"Should I stay or should I go?"

📨 Ask An Ex-Planner

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 #17. ✨

☀️ How was your week?

My beloved local dahlia garden

I finally saw the Barbie movie (Oppenheimer will have to wait). I went with my brother, a film school grad who was genuinely curious what on earth Greta Gerwig was going to do with the subject matter.

The rest of the world has written enough thinkpieces about Barbie: the beauty standards, the gender roles, the politics.

My takeaway? This was a movie about Barbie’s five-year plan going up in flames. So I felt something like kinship with “Irrepressible Thoughts of Death Barbie” and “Depression Barbie” when they made their appearances.

On to today’s letter!

📨 Ask an Ex-Planner

Life is full of change, transition, and uncertainty—all things that are better navigated together. So in this column, I hand over the mic in order to address what you’re struggling with or curious about.

Want me to respond to your question? Make an anonymous submission right here—or just reply to this email.

Dear Maddie,

I’d like to hear your thoughts on quitting. What’s your decision-making process when quitting something you’d previously planned for?

And if the next step after quitting requires stepping up in some way, how do you know if you can become who you need to be in your new situation?

Dear reader,

Sometimes, your plan goes up in flames because something—or someone—has quit on you. But almost as often, your plan goes up in flames because you’ve committed arson.

That’s actually an evidence-based assertion—one put forth by

Bruce Feiler

in his marvelous book Life is in the Transitions: Mastering Change at Any Age. (This book is currently on my nightstand, and I’m churning through its pages at breakneck pace, highlighter in hand.)

Feiler writes about “lifequakes,” a term he coined to describe exactly the kind of plan-in-flames moment we talk about here, but swapping the Richter scale for the matchbook and kindling.

He defines this phenomenon as a “forceful burst of change in one’s life that leads to a period of upheaval, transition, and renewal.” Feiler interviewed 225 subjects about their own lifequakes, mined each story for data, and uncovered patterns that can help us all learn how to master the skill—yes, the skill!—of transitioning.

In his research, he found that approximately four in ten lifequakes were undertaken voluntarily. And that gets to the heart of your question about quitting, I think.

Since voluntary actions are at the center of so many upheavals—and, done well, can unlock positive change over the long-term—we’d all do well to consider how to quit better.

The directive to “quit better,” though, can freeze us up for weeks, or months—even years. Because inevitably, we view these decisions as forks in the road, our own personal Sliding Doors moments. Which of the two futures do we choose?

A confession: I received this reader question almost two months ago, but didn’t have the courage to answer it then.

After all, what quitting-related wisdom can I possibly offer? I’ve only quit…let’s see, two cities, five relationships, one marriage, countless creative projects, and five full-time jobs. (We won’t count the part-time ice-cream scooping role that, after three days, I found Teenage Maddie simply didn’t have the upper-body strength for.) I’ve quit using purchases I made in the heat of the moment, thinking that they’d solve an unsolvable problem.

And I don’t have a bulletproof framework to offer, like former professional poker player Annie Duke presumably does in her book Quit: The Power of Knowing When to Walk Away (that one’s still in my Goodreads queue). Or like my writer friend Zac Solomon did in this nuanced and helpful piece.

It’s not for lack of trying; I’d love a step-by-step instruction manual for aspiring quitters.

Once, when I felt desperately stuck in my decision to stay or leave one of those six aforementioned relationships, I read a book meant to help me decide.

Each chapter covered a different relationship challenge, interviewing partners who had experienced that challenge and stayed, or experienced the same challenge and left. For those who stayed, and those who left, the author asked: in hindsight, did you make the right choice?

Based on their answers, it became clear which challenges proved so intractable that quitters ultimately felt relieved about their decision. It was a tidy, actionable resource that I read cover-to-cover.

Yet, at the end, I felt as stuck as before. How could a precious, maddening, beautiful, complex connection between two people be reduced to…a decision tree?

Maybe it’s because I’m a Myers-Briggs type INFJ—the N standing for “intuitive”—that, years later, I found my answer in a question.

It was posed in Oliver Burkeman’s final column for the Guardian to wrap up his decade-long gig there; clearly, the topic of “quitting” was top-of-mind.

Here, in Burkeman’s words:

When stumped by a life choice, choose “enlargement” over happiness. I’m indebted to the Jungian therapist James Hollis for the insight that major personal decisions should be made not by asking, “Will this make me happy?” but “Will this choice enlarge me or diminish me?” We’re terrible at predicting what will make us happy: the question swiftly gets bogged down in our narrow preferences for security and control. But the enlargement question elicits a deeper, intuitive response. You tend to just know whether, say, leaving or remaining in a relationship or a job, though it might bring short-term comfort, would mean cheating yourself of growth. (Relatedly, don’t worry about burning bridges: irreversible decisions tend to be more satisfying, because now there’s only one direction to travel – forward into whatever choice you made.)

I recalled each time I’d quit something, replayed the tape through the enlargement-or-diminishment lens, and realized: this had been the question that guided my choices all along. And when I chose growth, it always ended up being the right decision.

In some ways, this was an unexpected place to find an a-ha moment on the subject; Burkeman now writes, primarily, about…time management.

But since, as he puts it, our lives are “absurdly, terrifyingly, insultingly short,” this is ultimately a question of how we’re using our finite days on Earth, and all the more reason to quit things exactly when they require quitting.

Two brief caveats.

Often, we want to quit things that make us uncomfortable. Healthy levels of discomfort, though, can indicate that we’re growing, or being called to grow. So in some cases, the enlarging (albeit counterintuitive) choice might actually be to stay.

And, of course, when our plans are inextricably linked with someone else’s, there’s a higher standard of ethical care required when quitting. The greater someone’s investment in a shared future, or the more they depend on you, the more thoughtfulness and empathy you should bring to your decision.

As for the final part of your question: how can you know if you’ll become who you need to be as you step into your new, uncertain future?

The short, unsatisfying answer: you can’t. You can try to give yourself the best odds of success. But the fundamental truth about the future is that you can’t predict it.

But if you choose growth, you don’t need to. You’re guaranteed to win either way. Not necessarily by achieving the specific outcome you’re hoping for, but certainly at the infinite game of growing into the next iteration of yourself.

💬 What do you think?

I’m curious to hear from you. What would you like to share with the reader who wrote in?

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