Uprooting our life and moving to Asia, cannot decide.

My wife and I are both in our late 20s and are trying to decide if we should uproot our entire life and move to either Tokyo or Taipei. We currently live in Canada (I grew up here, she moved here when she was 14). I am a dual-citizen of Canada and Taiwan. She is a dual-citizen of Hong Kong and Taiwan with Canadian PR. We are both ethnically Taiwanese and her grandma and my parents live in Taiwan.

For the record we are child-free and dual-income and do not want children period. We have a dog and cat and own our home (with a mortgage) and our car. We have friends in Canada, but no family. We are not particularly attached to this place other than our friends and current lifestyle.

Reasons we are thinking about moving to Toyko or Taipei:

Pros:

-between the two of us, we speak English, Mandarin, Cantonese, Taiwanese at a native or near-native level, and Japanese at N3 level

-life in Canada is more and more un-affordable with high inflation and interest rates and generally high income and consumer taxes. The healthcare system is universally free, but it is garbage and we have a severe lack of housing and medical professionals and a huge immigration burden

-Tokyo is clean, polite, safe, convenient, and has amazing food and vibrant youth scene with many activities to do and places to visit. The culture is something we enjoy having worked and lived there for a few months years ago. We love visiting on vacation

-Taipei is polite (sort of), safe, convenient, and has amazing food and vibrant youth scene with many activities to do and places to visit. The culture is something we grew up with and know we can quickly re-integrate into

-She runs a digitally-based business related to art, but client base is all mainly within USA and Canada, not Asia. She would need time to reinvent and change aspects of her business to adapt

-I work a high-paying job in tech at a mid-career level and luckily there are a good amount of options in Tokyo even with limited Japanese. The same applies to Taipei, and my Mandarin is even better

-we have some family in Taiwan

-Japan and Taiwan both have a lot of natural beauty to offer (although so does Canada, but without the food and infrastructure to make it enjoyable during travel, let’s be honest here)

-excellent healthcare systems in Japan and Taiwan that won’t be host to a number of huge problems like in Canada (ridiculous wait times, etc)

Cons:

-working for a Western company in Tokyo or Taipei is one thing, but if I end up working for an Asian-styled work environment down the line, that would be a huge detriment to my work life balance

-certain cultural elements preventing us from easily integrating or making friends, i.e. polite and shy culture, fakeness, etc (this applies more to Tokyo than Taipei)

-having to sell our house in Canada, move our pets and say goodbye to decades long friendships will be difficult

-having to start over in a new country (effectively) and try to make new friends and create a support system in our late 20s is definitely an endeavour

-xenophobia in Tokyo, although this applies less since we are visibly not a minority, but it would probably still affect us somehow

-value differences in feminism, lgbtq support, multiculturalism, honesty and directness in interactions and friendships, etc.

-needing to put more work into increasing language ability in Japanese (and to some degree, Chinese)

This is a huge move, and overall, we know we would eventually like to live in Asia at least for a few years and to retire there for the convenience and healthcare in old age. Do we do this now while we’re relatively young or later when it’ll be even tougher of a career and friendship move?

by SassyNihilist

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