Ask for days off as soon as you can
If you aren’t lucky enough to be your own boss, you need to make sure your real boss knows about your days off as soon as possible. You want to be specific, straight, and to the point when requesting time off so there are no misunderstandings. Make sure to send your boss an email after the meeting to specify the dates you discussed. See? Simple! Also, if you and your coworkers have a good relationship, you can strategize your vacations so you’ll be able to cover for each other when you go on your respective vacations.
Have your email support you
An out-of-office autoreply is a vacationing employee’s best friend. But before you set on up, you might want to send another email to your coworkers/clients/patients/whoever, telling them you are about to take some time off. A week before you leave is usually a good time to do that. Ask them if they have any pressing issues you can help them with before you leave, tell them when you’ll be back, and let them know who their point of contact is while you’re gone.
Airport preparation
Airports (specifically airport security) can be stressful even if all you have in your carryon are an energy bar and two pairs of underwear. But arriving early can help de-stress the whole situation. If you fly internationally, try arriving two-three hours before boarding. The security and check-in lines will be a lot friendlier and less busy, and you’ll still have some time for a relaxing cup of tea before boarding.
Back it all up
Any kind of electronic device you take with you, be it your phone, your laptop, your iPad, or your Kindle, MUST have a backup. Get a good hard drive or use a cloud account to make sure none of your information gets lost. This way you can access it even if the devices get damaged or stolen (the horror!). Also, you would do well to email yourself all the important information, such as a copy of your reservations, passport, or visa. This way they will be easy to access in case of emergency, but remain password protected.
Don’t pack too much
We’re going to assume your vacation destination is a place with human civilization. This means that most items you forget can usually be bought there once you realize you forgot them. The best thing about packing light is that your luggage can be taken on the plane as a carry-on! This way you don’t need to worry about it getting lost or stolen, and you’ll have fewer items to keep tabs on.