Quitting Work to Travel/Live Abroad

[Jacob1234098]

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?

[AZDude]

I did not work abroad, but I did ask my employer to work remotely, and they agreed. Questions you should ask yourself:

1) Do other employees work from home/remotely?
2) Do they have the infrastructure in place? IE: VPN, company laptop you can use, etc...
3) Make sure you have a strong internet connection that is not going to be on a public wifi wherever you go.

As far as taking a sabbatical, there is probably a maximum length they would be comfortable with. Like 6 months, maybe. Any more than that and they would probably tell you they would love to have you back, but no guarantees. Good news is that the tech job market is good right now, and assuming the economy does not crash, you could likely land a job quickly when you get back.

[Paul der Krake]

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?

I am currently looking into doing this, with a tentative "exit" date of summer/fall 2016 to set up shop in the tropics. The career aspect doesn't bother me because I don't give a hoot about my career.

[humbleMouse]

I work in the same stack as you!   If you have 5 years or more experience working in oracla/java you should have no trouble at all returning to the workforce if you would like to get another job after a year or 2 or 3. 

Furthermore, I would suggest reading hacker news "who is hiring" posts like the one for sept 2015 I have provided below:

https://news.ycombinator.com/item?id=10152809

There are many people looking for competent remote devs.  Just make yourself a nice looking bootstrap website shamelessly promoting yourself and go from there.  Also, I have researched cheap places to work remote from extensively and found that greece and portugal are two prime locations with very cheap rent and real estate.  Large cities in Brazil, argentina, and south africa are some other places where your dollar will go very far. 

[StetsTerhune]

I agree with humbleMouse -- you won't have a problem getting a job when you come back as long as it's some reasonable amount of time (I'd say less than a year is no problem, less than 2 years is probably still fine).

What I would do (and I did a very similar thing a couple years ago) if you have a good relationship with your employer is to go to your manager and tell them exactly what you're planning to do. Don't start with asking what works for them, start by saying (e.g.) "I'm going to travel in Europe and Southeast asia for the next year." Then everyone is on the same page, and you should be able to have a frank conversation about what options (if any) there are for continuing the relationship with the employer.

My other 2 cents, as someone who has both worked remotely while traveling and taken time off to travel -- try hard for the sabbatical/ just-quit option. There are just going to be a lot of things you can't do because you need to stay "connected".At least for me I'm still left wanting more when I travel and work. Not that travel/working isn't awesome, it really is. But being fully free and traveling is a completely different thing, and something that you should do "in your youth" if you want to and can.