The uncertainty diaries
All the tools and resources I’m loving in spring 2024
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 #44. ✨
Over the last few months, I’ve published personal essays and thinkpieces about topics weighing heavily on my mind. They’ve helped me clarify my ideas; they’ve also helped me process important experiences, like the first anniversary of my mom’s passing.
But today, the Pacific Northwest sky is miraculously blue, birdsong fills the air, and the magnolias and cherry blossoms are popping. Plus, I’m enjoying a blueberry muffin at my favorite bakery. It feels like a moment to approach my writing, and this space, with an extra dash of joy.
In that spirit, let’s take a lighthearted peek behind the scenes!
This is the first in an occasional series I’ll call The Uncertainty Diaries, with a nod and hat-tip to the excellent Money Diaries column that
, author of , ran for Refinery29.When my own five-year plan went up in flames, I found that four major fears kept coming up:
💪 “Can I handle what lies ahead?”
🧠 “How can I feel better along the way?”
👯♂️ “What if I need help?”
🎨 “How do I build something new?”
After lots of reflection (and trial and error), I cobbled together a framework of four strategies that helped me answer each question:
💪 Sharpen my self-advocacy skills, and start investing in myself.
🧠 Adopt a flexible, joy-seeking mindset.
👯♂️ Shift my focus from independence to interdependence.
🎨 Immerse myself in creativity.
That’s why all of my writing touches in some way on the topics of self-advocacy, mindset, interdependence, or creativity: because, collectively, they helped me begin to embrace my own uncertain circumstances.
Here’s how each topic is factoring into my life right here and right now.
Recently, uncertainty has taken a number of forms in my life, including a relentless construction project that I’ve already complained about.
As of yesterday, another big unanswered question was “Where am I supposed to fix a flat tire if my mechanic is busy?!”
But over the past few months, the bigger-picture source of uncertainty has been professional: what do I want to do with the rest of my life? (No pressure, of course.)
💪 Self-Advocacy
To begin exploring that question, I started with something I was certain about: an unrelenting curiosity about web design that wouldn’t leave me alone.
That curiosity appeared years ago, when I started tinkering with my now-defunct WordPress blog. I modified theme templates and—when the results didn’t pass muster—learned to use drag-and-drop visual page builders that gave me more creative freedom.
Still, I wasn’t satisfied. I wondered how real web designers sketched out their visions, and how developers brought them to life.
I became obsessed with Charli Prangley’s design-focused YouTube channel. I learned HTML, CSS, and JavaScript “just for fun.” I spent as much time creating the hand-drawn logo and page dividers for this newsletter as I did the early content. And, starting this past December, I learned the basics of design and development platforms Figma and Webflow so that I could finally make beautiful websites from scratch.
Given the longevity and persistence of this particular curiosity, I’m pretty sure that it’ll continue to capture my interest. As I overhaul my own personal website, I’ve already found myself getting lost in the flow of that work—always a good sign!
Here’s what I’m not sure of, though: will I be able to sit with the discomfort of being a complete beginner, inching through the mountain of questions that arise each time I attempt a new technical task, for long enough until I actually know what I’m doing? Will I ever be good enough to call myself a professional?
When these fears arise, it’s been empowering to identify what
—in her excellent newsletter —calls “One Foot in Front of the Other Time.”
“One foot in front of the other” is exactly what professional self-advocacy has looked like for me these days: commit to watching one Figma or Webflow tutorial. Then, apply its lessons to my own project. All the while, remind myself that the only thing I need to worry about is the single next step.
Stack together enough single steps, and that’s how you get a flywheel spinning.
🧠 Mindset
I’ve picked up countless insights from finance influencer Ramit Sethi. One of my favorites? That he’ll buy any book that sounds interesting, without hesitation.
That’s because reading a book is the cheapest, easiest way to sponge up a lifetime of someone’s expertise. That’s also why so many of my recent mindset shifts have come from books.
Here’s a sampling of the nonfiction books I’ve loved (and am loving) this season—all of which have deepened my understanding of how to live well in an uncertain world.
Wintering: The Power of Rest and Retreat in Difficult Times and Enchantment: Awakening Wonder in an Anxious Age. I finished the first, and started the second, by my Airbnb’s fireplace on a recent weekend trip to Victoria, British Columbia. It was the ideal setting for enjoying
’s gorgeous—and always relatable—prose.Master of Change: How to Excel When Everything Is Changing - Including You. I’ll be roasted by
for this one; we started reading Brad Stulberg’s book at the same time, but I’m lagging woefully behind. That’s because it’s a dense read—but that also means there’s zero filler. My copy is littered with notes and highlights; every other sentence contains practical and insightful advice for living in a changing world.1000 Words: A Writer's Guide to Staying Creative, Focused, and Productive All Year Round. During a recent uninspired stretch, reading
’s book felt like a warm, encouraging voice note from a writing buddy. The take-home message: you don’t need to know exactly where your writing is taking you. Just get 1000 messy words onto the page, and go from there.Slow Productivity: The Lost Art of Accomplishment Without Burnout. It’s easy to default to frenetic busyness, particularly during times of uncertainty, because completing lots of checklist items provides us with a false sense of control. Cal Newport makes an impassioned argument for thinking about productivity in an entirely different way. This one’s a must-read!
On a related note, I bought the cheapest possible Apple Watch for the express purpose of listening to audiobooks while walking outside—so I can leave my phone and its incessant calls, text messages, and notifications at home.
It’s the most buggy Apple product I’ve ever owned. It’s annoying to navigate. But, judged by the simple statistics of miles walked and audiobooks finished since my purchase, it’s been a fabulous investment.
👯♂️ Interdependence
There’s so much I could discuss on this front!
There’s the trip I’m planning to visit my dad and stepmom, or the monthly “study group” my former financial planning colleagues still invite me to, even when I have nothing constructive to add. (Love y’all.)
There are the real-life writerly friendships I’ve forged from connections made through this newsletter, thanks to Zoom and text messaging. Nurturing these fledgling but genuine connections has been wildly rewarding—more, please!
But fittingly, the best wisdom on this subject has come to me via the words of others. Here are my favorite recent reads on the subject of interdependence:
- ’s incisive, gorgeous meditation on connection.
- and ’s entire friendship training program (start here!).
- ’s essay “I don’t want friends, I want connection.”
Just about everything that
publishes on .
🎨 Creativity
Next month will mark this newsletter’s first birthday!
To celebrate, I’ll write about creativity all through April: sharing my writing setup and process, the lessons I’ve learned from a year of publishing, and—maybe!—what’s next for my writing. (Though frankly, I’m still figuring that one out.)
This series is inspired by my friend Anna, who recently asked how I put each newsletter together. If you, too, have a burning question on this topic, I’ve got you covered:
If all goes well, this series will be the writerly version of “Stars: They’re Just Like Us,” in which you find out that D-list actors pump their own gas.
It’s entirely possible that any wisdom I relay won’t be transferable. But if you’re struggling with uncertainty around a creative project of your own, humanizing the process can be energizing. We’re all fallible humans, fumbling around and figuring out this creating-in-public thing together.
💬 What do you think?
I’m curious to hear from you. What are the big, unanswered questions you’re wrestling with this spring? What’s been helping you cope with that uncertainty?
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 hear from you. What are the big, unanswered questions you’re wrestling with this spring? What’s been helping you cope with that uncertainty?
I love all of this, Maddie! And also feel like I could have written it myself! Definitely feel like I'm living through a period of uncertainty, which isn't all bad but can definitely be challenging! I needed the advice of one foot in front of the other this morning!