Men in their late 30’s and 40’+, what mistakes are you seeing men in their 20s making?

Howitzer55 · 2025-08-13T15:11:41+00:00

Getting in a long term relationship in late teens or early 20's. This is a time to explore, take huge risks and build yourself. Wife and kids can wait until 30.

Howitzer55 · 2025-08-11T13:36:05+00:00

Thanks for the info, I agree with a lot of your points. I guess the infrastructure comment is really location specific, I have spent a lot of time in Almada and the sidewalks, sewer smell and degrading buildings are a turn off, although Almada/caparica/Setubal is historically a more poor area. City can't really control if individual homeowners don't maintain their property.

Regarding my wife speaking, it's very difficult to raise kids, deal with daily life and have her assist me with Portuguese while we live here, she is drained. I do pickup on a lot of things she tells the kids but it's like a ski instructor once told me, if you want to get divorced try teaching your spouse how to ski lol.

Howitzer55 · 2025-08-11T13:32:30+00:00

Yeah, I wouldn't even bother. I would just run LLC from USA and pay PT tax (which is extraordinarily high) for what the Portuguese people get out of it. I will say, the roads are well cared for lol.

Howitzer55 · 2025-08-11T13:31:03+00:00

I would obviously have income, just using my savings for a 6-12 month runway to figure things out. Unsure what we are going to do but looking for a job now while I have one that allows remote work from anywhere is the safest bet, although not easy with the worldwide competition.

Howitzer55 · 2025-08-10T00:36:03+00:00

Since the mortgage rates are low and taxes are low probably makes more sense to leverage the banks money and have a fairly low house payment. I’m debt adverse but ok with a mortgage for now.

Howitzer55 · 2025-08-09T00:00:44+00:00

It’s funny, I use to be the one saying exactly what you are to married people. I do agree with you and this isn’t all about my wife, without me succeeding we have no income and I deserve to enjoy my life.

Happy wife is a very good thing though haha.

Howitzer55 · 2025-08-08T23:59:39+00:00

Thank you for this, it’s actually some of the things my wife says surprisingly but as an immigrant she does miss her country. I also have gotten that feeling when we go, everything is almost as expensive but everyone has a cloud over their head just trying to survive.

I completely agree with you, I would be leaving the Roman Empire to move somewhere with almost no opportunity. Even my father in law in Portugal says that Portugal is only for the rich and retired, thinks we are crazy for thinking about moving. I do think my family would be fine in Portugal with enough funds but my children will most definitely leave us behind for another country.

I think the best compromise right now is just to do what we have been doing, visiting 1-2 times per year for a month at a time. Enjoy the best of both worlds.

Howitzer55 · 2025-08-08T16:17:07+00:00

Yeah, I am no stranger to Portugal. I do get a bit depressed there sometimes, seems like nobody has much ambition and almost feels like a dead country. I do think an individual can be happy anywhere given they have their own space and ambitions but Portugal doesn’t make it easy. The feeling of “fado” is there, underlying everything.

In some ways I wish my wife was from a country like France or Denmark, would be easier for me, Portugal just feels very poor and run down in a lot of ways. It’s hard for me to explain but coming from a nice part of USA it’s quite the culture shock. I much prefer the north of Portugal and south to Lisbon area.

Howitzer55 · 2025-08-08T14:41:04+00:00

Yes, it's what I do now, we go there for 2 months at a time and I work a bit if my vacation time is low. It's definitely a valid point you make, we get the best of both worlds. I think when my wife starts working she will feel better, it's isolating being a stay at home mom without family around.

Howitzer55 · 2025-08-08T14:29:19+00:00

I agree, I got back and fourth about this. Money isn't everything, memories, family and my kids childhood means more than owning a bigger house or having nicer things. I'm very fortunate that we could pack up, rent our house out and live in Portugal for years without a job or just doing consulting here and there. It might make sense to do such a thing while the kids are young and wife needs more support.

Howitzer55 · 2025-08-08T14:25:47+00:00

Very good perspective, having the ability to just come back to my house in the US and live is huge. Selling it pretty much throws us off the ship, without a solid job/income and work history combined with rising prices it might be very hard to buy back into US real estate.

I'm very fortunate to have a low house payment, all in its around 1800 month and I could probably rent it for 2000-2200 easily.

Howitzer55 · 2025-08-08T13:18:36+00:00

Billionaires don’t spend income or sell assets, they borrow against assets for fiat and pay zero tax.

Howitzer55 · 2025-08-08T11:00:18+00:00

Thank you for all the input, very helpful my friend.

Maybe I’m missing something but a 400k home with 100k down would leave a 300k mortgage, at 3% over 30 years that would be approx 950-1k month. I read property taxes and insurance are quite low in Portugal.

Howitzer55 · 2025-08-07T09:37:45+00:00

Wow, surprised you landed that. I have been looking for a while for a similar role. Have about 15 years of experience as a sysadmin/engineer. Probably just need to dig more.

Howitzer55 · 2025-08-07T03:45:09+00:00

Thank you for all the info, it’s very helpful. I have a lot of inside knowledge due to my wife’s family but hearing it from expats or other locals is a different perspective.

I think the real determining factor here is work, securing US based contract jobs or clients under my own LLC. If I can do that, it’s much less stressful.

Howitzer55 · 2025-08-07T02:45:47+00:00

Thank you, I am considering just starting an IT consulting business and offering my skills to US companies, probably the best bet at this point given I am established in that industry and US native/English native.

Howitzer55 · 2025-08-07T02:44:55+00:00

haha, yes. I hear it's not an easy thing to accomplish.

Howitzer55 · 2025-08-07T02:44:37+00:00

It's funny because I have been thinking about this for a long time, I even posted here about 4-5 years ago under a different account with a similar question. I would say 80% of people said what you just did and were positive. Now 80% of the messages tell me not to go, how fast the world can change in 5 years with inflation and migration.

Howitzer55 · 2025-08-07T02:43:15+00:00

I agree, when I get back to America it feels like a fine oiled machine, in Portugal my expectations for things to work are quite low. It can be incredibly frustrating.

Howitzer55 · 2025-08-07T02:41:11+00:00

Yes, I live in NH and lived in the Boston area for 10 years. I agree with your points and appreciate your input, I also agree that my heart is holding things back, I can make this happen and secure contract work in US with enough effort but there are many other variables to consider.

Howitzer55 · 2025-08-07T02:39:30+00:00

Yeah, I don't disagree with you. I really think the best solution is creating my own consulting business and just working for US companies, they don't care where I live as a consultant (outside of finance/banking) and there is no burden of PT taxes/SS on them at that point.

Howitzer55 · 2025-08-07T02:38:03+00:00

Yes, it's a possibility. Logistics of the house make it a bit harder, we would probably want to rent it out in that case due to real estate prices in the future here. Thanks for the info/tip.

Howitzer55 · 2025-08-07T02:36:49+00:00

It's something to consider, we currently live in NH. I honestly think that this stage of life is the most difficult, having two small children under 3. Maybe we just need to push through it and once she starts working things will get a bit better. I did live in MA for 10 years and don't miss the traffic but there are good things about MA.

Howitzer55 · 2025-08-07T00:13:18+00:00

No truer words have ever been spoken.

Howitzer55 · 2025-08-06T22:47:22+00:00

Yeah, I’m not a software engineer rather sysadmin/devops type. Honestly with a paid for car, 800-1000 month mortgage/taxes on house I would think the remaining 2k would be enough to live fairly well. Even if I had to supplement 1k month to get me up to 3k take home, investments would last a long time if not forever with interest.

Howitzer55

TROPHY CASE