This may seem simple, but it is effective. Every six months, dump the contents of your wallet onto a copy machine and copy the front and back of everything. Be sure to file it someplace secure, so that if you lose your wallet, you will have a checklist of everything inside including, account numbers, and on the back, the phone numbers to call.
When you go on vacation, do not bring your entire wallet with you. Bring only the essential identification (that includes health insurance!), and credit cards that you will need. Do not bring all of your credit cards — maybe just one or two from different companies (e.g., an American Express and a Visa). More than this is generally not necessary. This way, if you lose your wallet on vacation, you only have a few missing documents and cards to deal with, and if you have a photocopy of the documents and credit cards, it will be much easier to contact all the necessary people and companies. All this preparation may seem excessive, but vacations should be relaxing! If you lose your wallet or a single document, being prepared will help resolve the problem quickly and with a minimal amount of stress.
If you are traveling with your passport, make sure to bring AT LEAST two copies of your passport with you. Keep your actual passport and the two copies, all in different places. If you lose your passport while you are out of the country, it will save you a lot of time at the Embassy (if you are out of the U.S.) if you have a copy of your passport as verification of who you are and the identification number on your passport (if there is one).
Lastly, make a list of your passwords for any accounts that require them. Having passwords protecting your account numbers may not be useful in the event that someone else is trying to access funds on your behalf.
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