When the Plan Ain’t the Plan: A South Side Leap of Faith

They say life begins at the edge of your comfort zone. But if that’s true, mine began in an aisle at Trader Joe’s, clutching a bundle of kale like it held the secrets of the universe. Let me explain.

I wasn’t supposed to be there—literally or metaphorically. At 29, I had an exact vision of how my life was supposed to unfold: published novelist (check, with a little asterisk), steady relationship heading for “next steps” (zero checks, no pen in sight), and firmly rooted in Chicago (with the gloss of Paris still in my Instagram captions). Instead, I was aimless, newly single after what turned out to be a situation-ship, and shopping for kale because... well, I thought kale would somehow fix me. Or at least make me “look” fixed.

But here’s the thing about comfort zones—they’re deceptively named. They’re cozy until they suffocate you. And in that parking lot, trying to jam too many bags into my trunk, it hit me: I had to shake things up. For real this time.

The First Leap: Breaking Up with "The Plan"

I’m not going to lie: I’ve clung to a plan like a Chicagoan clings to a space saver in February. Plans have always been my emotional armor against uncertainty. My academic life was a plan. My writing career, however turbulent, was still technically a plan. But relationships? Those were always where the plans got personal—and messy.

When I broke up with my then-partner, it wasn’t because we fought. It wasn’t because something catastrophic happened or because Beyoncé dropped “Lemonade” and planted ideas (though it’s incredible, right?). It was because I was too scared to admit the person I was becoming didn’t quite fit the plan I was crafting.

For two weeks, I mourned the life I’d built in my head—a neat apartment in Bronzeville with exposed brick walls; shared morning coffee routines that no Spotify playlist could hope to replicate. Then came a moment of uncomfortable clarity: maybe life wasn’t about fitting into the plan. Maybe it was about writing new ones.

Leap Two: Saying Yes to Paris... Again

Here’s the twist: When an old college friend asked me to visit Paris for three months to help her launch urban African art workshops, I almost said no. Not because I didn’t want to go (trust me, Paris always calls me back), but because it wasn’t convenient. You know what was convenient? Wallowing. Letting my identity calcify in the safety of "I’m figuring things out."

But something—or maybe someone (thanks, Mom)—reminded me that the only cure for self-pity is action. So, I said yes. I booked the flight. I didn't have a solid plan beyond landing at Charles de Gaulle and texting my friend, but that was enough.

And let me tell you: eating pain au chocolat solo in a Marais café hits different when you’ve decided to stop caring how it looks to other people.

I spent those three months doing what I’d thought was impossible: putting myself first. Living without autopilot. Wandering without needing a destination. And somehow, amidst hosting storytelling workshops for teenagers, touring Montmartre with too many croissants in hand, and marveling at the casual confidence of French flirtation (a je ne sais quoi I’ll never unlock), I discovered something liberating: being untethered isn’t failure—it’s freedom.

The Risks Worth Taking in Love (and Life)

Now, let’s get something straight: I’m not saying your leap of faith has to involve Paris. It won’t always look romantic or cinematic. Sometimes, the leap is applying for a new job, having the “Where is this going?” talk, or finally deciding to stop texting that ex who only hits you up after 11 p.m. For me, it meant unlearning habits disguised as ambition and rewriting what success meant in my relationships.

Here’s what I learned when I took The Leap(s):

  • Don't let a Plan define you. Plans can be like IKEA furniture—looks good on the box but maybe doesn’t hold under pressure. It’s OK to pivot, rebuild, even start over from scratch.
  • Invest in the mess. Love, like jazz, thrives in improvisation. It’s not always about following sheet music. You have to be willing to take the wrong notes until you get the groove right.
  • Say yes—when it scares you. Whether it’s a solo trip or a new experience, leaning into fear is often where growth hides. Sure, sometimes you’ll metaphorically fall flat on your face, but those lessons? Unbeatable.

Leaping Towards Home

Eventually, I returned to Chicago. The South Side was still the South Side: bustling, flawed, musical, and magnetic. The leap didn’t magically make me the “perfect catch” or land me in an immediate, mystical meet-cute. But it gave me clarity: love is less about perfection and more about showing up fully, flaws and all.

Now, years later, the risks still come in different shapes and sizes—whether it’s trying to communicate better in a relationship or accepting that vulnerability is necessary (even when I’d rather channel stoic Miles Davis energy). I don’t have all the answers. To be fair, no one does. But what I do know is this: taking those leaps, however small or uncoordinated they might feel, is worth it. Every time.

So, to you, dear reader: what leap have you been avoiding? What risk looks scarier than it actually is? Maybe it’s time to grab your version of kale and just jump.

Go ahead. I’ll be cheering you on from wherever leaps take us next.