I still remember sitting at the Portland Airport on January 5th, 2010.
I was feeling pretty much every emotion possible. There was the intense fear of stepping into the unknown and moving to a new country (on a new continent) where everything would be foreign to me.
There was unbridled excitement to finally be doing something with my life and breaking out of the mental and physical rut and routine I’d been living in for the previous few years.
There was an unbelievable amount of uncertainty which I’d only just recently begun to conquer.
But the bottom line was that despite the uncertainties and fears, it was all good.
I was about to embark on an adventure that few people would get to experience in their lives and one that I wouldn’t understand the true importance of until years later.
But not all trips are so long and intense. And if you’re not used to traveling even a week long vacation can seem daunting and stressful.
This week I embark on the longest trip I’ve taken since that 7-month stint in Thailand.
My wife hit 10 years at her job, and we’re taking a 2-month sabbatical and traveling around the world to knock off a bunch of bucket list items together.
So for the past few weeks, my head has been swirling as I’ve been preparing to dive back into the unknown and wrap up stuff at home and in the business so that I’m able to truly enjoy the trip.
In today’s post, I’m going to share with you ten things you can do to ease your stress and make you feel as prepared as possible for an upcoming trip. It doesn’t matter if your trip is 2 weeks, 2 months, or 2 years – taking care of these basics will help you feel more prepared and more excited than you thought possible.
1) Address the stress
Let’s put it out there, most people reading this post who are preparing for a big trip are stressed.
Right this second, not gonna lie, I’m pretty stressed out.
Stress has a way of taking over and making things seem worse than they really are.
I’ve got a lot of things on my mind and a lot of things to do, but the reality, is usually there are only a handful of those that are truly causing me to stress out on a fundamental level.
To address that, whenever I find myself feeling overwhelmed I create what I call a “stress list.” And I write down the things that truly make me feel anxious when I think about them.
Out of 20 to do items, it’s usually only 3-5 that really makes me have a physical reaction to not having them done.
Once I have that list, I prioritize doing those things first – and then the rest of the planning and packing tends to go smoother.
Obviously, this doesn’t reduce ALL your stress, you’re taking off on a big trip after all! But it will usually help me reduce it down to something much more manageable.
For more tips on this check out:
2) Don’t worry about the things you know won’t get done
There will always be things you wanted to do that won’t get done before you leave.
If you’re currently preparing for a trip, I bet you have a pretty good idea of what those are.
Let them go.
If you know something won’t get done, or even if there’s a good chance it won’t get done. Don’t worry about it. Go focus on the things you know you can and need to do, and let the rest wait until you get back.
Right now I really need to clean out my garage for instance. I’ve been meaning to do it for months, but it’s clear that it just isn’t going to happen.
So I let it go and feel infinitely better for it.
3) Understand your preferred travel style
This is a big one because it will help you manage your emotions all the way through your trip.
What I mean by your preferred travel style is primarily: are you a planner or a fly-by-the-seat-of-your-pants kind of person?
If you’re a planner, and you know this about yourself, then spend the time now to get all of your plans and itinerary set for the trip.
You’ll feel much better knowing it’s all handled and taken care of.
A couple weeks ago we told some friends (who are planners) we hadn’t booked a hotel or flights for Oktoberfest in Munich (we were about a month away).
And they looked at us like we were completely insane.
“You HAVEN’T BOOKED ANYTHING?! Well, then you’re probably not going…”
While sure, Oktoberfest in Munich is a huge draw and things book out quickly, it wasn’t a huge source of stress for me. I actually tend to get more stressed out the more I plan because so many of the best opportunities come up last minute.
Long story short, I booked our Airbnb yesterday for a totally reasonable rate, 10 minutes from the festival grounds.
All is good.
I know personally booking flights too far in advance will make me feel obligated to that itinerary, and know I might be missing out on better opportunities to use miles. You know, like this.
For most people, planning is essential to sanity. So understand how you roll.
4) Create a “Central Planning HQ”
There are a lot of components that go into planning to leave for a trip.
And if you don’t have some semblance of a plan, it will leave you flailing wildly, forgetting crucial things, and once again, feeling stressed.
The absolute game changer for me has been integrating my travel planning into my daily project management system: Asana.
I have a project for everything trip-related including a packing list, to do items, a list of things I need to do upon returning – and it’s made all the difference.
Whether you use a physical notebook, Google Doc, systems like Asana or any other software – have a place for every to do item, brain dump, or task that you want to track.
5) Make a packing checklist
Weeks before you ever begin to think about packing for your trip, you should start making your packing list.
It’s kind of like creating a bucket list in the sense, that you can’t just sit down and bang it out in one 10 minute sitting.
There will always be things that pop in your head or come to mind later on, so if you make your list the day before you leave – you’ll inevitably forget things.
I use my “central planning HQ” for this and add it to Asana. Then I add things as I remember them, and check them off as I get them packed.
6) Take a break to be excited
This might be one of the most important items on this list.
As you get older it gets harder to be truly excited about things.
I’m talking like 7-year-old the night before going to Disneyland kind of excited.
This is in part because there are so many stressors and things to clutter your head in life, but especially before a trip, that keep you from being able to experience the simple joy of anticipation.
So do this right now. Take two minutes, put all of the other stuff aside, and think about the one thing you’re most excited for on your trip.
7) Do at least a little cleaning
Coming home from a trip to a disaster of a home is one of the most unpleasant experiences possible.
Take an hour or two and make the beds, do the dishes, and pick up the clutter, so that when you come home and are preparing to go back to work, you’ll have one less thing on your plate.
Do this, unless of course, this is one of those things you know you won’t get done (see point #2), in which case, let it go and don’t think about it again until you get home.
8) Make any last minute bookings or necessary arrangements
No matter how much or how little I plan, the one thing I always try and do is have a place to stay booked for my first night or two in a new place. From there I’ll go with a little less planning, but when you first arrive the last thing you want to deal with is finding a decently priced place to stay.
Here are some of my go to spots for booking things:
- Hotel Engine: If you have a business try and sign up for an account here. It gives you access to corporate rates, that has often saved me an additional 25% off the best rates I’ve seen on Expedia
- Hotwire: I use the Hotwire Hot Deals all the time when I travel. You won’t know exactly which hotel you’re going to get, but you’ll know the general area, price, and star rating. I have yet to be disappointed with one, and often get as much as 50% off the published rate.
- Hipmunk: This is great for getting a visual view of different flight options, and I often use it when comparing different flights and times while trying to find the best fit for me.
- United MileagePlus: This is my go to spot for rewards bookings. You can transfer Chase Ultimate Rewards Points, and it led to a round the world business class redemption for my wife and me on our honeymoon. We’re also booking nearly all our flights on this trip using it as well.
- Chase Sapphire Reserve Booking Portal: The Sapphire Reserve is my favorite credit card out there, and the travel benefits are amazing (3 to 1 points on dining, Priority Pass, etc).
But one of the very best benefits that few people know about are the rates on rental cars when booked through their travel portal. It is routinely half the price for a better car than any other public place I’ve tried to book.
6 days for a Mercedes in Scotland? $221.
The fee for this card is steep at $450 a year, but it’s totally worth it considering the sign-up bonus, and the fact you get $300 right back annually in travel expenses.
9) Think about how you want to document the trip
I can’t tell you how many trips I’ve taken where I had goals of shooting tons of photos, or editing vlogs, only to do hardly any of either.
Doing this (especially video) takes a little extra time and planning. So think through before hand what you want to do for documentation.
Is it simply shooting photos of your kids with your iPhone? Great, not much planning needed.
But if you want to get professional sunset photos of that beach trip, you’ll want to pack a DSLR, tripod etc.
Make sure you have a story to tell and think through what that is before you go. For instance, this video of our honeymoon took a more planning and discipline than you might expect:
Then force yourself to shoot video, even if you’re tired, cranky, or uncomfortable. That usually makes for the best story elements anyway.
10) Remember to enjoy the ride
These days travel is stressful. It can be even more so if you don’t do it often or have kids with you.
But often, it’s the worst, most miserable situations that lead to the best stories.
Getting trapped in Atlanta in April for 3 days due to Delta canceling flights? Miserable, but had some pretty entertaining stories come up because of it.
My wife not being allowed to fly into Indonesia (after already getting halfway there):
All sucked, but are all still stories I tell on a regular basis.
So if and when something on your trip (or before your trip) doesn’t go your way? Relax and think of the stories that will come from it later.
Because at the end of the day, the person who wins in life is the one who has the most stories.