When the path to clarity is paved with pie crust

Working at a bakery was the sweetest career transition I ever made

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 #31. ✨

For years, I worked as a financial planner. The irony? My life hasn’t unfolded according to plan.

In this series, I share what helped me navigate each chapter of my money story with resilience and flexibility. (And this chapter just happens to have a timely, delicious Thanksgiving tie-in!)

When the path to clarity is paved with pie crust

Shot while working at the bakery (this photo ran in Food & Wine magazine!)

The world was asleep as I walked the deserted, mile-long stretch from Berteau and Ravenswood northwest to Lincoln Square. I was following the El tracks, so the empty brown line cars clattered overhead every twelve minutes.

In my previous life as a desk jockey, it hadn’t really mattered if I strolled into work ten minutes late. But now that I was working a bakery’s opening shift, it didn’t matter how groggy I was when my alarm blared.

I had to slip out my front door promptly at six o’clock because, by seven, there would be a line of people clamoring for to-go cups of strong coffee and warm cinnamon rolls.

My own peach-blackberry pie, baked after Kate McDermott’s pie class

I should probably explain how, at age 27, I arrived behind the bakery counter.

After two happy but low-income years, I left my university job in the suburbs for a boutique investment consulting firm. It came with a $20k raise and big-city delights like a commute into the Loop, where I shared the sidewalk with busy people on their way to important meetings.

But after two years of tabbing through Excel formulas all day, I was left feeling…bloodless. I craved warmth and messiness in my work.

So I was primed to jump ship for a front-of-house bakery gig; I needed a change of scenery while I considered what I wanted to be when I grew up.

Miniature blood-orange tarts

It wasn’t just any bakery. Baker Miller was about to open its doors to foodie buzz and fanfare; they were leading the whole-wheat pastry charge in Chicago.

Their flour was unlike any I’d ever tasted. Milled in an empty storefront next door, it was An Ingredient in its own right—not the bleached, flavorless filler I was used to.

But it was extraordinarily temperamental. While my new coworker Maria and I brewed the first carafes of coffee each morning, we’d ask Sarah—who’d been baking through the predawn hours—how the cinnamon rolls were doing.

Half the time, we’d get a head-tilt and a sigh in return. “They’re…a little wonky today,” she’d say with furrowed brows.

Maybe the humidity had shifted, or the amount of wheat bran and germ that remained after sifting. But even when the pastries came out uglier than desired, the sweet, nutty flavor of the shop’s own flour made a convert of anyone who tried it.

Strawberry cream-filled donuts with rhubarb compote

Somewhere between refilling a Mason jar with silverware and wiping butter from the surface of a four-top, I decided on my next career move. While I was busy mopping floors and disinfecting countertops, my mind was working on the problem in the background.

I’d learned about financial planning a few months back—it sounded like a good fit for a concrete thinker who also loved working with people—but I wasn’t ready to commit to the first steps. Clarity of purpose never seemed to arrive when I was sedentary, overthinking.

But it arrived at the bakery: when I was tired in the best way, from genuine exertion, and when I was immersed in connections—the flow of eager customers, and my new, slightly-dysfunctional work family who bickered over menu changes while breaking bread.

Clarity tends to arrive when it’s good and ready. For me, that happened when my employee benefits no longer included health insurance or a 401(k), but did include a butterscotch pie to take home to my family on Thanksgiving.

Blood-orange tart, captured on Kodak Portra 400 film

At the bakery, working the closing shift was like hitting the sugar lottery. Any sweets that remained were fair game to bring home: sugarplum muffins, or the pecan sandies whose thumbprint indentations were dotted with jam.

Those first few weeks, I locked the door at the appointed hour, then greedily filled my doggie bag like a squirrel preparing for Chicago’s interminable winter.

After some time had passed, though, that impulse softened. I realized that my baked-good scarcity mindset was an evolutionary vestige not entirely based in current reality. I didn’t need to hoard all six leftover cinnamon rolls—which, after nine hours on the shelf, had gone slightly stale anyway.

There would be an abundance of sweetness tomorrow, and the next day, and the day after that.

🥧 What about you?

Let’s meet in the comments section to dish. I’m curious:

• Have you made career pivots that made more sense in retrospect?

• If you’ve worked service-industry and desk jobs, what lessons did you take from each?

• What’s your go-to order at your favorite local bakery? Inquiring minds must know!

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

PS: New to heirloom flour, but want to give it a try? I use the high-protein bread flour from Janie’s Mill in this foolproof bread recipe—and have made more than one Thanksgiving pie crust (using

Kate McDermott

’s recipe!) with Cairnspring Mills flour. 🥰