The Waiting is the Hardest Part

How to make your vacation countdown more bearable


So you’ve finally done it: you’re going on that trip of a lifetime. You booked the dream cruise, or you reserved the flights to those faraway lands you wanted to see all your life, or you’ve mapped out that cross-country road trip and reserved hotels along the way.  You’ve put in the request for time off from your job, and you’ve even signed up for a class in conversational Italian/Russian/Japanese/Whatever.

The problem: Because you’re a highly organized, plan-ahead individual who makes arrangements as far as possible in advance to get the best prices and allow the most time for ironing out any potential problems, you now find yourself with a lot of days, weeks, months or even years to wait before your journey actually commences. The long, slow ticking of the clock that stretches out in front of you seems almost unbearable. How can you maintain your enthusiasm and make the time seem to pass a little more quickly?

The anticipation makes it better


I know there are some people who make their travel decisions, make all the necessary reservations, send the payments, set a reminder on their calendars and then don’t think much about it until it’s time to pack up and head to the airport.

If that’s what works best for you, okay – different strokes for different folks. But to me, that sweet anticipation leading up to the trip is almost as much fun as the vacation itself (and truth be told, now and then it turns out to be the best part of all).

Anticipation – eager expectation that looks forward in excitement to something that’s going to happen – is the opposite of anxiety, which is about fearing and dreading what’s ahead. I don’t want to quash my anticipatory feelings; I want to leverage them to get maximum enjoyment out of my trip even before it happens.

Anticipation, together with memories that you savor long after it’s over, can turn your two-week adventure into months or years of repeated pleasure. And I’m all for getting the most bang for my buck.

Sharing the wealth


If you want to really enhance those daydreams about all the fun you’re going to have when that day finally arrives, share them with others.

Whether you’re going on a cruise with four thousand other passengers, a small group tour with fifty people from your company, a family reunion trip with twenty aunts and uncles and cousins, or a romantic getaway with your favorite person in the whole world, making plans and talking about your expectations together will help keep you excited and optimistic about your vacation.

What if  you’re going solo? Traveling alone can be one of the most exciting and/or most relaxing experiences you’ve ever had – take it from one who’s been there, done that, and will do it again and again. But even if your dream is to get away from it all, including everybody you know, that doesn’t mean you can’t share the excitement with them before you go. Go ahead, rub it in – and let those who aren’t able to join you enjoy living vicariously through you as you count down the days.

One great way to share is to join an online group of “fellow travelers.” If you’re going on a cruise, join or start a group for that sailing and get to know some of those who’ll be on board with you, and sign up for group activities if you’re so inclined. If you’re going on a trip to Italy, find a group of those who love Italia and talk up your trip with them. If it’s your first time to a new country or on a new ship, those who have already done it can give you loads of great tips and tricks that will make your own vacation go more smoothly. Which brings us to the next point:

Create a pre-trip notebook

It’s enormously helpful to collect all the information about your upcoming trip in one place. This serves several different purposes:

  • Makes it easier to plan your itinerary
  • You have confirmation numbers, contact data, receipts proving you paid, etc. all handy if you need them, either before or during your trip
  • It can be used to refer back to after your trip if questions come up about where you were at what time or what you did


You can either use a paper notebook or an electronic version, such as OneNote or EverNote. I organize my trips (and my entire life) in OneNote. Every time I make arrangements for flights, hotels, cruises, dinner plans, transport in my destination locations, etc., I put a copy of the email, web confirmation, or a scan of the paper confirmation in a OneNote page dedicated to that trip.

It can also be helpful to use an online service, such as TripIt, for keeping up with your travel plans. I use this along with OneNote. It’s important, though – especially when you’re traveling – to remember that sometimes Internet connectivity isn’t available. Although I save my OneNote notebook to secure cloud storage that I can access from my phone, tablet or laptop over the ‘Net, I also always download a copy of the file to my devices and print out a paper copy, just to be safe.

Of course, all this saving and organizing and just browsing through my notebooks before the trip also helps to pass the time and keep the excitement level high.

Make a list and check it twice


One way to put all that time between the planning stage and the going stage to use is to make list to help ensure you won’t forget something important in the weeks and days leading up to  your trip. I make a lot of different lists for each of my travels, and I keep them handily accessible in (you guessed it) OneNote.

  • Packing list. I have a master packing list of items that I always take with me, and I copy that and then add items specific to that trip. I use OneNote’s checkbox feature so I can check each off when I pack it. Thanks to this habit, I rarely find myself frantically searching for a Walmart in the middle of the Caribbean, or paying the exorbitant prices for normally cheap toiletries in a ship’s or hotel’s shop.
  • To do list. This is a checklist of things that I need to get done before leaving, such as renew my passport, or go to the bank and get cash in small bills for tipping, or download ebooks to read on the plane, and so forth.
  • To get list. These are things I need to buy for the trip, such as a birthday gift for one of my friends with whom I’ll be traveling, or door decorations for my cabin door, or a pair of warm gloves for the Alaska adventure, or a new piece of luggage to replace the one that was destroyed by the airline baggage handlers last time, and the like.
  • On-board list. For cruises, I make a list of things I want to do or check out on the ship, especially if this is my first time on that particular vessel. Maybe they have a new specialty restaurant, or someone has recommended attending the cooking demonstration, or I want to remember to go to the liquor tasting, or attend the veterans’ appreciation event, or try out the ropes course or the new sky ride.
  • Sight-seeing and activities list. For formal excursions and tours and such, I make reservations in advance and keep that info in OneNote as mentioned above. But sometimes the plan is to have no rigid plan, but to simply “wing it” in a particular port or destination city.  However, being who and what I am (just a tad OCD, according to pretty much everyone who knows me), I still do my homework to find out what some of my options will be, and list them along with pertinent information, addresses, open hours, etc.
  • Bring-back list. Things to buy in the places I visit: souvenir magnets or shot glasses from each port, that brand of rum that’s only available on that one Caribbean island, vanilla from Mexico for my friend who loves it, and so on.

These are only a few of the lists that I make to keep me organized and in “getting ready” mode during the long wait.

Make a game of it


If you’re going with a friend or family member, challenge him/her to this little game: Set up a list (you should be good at lists by now) of various milestones in your travel preparations. Then the first one to complete each of the milestones gets a point. Whomever has the fewest points on flyaway or sailaway or driveaway day has to treat the other to a nice dinner during the trip, or buy the other a drink, or whatever “prize” the two of you agree upon beforehand.

Here’s another that you can play all by yourself – and get in better shape and end up with more spending money on your trip, too.If you’re one of many who wear a fitness band these days, set a daily goal (for example, 10,000 steps) and every time you reach it, “gift” yourself with a dollar or five or twenty – whatever works for your budget. The money goes into your “cash cache” and you can use it on the trip to buy yourself a special souvenir or put it in the slot machine or take that helicopter excursion you’ve always wanted to do if only it weren’t so expensive.

The art of waiting

If you’re the creative type, unleash your talents to make reminders for yourself and your friends of all the fun that lies ahead. Draw pictures, write songs, Photoshop, or write long and rambling Facebook posts about the trip ahead. Some people even shoot elaborate videos. I enjoy making electronic countdown posters, myself, and sharing them in my cruise groups. Fellow group members have told me that they watched for my countdown each day and that it kept the anticipation high for them, too.

In the end

No matter how far ahead you make your plans, or how “last minute” your decision was, in one way it’s going to feel as if that vacation is never going to get here. Time will slow down to a crawl as you chomp at the bit for the big day to arrive so you can throw off all the demands and worries and responsibilities of everyday life, just for a little while, and relax.

In another way, time will seem to accelerate and you’ll find the day that seemed so far away is suddenly coming at you like a freight train as you scramble to get everything done that needs to be done before  you can leave work, house, etc. in someone else’s (most likely perfectly capable) hands, and that’s anything but relaxing.

You can be sure, though, that whether too slowly or too quickly (or both), your countdown will proceed, one day at a time, and before you know it, you’ll look up and see that the calendar pages have all been torn off and the hardest part is over. Now it’s time to simply:



About debshinder

Technology analyst and author, specializing in enterprise security. Author of or contributor to over 25 books, including "Scene of the Cybercrime." Fourteen-year Microsoft MVP, married to Microsoft FTE Tom Shinder, and proud mom of two wonderful grown-up human children and three amazing Japanese Chin pups. In my spare time, I love to travel - especially on cruise ships - and write about my grand adventures.
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