Hey all,
I'm 28 and finally looking to live abroad after missing the chance post-graduation due to COVID. I'm seriously considering moving to Japan this winter on a working holiday visa, working through the winter and traveling around the country in the spring.

My big question: Is it better to work a full season at a ski resort, or base myself in a city like Tokyo or Osaka OR SAPPORO? doing background acting/freelance work and take weekend ski trips?

Here’s my background:

• I’m an expert-level skier who used to compete in both racing and freestyle.
• I’m a high-level commercial/film video editor by trade — I’ve worked on several award-winning projects in Canada.
• I have freelance editing clients back in Canada, but the time zone difference might make it tricky to keep up with that work consistently while in Japan.
• I speak English and basic Spanish.
• I’d love to have my own room if possible (not a big fan of packed dorm living).
• I want to make decent money while still skiing regularly.

Option 1: Work at a ski resort

Pros:

• Free/discounted lift pass and living right on the mountain
• Daily access to skiing
• Housing sometimes included

Cons:

• Pay is low (~¥1,000–1,200/hr)
• Rooms are often shared
• Hard to do freelance work unless the resort has decent Wi-Fi and flexible hours
• Unlikely to use my editing skills unless I find a rare media-related position

Option 2: Live in a city and do background acting or freelance

Pros:

• Better pay and more flexible schedule
• Easier to find private accommodation
• Potential to tap into Tokyo’s creative/production scene
• Easier to manage freelance editing work if I can sort out the hours

Cons:

• Skiing would be limited to weekend or day trips (e.g., Gala Yuzawa, Hakuba)
• No free lift pass or guaranteed regular income

This trip is also a bit of a reset — I’ve been thinking about a career shift and have always wanted to experience living abroad. I’d love to hear from anyone who’s done a similar working holiday or balanced freelance work with mountain life in Japan.

Any tips, insights, or experiences would be really appreciated!