Three Steps to Headache Free Travel

UPDATE: I first wrote & published this piece on my personal site. It’s been updated before reposting here.

You’d be hard pressed to find anyone who claims they don’t enjoy traveling. I find that to be a generic statement; most of us enjoy vacationing and weekend getaways. We don’t necessarily enjoy business trips. And preparing for travel can be a headache.

I’ve done my share of travel over the years. I still recall how excited I was for my first “business trip.” So excited that, by the time I was done packing and adding “one more thing,” I ended up with enough luggage that it looked like I was embarking on a cross-country tour, not a three day training a couple hours away.

Over time, and after lots of fine-tuning, I came up with my own system to avoid the headaches and enjoy the journey, so to speak. Today, I’m sharing the headache prevention parts of my system — pre-trip, homecoming, and everything in between.

Be Ready

Most of us going on a vacation make a mental list ahead of time of what to pack. What about the trip that’s unplanned? Whether its your boss saying he needs you in another state tomorrow, or a family emergency, having things prepared can greatly reduce stress or, better yet, make the decision to take an unexpected getaway easier.

It’s no secret that I love templates and automating all the things. After my share of impromptu trips, I sat down and made a few templates, then organized all my travel gear to store in my suitcase. Now, an impromptu trip means a little copying and pasting, and I have a plan in place so I can get done what needs doing, and pack what needs packing. No extra stress, no worries of forgetting something.

Your own template needs may differ, but personally, I have three templates for travel: a fairly exhaustive packing list, a work to do list (set up out of greeting on office line, email clients if availability will be affected, etc.), and a home to do list (more on this in a bit).

Again, we’re not idiots and know what we need to pack to go on a trip. But having a list you can copy and paste not only saves time, but reduces stress. It may be clear and simple to remember everything you’ll need to pack or take care of ahead of time, but add in the stress of a death in your family or the excitement of your partner wanting to whisk you away for a weekend, and it can be easy to forget something. ​

If something changes, make it easy on yourself to make itinerary changes…

Have you ever booked a trip using Expedia or Priceline and end up having to cancel or change your reservation? Ever try to get your money back? To say it’s not easy is an understatement — in my experience, and for many people I know, it’s practically impossible.

While you may think there’s no reason you’d cancel, well, you just never know. Unexpected illness, family emergencies, inclement weather…the list of reasons for an unexpected cancellation go on and on. When you book direct, changing reservations is much easier. I’ve had to change many a trip at the last minute, and never ran into issues when I booked direct — a simple phone call took care of cancelling reservations and avoiding charges. And its not just for cancellations — maybe you’ll need to fly back early, or are having such a fantastic time you decide to add a waypoint on your route home.

Save the travel sites to research prices, but unless you’re scoring a “too good to be true” deal and can deal with a cancellation without getting your money back, book direct. ​

Get ready to go, but get ready to come home, too.

Regardless of the length of your trip, it’s always good to get home to familiar surroundings. Before we leave, most of us are sure to take out the trash, clean out the fridge, and wash all the dishes. But a few extra steps of prep can be a game changer when you walk through your front door after a long flight or drive.

Put fresh sheets on the bed. Hang a clean towel in the bathroom. Be sure you have not only have comfortable, clean clothes to sleep in that night, but have a “reliable” outfit ready to wear the next day, too (especially if you have a big meeting or a monster to do list). Plan your first meal home, whether its something simple to microwave for dinner, or leaving room in your travel budget to order a pizza.

Basically, make your Current Self treat your Future Self by creating an environment where coming home doesn’t add any stress or tasks. And, if you’re using templates, this is easy enough — add “wash dishes” and “change sheets” to your home to do list template, and you can knock it all out before you even walk out the door. ​

It’s not always fun to work on travel prep or plans when you don’t have a trip scheduled, but you’ll be thanking yourself when something comes up and you’re ready to go in record time, have a successful trip and come home to a clean house. I can’t promise a headache-free trip (especially if you’ve got a long flight in coach!), but the tips presented here can make life easier.


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