One year I did the Pacific Coast but did it in three separate chunks:
- Week of Memorial Day, I went from Vancouver, BC to Eugene, OR
- Week of 4th of July, I went from Eugene, OR to San Jose, CA
- Week of Labor Day, I went from San Jose, CA to Tijuana, BJ MEX.

I've managed software teams for many years and during that time, I've taken breaks of 6 weeks, 3 months, 12 months, 10 months and most recently 6 months for long bike trips. There are a few factors that have let me do this:
- I've been fortunate in my choice of employers to let me do this as well as establishing good track record and rapport with my boss.
- I ask way early. If I were to have a discussion today about taking off most of 2014 - chances are good I'd be looking at a change in employers. However, if I were to have discussion about taking off most of 2016, then it might be a different story since that seems further away than typical cycle time on current projects. Once on the "calendar", it slowly gets closer over time. In meantime, I'm taking shorter trips as vacations.
- I work with my bosses on it and do whatever I can to eliminate my job and/or coach and grow my successors so company does well in my old role and I'm ready to do a new role on my return. Often I've found that it takes 12-18 months to get really good at what I do and I want to contribute for a time. However, after a few years in a role, I'm not growing/learning as much as I did when things are new and at some point both myself and team can benefit by something new. So the ideal time between really long trips is ~4-5 years , which is what I've been able to do and also worked with my bosses.
- Most all these breaks have been under a "leave of absence" policy at companies I've worked for. Companies have to have plans for certain legally sanctioned leaves (e.g. maternity, military leave, FMLA) so they figure out how to make those work. However, for good performers who work with their bosses and give sufficient notice there might be other ways to request a "personal leave of absence" and make it work too. However, if for some reason I needed to switch employers I've also built up both enough skills and contacts - and have some flexibility in where I work - that I have reasonable confidence that I could find something different if I needed to (*). I've also lived a fair amount below my means to give me some additional flexibility.
- No spouse, no pets
- Been fortunate and lucky - but also made some explicit choices in my priorities that these extended tours are important for physical and mental health so found a way to do them.

(*) I learned one lesson early in my career when suddenly the software team I was part of was shut down and work was moved elsewhere. That gave me perspective both that I need to be able to switch and find other work if necessary - but also that I can be the one initiating such change by purposefully deciding to take an extended leave and then seeing what comes next in my employment. In both cases, what is necessary is similar: keep skills/contacts current, have some flexibility including keeping extra savings. For me it then became a question of priorities - how important was it to prioritize and find situations that let me take extended trips every 4-5 years vs. other priorities. I'd rather take such trips now when I'm younger and able to do it, than wait many years to retirement and then discover I no longer had ability to do as much.