Are you still enjoying the climb?

Or is it time to revisit the map that led you here?

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 #43. ✨

Are you still enjoying the climb?

Mount Rainier’s Skyline Trail, captured on Kodak Portra 160 film

The only clue that we were in the presence of a celebrity was her oversized ivory Loewe sunglasses.

My boyfriend and I had just pounced on the only open table in a buzzy new bakery. We had a spread that included coffee cups, pastries, and books, but there was still plenty of room to spare at our six-top.

When the stranger sat down across from us, we exchanged smiles, then left each other alone to eat and read in peace. But after everyone’s last bite, my boyfriend broke the ice with a polite question—“Did you like what you ordered?”—and those niceties eventually morphed into conversation.

That’s how we found out she was in town to headline a series of comedy shows.

It wasn’t entirely surprising to learn that Zainab Johnson, our new bakery acquaintance, also commands the stage in an excellent Amazon Prime comedy special. After all, she had an aura of approachable, easygoing confidence.

After chatting for fifteen minutes, I had one more burning question to ask.

In the last decade-plus of her career, she’d clearly “made it” in every conventional sense. Still, she had an unmistakable energy and drive, so I guessed she might have bigger ambitions, too. I wanted to know: what does inhabiting that middle space feel like?

She took a long, reflective pause before answering. “Looking back at where I started, I’m so grateful to be here,” she said. “But I’m still enjoying the climb.”

When we make choices about our careers, we’re also making choices about money. So Zainab’s words loomed large as I started writing this latest chapter of my money story, one that centers around my decision (after a brief but tasty detour!) to become a financial planner in the first place.

At age twenty-eight, I began commuting from my suburban university day job—which offered stellar education benefits—to the downtown Chicago campus where my CFP® certification classes took place.

When I had a night class, there wasn’t a moment to spare between leaving work and hopping aboard the train, meaning that dinner was a peanut butter sandwich eaten aboard the El.

In a pivotal scene from Risky Business, Tom Cruise and Rebecca De Mornay’s characters steam up the plate-glass windows of an El car as the ethereal strains of Tangerine Dream’s “Love on a Real Train” build to a crescendo.

When my boyfriend mentioned that this sex scene was the stuff of teenage boys’ fantasies, I recoiled: “I’m sorry, babe, but do you understand how disgusting the El is?”

I may be a public transit devotee, but the El is quite possibly the worst setting for exhibitionism—or, for that matter, eating.

So when I tell you that I ate on the El, happily and regularly, whiling away my commute with a steady stream of financial planning podcasts, that’s my way of telling you this: at the beginning, I was genuinely enjoying the climb.

Our goals are products of the paths that led us to them, and by twenty-eight, my own path had me pining for financial security.

In plain English, I’d grown tired of pinching pennies, and that meant I needed to grow my income.

By then, I’d held a series of jobs, but what I craved was a capital-C Career. When someone asked what I did for a living, I didn’t want to tell them where I happened to work at that particular moment. I wanted to be able to tell them who I was.

I also wanted to narrow the wage gap between me and my then-partner, one that was growing with each passing year. If we had kids someday, as I figured we would, I wanted a salary bigger than our daycare bill.

Even in the most egalitarian relationships, money is still a source of power, and I didn’t want to be left without it.

If I did leave the workforce for a hot second, though, I wanted a professional certification that I could retain, those three letters behind my name that would vouch for my worthiness.

Almost a decade later, some of the things I wanted then remain true: I still want, more than anything, to help other people. And I still want to tackle technical questions, ones that help me learn and grow.

But so much about my life has changed since I chose my financial-planning career path—and it’s interesting to consider how few of my original motivations are still applicable nine years on.

Over time, even the most carefully-selected climb can become a slog, a series of moments that turn into longer, teeth-gritting stretches, ones that find you pushing joylessly toward the summit for no other reason than you’ve already committed to getting there.

Lately, I’ve been reading Cait Flanders’ excellent Adventures in Opting Out: A Field Guide to Leading an Intentional Life.

It’s a book about experimenting with new paths, like Cait’s decision to leave her home base in favor of full-time travel—a big adventure with big unknowns. And she explores how the rest of us might approach choosing new paths through the (very appropriate!) guiding metaphor of a hike.

In reading this chapter of Cait’s story, it struck me how infrequently most of us stop to revisit the map that led us here, even when we have the immense privilege of choice. I sure didn’t—not until a confluence of low moments forced me to.

Revisiting that map is important because the act of walking any path teaches us things we didn’t know at the outset.

At twenty-eight, I didn’t know these important things about my relationship to work, all of which are clear now:

✳️ As Annie Dillard said, “How we spend our days is, of course, how we spend our lives.”

My financial-planning career was centered around meetings and an ever-swelling inbox. If your best life involves lots of communication and relationship-building, that can add up to a life well-spent! But my own best life has always involved producing tangible, creative work—and a healthy dose of solitude.

✳️ Go against these natural preferences for long enough, and they’ll probably become a source of chronic stress.

I used to think that stress was “just a feeling,” one that I could safely ignore, but stress is actually a physiological process with physiological consequences—ones that compound over time. Ignore them at your own risk.

✳️ You can outgrow an otherwise-great career.

For many years, I adored spending forty hours a week talking about personal finance—until I didn’t.

✳️ You can be amazing at a job that doesn’t serve you.

I was a talented financial planner, in part because the role rewards those who love planning. (Shocking, right?)

But leaning into my overthinking, overplanning tendencies came at a personal price—which was hard to see lurking behind the cover of professional success.

✳️ It’s easy to get stuck in a “shadow career.”

The kind of work that isn’t the highest and best use of your talents is what author Steven Pressfield calls a shadow career:

Its shape is similar [to a true calling], its contours feel tantalizingly the same. But a shadow career entails no real risk. If we fail at a shadow career, the consequences are meaningless to us.

And that’s exactly how I got stuck building someone else’s business when I really wanted to build something of my own.

Now that I’ve integrated these lessons, I’m back to enjoying my own meandering but self-determined professional climb—yes, even the frustrating stuff, which is ever-present.

Revisiting the path that led you here doesn’t necessarily mean bailing on it, even if you’re grappling with a low moment. With a nod to Cait’s wise advice about hiking and life, it might simply mean that you need a snack.

But if the act of revisiting brings clarity that a rest stop can’t fix, just remember: it’s never too late to pick a new destination.

💬 What do you think?

I’m curious to hear from you. When’s the last time you stopped to reassess the route you’re traveling?

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