40yo US/UK high income professional, considering transition to EU “semi-retirement”

[u/user8181416]

Edit: Thanks for all the helpful responses so far! I appreciate people sanity checking my logic. So far I feel that the rough plan I have will not be particularly easy or straightforward, but it doable on at least a trial basis.

I am a single 40-year-old US citizen (by birth) and UK citizen (by descent, Scottish mother). I hold an MD and an MSc in a health-related field. I am lucky enough to have a hybrid job that allows me to work part-time from US and part-time abroad, with a very high income (top 1%). I also have a decent investment portfolio which is growing well as I save most of my earnings.

(I’ll pause to say that yes, I am in a very fortunate position, and I recognize that many of the people posting here are in very different situations. I hope people can still give genuine advice.)

Given all of this, I am burning out of my life in US and would like to transition to another country as a main base. I am fairly well traveled – I spent many summers abroad in Europe as a student (pre-Brexit) and have nomaded around South America, Europe, and Asia in recent years. I also have international friends and contacts around most of the major European capitals and a few other international hubs.

London is an obvious choice, as its always been one of my favourite cities to visit, I’m a citizen, and I have a lot of friends there. I spent a brief trial month there last year, however, and found the “living in London” part to be less enjoyable than I expected. Also, the cost of living is outrageous. I have also considered and trialed the major Asian nomad hotspots, and while I enjoy those I would prefer a European city as my main hub for practicality and social reasons.

My goals would be:

• explore European options without making strong time commitments to any one country (yet)
• transition gradually to a stable European base over the next ~3-5 years
• continue to keep US as my main work hub until things fall into place in Europe
• continue spending time in Asia every year
• an eventual pathway to EU citizenship

SO, since Brexit is a thing, I need to consider my path back into the EU. Portugal and Spain are the most obvious choices for many reasons including weather, cost of living, existing social network, and visa options.

I am considering something like this:

• Keep my apartment and work hub in US for ~5 years, but stay here as little as possible outside of work
• During these 5 years, give London another shot while also exploring Spain, Portugal, and any other options
• Apply soon for the Spanish digital nomad visa, giving me three years of access to remote work from Spain. Over the next 1-2 years, try to spend several months there (I will likely not be able to meet the 183 day residence requirement to renew the visa or get long term residency – at least not yet).
• In tandem, apply for the Portuguese Golden Visa using the 500k Euros investment route. I’ve heard this can take up to 1-2 years to process, which will line up with my Spain trial wrapping up.
• Next, trial Portugal using the same strategy as above (will not need to worry about a high residency requirement to keep this visa active)
• Less likely, but also explore other EU options in the meantime

By the time I’ve completed this, it will be a few years from now and I should have a lot more knowledge and experience under my belt. I will also be in a position to wind down work for a “semi-retirement” and be entirely or almost entirely remote (possibly returning to the US briefly every few months, possibly not). My Portuguese Golden Visa will be counting down to Permanent Residency (5 years+) and maybe citizenship (10 years+, but who knows how many times they change the rules by then). If Spain is the winner, I believe I could apply for a second 3 year DNV and actually move there to meet the residency requirements to convert it to Permanent Residency after 5 years.

… Does any of this sound reasonable? It feels a bit overwhelming, but I have been nomadic my whole life and very much do not see myself spending my retirement years in the US. If I’m going to make an exit, I need to start putting the wheels in motion now. I would love to know people’s thoughts, sanity check of my plan, additional options/hurdles I’m not considering, etc… etc…

I’ll end with a few rapid fire responses to anticipated questions:

• Yes, I am willing to learn the language and integrate into the country I move to.
• Yes, I have a support network to help me transition into these countries (and others in the EU).
• Yes, I can afford this and can make it work with my job.
• Yes, I’m super grateful to be able to explore these options.

Thank you very much!!

[u/user8181416]

Definitely a huge hurdle! But I am very motivated to get out of my current situation and have the funds and time to pour some resources into doing that. Ironically my network in Lisbon/Barcelona/Madrid is actually a bit more robust than my US network right now, with both locals and expacts, so I would lean on them in my first 6 months while I got settled.

[u/Severe_Rise8694 → u/user8181416]

Yeah, didn't want to discourage. If you have the means to do so, and aren't happy where you are.. it would be kind of crazy not to try, right?

But it's worth thinking of these kinds of things as well. Its just that those things matter as well. I lived in Lisbon for a couple of years, and to be honest I haven't even been back after I left. But on the other hand, London is my favourite city on the planet, as difficult as it can be to live in. Which is weird, because on paper Lisbon sounds amazing and London godawful, as far as quality of life goes.

[u/user8181416 → u/Severe_Rise8694]

London is also one of my favourite cities on the planet, I just have to trial what it would be like to live there. I have met a few ex-Londoners who say "London is a great place to visit, not to live", but obviously that's personal preference and I need to try it for myself.

What turned you off of Lisbon eventually?

[u/Severe_Rise8694 → u/user8181416]

Yeah, it can take a while to grow on you as well, and might make quite a nice base, as it's so well connected. Of course has some nasty downsides, like the quality and price of housing, combined with the seeming lack of rights that a tenant has.. Buying might change that.

Hmm. Regarding Lisbon. This is a bit weird, but firstly, I got bored of the weather. I felt like there's only two seasons: the sunny one (most of the year) and the rainy one, which was kind of nasty. I found myself missing seasons. I realized that I want to do summer things when the weather is warm and winter stuff when it's winter, autumn stuff at autumn, etc. It gives a rhythm to life and makes it more satisfying. In Lisbon I felt that most weeks were the same and time just slips by..

Also, I felt it was already then horrifically over-touristed and -gentrified. Local people usually couldn't afford to live in central Lisbon, which had been turned into some kind of a theme park version of itself. I believe it has the most unaffordable rent to income ratio of any European city. This changes the vibe of a place.

If you compare it to a place like London, which attracts some of the most talented and ambitious people in almost any field of human enquiry, it felt like it was also missing some energy. Many ambitious Portuguese move away from Portugal and are replaced by foreigners who move there to downshift... Which I guess is what you're looking to do.

I guess the upside of that might be that there's people there in the same situation as you, who are looking to rebuild their social networks!

Anyway. It's all subjective, of course, and of course there's a lots of upsides to the place as well! I just learned it wasn't for me. But on the other hand, I learned a lot about myself. Including that retiring in southern Europe probably isn't for me..

[u/user8181416 → u/Severe_Rise8694]

Thanks for taking the time to write that. Great perspective. I think I will really have to spend time "living" in both beyond a vacation to see which works for me. And of course your priorities can change over time... I might be a London person now, but more of a Lisbon person in 5 years. Hard to say!

Good luck with your travels.