It's generally not advised to settle in a place until you've tried it out for a year or two first. Bounce around the world for a decade, get some international work experience. By the time ten years are up, you'll have more adventures under your belt and a better idea of where/if you want to live overseas long-term, there'll be a new prez in office, and you can reevaluate.
If you're not FI or in high-demand positions (secondary STEM, special needs) start by teaching in places more likely to hire you without international experience, and where you can save: Asia or the Middle East (if China's not your thing, Kuala Lumpur, Bangkok or Jakarta have some good schools that pay quite well after you've done a contract overseas). Or even the Outback -- one of the few regions I've considered worth getting teaching certification for.
After some time working internationally, if interested, you'll be more marketable for Europe, which is more competitive, and many countries in which pay a good deal less, esp. after the 2-year tax-free salary treaty with the US is up. Switzerland is considered an ideal 'retirement job': they require high levels of training and experience but provide great savings and benefits, good environment, relatively low taxes, etc.
