Reinvention Stories

There’s nothing quite like the moment you realize you need a reinvention. It’s a vibe shift with consequences—a little like switching from regular coffee to oat milk lattes because someone told you they’re “better for you,” except this time, it’s your entire self on the line. Reinvention isn’t just for Hollywood montages or Beyoncé’s ever-evolving eras; it’s for you and me too. And sometimes, the need for change sneaks up on you in the most random places—like my dear friend Craig realizing he was terrible at breakup conversations while standing in line at Harold’s Chicken Shack with teary-eyed resolve and a soggy paper napkin. (More on him later.)

Let’s be honest: we’ve all hit a point where our old selves felt too tight, like a bad suit you thought was tailored correctly but pinches in all the wrong spots. Maybe you stayed in a stale relationship because it was easier than drafting a breakup text. Maybe you’ve clung to the same pattern—the same situationships, same excuses, same wardrobe full of sweatpants—because change felt too daunting. But real transformation? It’s intentional, messy, and surprisingly rewarding. I’d know. Been there. Twice.

The Breaking Point(s): When You Know It’s Time to Change

For me, the first big reinvention came in college. Northwestern is full of achievers. Everyone’s running some club, learning to play the saxophone, and hosting a podcast, sometimes simultaneously. I kept trying to keep up, but I felt like everyone had it figured out except me. My “aha” moment didn’t happen at some deep self-improvement seminar or solo hike (who has time for that in Chicago winters?). Nope, it hit me in a dorm room comparing myself to everyone on Instagram. Everyone was pursuing their passions with their whole chest, while I was fumbling through life trying to sound like I’d read the entire syllabus.

That day, I decided: no more comparing my behind-the-scenes to someone else’s highlights reel. I started taking creative writing workshops and telling stories that reminded me of home, of growing up on 79th and Luella, of bike rides under hazy summer skylines. I wrote my way back to myself—a self that felt real.

The second reinvention came years later. Picture this: I’d just gotten out of a situationship that had me doubting whether I was even good at relationships. The kind where you’re together long enough to have inside jokes but short enough that you never officially meet each other’s families. Y’all, I was spiraling. Then a mentor—wise, sharp, one of those people who can see through your nonsense—hit me with some brutal truth: “You’re so good at writing characters. When was the last time you worked on the character of yourself?”

It stung. But they weren’t wrong.

Step One: Name a Truth You’ve Been Avoiding

Here’s a fact that’ll change your life: reinvention starts with naming the thing you don’t want to face. If you’re stuck, there’s a reason. Dig into it. Avoiding conflict in relationships because you don’t want to upset anyone? Guilty. Filling your time with distractions instead of making room for things that scare you? Been there. Eating Harold’s Chicken on the couch three nights in a row, claiming it’s self-care? Okay, maybe that one was just Craig.

If you don’t address it, that stuck feeling lingers. Think of it like your favorite jazz tune: you can glide through a few dissonant notes, but at some point, you gotta resolve the chord. Journaling can help, but also ask yourself the tough questions: Is this who I want to be? Or, even deeper, how did I get here?

Step Two: Play with the Possibilities (And Be a Little Delusional, It’s Fine)

There’s a certain magic in imagining the “you” you want to be, even if getting there feels impossible. When I was stuck in that aforementioned situationship, I started imagining what a decisive, confident, emotionally mature DeAndre would do. Sure, I didn’t feel like that guy yet, but pretending gave me a road map to work with.

Would “new me” over-apologize, or would he state his needs clearly? Would he keep brushing off friends’ concerns, or would he actually take their feedback to heart? (Spoiler: he’d listen.) Reinvention isn’t about overnight success, so take it slow. Change your routine. Sign up for that salsa class your friend keeps inviting you to. Dare yourself to text back first without overanalyzing your tone. Small wins lead to bigger leaps.

Step Three: Take Your L’s, Then Laugh About Them Later

Reinvention isn’t smooth—it’s awkward, uncomfortable, and sometimes downright embarrassing in the moment. Like that time I went to a networking event in Paris and accidentally started debating French existentialism with a stranger. (He was, apparently, the keynote speaker.) But reinvention thrives in those cringey moments because they teach you resilience.

You don’t grow by being perfect; you grow by failing spectacularly and realizing you’re still standing. So go ahead—botch that karaoke night. Stumble through that first date. Cry through your first therapy session. You’ll be better for it.

Step Four: Build, Don’t Rebuild

The secret to reinvention? You’re not scrapping the old version of yourself entirely. You’re adding layers. Think of it like Chicago architecture—beautifully complex, blending old and new together. Reinvention is about honoring where you’ve been while creating room for what’s next. That’s why Gwendolyn Brooks’ work hits so hard: she captures the history, joy, and grit of the South Side without losing sight of its possibilities.

You’re not just starting over; you’re starting better. Maybe you’re more mindful of how you choose relationships now. Maybe you’ve learned to own your joy without waiting for permission. Maybe you’re just learning to show up for yourself, no matter the noise.

The Encore: Becoming Takes Time

The funny thing about reinvention is: it’s never really done. Just when you think you’re settled, life throws you a curveball, like an unexpected job opportunity or someone sliding into your DMs with way too many emojis. The beauty is, reinvention teaches you to embrace the unknown. It’s not about being flawless; it’s about being fearless enough to evolve.

So here’s the takeaway: you’re allowed to change. Sometimes that means trading one life for another, shedding your insecurities like an outdated coat. Other times, it’s subtler—a shift in the way you speak your truth, the way you prioritize yourself, the way you never settle for less than love that feels expansive and true. Wherever you are in your reinvention story, remember: your journey isn’t linear, but it’s yours.

Take that first step. The version of you on the other side? They’re waiting. They’re worth it.