Put yourself in my shoes, what would you do?

You only get one life to live, so make the most of it.

Me, I wouldn't do it. You, go for it. Go big or go home. Just have a Plan B to fall back on if things don't work out.

+1
You will always wonder what could have been, but definitely have a plan B.
 
My son is able to live on his income and save money. He doesn’t have to use his savings. My friend’s son just returned from 10 years in Thailand working. He was able to land a decent job here. I think the key is that he wasn’t unemployed so no gaps in his work history.
 
The pain of regret when you’re old, will cut far deeper than the pain of losing money when you’re young
 
i agree. Dropping out of the USA in the prime of your life carries high risk. You lower your risk if you start a teaching career in another country. Vietnam is super cheap so you can live like a king provided you have a source of local income and not totally rely on your life's savings.

In USA, teachers appear to be treated like dirt. However, in Asia, teachers are treated with higher respect because of the Chinese's influence in that the teacher has superior knowledge and the Asian students are taught to listen to wisdom.

Wealthy Asian parents pay big bucks to a private teacher/tutor so their child can get into the better colleges. Any teaching experience/credentials is a plus.

I have to disagree here. Teachers in USA focosed on the end game usually make out well. Of courses there's extremes. https://www.businessinsider.com/teachers-early-retirement-traveling-the-world-2017-1

However I completely agree with your statement that "Dropping out of the USA in the prime of your life carries high risk."
I'd suggest the OP focus on becoming FI.
"Make hay while the suns shining is one of many euphemisms"
Good Luck!
 
Hold on here, care to flesh out those numbers?..you are 36 have made 65K in two years sports betting and own a house.

Yet you have a total of 100K assets including your home equity and at 36 and single have only 35K in retirement funds..these numbers absolutely do not add up. Care to elaborate otherwise I'm putting on my skeptic hat...

+1
 
If you you were bored with your most recent significant other, maybe examine if that was actually boredom with your life, or if you were lazy in your choice. Course correct next time.



Don’t confuse boredom with life and boredom with SO.



If you really were bored with the SO, keep looking for a life companion. It may be the deepest purpose and comfort in your life, which you cannot appreciate until later.



Have you figured out that the first couple of years of any relationship is just a prelude to the real thing? The real thing is a shared life, the good but especially the bad. It’s hard to put into words what this is until you have experienced it.



Examine why you don’t like having a job. Entry level jobs are often hazing exercises as test and prep for providing actual value in mid and end of career. The serious money/commercial world is largely dominated by large corporate teams, and free lancers face impossible odds against rising above hand to mouth subsistence outside these systems. Corporations are actually gangs, and you need to be part of a big, tough gang to compete.



Learning to meld with a team, submit to authority, often not gently administered, is a big part of growing up, and actually becoming valuable. There is a spiritual aspect of ego taming that is part of becoming fully human. As one very high flying official said in a workshop, you have to find your crowd, your level of organization, a job that challenges your abilities.



Late twenties is decision time for settling in to a path to create an adult income stream, begin and dial up a flight path to financial independence, at some age, and start dating girls who are prospective lifetime partners.



My value system is to have no drama with marriage, career and investments, but entertain myself with crazy **** around the edges of that.



You can have a wild bad ass time with the right girl, the right job, the right investment approach, and completely open up, retire, after a couple of decades if you do it right.



Yea, but don’t think the OP was asking for a philosophy lesson, nor for the answer to life, the universe and everything. Your value system is not his, his goals are not yours, and I’m not sure he needs to be given the rules to run his life along. I think he was asking for opinions on the financial feasibility of HIS dream.

OP there are no guarantees in life. You might die tomorrow, or next year and all the savings in the world will do you no good *shrug* .Live the life YOU want live. SInce you asked what I would do, I would take the chance the chance - since there are no current commitments - and see how it goes. I’d be constantly re-evaluating the situation, and trying out different scenarios. After six months to a year, I’d really go into contemplation mode, to decide which would truly make me happy - lots of money and the rat race, or a more leisurely lifestyle.

There’s no one answer for everyone, but we most often regret the things we never attempted.

Good luck and stay in touch.
 
...and whether or not I could afford my current choice *grin*
 
Mid thirties no established relationship nor career, nor wealth, it’s a train wreck in slow motion.

Had a cup of coffee with a guy last year who was one of these perennial drop out drifters, most of his earnings were off books so not even any social security.

Pushing 60 with a bad back kicked out of his sisters house with no options other than homelessness or suicide.

I tell young people, illness, poverty, isolation, and old age are hunting you down, you have a head start, start running.
 
I have a friend who did the SE Asia thing for a couple years about 8 or 10 years ago. If you're resourceful and don't have trouble finding work, it could be fun and worthwhile. However if you're like me, and count my blessings I've been employed a long and steady time, I would not do it. Luckily for me before, I was able to do study abroad in Japan while at University for 1 year while 23-24 yro - outstanding memories of that. Note when studying abroad I had considerably less assets than what you give, however I received a scholarship and subsidized housing.
 
This is an interesting post and the responses have been facinating. One question: how is playing poker for 40 to 60 hours a week NOT a "job?" Seems like a regular job plus overtime!
 
This is an interesting post and the responses have been facinating. One question: how is playing poker for 40 to 60 hours a week NOT a "job?" Seems like a regular job plus overtime!



Yeah. And after a few weeks I am not at all convinced it’s any more fun than a ‘real’ job which is likely to be more lucrative
 
... I tell young people, illness, poverty, isolation, and old age are hunting you down, you have a head start, start running.

I have been running all my life, starting from elementary school. :)

At this point, I think I have far outpaced isolation and poverty, and I should be safe from them.

Illness and old age will eventually catch up with me. I will be running until I drop. :) Illness almost got me 7 years ago. Whew!
 
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Life is full of regrets sometimes (would've, should've, could've). If you don't at least try it, you may regret it later in life. Try it for a year or two and if it is working out for you and you are happy, great. If not, you can always come back to the US and pickup where you left off
 
Disclaimer: most people on this site have never worn your shoes or by the time they got here they have forgotten how they fit.

I somewhat admire your ability to do want you want vs what is traditional. Although I can’t give advice to that mindset.
 
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