Maggie - I second Thatsagirl's advice about teaching part-time while having a part-time or full-time or consulting gig in your "day job" in IT or something related to your old career.
I'm assuming you'd be moving to Canada rather than to the US or the continent, if you go for this. You wouldn't likely be able to get an H1B (the visa that lets you work for years for a US corporation - like we don't have enough underemployed US IT people
) but probably you could get into Canada easily enough since it's in the Commonwealth. I'd expect there's enough of a demand for IT-related fields in Canada in locations reasonably close to good skiing. For example, Calgary or Vancouver.
That's pretty much the model I'm doing in the States - blew off the corporate job, moved to Summit County Colorado, right around Breckenridge, Keystone, A-Basin, Copper, and Loveland, and only 35 miles from Vail, 45 from Beaver Creek. Also only 70 miles from downtown Denver, where I was able to land a part-time gig at an IT firm. That job takes up a couple of days per week, usually one down in Denver and parts of a few other days remotely as needed. That pays my benefits and keeps me in the IT game in terms of career currency.
I once told a friend that I felt lucky, because I'd found 3 occupations that I'd loved doing, and had taken a chance at times on all of them - at least enough to have no regrets: Working in radio, acting, and then working with computers (which became the only one I could make "real money" in). When I got hired at Breckenridge last season and then got my PSIA Level 1 this season, I privately added "teaching skiing" as the 4th.
Somewhere in an alternate universe, there's a MarkXS back in Boston full-time, burnt-out in a cube trying to balance too many projects, too much demand on him and his team, never getting time to get out in the outdoors, getting sicker and weaker instead of healthier and stronger, coming to hate the career choice that he once loved due to buying in too much to climbing the ladder, desparately politicking for the next promotion to Director and trying to wrangle a way to become VP.
Meanwhile in this universe: I just wrapped up teaching for my second year two weeks ago, still have a few weeks left to ski for free with friends at A-Basin, I'm in rehearsal for two different shows that will keep me onstage from May through August, I'm involved in IT on a non-career-climbing level that I'm finding satisfying again, I've been back in a radio studio a couple of times to do some voiceovers for my wife's ski fitness studio's spots, and I'm even going to finally learn to ride a damn bike at age 53! Those bike paths all around the county are looking too appealing.
Tomorrow I unload the last vestige of my former corporate/city life: my charming condo (which was my "security" and largest investment) in Boston becomes the property of a couple of girls going to university near here (well technically the property of their rich parents who want to give the little darlings a good start on the way up the ladder). Meanwhile I'm taking a break from loading up the last couple of boxes of my former life into a car to start my last road trip back home, to the mountains.
Go for it. (Of course asking about it here on epic is like a drunk asking a bunch of other drunks if she should have another drink!
: We're not exactly the AA meeting here.)