆚 a hot mess Google Doc
In an ideal world, I capture my ideas in a pristinely-organized document. In reality, it’s a word-vomit situation.
More than once, I’ve gone back to categorize everything that was unceremoniously dumped into my “newsletter ideas” Google Doc. I’ve also put considerable thought into systematizing my idea-capture process.
But those attempts have fallen flat—a fact that used to bother me. (Clearly, I need to avoid the aspirational YouTube subculture that glorifies “building a second brain.”)
I’ve since realized that all it takes to start the week’s newsletter is one single resonant idea. And I can pick one of those out of my Google Doc at a moment’s notice, even if it’s an organizational dumpster fire.
Ready-to-go topics 🆚 unripe topics
In an ideal world, every idea I have would be equally ready for primetime. In reality, many of them arrive unripe.
Oliver Burkeman once mentioned that he tries to avoid thinking about potential writing topics as “good” or “bad,” but rather “ripe” or “unripe.” Now, when I can’t make progress on an essay, I think about what it might need to ripen.
Sometimes, a topic needs time to sit untouched in a paper bag on the counter, like an avocado: no amount of proactive work will hasten the ripening process. Other times, I can hasten the process—something I do by brainstorming on my reMarkable tablet.
At any given moment, I have ten separate drafts in progress on my tablet, each with hand-scrawled, stream of consciousness notes about the prompt under consideration. After a few days or weeks, that process renders the idea fit for public consumption.
Writing a little bit every day 🆚 binge-writing
In an ideal world, I’d write for an hour each morning. In reality, I avoid my writing for days—then attack it in feral, unshowered, obsessive stretches.
This preference used to make me feel undisciplined, until I read Cal Newport’s Deep Work: Rules for Focused Success in a Distracted World.
In it, he argues that there are four types of deep work “philosophies,” or methods of integrating a deep work habit into our lives: monastic, bimodal, rhythmic, and journalistic.
Many writers extol the virtues of the rhythmic philosophy (write a little bit, every day!). But as it turns out, the bimodal philosophy works better for me.
In Newport’s words:
This philosophy asks that you divide your time, dedicating some clearly defined stretches to deep pursuits and leaving the rest open to everything else. During the deep time, the bimodal worker will act monastically—seeking intense and uninterrupted concentration. … The bimodal philosophy believes that deep work can produce extreme productivity, but only if the subject dedicates enough time to such endeavors to reach maximum cognitive intensity—the state in which real breakthroughs occur. This is why the minimum unit of time for deep work in this philosophy tends to be at least one full day.
If you’re struggling with your ability to work deeply, consider reading about the four philosophies of deep work. You might find that you’ve been trying to adopt someone else’s preferred philosophy when there’s a better option for you.
Spending a consistent amount of time on the newsletter 🆚 🤷♀️
In an ideal world, I could predict how long each newsletter would take to write. In reality, it’s a moving target.
Sometimes, a complex piece gets done breezily in one day. Other times, something that seems simple and straightforward takes forever to eke out.
I loved
’s recent meditation on the topic of “enoughness” when it comes to publishing work: in her words, it involves “giving your brain very specific, concrete details and directions about the outcomes you’ll consider as ‘enough’ for a task.”For her, whatever writing she’s completed at the end of four hours—the time she’s decided ahead of time to devote to her newsletter—is what gets published. It’s an approach I’ll be keeping in my back pocket, ready to deploy in the future.
Writing at my desk 🆚 writing from everywhere
In an ideal world, the ergonomic setup I shared is where I do all my writing. In reality, it happens there…and at the kitchen table, and on the couch, and in the wild.
Recently,
admitted she was “currently typing from an auto repair lobby as I wait for my car to get fixed.” Reader: I gasped!Before that moment, I hadn’t considered how little it matters if your words are tapped into existence by your thumbs during stolen moments between obligations.
If you translate the ideas in your head into words others can consume, you’re writing, whether it happens under ideal circumstances or at the mechanic (which is where I’ll be sitting when this newsletter is published).
Knowing what you want to read 🆚 knowing what I want to write
In an ideal world, I’d know exactly why you subscribed to my newsletter. In reality, I have no clue.
Perhaps if I knew your story, your fears, your obsessions, and your dreams, I could speak directly to each of them. Unfortunately, in most cases I don’t.
So each week, I look to my own life and consider what feels most important, hoping that (more often than not!) the resulting piece is as meaningful to you as it is to me.
It’s a real leap of faith—one that I’m grateful you’re taking alongside me.
💬 What about you?
I’m curious to know: Where in your life right now is someone else’s ideal departing from your actual, lived reality?
US-based subscribers, don’t forget to enter the book giveaway by dropping an emoji alongside a comment: 🚀 for Bruce’s book, ⛰️ for Cait’s, or 💰 for Myra and Abby’s!
Had your own plan-in-flames experience? Taking a leap into the unknown? I’d love to hear more. Just hit “reply” to get in touch, or introduce yourself here.
Warmly,
Maddie
I’m curious to know: Where in your life right now is someone else’s ideal departing from your actual, lived reality?
US-based subscribers, don’t forget to enter the book giveaway by dropping an emoji alongside a comment: 🚀 for Bruce’s book, ⛰️ for Cait’s, or 💰 for Myra and Abby’s!
🚀 currently one year out of undergrad and applying to graduate school. And in the next week I have to make the hard decision to turn down all the ones that I have gotten into because none of them are right for me this moment. So, I’m looking towards the future and figuring out what comes next. A book about transitions might just be perfect.