Advice sought re: annual leave

This is a strange situation I find myself in and I’m mostly asking for any real life advice. I very rarely post in any public setting because I realise how people might judge me, but basically, I came to Japan when I was very young, straight from University, never really planned to stay and in an era where things were a lot less concrete in terms of getting actual labour related advice etc. (2001 was when I arrived).

I worked for one of the big English schools initially and then a small family run company for about 6 or 7 years, and then to my current situation where I am working at two different places as well as doing a lot of creative work. I’m employed as a private contractor at one of the jobs, and part time at the other, where the hourly rate of pay is very good and until a few years ago it was basically a perfect situation in terms of my work hours and days and the freedom it gave me to pursue and fund my artistic life.

I have always been the sole employee there, and until a few years back my employer was a very decent person. I feel incredibly naive and stupid saying this, but because of my background (my first two jobs here I was a full time employee) it honestly never occurred to me until a few years ago that I was entitled to paid annual leave as a part time employee. I say this knowing full well that people will think I’m stupid and I actually feel incredibly frustrated at myself for never knowing my rights in this regard, but it was just something that honestly never occurred to me, particularly with my hourly rate of pay.

Anyway, around 2022 I asked my boss about this after a very random conversation with a friend about the topic, she was shocked that I wasn’t given any annual leave, including payment for sick days or weather emergencies etc., and my boss denied that I was able to get annual leave, and it wasn’t until early this year that I finally decided to demand that I was paid.

The situation now is extremely tense, there is a lot of guilt tripping etc, and as I’m the sole employee and I fully understand that it’s difficult to take long holidays apart from my normal (unpaid) days off in Golden Week, Obon and over New Year (which basically is what I wanted to be paid for), I raised the possibility of being paid some of my accrued leave as blocks of hours rather than full days off, there are many days when I have unpaid gaps of up to two hours at a time and I’d like to be paid for this wasted time (one extreme frustration is that they won’t actually tell me how many days I’m owed, I’m there three or four days a week and have been there since 2009 so it is at least 8 days a year and there is a minimum of three years owed from my discussions with the labour board).

Basically, I’m obviously on the way out, what I want to know in terms of anyone with personal experience is if I have any legal recourse in getting some of this money paid to me (there is 16 years of non payment) and also if I’m within my rights of requesting blocks of hours of leave (the labour board said that as long as they agree to it this is perfectly ok). I feel incredibly overwhelmed and exhausted because they literally won’t discuss it with me, they get angry and defensive or ignore direct and explicit requests, I’d really rather not have to take it any further and I actually doubt I’d have much luck with it but I’d like to hear from anyone who has actual experience of it.

I’m always very nervous posting in Japan related stuff from the early forum days and the kind of responses these kinds of questions would generate, and I understand that it seems like an insane situation to have let happen to myself, I feel the same way, I have such a busy and full life outside of work and honestly until a few years back never ever had the slightest stress about the job or being there at all (I still actually love the job itself a lot), it’s just a very weird shift and would appreciate any advice at all.

by autumnleaves744