What If the Detour Is the Path?

Lately, I’ve been grappling with a question that seems deceptively simple but has profound implications: Should we plan our lives, or let them unfold naturally—improvising as we go and trusting what comes?

We live in a world that celebrates goal-setting, vision boards, and five-year plans. From a young age, we’re taught to map out our futures like GPS routes—college, career, marriage, home ownership, early retirement. And for a while, I was all in. Planning gave me a sense of control, direction, even identity. But life, as it tends to do, threw me a few unexpected curveballs. And those detours challenged my belief in the power—and limits—of planning.

I used to be a HUGE planner. I planned to study psychology in the U.S.—and I did. I planned to pursue a PhD in Psychology—check. I even crafted a five-year plan to land a job at my dream company, and by year three, I’d secured an internship there, right on schedule.

But life had other plans. Then came Spring 2020.

I was visiting my boyfriend (now husband) in Boston when I got a text from him at work: "There’s a pandemic. We’re going remote starting tomorrow." I was in the thick of my PhD thesis. The world was unraveling, and my meticulously laid plans suddenly felt irrelevant. I ended up staying in Boston through July. That summer, we drove back to Minnesota, loaded up my belongings, and left—no goodbye parties, no closure. Just a quiet, disorienting sense of fleeing one chapter—without closure, and without knowing what kind of life we were driving toward.

Determined to stay in the U.S., I applied for OPT, giving me 90 days to find a job. With several strong internships on my résumé, I was optimistic. But as the pandemic dragged on and the job market contracted, my confidence cracked. Weeks turned into months. I later learned that the role I’d been aiming for—on the very team I had interned with—had been filled. My five-year plan had officially fallen apart.

It’s important to acknowledge that having the opportunity to plan your life is, in itself, a privilege. To be able to set long-term goals, explore different paths, or even dream about what you want to do assumes that your basic needs are already met. It means you’re not in survival mode—you’re not consumed by immediate concerns like putting food on the table, securing stable housing, or navigating crisis after crisis. Planning requires mental space, emotional bandwidth, and often, financial security.

So what about those who don’t have that luxury? When survival takes priority, the question shifts: not “What’s your five-year plan?” but “How do I make it through this week—and still hold onto hope?” How can you stay resilient, creative, and open-minded even when life doesn’t give you much room to maneuver? Sometimes, the most powerful kind of planning is simply creating enough stability to make it through the day—and trusting that clarity and choice will come with time.

Before Jimmy Fallon became host of The Tonight Show, he faced harsh rejection—and even lived with cardboard furniture before reaching his dream of comedy stardom. Todd Owyoung/NBC via Getty Images

That’s why stories like Jimmy Fallon’s are so captivating. They offer a kind of clarity that few of us have. At age 12, he knew he wanted to be on Saturday Night Live. He stayed focused on that dream, designed his entire life around it, and eventually made it. I was mesmerized. That was the kind of narrative I had once envisioned for myself: dream job, dream company, perfectly timed execution.

Instead, I landed a six-month contractor role. And then, almost accidentally, I found myself in my current job. While it didn’t come from a carefully crafted plan, it has turned out to be deeply fulfilling. It satisfies my need to make an impact, gives me a sense of purpose, and allows me to contribute meaningfully without overwhelming other parts of my life.

For one, I sidestepped the massive layoffs at my dream company at the time, which included the very role I once coveted. And in an unexpected way, this job gave me something even more valuable: freedom. It doesn’t consume me or define my identity. It doesn’t define my worth or identity. Because of that, I’ve been able to build a rich life outside of work—one filled with creativity, new interests, and space to nurture other aspects of my well-being.

Looking back, I know myself well enough to say: if I had landed my dream job, I would have burned out trying to prove I belonged. I would have chased perfection and sacrificed everything else. So while I didn’t get the job I dreamed of, I might just be living the life I once dreamed around.

Then in 2024, my life was turned upside down again. After I lost the H1B lottery for the final time, I had to do what I’d long feared: leave the U.S. and spend a year in Hungary, far from my husband and the life I’d built over 11 years. Thankfully, I was able to keep my role and continue working remotely in the comfort of my childhood home and have the unique experience of living with my parents as a 30-year old adult.

Looking back, I’m surprisingly grateful that I didn’t land my dream job. If I had, it might have reinforced the illusion that I could control every aspect of my life—and made this setback feel even more devastating. Sometimes, too much early success can set us up for even greater heartbreak. Instead, I learned that even when plans unravel, life continues—and sometimes creates unexpected room for growth, clarity, and resilience.

Lee Jung-jae (right) in "Squid Game" (Netflix)

This shift in mindset reminded me of another kind of story: Lee Jung-jae, the star of Squid Game. Unlike Fallon’s laser-focused ambition, Lee never planned to be an actor. He was discovered while working at a café, started modeling, and fell into acting almost by accident. His rise wasn’t planned—it was spontaneous, unforced, shaped by serendipity and timing. Yet here he is, globally recognized and widely admired. His journey suggests a different truth: success doesn’t always come from clarity of purpose. Sometimes, it’s about openness to unexpected paths.

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So, should we plan our lives? 

Maybe the better question is how we plan. Rigid, linear plans give us direction—but they also create fragile expectations. Life is full of detours, delays, and delightful surprises. Some of the best things that happen to us aren’t part of any plan—they show up in the in-between moments, the detours we never intended to take. Perhaps the real secret is to plan with intention but hold those plans lightly. To dream big, but also stay flexible. To allow life to surprise us. After all, it’s in that balance—between vision and surrender—that we often find something even better than what we planned for.

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