A friend of mine is moving out of the country. While my friend and his wife are really excited, they are doing a trial period (like 4-6 months) to see if it's really what they are looking for and expecting. That said, even with the thought that they may choose to return in the long term, there were a lot of things to consider during the process. (It's also similar if you 'winter' in a different state from where your more permanent residence is. Some of the same considerations apply!)
(1) Where are you going to bank?
While the comforts of the internet have allowed for conveniences not previously known to us as a species, there are still some vital points to remember. Yes, you can pay most of your bills online, but what do you need to do for short-term cash needs? The best thing to look into is joining a bank that has international branches or partners in the area you are going to be. For example, Bank of America or Chase may partner with banks in your country of choice. This means that, while you won't be walking into a Chase or BoA bank in your new home country, there may be a bank there that still affords you the same privileges: deposits, ATM withdrawals without fees, and investing options. While it may not seem like a huge deal, there will be that clutch time when you need access to your money and you either can't or don't want to pay the fee or wait the required timespan to obtain what you need. These partnerships are vital. Do your research, and know what your options are.
(2) What about your mail?
Unlike banking, mail is still very physical. The internet hasn't put the monopoly on this one yet. That means you probably should check the forwarding restrictions on your new location. If you're within the same country, you may be able to forward your mail for a short period of time without much difficulty, or at least put it in a PO Box until you return. If you are traveling across boarders for a substantial period of time this may prove more challenging. First, understand the kind of mail you get. If they're bills and things, transfer them to online payments. If they're investments, ensure you can manage them from online as well. If you have regularly shipped packages or prescriptions, see if your new host country or location can fill them or if you would even be allowed to ship them internationally. If so, forwarding to a trusted friend or family member may be a great option. They can collect your mail and send you a large package at regular 2-4 week intervals or every 1-2 months, depending on what you need and how much is sent to you. However, check the stipulations of what would be included in that package!
(3) Any belongings you leave behind need a home.
If you're only going for a short time and returning to your same home, most of your belongings can probably stay in-house as long as you appoint someone to come in regularly, make sure everything is running properly, and just generally check on your property. If you have a car that 'lives' outside, though, maybe you want to leave it with a friend while you are gone or rent a large enough storage unit to ensure it's stored safely. The last thing you want is to come home to disarray that could have been avoided with a little forethought.
(4) Phone plans.
If you're staying in-country, this probably isn't such a big deal. If you are traveling abroad but you want to try to keep your number, you may have to go to your phone provider and understand their international plans. Some phone companies now allow for unlimited texting to certain countries. Some allow for unlimited texting regardless of country. Some allow for add-ons such as X-minutes of calling from or to certain countries. Others charge heavy fees and you may find options like Skype, Viber, Zoom, etc, are more to your auditory needs, especially if it's only for a limited amount of time and if you still have texting enabled. Yes, you may have to plan your phone calls more carefully, but everyday issues can be handled by text making the voice requirement less of an issue. But either way - check! The last thing you want is an exaggerated phone bill to show up when you log-in online to your account and had no idea it would be there!
Otherwise - have fun! Check food/dietary restrictions/language barriers and customs as hopefully you would even if you were traveling for only a short period of time. Insurance is also really important, but I know and understand that in a very very very limited capacity. Enjoy the world, enjoy your time away, and just enjoy all the beauty and perks life has to offer you.
...and now you can enjoy them with even more convenience and peace of mind.
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