I am a full-stack software engineer working with Java/Javascript/Oracle. I have worked 5 years for the same company, saved up 250k, and am about to turn 29. I really want to travel the world in my youth, and feel a pressing need to do it soon. I would ideally like to work while living abroad, maintaining a decent US salary (otherwise it makes more sense to continue working here and continue saving).
My plan is to:
a.) ask my employer for permission to work remotely.
If fails, b.) Seek new full-time remote development opportunities.
If fails, c.) Ask my employer if I can take an unpaid sabbatical.
If fails, d.) Quit my job and move abroad, studying new technologies in my free time, and maybe trying to build a start-up, though I know nothing about start-ups. This would mostly keep my resume looking good for when I return to the states.
This whole process is really scary for me. I need advice from someone who has been through this before. Am I nuts if I actually go through with this? Would this be a step backwards in my career?