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 #4. ✨
☀️ How was your week?
I took a drawing class—and actually had fun making mistakes. After discovering
and his fabulous Substack , I was enamored with the idea of learning to draw “tiny people.” So I grabbed a sketchbook and pen, and fired up my laptop for his Zoom class.I’m a total beginner—and a recovering perfectionist, so making terrible art was uncomfortable. But Nishant noted that mistakes are important; your imperfections and idiosyncrasies are the foundation of your personal drawing style. I can’t wait to visit a coffee shop and (sneakily) practice my fledgling skills.
On to today’s letter!
A declaration of interdependence
“We are mirrors reflecting one another. The people with whom we surround ourselves shape us, and we shape those around us, too.” –Brad Stulberg
During the heyday of inane Buzzfeed quizzes (“Which Glee Character Are You Based On The House You Design?”), the satire website Clickhole launched, responding with its own flurry of increasingly absurd content.
There’s one quiz I remember vividly: “Are You An Introvert, An Extrovert, Or A Sea Monster?”
Answer five simple questions, and you’ll find out if you thrive in lower-stimulation environments, higher-stimulation environments, or prefer to “live undisturbed for decades in a secluded cove untouched by man or time.”
Since my typical Friday night plans involved avoiding the rest of humanity while “brushing against the underside of a Portuguese fishing trawler,” Clickhole deemed me so introverted as to be, in fact, an actual sea monster.
At age fifteen, I got my first full-time summer job. (In retrospect, this specific job was a terrible choice. Babysitting for two hours on a Friday evening had been a piece of cake. Babysitting for 40 hours per week? A different matter entirely.)
Even at the sub-minimum wage of $5 per hour, I found myself rapidly amassing twenty-dollar bills, which I stashed in my underwear drawer. By the end of the summer, I had more than a thousand dollars to my name.
My parents had been through a bitter divorce, and the conflict felt destabilizing. For some reason, having money of my own brought me comfort. In a moment where I wasn’t totally sure what I could rely on, I had the growing sense that—cash in hand—I could rely on myself.
The 2010s were the golden era of self-reliance.
In 2012, Susan Cain published her sensational bestseller Quiet: The Power of Introverts in a World That Can’t Stop Talking. Before reading Quiet, I didn’t understand why being packed into a dorm room—one of many sardines in my big-city college campus—left me irritable for a full four years.
After reading Quiet, I understood that introversion wasn’t a character flaw. Harnessed wisely, it could be a powerful strength.
The FIRE movement was ascendant in this same moment. For those uninitiated, the acronym stands for Financial Independence, Retire Early. Blogs like Financial Samurai, Early Retirement Extreme, and Mr. Money Mustache showed that you could gain financial independence decades before collecting Social Security by supercharging your savings rate and relying on the magic of compound interest.
They made a compelling case for dedication to this cause. “Follow my lead,” they argued, “and you’ll never have to depend on anyone else again.”
I spent my early adulthood listening to these cultural conversations, and perhaps unsurprisingly, found my outlook on the world defined by them.
I gave myself ample, guilt-free alone time. I lived for DIY projects. I never developed a side hustle, but I sure felt inadequate for not having one! And I steeped myself in so many personal finance blogs that I found myself a career path.
So I’d mastered independence. But as life’s challenges stacked up, it was time to learn the art of interdependence. By definition, I couldn’t learn about interdependence on my own; I’d have to turn toward my community, and my mom’s, for that.
My mom’s initial diagnosis came in 2020, after the pandemic started, before vaccines were available. I couldn’t fly home—so I started a meal train. I picked a digital platform, worked on the setup logistics, and when the site went live, was knocked over by the flood of responses.
It’s a testament to how fiercely people loved my mom: for months, she was absolutely drowning in casseroles and cakes.
She was buoyed by community in all aspects of her initial treatment and recovery. Friends drove her to every chemotherapy appointment, neighbors came over each Tuesday to take out the trash, family dropped by to share masks-on, windows-open time together.
She’d always been there for others; it wasn’t a heavy lift for them to show up for her.
Months later, after telling her about my separation, she started texting me each morning—each note accompanied by a gif of Chippy the dog, reminding me that I was loved—until my spirits improved.
When my mom’s cancer came back, it was my turn to send her daily Chippy gifs punctuated by love notes.
That’s how interdependence works: one person needs support for a stretch; then it’s someone else’s turn. And on and on, forever.
The previous flood of support for my mom gathered tsunami force, now that everyone was vaccinated and could gather in person. In her final weeks, loved ones filled her social calendar, and flew in for emergency visits when emergencies happened. They FaceTimed, texted, emailed, sent flowers, wrote letters and cards with baby photos tucked inside. They reminisced over takeout meals. They brought ice cream and chicken soup and cheesecake. They sat by her hospital bed when she was aware of their presence, and again when she wasn’t. They were there for her, but they were there for me, too.
Brad Stulberg writes in The Practice of Groundedness, “It’s a one-two punch: community keeps you from falling, and if you do, it picks you up.”
I’ll tell you this: the only reason I’m able to be lit on fire by a series of challenges is because of the support system that materialized around me.
A certain degree of self-reliance is admirable, important, and necessary. But when it comes to living a good life, it is simply not sufficient.
observes in The Pathless Path that “people aim for ‘financial independence’ only to realize when they achieve it that they’re only independent in the narrow sense of being able to pay for everything.”After my mom died, I was nagged by a persistent sense of guilt. How could I ever repay the countless people who’d offered me so much of themselves?
But there is no “repayment.” Interdependence is not a series of transactions. Next time someone in my community experiences hardship, I’ll be there for them—but not because I owe them something. I’ll be there because there’s extraordinary beauty in relying on others, and being relied on by them in return.
💬 What do you think?
I’m curious to hear from you. Tell me about a time you leaned on your community instead of opting for self-reliance, and what the experience taught you.
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