Let me set the stage for you. It was a sweltering summer evening in D.C., the kind of heat that makes asphalt shimmer and patience evaporate. I was 26, fresh out of college and working long hours on Capitol Hill. My life was spreadsheets and talking points by day, and post-work happy hours with lobbyists by night. The grind was all-consuming—steady, predictable, even comfortable in its own exhausting way. But deep down, I knew the trajectory was wrong. Something was missing, and it wasn’t just sleep.

Then one day, like something out of a rom-com with questionable plot development, I walked into a bookstore in Adams Morgan. Foolishly, I thought I’d just browse and decompress. Instead, I came across a local author hosting a Q&A for his debut novel. He was magnetic. The way he spoke about the world-building, his characters, and the sheer joy of storytelling hit me like one of those cliché “I’m in the wrong movie” moments. My heart was racing, not over him but over what he represented: freedom, creativity, and something unapologetically mine.

The risk didn’t come in realizing I wanted to write. It came afterward, in choosing to actually pursue it.

The Choice You Can’t Rationalize

Let’s talk about the pressure cooker that is D.C. career culture. It’s less about what you do and more about who nods approvingly when you say it at cocktail hour. I had all the ivy-covered qualifications and a boss whose connections could open big doors, but the thought of continuing on that path made my stomach churn. On paper, I was winning. In reality, I felt like I was drowning in someone else’s idea of success.

One night, over a curry goat dinner my mom had cooked, I broached the subject with my parents. My dad barely looked up from his plate as I stammered through phrases like “creative fulfillment” and “alternative path.” When I finally blurted out, “I think I need to leave my job to write,” my mom tilted her head and gave me a long look—the kind filled with both wisdom and wicked sharpness.

“You want to leave a good job? With benefits?” she asked, her Jamaican accent heavier than usual—always a sign that I was treading dangerous ground. I nodded. She set her fork down and narrowed her eyes. “So, what you’re saying is... you want to leave stability for what? Scribbling and hoping?”

“That’s...not exactly how I’d put it,” I muttered, face flushed. Let’s just say the dinner conversation that followed included phrases like “back-home struggle” and “better opportunities.” I don’t blame them; their sacrifices had brought me here, and dream-chasing felt disrespectful in contrast to their grit. But deep down, even I wasn’t sure if this pursuit would work out.

Afterward, I Googled things like "how to know if you’re making the worst decision of your life" (not helpful) and cringed through YouTube videos from self-styled “life coaches.” None of it gave me an answer—it just reminded me there was no answer. Eventually, I realized this was a call I had to make, and in the end, it wasn’t about certainty. I wasn’t certain. It was about choosing to bet on myself anyway.

Freefalling into the Unknown

Here’s the unvarnished truth: My “leap of faith” was anything but graceful. Romanticizing this would do you (and me) a disservice. The first six months were an unholy cocktail of anxiety and ramen noodles. One day, I’d feel unstoppable as I outlined the twists for my novel. The next, I’d spiral over the very real financial gap this decision had created.

To survive, I started freelancing—writing op-eds about D.C. politics and, occasionally, ghostwriting speeches. If you’ve ever tried to balance paying the rent while also scribbling fiction at three in the morning, you know there’s nothing glamorous about the hustle. But slowly, piece by piece, progress started to emerge. I self-published a collection of short stories first, then finally secured an agent for my debut novel.

Through it all, though, I learned something crucial about taking big risks: stability doesn’t follow you overnight, but neither does regret. When the payoff began gaining traction, it wasn’t just about personal pride. It was about proving to myself that the things we dream of—the ones that seem wildly improbable—are worth the messy in-between.

What Risk Taught Me About Love (Yes, This Comes Back Around)

I’d be remiss if I didn’t mention how much this journey also shaped my views on dating. I used to think—and tell myself—that relationships thrived on set plans and predictability. That love meant certainty, and certainty was what I needed in everything.

But love, much like leaving a safe career, will humble you. It won’t always look like the formulas in Pinterest quotes or the spreadsheets in our heads. There’s risk in opening up to someone, in sharing your uncensored self to see if they’ll still pull you close. And relationships that thrive don’t avoid fear—they include it and push through anyway.

When I met the person I’d eventually be with, I wasn’t the guy with “stability.” But I was someone proving I could commit to the scary parts of life wholeheartedly, and that mattered more. Creativity, love, and connection—all of it demands risk.

Some Free Takeaways (Because I Like You)

Here are three things about taking a leap of faith that might just apply to your own life—even if you’ve got no plans to channel your inner Hemingway.

  1. Listening to your gut isn’t selfish—it’s necessary. If you’ve been conditioned to suppress what you feel for the “greater good,” I hear you. But here’s the truth: your instincts are rarely wrong. They might be inconvenient, yes, but they point to where the real growth lies.

  2. Failure isn’t the weight you carry—it’s fuel. Failing doesn’t mean the risk wasn’t worth it. Some of my most epic stumbles taught me how to trust myself more, not less. If you’re taking a chance, be ready to trip. But also? Be ready to learn how to recover.

  3. Betting on yourself changes how others see you too. Confidence isn’t about being perfect; it’s about choosing forward momentum even when the outcome isn’t clear. That energy can transform not just your path but the relationships you’ll gravitate toward.

So, if you’re mulling over a leap of your own—whether it’s a career pivot, a romantic confession, or just trying guava juice for the first time—consider my unsolicited advice: forget chasing certainty. Chase possibility instead. I took my greatest risk not knowing if the net would ever appear. But as it turns out, sometimes the net is you.