After four years of coursework, practicums, and part-time jobs, graduating felt like a huge accomplishment. I finally had room to breathe. Then fall approached, and it was time to get a “real job”.
I earned my bachelor’s degree in social work, picked up ESL teaching certifications along the way, and assumed I would either go straight into the field or head to teacher’s college.
It felt like the responsible choice — one that made sense to my family, to my need for stability, and to the unspoken expectation that, after graduation, you pick a path and stay on it.
That summer, I came across a college instructor position I was technically qualified for, so I applied, interviewed, and overcame some serious impostor syndrome. By September, I was teaching my first college-level courses from home.
At first, I felt great. The hours were good, my students were kind, and my family was proud of me. I was even teaching future community-service workers.
On paper, it was a dream job. It felt grown-up, fit my background, and seemed like the right thing to do. Over time, though, that feeling faded.
I wasn’t ready to settle down, and I could feel it
Alessa Hickman
Between life changes, teaching burnout, and a growing disconnect from my passions, I felt stuck.
I’ve always been creatively inclined, whether that meant writing, making videos, cooking, or creating digital resources in my free time.
Instead, many of my nights were spent prepping lessons, grading assignments, and reading essays, leaving little room for the hobbies that filled me up.
Gradually, the work took a toll on me, but the expectation that a “good” job is one you stick with for years made leaving seem like breaking the rules.
In my early 20s, I felt boxed into this pipeline that didn’t suit me, and I didn’t want to follow a version of success that didn’t feel sustainable.
I’m entrepreneurial by nature, constantly chasing new ideas, certifications, and ways to apply them. So when I started exploring what else I could do with my skill set, freelance writing made the most sense.
With my husband’s support, I decided to leave teaching and pursue freelancing full-time — a move that raised quite a few eyebrows.
My craving for something radically different pushed me to leave my job and my country
Alessa Hickman
Around the time my teaching chapter closed, I learned about Japan’s Working Holiday Visa program. My husband and I first visited Japan in early 2024 and instantly fell in love with the country.
Back in Ontario, that feeling was hard to ignore. We were renting an apartment with a lease ending in October, and after spending my entire life in my hometown, staying felt more limiting than comfortable.
Between the rising cost of living and a sense that I had outgrown my routines, I wanted to explore something new.
Alessa Hickman
We applied for the visa, were approved, and sold most of our belongings as our move-out date approached. In December 2025, we flew to Tokyo and rang in the new year halfway across the world.
Living here has been incredible. Learning Japanese, navigating a new culture, and building a life in Tokyo have been exactly what I needed. And yes — the food’s been amazing, too.
Moving abroad and changing paths didn’t mean abandoning my education or values. Instead, it meant reframing them.
Read more stories about moving somewhere new
My definition of success looks different now
Alessa Hickman
I’m no longer in a classroom, but my background in social work and teaching continues to shape the work I do.
I create and edit content that’s rooted in helping others, and I’m lucky enough to write about my life and experiences abroad.
When I told people I was quitting teaching, and later that I was moving to Japan, it was seen as somewhat unconventional. My husband even left his stable job to come here.
However, the move opened many more doors than it closed. Living in Tokyo has brought new experiences, stories, and opportunities I would’ve never had otherwise.
I’ve learned that postgrad life doesn’t have to be linear — and maybe it shouldn’t be. For some people, stability is the right choice. But for others, taking a detour can lead to growth you’d never find by staying put.
For me, choosing uncertainty meant choosing myself.
I don’t know what my life will look like in two or five years from now, but I do know that I’m building it on my own terms. That feels like a pretty good place to start.
