Change of plans? Join the club.
Here's the framework that'll help you embrace uncertainty—not just tolerate it.
Welcome! 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. Either way: this is your trusty companion while you’re writing the next life chapter.
Life is change, which makes uncertainty an integral part of the human experience.
Whether the change in question is characterized by grief or joy—or both!—transitioning into something new often brings anxiety and possibility.
After navigating three unexpected life transitions, I should know.
I, quite literally, made (financial) plans for a living, until life unfolded in ways I couldn’t have planned for:
When my own plans went up in flames, I had to learn the mechanics of embracing uncertainty by mining my own experiences—and talking to others about theirs.
Four major challenges kept arising:
💪 “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?”
These are big questions. It took many conversations, and lots of reflection (and trial and error!) to learn how to even start answering them.
But eventually, that fuzzy picture came into clearer focus.
Here’s how we can address each challenge and begin to embrace uncertainty:
💪 Sharpen our self-advocacy skills, and start investing in ourselves.
🧠 Adopt a flexible, joy-seeking mindset.
👯♂️ Shift our focus from independence to interdependence.
🎨 Immerse ourselves in creativity.
These directives can make us more resilient, empowered, even antifragile as we transition into…whatever comes next. Taken together, they form a concrete framework for learning to embrace change, transition, and new beginnings.
Every edition of the newsletter explores these themes from a different angle or perspective. And since I’m learning along the way, you are cordially invited to contribute your hard-won, considerable wisdom.
So let’s dive into each theme below! (If you’d like to dig deeper, follow the links in each section.)
💪 Sharpen your self-advocacy skills, and start investing in yourself.
“Explore life from a position of power.” –James Clear
We don’t have control over the future, but we do have boundless agency over how we approach and respond to our life circumstances. That involves choosing better inputs whenever we can; it also means building self-trust, and durable skills that no plan-in-flames moment can take away from us.
One crucial skill? Self-advocacy, which helps us step into our own power. Because embracing uncertainty does not mean “letting life happen to us.”
Investing in yourself, even without knowing where it’ll lead, is another secret weapon during times of uncertainty. That could mean shoring up your professional ties, your physical and mental health, your finances, your relationships, furthering your education, or learning new skills—because you are your best five-year plan.
And speaking of investing: as a former financial planner, I can’t not talk about personal finance, especially because my experiences of loss and transition shaped how I think about, use, and manage my own money. My hope is that sharing my money story will provide food for thought as you write your own.
Find all past editions on the theme of self-advocacy right here.
🧠 Adopt a flexible, joy-seeking mindset.
“We need to transform our relationship with change, leaving behind rigidity and resistance in favor of a new nimbleness, a means of viewing more of what life throws at us as something to participate in, rather than fight.” –Brad Stulberg
Adopting a gift-giving mindset is an effective, fun way to balance our Present and Future Selves’ needs, especially in times of uncertainty. It’s an approach I explain here:
There are certainly occasions when planning is an appropriate tool for the job at hand. But when it isn’t, we have other tools at our disposal. We can use frameworks, which offer a gentler form of structure, or run experiments when we’re trying on something new for size.
Other mindset shifts that make uncertainty more bearable: embracing slow productivity, finding certainty anchors, and listening to our body’s signals.
Find all past editions on the theme of mindset right here.
👯♂️ Shift your focus from independence to interdependence.
“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.” –Paul Millerd
When I worked a financial planner, achieving financial independence was a ubiquitous goal. Everyone was striving for it. And it’s a worthy aim, as long as we also recognize that it’s wildly insufficient.
In my experience, aiming for interdependence—which includes going above and beyond for the right people, and learning how to offer and request help from others—is key to navigating life’s most uncertain moments. Banking memories, prioritizing “joy dividends,” and fostering genuine connections is non-negotiable.
That’s why this newsletter offers a way to learn from each other’s stories and experiences, through the Ask An Ex-Planner column, the Change Of Plans series, and the occasional, delightful community roundup.
Don’t sleep on this evergreen reader-introduction thread, or the comments section of each letter. I want to hear from you—this isn’t a monologue, it’s a conversation. We can all benefit from your hard-earned wisdom about navigating uncertainty.
Find all past editions on the theme of interdependence right here.
🎨 Immerse yourself in creativity.
“We’ve become accustomed in recent years to the language of resilience, and to the idea that after a massive interruption we revert to the norm. … But far more frequently, we actually move in new directions. Instead of going back to what we were before, we go sideways, forward, or some unforeseen place entirely.” –Bruce Feiler
After you’re lit on fire, you won’t return to the person you were before. And discovering who that new person is? Well, that’s a creative act.
And staying grounded in creative pursuits helps you craft meaning from the ashes of your five-year plan. For me, that looks like writing this newsletter and snapping photos on Kodak film; your creative outlets might look radically different. (And, like flywheels, they might require considerable effort to get spinning!)
That’s why I’m inviting you to the adventure that unfolds when your plans go sideways. As Yvon Chouinard said, “It's not an adventure until something goes wrong.”
When something goes wrong, you’ll need time, support, and probably ice cream to grieve properly. But then, you have a choice: view uncertainty as a curse, or as an opportunity.
Crafting intricate plans and clinging to the illusion of certainty might feel comforting, but here’s some tough love: it’s also really boring. Certainty is the enemy of creativity. Creativity loves uncertainty. And as fundamentally creative beings, we should, too.
Find all past editions on the theme of creativity right here.
In the spirit of interdependence, let’s step forward into life’s profound uncertainty together.
Warmly,
Maddie