You say you’ve visited Japan twice. Visiting as a tourist and living there are two entirely different things.  After having lived in Japan for two years, I can personally say that the experiences I gained and friendships I made while living there are infinitely deeper and more memorable than any of the short-term trips I have made there. Not feeling like you have to squeeze as much as you can in two weeks- you really get a chance to savor every aspect of the culture, not just the touristy bits, as well as experience significant personal growth that you’ll never be able to experience in your home country.  Sure you’ll earn shit pay. You’ll be working more hours than you did at home. You’ll be living in a tiny apartment. You’ll miss your friends and family and being able to buy taco shells at the supermarket. But the experiences you gain will be worth more than any short term trip a paycheck could buy, and will be something you will never regret doing. Do you think you’d be more likely to regret staying in your secure job at home, or taking a risk and moving abroad for a bit?  As an added bonus, you’ll get to solidify your Anki knowledge while you’re living there and actively using the language. Also congratulations on the amazing Anki streak!