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The Expat Who Regrets Being an Expat in Latin America

Published March 20, 2022 in Personal Stories & Opinions - 0 Comments

When you listen to other expats talk about their life down here, most seem to be in agreement that their life is better as an expat in Latin America than back home.

After all, some find it easier to have more sex down here.

Others enjoy the lower cost of living.

Of course, we all get the benefit of travel and how cool that can be.

For the non-Americans, it can be easier to reduce the taxes you are told to pay each year.

Cold winters replaced by year around sun or spring temperatures.

So on and so on.

However, there is a certain type of expat who seemingly regrets his past decisions with this life.

He might not necessarily regret being an expat though but maybe looks back at more “degenerate” aspects of his life abroad with some regret.

Perhaps shakes his head as he matures and thinks “I could’ve done better.”

Though, to be fair, I think plenty of people – expats or not – come to an age where they mature and regret some of the things they did in life.

Nobody is perfect.

Still, for the more degenerate expats who started down here a bit younger, they might look back at their time as a little bit of a “waste of opportunity.”

Thinking about the academic success they could’ve had earlier on.

How smart they were as kids.

All the potential to be more successful.

For others, some might turn to a religious conversion.

Like a stereotypical woman who turned 35 yesterday and now “has found Jesus” after fucking every dick in the neighborhood.

This type of “regret for being an expat” isn’t USUALLY seen among folks who started out being expats at an older age in my experience.

And I only emphasize “in my experience” quite strongly.

As you should be aware, this is just a blog and I’m only putting down words on what I have seen personally.

The man who came down here when he was 40 or 60 might very well have regrets about his earlier years but they don’t have much relation to “being an expat” because he wasn’t an expat just yet.

And, for the man who is in his 60s already, he perhaps is less likely to have regrets about wasting career potential.

At least when compared to the young 20-year-old expat who is broke for such a long time trying to figure out how to make ends meet in a local economy down here where most jobs are not realistically obtainable for us in Latin America and where many try to be self-employed with varying degrees of success (or failure).

Perhaps, for those reasons, it’s a little more common to hear about the expat who started down here when he was in his 20s but then has deeper regrets about how he did things when he turns 40.

He might still have chosen to be an expat if given the chance to do it over again and quite likely has a lot of cool experiences.

Only that said expat might’ve wished he took his career a little more seriously.

Perhaps tell his younger self to take money more seriously and spend one less night a week drinking, doing drugs and chasing pussy.

And, in some cases, maybe said expat wishes he spent more time with family back home before leaving.

A relative – brother, sister, dad, mom or whoever – dies and you spent so much time away that you wish you could have back.

Finally, another detail about this type of expat that I have noticed – and my experience only might not reflect yours – is that they might be “running from something.”

I hate to use that term because it’s a stereotype of us expats.

But, for some younger expats, there’s some truth to it!

Of course, the stereotypical version is the young dork who couldn’t get laid back home and uses all his time chasing pussy abroad.

With more nights paying for it in a whore house than he cares to admit.

For other expats, there might be deeper issues at work.

We could always mention the type who couldn’t make it work financially back home.

But, on a deeper level, you got that type who had a “rougher” childhood.

Maybe a dad who screamed at him one too many times (with how much liquor to drink).

A dad who might’ve been more physically abusive (not always but could be the case)?

For some expats, there might’ve been sexual abuse as a kid.

Perhaps, for others, they got bullied as a kid quite often for being different or whatever reason (like being a kid of immigrant parents in a small town like one chick I knew).

Maybe a relative died early in life that impacted them strongly.

We could go all day theorizing all the ways said expat was hurt as a young age.

You get the idea.

And so said expat, when he travels to Latin America at a young age in his 20s, might engage in the vices that are more easily available down here than up there.

Give it time.

He ends up dead, in jail or perhaps “on a better track” someday.

He might get his shit together before facing some serious consequences.

And, in either scenario, he looks back at his younger years and thinks “maybe I could’ve done things better. Was I acting a bit foolish?”

Of course, it doesn’t have to be THAT extreme.

It could be something without the abuse and the coping where said expat is just a lazy fuck who comes down here, gets comfortable making 500 bucks a month and never aspires for more in life.

Roll the clock.

And he arrives to a life a little bit older and thinking “shit, I only got $13.04 in the bank.”

Reminds me of this guy here who went to Thailand for some odd years and blew all his money away.

Does he regret being an expat and going broke? Who knows.

Or you have the Roosh example here where the dude, after decades of traveling abroad to have fun, now has spoken, to some degree, against his old actions.

Next, you have the type of expat who wasn’t degenerate at all. Chose to give the expat life a shot, found out he doesn’t like living abroad and decides to throw in the towel.

Some will regret it and think it was a “waste of time” but most probably at least appreciate the experience of travel and seeing what it is like.

But did they waste their time?

Did They Waste Their Time?

For the expat who might regret being an expat entirely or the one who just regrets his more degenerate activities, the question of “did he waste his time” is one that could truly only be answered by him.

I will throw in my 2 cents but a real answer is entirely dependent on the individual who has that right to evaluate their own lives without us doing it for them.

Still, we can talk in generalities here and not for anyone specifically.

First, there’s a part of me that is inclined to believe that it isn’t all a waste, is it?

After all, even if you regret your more degenerate behavior from before, you still lived life more than most people if we’re being honest.

Got to travel. See the world. Party. See much of some of the coolest sights to see on the planet. Hookup. Maybe do some drugs. Whatever.

Let’s be real here – plenty of folks from back home aren’t doing cool shit like that and life ends for them when college is over and there’s no more fraternity parties.

Or, in worse case scenario, life ends after high school is over and they end up as a “wagie” at Hy-Vee.

In short, we as people tend to compare ourselves to people we knew from high school and college where those same folks project the best on social media but we don’t know the “lesser” nice details about their lives while a few of them, ironically enough, might be jealous about how we live abroad

And, on top of that, you got to live life in your 20s before “behaving more seriously.”

What else were you going to do in your 20s?

Most people won’t take a 20 year old kid seriously in the job market anyhow.

And what sounds cooler?

Doing drugs with a hot slut in Colombia or filling in paperwork at a cubicle?

So don’t judge yourself too harshly.

Second, obviously if you never get your shit together, then it’s a bad look.

I remember meeting a 50-year-old alcoholic German man begging me to “help him find his Costa Rican wife” as I wrote here.

Suffice to say, that was a scary moment.

Not because I feared he would mug me but because a look at that makes you think “fuck, if I don’t get my shit together, this is who I’ll become.”

Though I prefer having a Paraguayan wife.

Third, for those who are “coping” with the past (especially if it involved heavy childhood shit), do try to give yourself a little bit of a break.

Of course, it’s still fucked if you take that to your 40s and 50s without ever having done ANYTHING to move past it.

But, if you spent your 20s down here fucking around and coping with shit like that, I’d consider that forgivable.

Let’s be real here – plenty of folks back home who went through the same had rough times up there also.

The difference is you get to do cool shit like travel while dealing with it.

Our environment as kids impacts us anyhow even if it’s our responsibility as adults to learn how to deal with it in a healthier way someday and have more productive lives eventually.

Might be hard to do for many but just understand that.

Fourth, if you were a young man in his 20s though having fun, understand you are just that.

A young man in his 20s having fun.

You were full of testosterone and having a fun as fuck story.

While the older man in his 40s or 50s with less testosterone and more maturity might wish he had done things “more intelligently,” he should give him some slack on this point also.

Fifth, you also have some expats who felt like they wasted so many years chasing pussy and wondered if “that one chick” that they cheated on, only used as a fuck toy or wish they took more seriously was still around.

Now they are in their 30s or older and maybe regret not settling down quick enough.

Hard to comment on this one.

It’s more of a “squandering romantic options” than financial.

Well, I’ll say this.

For one, I don’t really like the idea of a man settling down when he hasn’t had “enough experience” messing around.

But, on the flip side, a man who lets go of a woman who he truly loves and is compatible with is being “a little bit silly.”

Maybe someone would offer a few harsher words for that but it is what it is.

Sixth, if you wasted your time financially where you are in your 40s without good job prospects and no real savings, I can get the “disappointment with yourself” stuff.

At the end of the day, you might have a family to take care of now and, even if you don’t, the idea of retirement is probably more of a topic than when you were 20.

So I can get to some degree why some would look at their “degenerate years in Latin America” as being a waste if they ended up in their mid-30s to 40s broke as shit.

Because, at the end of the day, no amount of “rationalizing” from the points above is going to convince the older expat that he didn’t waste his years.

I think such a character should maybe be less harsh on judging his past and what opportunities he might have squandered but we can all get that feeling of wishing we did something better (especially the older you get perhaps).

Anyway, that’s all I got to say.

Drop any comments below.

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And thanks for reading.

Best regards,


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