I've been in NYC for ~8 years, and I've been thinking hard about my next stop. I can work remotely 100% of the time, and location is not an issue for me.
I've taken a couple of trips this summer to a few tropical places, and it's really gotten me thinking about quality of life. I love NYC, but I'm considering heading somewhere like the Bahamas, Turks, Costa Rica, or the DR for at least a year. I'd even consider Europe, but I have to work ET and don't want to be working weird hours (so that's out of the picture).
1. Anyone have any ideas on places I should check out? Already aware of MIA, FL, etc. and that's on the back burner
2. Anyone have any experience living on an island in close proximity to the US?
Where's your fam? Would consider living near them for a while
SD is also great, though 3hr time diff from EST can make it tough. Dunno you're appetite for that. On East Coast, the best you're gonna get is Miami / Tampa frankly
Thanks for the feedback. Yeah SD is definitely not my vibe. Folks are in FL but a sleepy part. I’ll check out Tampa and maybe do some more research into MIA.
I’m a fan of Colorado…
Thanks - have a few friends that visit there a bunch and have nothing but good things to say
You’re in a legit investment professional role at a HF and can work from anywhere? That’s incredible. I would just hop around from various furnished apartments every 3-4 months
I don’t think island life is for me. It has to feel claustrophobic after a while.
If I was in your shoes I’d be in Miami for the winter months, orange county for the summer.
Yeah definitely thinking about snowbirding for sure. And yep - have incredible flexibility. I’ve recently launched my own firm and it has a ton of advantages including the fact that I’m in complete control of my schedule.
Costa Rica would be a top choice if you want to have a reasonable working schedule. Go to a surf town such as Tamarindo for 3-6 months and see if you enjoy the lifestyle there. I left London to spend the summer on a (large) island in Italy and the lifestyle here is insanely different. It definitely isn’t for everyone (particularly if you don’t like the beach/outdoors), but it can be amazing. You really need to try it to find out for yourself.
Depending on if you need to travel for work at all, you could go deeper into South America. Medellin or Buenos Aires would probably be solid places to visit.
If you’re looking for something more dynamic, check out programs through Remote Year or Hacker Paradise which will have you changing countries every month. They do set you up with remote work space and solid internet connections though, so that handles probably the most important ‘career risk’ aspect.
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