Sink or Swim: Taking Risks in your 20’s

I’ve been thrown into a lot of sink-or-swim situations over the years. Right now, I’m in the midst of the deepest waters I’ve ever faced, trying hard to swim, learning the art of survival in real-time. I can’t offer wisdom from a place of having it all figured out—because I don’t. But what I can offer is my story, with all its missteps, moments of clarity, and everything in between.

I’m one of the many people who didn’t follow through with the degree I earned after graduating. In university, my only thought was to get through it as quickly as possible so I could get on with life—real life. The goal was always to finish school and then dive into whatever fascinated me at the time. Looking back, I did get to do some pretty cool things. I became a flight attendant, soaring through the skies, living a fantasy I’d always dreamed of. The idea of constantly being on the move, discovering new places and new faces, filled me with excitement. I’d romanticized the entire experience, and for a time, it was as exhilarating as I’d imagined. 

Life has a way of throwing you into unexpected situations, and soon enough, I found myself in the car sales industry—something I could never have envisioned. Luxury car sales, no less. Imagine the shock: I didn’t even have my full driver’s license, and suddenly, I was selling cars worth 6-figures. There were brief moments questioning, “How did I get here?”. Yet, there I was, in a high-stakes environment where competition was fierce, and success meant making people trust you with their most extravagant purchases. And they did. Even now, it’s still kind of shocking that someone trusted me with a sale like that.

Of course, I’ve done some not-so-glamorous things, too. I’ve had jobs that were tough—really tough—but they taught me a lot. One thing that stands out is how much I’ve switched jobs compared to my peers. While it’s given me deep, valuable lessons early in life, but it also opened the door to a lot of self-doubt. Was I capable of staying in one place? Did I even know what I wanted anymore?

When I was younger, I had a lot of dreams probably like yourself. You know those first-day-of-school sheets where you had to write down what you wanted to be? My answers were always changing, sometimes wildly. At first, I wanted to be a rabbit (yes, seriously). Then, a fashion designer, followed by a diplomat, a business owner, and, at one point, a lawyer. Most of those dreams are still a part of me—minus becoming a rabbit, of course. My parents, of course, gently pointed out that that one wasn’t really possible.

I could dig deeper into each of these jobs, but the truth is, I often quit—not because the work was too hard but because I’d look at the senior people in the industry and think, Do I want to live like them? The answer was usually a resounding no. I didn’t like what I saw. I wasn’t scared of hard work, but I couldn’t picture myself living a life like theirs. I was often told, “Just stick it out, and you’ll get there.” But these people didn’t seem happy themselves; they seemed stuck. I had to remind myself—this isn’t just about proving I can endure hardship. It’s about living a life that feels true to me, a life where I’m in control of my own happiness. It was about listening to myself and holding myself accountable to the life I actually wanted.

Fast forward to now—two years after graduation, unemployed, and I’ve moved back to the city. Understandably, this decision raised some eyebrows. And yes, people thought I was crazy. “Are you sure about this?” they asked, their voices full of concern. The truth is, yes I am out of my mind and I do not care. I was desperate. Life after graduation felt lonely and confusing, and I was willing to do what I want and make it work.  So, I jumped headfirst, and somehow, the path of least resistance began to form in front of me.

The truth is, I’m still learning how to swim. Every day presents a new challenge, and each challenge offers an opportunity to grow. This period of my life has probably been one of the most fun- the roll up your sleeves and figure it out or have crippling anxiety attacks kind. It’s like a crash course in problem-solving, where each challenge teaches you a new lesson. I’m savouring every part of it and smiling hard at my future self. 

One thing I do well is set goals and constantly evaluate and reevaluate them. I like to plan, and I absolutely hate gambling on things I’m not prepared for. I ask a lot of questions and actively seek feedback—even when it’s hard to hear—and I try to listen. That’s the approach I’m taking to make it here. Every day is a new test, but I’m determined to keep swimming, no matter how hard the tides gets.

I’m still figuring it out. This is the hardest swim I’ve ever done, but maybe that’s the point. This journey isn’t about perfection—it’s about progress. It’s about moving forward, even when you’re not sure what’s ahead. Because sometimes, the bravest thing you can do is dive into the deep end, knowing you’ll figure out how to swim once you’re in the water.

This isn’t a neat, finished story with a perfectly tied-up ending—it’s a work in progress, just like me. But if there’s one thing I’ve learned so far, it’s that sometimes, you have to jump in without all the answers. You won’t always know what the outcome will be, but you have to trust yourself to keep swimming.

What part of the waters are you swimming in?