You thought you still had plenty of time, don't you? Now you need to pack everything by Friday, rushing to take the last summer getaway before summer ends. If your job gives you PTO, then using it shouldn't feel like an act of rebellion. Still, I know it's hard to request days off. It can involve more preparation than the trip itself. You finish your tasks early, leave detailed notes for the coworkers who will be covering you, you write the out-of-office message explaining when you will return, and set it to be sent automatically to every email that reaches your inbox during that time. Five minutes after logging off, a colleague asks whether you can join a quick call. No!! That is what the message was for.
The best trips are the imperfect ones. Will you remember the ones where you quietly sat by the pool one peaceful afternoon? I don't think so. But will you remember that road trip where you missed the same exit three times? Definitely yes. The most memorable memories come from the imperfections, from the funny stories to tell. A good example of this could be trips with family or friends, which are rarely peaceful from beginning to end. If you're traveling with friends, someone wants to change every plan, someone is hungry when no one is hungry, someone forgets the sunscreen, and you all have to come back to the hotel room because no one wants to end up badly sunburned.
One of the biggest travel fails always happens at the accommodation you picked. The room you booked online looked enormous because the photographer stood in a corner with a wide-angle lens. The "ocean view" promised in the room description requires leaning past the curtains and looking between two big buildings. But none of that matters when nobody expects you to answer an email. In fact, it becomes one of the funny memories you later tell your friends and family.