this post was submitted on 02 Aug 2023
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Thank you for all of your perspectives
Some more perspectives/information. I can see that my post is lacking important details: 70% of my work is like mostly talking with people on how to reach solution (and possibly fixing it), 15% project work and 15% misc. It is a weird mix of sysadmin, technical support, and "internal process consultant". Deadlines are not a problem and I could even make it an easy work-week, e.g. 6-hour a day. We have a good infrastructure, thus remote connection is not a problem from that perspective - but internet connection at a hotel or café could be an issue as some pointed out.
I do not have a wife and children, but living together with a gf and one cat.
Regarding price I had in my thoughts just to use some of those cancellation trips which makes it quite cheap (Greece, Turkey, Cyprus, Spain... lots of cheap flights when the vacation season is over).
With all of that said, I can see it work, but it mostly sound like a bad idea :)
I’ve spent most of my adult life working remote (also in tech) and have had some trips like this that were fantastic and others that were big hassles. The determining factor is whether the location you go to is conducive for actually working, otherwise you spend way too much of your time trying to sort out stupid logistical things (where can I hold a call? How flaky is the internet? How do I sync hotel checkout to work schedule? Etc). But some locations are designed for remote workers.
Look on the map specifically for coworking and read reviews and look at pics to get an idea. Consider getting a Spaces membership, which is a very large network of coworking through most of Western Europe and some other countries , where you can drop right in and everything “just works”.
I have a wife and kids now so it’s not as easy for me to float around as much, but I’ve had some excellent week long trips or even just long weekends through much of Western Europe. There are many places with budget flights and you wouldn’t necessarily go to on serious longer holiday, but are awesome destinations for this kind of travel. You get a chance to have a taste of those places and don’t use up your PTO.
A recent place I went like was to Taghazout, a cool beach town with a bunch of surfer tech nomads and lots of coworking spaces. I went in April on a $50 Ryan air flight (in/out Agadir). It was a great trip.