Considering Moving to Tokyo at 28, too late given life/relationship timeline?

I’ve been thinking about living in Tokyo for several years now, and I finally have opportunities to make it happen (either transfer within my company to a different org, or find a new position). But I’m questioning whether 28 is too late to do this given my other life goals.

Background:

  • 28, tech worker, NYC-based
  • Have been to Japan before – loved it but know tourism ≠ living
  • Basic Japanese language ability
  • No Japanese heritage/family connections
  • Haven’t built strong community in NYC after 5 years (friends moved, others drifted)
  • Feeling burnt out at current job
  • Want to get married/have kids eventually (ideally by mid-30s)
  • Last relationship ended recently – thinking before getting into another serious relationship, is this the time?

The opportunity:

  • 1-2 years in Tokyo (either transfer or new position)
  • Keep income while experiencing life abroad
  • Travel around Japan/Asia on weekends/holidays
  • Company would handle visa/logistics (qualify for the highly skilled worker visa)

What I’m realistic about:

Based on research and expat experiences I’ve read:

  • I’ll always be seen as an outsider (even after years and fluency)
  • First year will likely be lonely
  • Most friends will be fellow expats, not Japanese locals
  • Daily life involves language barriers at banks/doctors/government offices
  • Most expats leave after 5-6 years – this isn’t a forever home
  • Dating pool would most likely mainly be other expats
  • Systemic discrimination (housing, loans, workplace treatment)

My assumption:

  • Odds are I’d probably be leaving after a few years rather than living there the rest of my life
  • Though of course that could change if I really build a life there

What draws me despite knowing this:

  • I’ve wanted this specific experience for years
  • The expat community seems like my kind of people
  • Major city to major city transition (NYC to Tokyo) feels like good fit
  • Being the “new guy” will hopefully prompt me to go out, do new things, get out of old patterns, and meet new people
  • Travel opportunities in Asia while maintaining income
  • Daily life experience appeals to me

My main concerns/questions:

  1. Age/timing: Is 28 too late to do this if I have other life plans?
  2. Relationship/family timeline: If I’m not prioritizing dating in Tokyo (would be in experience mode), I’m coming back around 30 single. I want to be settled by mid-30s. Does this timeline work or am I cutting it too close?
  3. Community building: If I haven’t built strong community in NYC (where I speak the language), will Tokyo actually be different? Or will I face the same challenges?
  4. The return: For those who did 1-2 years and came back:
  • Did you feel satisfied you’d “done it” or wish you’d stayed longer?
  • How was rebuilding your life back home?
  • Did you feel behind your peers who’d stayed?
  1. Career impact: Did taking 1-2 years in Tokyo affect your career trajectory when you returned?
  2. Is this too risky given what I want long-term? I want deep roots somewhere with strong community while traveling extensively. Does Tokyo derail that or support it?
  3. Honest assessment: Does this sound like someone who should go, or someone who might be using it as an escape from problems at home?

The alternative:

Stay in NYC, travel more broadly (month or two in different places around the world), build community here, keep global flexibility. Or maybe just go to Japan for 3 months first to test it out.

Looking for honest takes:

  • Anyone in a similar position? How did you decide?
  • For those who made the move: was it worth it? Any regrets?
  • Is 28 too late to do this if I have other life plans (family, settling down)?

Edit: thank you everyone! Reading through and answering! One thing I think to note based on common questions is I’m a guy for context

by _wndrer_

49 comments
  1. Do it.

    I’ll be honest, when you’re 28 with no familial obligations or in a serious relationship and you make money well enough…do it.

    I’m 35 now, married. But when I was your age I packed my bags and left for France, then Japan. 7 years overseas and came back better for it.

    I can’t imagine moving again (I live in Canada) with the wife and I now thinking about buying property, but given your situation, now is the time to bite the bullet rather than later.

    Also your legs start to hurt as you get older so use them to travel now young man!

  2. I moved to Japan in my mid 30s through internal rehiring so 28 is not late at all. The pros vs cons points you raised are good but end of the day they are all just assumptions. How your life will turn out depends largely on what you end up doing and also some luck thrown in the mix. Assuming I were in same shoes I would go if I don’t have any debts or attachments back home.

  3. If you can get a transfer, continuing to receive US-parity salary and with the company handling your visa, it sounds like an excellent opportunity.

    If you were wanting to take a career break and teach English for a couple of years to experience Japan, it would be different and I wouldn’t recommend it. However, this sounds like a good opportunity.

  4. I moved here earlier this year at 37 (now 38), you really need to throw the timeline out tge window. You can have goals in life but don’t try to guess when it’s going to happen. I had planned to be married by now, I even had a fiance, but things changed.

    If you want to do it, have the finances to to do it, then do it. Yes, it is challenging when not knowing the language as much but you can still get things done, most places have English services.

    The plan for me is to move back in 2027 and I’m looking forward to it. This is due to my cat dying 3 months after moving here (I brought her with me). I don’t want to have another animal while in Japan (various reasons) so i will wait until I move back and am more financially stable.

  5. 1. No. If you’re unmarried with no kids, best time to move.

    2. I can’t say this for you, but I do think trying to hold yourself to certain life timelines isn’t good. Life happens when it happens, but that’s just my opinion.

    3. I guess this also depends, but I think it depends on what you mean by community. I think you can make a great community while living in Tokyo (I did it), but it takes years for that to develop. Not because it’s hard, but bc Tokyo is a very transient city. People are always coming and going. If you’re specifically want to get Japanese friends then I think it’ll be harder than NYC.

    4. I stayed nearly 6 years so can’t answer these.

    Personally, I say got go for it, especially if you’re an intracompany transferee. That’s like the golden ticket for Tokyo/Japan in general. You bypass a lot of the bullshit regular folk gotta go through. When you say “transfer or new position” what do you mean by that? Like searching for a job that would sponsor you a visa? If so, I’d first see if that’s even an option rn. Really, if you can do intracompany transfer then do it. I think most people would tell you they would’ve took that route if they could.

  6. If you have to find a local job (not via a transfer) it is very unlikely that you will retain a comparable salary. Honestly in my experience with SWE it’s unlikely even with an internal unless you’re very senior but I know that varies a lot. Also, since you have minimal language ability building a community will be difficult. Other than that, go for it.

  7. Hey Op,

    I moved here when I was 27 for a completely new career, main difference is I had learned Japanese. If work is already taken care of,
    then you can spend time picking up the language.

    Making friends and enjoying life here is still fine without Japanese (you should still learn though)

    It sounds like you really want to do this, and since you don’t have any relationship ties back home, and there is the possibility to move with work, now may be as good a time as any. I’ve known people that have come in their 50s.

    Regarding settling down, you can find your partner anywhere, especially when you’re happy, healthy and thriving.

    Do some more research and remember, you can always go back or head out to a different country if you give it a chance and things don’t work out.

    Good luck Op.

  8. What’s wrong with going there for a few years experience Japan and coming back?

    I mean this with love. Perhaps you should just relax and enjoy life rather than try to plan your life to the second.

    You never know what will happen.

  9. I moved to China at 21 and Taiwan at 24 – it changed my life completely and I’m itching to move away after having been in the US from 27-33.

    I met a few women that moved to China when they were 55 – one had worked on farms with horses her entire life and needed a change so came to teach English. She was so full of joy that I’m sure she wasn’t feeling before in the US.

    It is hard – you will never be looked at as a local even if you’ve lived there for 10 years and speak silent Japanese, and always being the outsider can be isolating. But making all sorts of friendships and connections you never would have otherwise is exhilarating. Small things can be exhausting, like changing your phone plan or dealing with an issue with your utilities, but there is a sense of accomplishment once you figure out how to resolve it.

    28 is not too late at all- do it.

  10. Well I moved to Japan in June .. with 29 and I’ve met people in their 40s moving to japan so no it’s not too late

  11. People need to stop asking for permission to enjoy their lives. Just do it. You’re not too old now and won’t be too old at 40, but it’s easier to do it the younger you are. If it doesn’t work out perfectly then so what, you can still move forward elsewhere, but if you never try you’ll just face a lifetime of regret or be asking the same thing when you’re 38.

  12. First visit to Japan at 28 (loved it), then moved in permanently at 31. Fast forward a few decades, no regrets other than the weak yen, making it difficult to visit parents / sibling abroad.

  13. Foreign guy here. I made the move, and seriously regret it.

    Dating pool for a serious relationship is very small for foreign men, and even more for those who don’t speak Japanese fluently.

    Most Japanese women don’t see foreign men as potential marriage material, even those Japanese women who speak English.

    For foreign women living in Japan the odds are better, because there’s far more foreign men than women.

  14. I’m moving there next year at 29. I used to feel the same with pressures of a timeline for marriage and kids, especially since I’m a woman and the biological window is shorter, but I’ve came to terms with the fact that having a timeline doesn’t actually mean I’ll meet the right person or where I’ll meet them.

    While you’re young and healthy enough, go for it. As you said, it might only be for a year or 2. 30 is still very young! I think you’ll regret it more if you don’t try.

  15. Lol you’re not 48, give me a break. Good luck settling down hope you meet a partner there

  16. I moved here when I was 28 and it’s been awesome! Let me know when you’re here and we can hang out haha. (I’m also in tech)

  17. My dude… Dude… Your life does not end at 30. 28 is your PRIME, man, the best time to make moves like this. You have the luxury of a whole life, years to see if it works or not. I tried to make the move at dang near 40, ended up in Fukuoka, then had to scurry back to the USA. I have zero regrets.

  18. I moved there at 32, stayed for 5 years and overall had a very good experience, 28 isn’t too old by any means.

  19. This is an amazing opportunity (especially considering you’ll keep your salary), you’re not bound by relationships or other responsibilities, why not just give it a go?

    You sound like a planner, but reality is that you never really know what life throws at you.

  20. Moved here when I was 29.
    28 is not that old. Do it. Don’t overanalyse.

    Have some fun before you real responsibilities kicks in. Such as having a family

  21. The party ended 35yrs ago. Early 2000’s there was still quite a bit of action. Post quake things really took a turn. Post Covid with this economy and anti foreigner rhetoric spewing from leadership. Can’t say I’d recommend coming here to start from scratch. It may be an upgrade or adventure relative where you are from but i feel we are in a bit of a dark period at present. Far less optimism in the air than decades past. At 28 career and upward mobility should be at the front of your mind.

  22. You’re massively over thinking it & creating issues that don’t exist. Does it matter if your friends are mostly Expats & that’s your dating circle? Plus, if you’re being transferred, they’ll be plenty of English-speaking Japanese in your office.

    28, single, with no real ties to NYC & a very high salary (presumably)…such an easy decision. Even if you only last 3 years, at least you gave it a go. 

  23. I lived there when I was 28, and it was the perfect age. Young enough to know I had plenty of time to waste and not care if it worked out or not, old enough to have some wisdom and life experience. I worked for Nova and they went bust, if I’d been in a decent company I may have stayed. Good luck with it all, it’s a crazy place.

  24. Japanese economy sucks right now. I wouldn’t come here. I came here around the same age as you. Actually much younger and I have been teaching English as a foot in the door. I am 40 and married and still stuck in this dead end job. Married too.

    You need fluency to even land a basic normal job outside English teaching. Find a different country where the economy isn’t messed up and the natives aren’t passive aggressive to foreigners.

  25. Is this a joke? 28? 28 is barely out of college these days if you have an advanced degree. I came to Japan about 2 decades older than this and it was fine. Seriously, who told you that 28 is “too old”? This is 2025, not 1825. 28 is very young in any developed nation.

    The main problem for someone who wants to spend a couple years working in a foreign country is the estrangement of relationships. 1-2 years isn’t that long though, but after that friends start dropping away and you get out of contact with many relatives. It’s also really hard if you’re rooted in a place: family, marriage, pets, etc. But if you’re single, don’t have a bunch of close friends in your hometown that you spend a lot of time with, don’t have a lot of material crap that you want to keep around you (and can’t just put in storage), etc., then making a move like this is really easy. Also, you didn’t mention any pets, so if you don’t have any, that makes it easy too. Japan in particular is very, very hard for pets, because it’s very difficult and time-consuming (at least 6 months) to import them, and even to find housing that allows them. So again, if you don’t have all this stuff weighing you down, go for it.

  26. I moved to Asia when I was 26 and thought it would be 1 – 2 years max which turned into almost 10. Still managed to get married and have kids by 40. Plans like that never really work out. Just do it. Imagine how much you’ll hate yourself later in life for not even trying when you had the chance. Once wife and family come into play things become impossible for a good number of years and then you’re actually old.

    Career wise I think time spent abroad is rather detrimental to neutral. 2 years won’t matter. 10 years make your experience much less relevant „at home.“ Unless you will join e.g. a Japanese company at home, then it’ll be a huge advantage. But in Japanese companies you’ll always hit a glass ceiling fairly quickly even when you’re fluent in Japanese.

  27. if your going to learn to be fluent in japanese, no

    if your not, even 22 would be too late

  28. Moved to Tokyo at 29. Stayed for 7 years then moved to NYC at 36. First three years in Tokyo were some of the best years of my life then started going downhill. Was so happy to be able to leave and move to NYC.

    If it’s just a year or two I don’t see any major reason that puts you at a disadvantage.

  29. 31 years old unmarried male that just moved to Japan 1 month ago. Even when I am older than you, the thought of “too old” has never occurred to me

  30. You’re overthinking it and you’re still young.

    Go and experience a new country. What do you have to lose? If you don’t, you’ll always wonder what could have been.

    The outsider thing is real, but only if you are trying to BE Japanese and integrate into a close knit rural community. Living in the city is very different

    Don’t worry about not making friends. Explore the city/country. Interact with people and this will come naturally.

  31. One thing I haven’t seen in this thread, but perhaps worth mentioning: if you do decide to move forward with it, and you’re in tech or a similar high-earning position (not uncommon for the scenario you’re describing), you should take an evening and peruse /r/japanfinance.

  32. I had a corporate executive position awaiting me so my move was worth it. If you don’t have a job with great salary and benefits lined up, don’t come. Japan pays crap wages to beginner workers and you are beginner here no matter your age if you start out as a newbie in a company. I built a brand new very large house as soon as I moved. A few months of living out of boxes was not fun, but awaiting the house was fun. Your salary will be nothing like NYC so why would you take a huge pay cut? You need to be investing, building up a retirement fund, and get a mortgage to have it paid off before you retire. Think long and hard. Research customs and culture here. It’s very different.

    You can not get a work visa here while on a tourist visa. You can not even apply for a job. It is illegal. Getting a visa will be your biggest challenge. You won’t have time for travel much as work hours are long here. I worked 12-18 hours per day, 6-7 days a week. I made great money, but all I did was work. Research long and hard!

  33. If your opportunity is a country transfer with the same company, and the duration is 1-2 years, it means it is probably 2-5 years if you come in as an expat. That implies US-based income with tax equalization (which is attractive because Japan’s progressive tax rates is worse than US)

    Have company sponsorship is very very useful for taking care of visa arrangements, and for finding a place to live. (because they are guarantor)

    In any temporary assignment, finding deep roots will be difficult, especially if you have no pre-existing ties or dont speak the language (yet). Tokyo has a lot of expats and the community is transient. I have seen them arrive in their early 20s, to mid/late 40s with families and children. Also, the expats can be kind of clique’d; based upon industry and/or country of origin. It’s fairly easy to meet people, but as noted, most will be expats.

    If you want to hang with the expats, then live in Hiroo, or Azabu juban and spend nights in Roppongi. If you want to meet more local types, learn the language and try a sport/activity. You will always be considered an outsider because you are a foreigner, but that doesn’t mean you can’t be accepted.

    I lived in Japan for 5 years, and left because of a transfer to another overseas location. I ended up traveling more around the region than within Japan. Keep in mind also that Japanese work culture is different than US.

    If you are worried about your career upon returning, then its important to understand the goals of an overseas assignment, what you can learn from it, and how your experience makes you more valuable when you return. Otherwise, it’s a great adventure and opportunity. Beats teaching English or cleaning rooms in a ski resort for a pittance.

  34. My advice would be to do it, you’re 28 (same age as me) you have no wife/kids (like me again lol) so why not just do it? Experience something new in your life or risk regretting not doing this when you had the opportunity.
    Maybe in a few years you still want to live and work in Tokyo but can’t due to other obligations (that you currently don’t have)

    OP, Whatever you do best of luck and all the best!

  35. Do it, 28? You’re young! Just please please please behave and don’t become one of the bad examples out there (but seeing your post you’re more likely to be one of the good ones!)

  36. Girllllll, I am in my 30s and I would do it if an opportunity came up like that. I grew up moving around so being in one place is driving me crazy lol.

  37. If you can transfer within a western company, that’s half the hard part squared away already 

  38. Don’t associate doing things for your life with age. OMG, you’re 28 years old!!!. Do as you please. You will only regret it otherwise in years to come. You’re overthinking it. Move to Japan. I moved to Korea at 43 , and loving it.

  39. Just grab every opportunity in front of you. Life is short. It would be challenging at the beginning, but you will get used to the life in Japan in a few years.

    Hope you meet great people in my home country.

  40. Thinking about the same too, but probably not going to move in the next couple of years until I managed to increase my savings.

    I am based in London though, M31, civil engineer and currently learning Japanese too. My biggest concern is I have no ideas on what my career path would look like if I moved to Japan. AFAIK civil engineering in Japan has a rather different system and overseas experience does not appear to be compatible, not to mention fluent Japanese in business level is an essential requirement.

    Gonna keep an eye on this post and I believe I will be able to get some insight here!

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