To date, I've been able to work rides within Europe around a little business but taking a "career break" this summer (three months) to get off the beaten track in Russia, Mongolia and the Stans. I'm self-employed and having to pull some work assignments forward and push one or two back but it's not seeming impossible right now. My only concern would be (and it's a possibility) that a new contract comes along that can only be fulfilled whilst I'm planning to be away. That'd put an "opportunity cost" of lost income on the trip that would make it a real hard decision to go.
There again, my brother buried his best friend at the end of last year. 48 years old; heart attack! Carpe Diem as they say. You're a long time dead and besides that, I don't want to be sitting in my armchair in twenty years time saying "Gee, I wish I'd ridden my bike a little more"!
"Every county of England, every country of Europe and every (part of every other inhabited) continent of the Earth" ... 83% complete!
What's left? Moldova, Ukraine, Belarus, Russia, Siberia, Eurasia, Central America, Mongolia, China, Central Asia, India, West, East, Central & Southern Africa, Australia & New Zealand.