Updated March 22, 2024

What Teaching English in Italy Taught me about Careers in Japan


Eri Ochiai

Japan Dev contributor

My first job right after graduating from University was teaching English in Italy. 

After getting the Certificate in English Language Teaching to Adults (CELTA), I became an in-company business English instructor in Milan. I taught people in various positions, from new hires to managers, and sometimes board members in large multinationals in Consulting, Banking, and Tech. I had students who were my age and students who were older than my parents. I ended up teaching several hundred students, many of whom I still remember their names and faces. 

Lessons were held in the office so my days consisted of going from one office to another while making pit stops at small coffee shops (called bars in Italy). I would walk past the Duomo, the central cathedral in the center of the city, every single morning on my way to and back from work. As someone who enjoys traveling and exploring, this job turned out to be something that suited me pretty well. 

What I found surprising about this job was how it taught me the most vital lessons I needed about careers. While I was the teacher, my students were also my teachers especially when it was about careers. They shared their perspective on the work they did, their future ambitions, and their concerns.

In this article, I will draw out a few lessons I’ve learned from this experience. When I think about what I do today, some key values and lessons have shaped the way I define a “Career” as a Career Coach and it may come to you as a surprise. 

What does “Career” mean? 

What do you associate with the word “Career”? 

When I was in school I thought that a career was like a train track, solidly laid out for me where somehow I would choose a path and stay on this track for however long I could or had to. If I fell off from it, then I lost my career. This made me feel limited and unseen as an individual. 

Despite feeling this way, I saw my friends wearing the typical black suit going to job fairs so I tried to do the same and failed. I can still remember the time I couldn’t even make it to the event because I was so sickened by the view of hundreds of job seekers wearing the same exact outfit heading towards the venue. 

I started to have a strong distaste for the idea of job hunting in Japan and the word “Career”. 

I wanted to escape from choosing a train track. A flame of defiance burned strongly and I promised myself I would somehow prove that my life would be different. This was how I was before I started teaching in Italy.

The joke’s on me because today I talk about careers and even have “Career” in my title! 

Here’s what I found on Indeed on the definition of “Career”:

The word "career" usually has two definitions or meanings. "Career" is often used to refer to a profession, occupation, trade, or vocation. A career could define what you do for a living and range from those that require extensive training and education to those you can perform with only a high school diploma and a willingness to learn….

Career has another definition as well, though. It also refers to theprogress and actions you have taken throughout the working years of your life, especially as they relate to your occupation. It is comprised of the different jobs you have held, titles you have earned and work you have accomplished over a long period. When viewed in this context, a career includes everything related to your career development, including your choice of profession and advancement.

-- What is a Career? Definition, Paths and Examples - Indeed.com

Your single career could include a variety of different paths. 

What I didn’t know back then was that a career wasn’t a single train track. Through the lessons I gained from teaching English in Italy and the experiences that followed later on I came to the understanding too, that “Career” is inclusive rather than exclusive of experiences. 

A Career is like a plate of spaghetti 

I once saw in the hallway of a University a funny comic strip of different everyday objects as representations of Italian culture. One that stuck to my memory was a plate of spaghetti. 

The way the long pasta would get tangled with the other pieces and the way it would mix with the pasta sauce… the seemingly chaotic dish that makes so much sense. I see careers like that today. Even when I was teaching English to people with corporate jobs, I often had students who had other activities that — for them — were essential parts of who they were as a professional. 

Some who came from rural areas would tell me how they were actively planning to start or even currently manage a Bed and Breakfast in their hometowns. Then there were also some who didn’t have a lot of plans for the future and were simply enjoying themselves. There were never two people who viewed their careers in the same way.   

I learned that a career is really about how you make sense of your plate of spaghetti, or in other words, experiences. 

Keep your eyes open because a single person can change your career

One time I made a student cry. We were in a one-on-one lesson that day and I had decided to have them watch Steve Jobs’s famous speech at Stanford. 

Something about the video and the questions I asked hit them differently that day and they started to open up. They told me how unhappy they had been in the previous months after getting what they thought was a prestigious job only to realize it was not what they wanted to do at all. 

I was deeply moved by their honesty.  I didn’t know what to say so I stayed quiet and listened. In my silence, they continued to talk and I noticed their voice shifted from feeling lost to something that sounded like determination. By the end of the lesson, they declared they were going to pursue what they really wanted to do.

This is not a story about how I changed my student’s career. This is a story of how they changed mine. When I think about the pivotal moments that shaped my career, I always think about them that day. I still remember as I walked past the Duomo on my way home, I thought to myself if there was any job out there where I could experience what happened with them, I wanted to do that for a living. 

Open your eyes to the possibilities that one person can have on you and the possibilities you can have on them. 

Every career is unique and valuable

I have to admit, there were times I would compare myself to my friends back home and wonder what kind of job I could have gotten if I hadn’t left Japan. 

I remember the times people had advised me not to move to Italy right after school as it could “damage” my career trajectory. That’s why in the back of my mind, as I was working as a teacher, I kept asking myself, “Is this job setting me up for success or failure?” I had no way to measure apart from how much I was getting paid and I wasn’t getting paid a lot. I would teach students who were my age working for the Big Four and feel a little insecure when my clothes didn’t look as nice as theirs. 

So, did I fail? What I do know is that for me, beginning my career as an English teacher in Italy was the best experience I could have ever gotten. I learned that teaching is not about saying what you know to others but about providing a safe space for others to grow and learn. I learned how to listen and ask good questions. I learned the value of partnering with my students where I’m a teacher and a student.

 I am so proud of having had this experience that it doesn’t matter what someone says to me anymore. I gained priceless wisdom and knowledge and met many inspirational individuals. 

That’s why when I work with someone I pay attention to their story and less on their title. I love hearing and reading stories like the one about Cornelius who went from an English teacher to a software engineer  or about Eric’s personal story about his career (this one’s in Japanese). 

I also interview people with an interest in learning about their journeys and wisdom along the way.

Knowing that your career isn’t a mere competition but an original book, a one-of-a-kind story will liberate you to powerfully write your next chapter. 


Teaching English in Italy was never on the list of things I wanted to do growing up, nor was it during my University years. Today, I am so grateful to have had the experience. 

To put it simply, it was a journey of self-discovery. I established foundational values through my students that have shaped the way I work and live today. I learned that a career isn’t just a single path that I must stick to but a colorful mix of experiences that come together often in surprising and unique ways. 

At the same time, knowing that any person can show up in my life and leave a profound imprint has nurtured my curiosity and openness to the world around me. Finally, I view every person as having a distinctive career and I’m able to acknowledge my own previous experiences. I have also gained confidence that any future experiences and challenges yet to come will always be the perfect addition.


Eri Ochiai

Eri is an Expat Career Coach in Tokyo. With a background in HR at an IT startup and expat life in 🇮🇹, she's partnered with +300 expat job seekers in tech. Currently, she specializes in supporting expats towards fulfilling careers drawing on her unique insight and experiences. On a constant quest for good bread.