I often mention that I’m very lucky to have found a way to travel on points. I don’t often talk about how I’m also very lucky to make enough money to pay out-of-pocket for things I can’t pay for with points, that I’ve got great friends to travel with, and that I live in a place with easy access to three major airports. While everyone can earn points cheaply, to travel the way I do really does require those last things, as well.
So it’s kind of sad when I say that probably my biggest impediment to traveling is time off from work; it’s a reality that most of us face. I’m very lucky to get more vacation than most, but all my travel has to be centered over a weekend, and for out-of-the-country trips, centered over a long weekend.
Since that’s reality, the best thing I’ve done is to try and maximize my situation. I do this in two ways: first, by being as open as I can about the situation and second, by being willing to do whatever it takes to make it happen.
My boss knows that I like to travel, so expectations have already been set that most long weekends, I’ll be going somewhere. She’s usually the first person I talk to when planning a trip. That may seem a bit ridiculous, but it’s very important to keep that line of communication open. She’s the gatekeeper for most of my trips (i.e. she’s one of the few who can determine whether or not I can go), so I do whatever I can to keep her happy. It also helps that I have a boss that is very open to these kind of things.
The other piece to this puzzle is being willing to do whatever it takes to make it happen. If I’m gone for a long weekend, my work can wait until I get back. If I’m gone for five weeks, it can’t. That means that my coworkers will be picking up the slack while I’m gone. One of the absolute best things someone with a 9-to–5 job who likes to travel can do is to jump on any chance to assist a coworker with a project when they need help. Maybe it’s when they go on a two-week vacation or maybe it’s when they get overwhelmed with a specific project, either way, it’s only a matter of time before a coworker has to pick up the slack for you. If you want to keep a good relationship (and to make sure they’ll help you out), happily assist them whenever you can.
For now, a regular job for me and most others is a reality. By constantly keeping my boss in the loop and by keeping my coworkers happy, I can minimize the impact that my job has on travel. Most people don’t consider time-off strategies when planning travel, but if you want to maximize both of these areas, it should be one of the first things you think about.