Apologies beforehand for rambling.
I recently returned from a month-long trip comprised of 2.5 weeks in Tokyo, a week in Kyoto and the remainder in the Nikko area. My expenses were mainly for housing and experiences, housing consisting of various capsule hotels and a business hotel for the last week.
I haven't felt as alive as I did in Tokyo since I moved to Chicago from my college town 20 years ago. By the time I left Tokyo I was already thinking of my hotel as "home". I lived out of a single backpack during the trip and my main gripe was that I didn't have my main PC with me and that I had to pack up and move so often. I would be happy with a room in a quiet sharehouse or perhaps a reasonably sized 1K apartment.
I'm pushing mid-40s and make just enough to qualify for the digital nomad visa (and WFH) and currently live in Chicago with a condo mortgage. I have a pair of bachelors degrees that I've never really used. I've mostly worked for startups and small companies in niche fields. I was a project coordinator for a decade and switched careers after a layoff. Now I work with JSON as an implementation supervisor in a small business.
My position is hardly unique, but I've only moved a handful of times in my life and each was a massive increase in quality of life. Smalltown Kansas to midsize college town, from college town to Chicago.
Due to the language issue I'll have to assume that I'll need to at least start with some sort of ALT/eikawa job for visa purposes. It's a massive pay cut, but I live well below my means in the US and have decent savings. My experience in Tokyo was that the majority of my real expenses were housing based. My last week I spent as much on a business hotel as I've seen listed for rooms in share houses. I don't mind living in older properties, etc., but I've read about all the issues with foreigners obtaining a lease.
I'm having a hard time getting my questions out:
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I need to sell my condo, but due to the visa issues, I don't know when I would be able to leave. Does anyone have experience with this? From what I've read so far I might be able to keep the condo until I leave the US and then sign sales papers via the US embassy in Tokyo. This way I wouldn't have to worry about interim housing or finding a place to live if the visa falls through.
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I'm very aware of all the just-plain-junk I've accumulated over the years. Does anyone have any advice on divesting this? I'll be doing this whether I ultimately am able to move to Japan or not. The majority of my life is digital and yet I've gathered lots of one-use tools and "someday I'll do this hobby" type of crap as well as a lot of old computer equipment that I've kept for "backups". I realize now that this stuff has no real value to me, but it's not quite trash. My feeling is that I could get most of what I want to take with me over in checked baggage and maybe one larger shipped package.
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Am I making a big assumption by assuming that I'll be able to get a foot-in-the-door working visa for a Tokyo based company? I've seen many questions asking about work outside of English teaching, but due to my current lack of Japanese language skills, I'm unlikely to be qualified for any of those. Other than soft skills my previous jobs don't have many transferable skills. My editing and writing skills have significantly declined from lack of use over the years and are, of course, based in English.
Overall, I'm just very daunted by what I need to do. However, they overall quality of life in Chicago has been falling significantly since COVID and based on my experience "poor" in Japan would be overall less stressful and more safe. I suppose I should handle question 2 regarding decluttering first. It should be said that as a single person with no extended family that should things go significantly sour in Chicago, I don't have a fallback (long term job loss for example) and I would be able to live significantly longer off my savings in Japan.
I'm also very willing to integrate to the extent that would be allowed and have started earnestly studying the language, though I don't expect that I'll ever be particularly fluent. I found the trip to be helpful for freeing up my capacity for language learning. It feels like I "get it" now whereas before it seemed incredibly alien.
by Ok_Nectarine11