Maybe next year…

“Someday” is a disease that will take your dreams to the grave with you. If it’s important to you and you want to do it “eventually,” just do it and correct course along the way.

Timothy Ferriss

Let’s face it, in today’s super-connected, multi-tasking world it can be hard to find the “right” time for a vacation. Why? Because there never is one, until you actually go and realize that not only should you have gone away sooner, but you should figure out how to get away more often!

We have seen the situation far too many times where a couple saves and sacrifices and waits their whole life for that milestone birthday or anniversary trip. When it finally comes time to go, illness or injury or even worse renders all those plans and sacrifices for naught. Tomorrow isn’t promised to anyone. Don’t wait!

Of course, how much time you take and how often you can travel depends on your unique circumstances. Here are some guidelines that help us figure out when we want to go and how to make the calendar our friend:

  • Look at your calendars holistically. Take into account any events that you know you don’t want to or can’t miss. For us, that means a couple of annual work conferences for which attendance is mandatory, and a few key Longhorn games in Austin or annual community festivals in Rockport. If you are a student or have school-aged kids, put all the relevant dates on your calendar as soon as the school calendar is released. Is your presence expected at certain family events, or are there other important milestones coming up? Put them in the calendar, too. No matter how flexible you think your schedule is, we all have some restraints that we need to plan around. It’s much easier to plan around them when you know what they are, and most are pretty predictable. If you do your best to anticipate when you’ll have calendar conflicts before you plan a holiday, you won’t be resentful when you have to change your plans or lose your deposit because you forgot that Grandma was turning 85 that weekend and you don’t want to be photoshopped into the family picture.
  • Take any major local events into account. For example, since I’m here in Austin, I block out the weeks and weekends around spring break, South by Southwest, and Austin City Limits music festival on my calendar every year. I don’t do this because I plan to participate, but because I want to be aware that flights into and out of Austin during those times are likely to be more expensive and scarce than usual. I personally don’t like to travel on 9/11 if I can help it, nor do I like to be out of the country on Election Day, even if I’ve voted early. Some people don’t like to be traveling over Christmas, and some companies have restrictions around time off during certain times of the year. You probably don’t want to plan for a romantic getaway during spring break if the chosen destination is also known for being a spring breaker haven. Mark it all down and take it into account before you finalize a trip that might have been hundreds of dollars cheaper had you just gone a week later or a week earlier.
  • Research your destination and take their local holidays or customs into account, too. Be aware of any country-specific holidays and understand the impact that will have on your itinerary. Sometimes, being in a country for an unexpected holiday can be a charming way to experience local culture, but it can also be a real pity if one of your bucket list items is to visit the Louvre in Paris, but the museum turns out to be closed on the day you planned to go. As someone who grew up on the Texas Gulf Coast, you won’t catch me booking any kind of tropical getaway during hurricane season. If you are planning to go to Europe in August, be aware that your chances of meeting any natives of the actual country you’re in will be greatly reduced since it seems like the entire continent goes somewhere other than where they live in August.
  • I block the days of trips on my work calendar as soon as we have a general idea of when we want to go somewhere. Even if we don’t have all the specific plans made, let your boss and colleagues know that you won’t be available on certain dates as far in advance as possible. It’s polite, but it also buys some goodwill if something comes up when you are going to be gone – “I’ve had this booked since January, I really cannot rearrange it now. Is there another time we can do this, or can someone else handle it?” We’ve all been there. Most of the time, the answer will be “of course. Enjoy!”
  • Dave and I have come to the conclusion that we’re good for up to about 10 days away from home at a time. You might prefer more time, others don’t want to be away more than 4 or 5 days. For us, after about 10 days we start to worry about what’s going on back at home and what we’re going to be coming back to, and that impacts our enjoyment of what we’re actually doing. (Not to mention, we don’t want our dog to forget us!)

Timing really is everything. There is so much that can happen that is not in our control when we travel. It only makes sense to try to anticipate and plan for whatever we can to avoid the disappointment and frustration of not being able to make the most of our precious and valuable time away.

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