My Journey of How I Went From Teaching English in Japan to a Career in Tech With The Coolest Company in the World

Oh So Bittersweet

The teaching life was an interesting experience while it lasted, but it was finally time to move on. There are of course elements and particular parts of my teaching experience that I will always love i.e. seeing those lightbulb moments on students’ faces, helping eager students progress toward their goals, sharing ideas of personal development & education.

However, it was ultimately the uninspiring environment (unproductive meetings, monotonous non-teaching related tasks, etc.), subpar working conditions (low pay, job instability, regular six-day-weeks, overtime, etc.), and inability to pursue my real passions that steered me clear of continuing on with the English teaching path.

After a little over six and a half years of teaching English in Japan (also the exact amount of time I’ve lived here), I made the change into a career I never knew I always wanted.

TL;DR
I went from an unfulfilling nine-to-five work life to doing something I truly love by helping make the web a better place for more than a billion people each month with the coolest 100% remote tech company on the block — Automattic.

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  1. Oh So Bittersweet

  2. Post-University Life

  3. Sapporo: My Second New Home

  4. My ALT Experience

  5. Living On The Poverty Line

  6. #NotAboutThatLife Part One

  7. #NotAboutThatLife Part Deux

  8. Learn To Code The Hard Way

  9. Democratize Publishing Part One

  10. Democratize Publishing Part Deux

  11. Welcome To The Chaos

11 thoughts on “My Journey of How I Went From Teaching English in Japan to a Career in Tech With The Coolest Company in the World

  1. Thanks for sharing your story, Paulo. Even though I knew the outcome I still held my breath a little there at the end, nervous for you! The GIFs were perfect too. Congrats on finding a career you love and on your beautiful family as well!

  2. I believe they’re always hiring. Lol. How long did it take you to do all those self-taught courses? I’m planning to apply, and I’m pretty glad I ran into your blog. I think I might do the same thing you did – take a lot of courses to prepare myself for the application.

    1. I’m pretty glad I ran into your blog.

      Thanks for stopping by! And I’m glad you were also able find something useful 🙂

      How long did it take you to do all those self-taught courses?

      In total, give or take 3 years — a bit long, but this was on top of a full-time job, parenting, and not having any background in web development. And I literally dipped my hand into everything i.e. programming, digital marketing, design, etc.

      I might do the same thing you did – take a lot of courses to prepare myself for the application

      Yeah, that would definitely help! If I were to look back on what I could have done to prepare more effectively, maybe I would’ve considered focusing more on CSS proficiency, WooCommerce, and making sure I know how to work & navigate the WordPress.com platform like the back of my hand 😄

      I’d be glad to answer any other questions, so feel free to shoot an email anytime: https://peaeb.blog/contact/

  3. What a journey! I recently applied to become a Happiness Engineer, and I’m very anxious. This would be my dream job and I can’t wait for my first interview.
    I’m currently learning JavaScript with TreeHouse and Codecademy at the same time, using the second to practice rather than as the primary source of learning tool. I’ve also learned CSS, HTML and Python from Codecademy but I might need to practice and start working on some websites of my own, to experiment and stuff.
    While the degree I’m pursuing at university is not related to tech at all, I really want to be a developer and I think the best way to do it debt free is through self-teaching.

    1. I recently applied to become a Happiness Engineer, and I’m very anxious. This would be my dream job and I can’t wait for my first interview.

      Nice, and best of luck! If you haven’t already, check out the Happiness Engineer blog:

      https://happinessengineer.blog/

      I really want to be a developer and I think the best way to do it debt free is through self-teaching.

      Absolutely. Being self-motivated to continuously learn is an invaluable quality to have. Keep at it, and you’ll eventually find that many opportunities start opening up for you 🙂

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