Black and white photo of a lone traveler in the water

Last Update: 17/7/2023 | July 17, 2023

Planning a trip can be stressful.

Where do you start?

What's the first step? What's the second step? Will everything go well? Is there a best route to take? How to find out what to do? What do you order first?

There's a lot to think about, especially if you're going on a really long trip.

Taking time off and traveling the world is a big life change, and it's easy to feel overwhelmed. Multi-month trips don't just happen. There is a lot of planning needed to make your dreams come true.

And an endless to-do list can sometimes overwhelm you.

So how can you stop feeling overwhelmed?

It's not as hard as you might think — and I've developed a unique four-step process to help (patent pending):

First, buy your plane ticket where you want to go first. (Not sure where you want to start? Simple. Where is the cheapest airfare to start.) All you need is your first flight.

Second, shut down the computer and stop visiting 93,754,302,948,320 websites about travel (except mine — you should always read mine!). You will suffer from information overload if you don't.

Third, go out with your friends and celebrate the start date of your trip.

Fourth, smile.

There – that's all. You buy your plane ticket. you will go. There's no turning back. No need to worry anymore. All other planning is secondary.

I've heard at industry events that people will view up to 20 websites for 40 hours when they plan a two-week vacation. That's crazy. You don't need to do a lot of research.

No wonder I get so many emails from people saying “Matt, I feel like I'm in over my head.”

Information is power, but in our information overload society, too much information leaves us conflicted and powerless.

I understand you may be feeling a lot of anxiety planning your trip because you want to make sure everything goes well. I remember how it felt when I planned my first trip. I have every guidebook under the sun in my room. I make spreadsheets. I researched everything. I have made several itineraries. I have list after list. I constantly worry about the “perfect ride”.

I've been there but I can tell you from years of experience that the more you plan your trip, the more anxiety you'll have. You will flood yourself with so much information that you will do nothing but stress over it.

Planning gives you a sense of ownership of your trip. There is joy in it. That's one of the best parts about traveling.

But excessive planning will cause stress and I can tell you that, once you hit the road, all your plans will change.

Someone will tell you about a new destination and you will go there instead of going to Amsterdam.

You will wander the streets and walk into unexpected restaurants.

You will meet a group of people who will convince you to stay on that tropical island with them a little longer.

All you should have as you go is a general idea of ​​the direction you want to go and plan your first few stops. After that, let the wind carry you.

(This rule applies even if you're just taking a short trip. Come up with a few things you want to see each day and then let the rest of the day take care of itself. Go with the flow!)

In 2006, my first European itinerary should have looked something like this:

Oslo –> Prague –> Milan –> Florence –> Rome –> Naples –> Corfu –> Metorea –> Athens –> Greek Islands –> Athens

But ends like this:

Oslo -> Prague -> Milan -> Florence -> Rome -> Venice -> Vienna -> Amsterdam -> Costa del Sol -> Barcelona -> Amsterdam -> Athens

Almost nothing worked out the way I planned. It worked better. Cooler stuff, more interesting, and people pulling me in different directions.

A recent trip to Southeast Asia completely took a turn when a friend said, “Wanna come see me in Chiang Mai?”

Instead of flying to Bangkok, I ended up in Chiang Mai and then on to Laos!

I rarely keep my original plans. I don't know many travelers who have.

Once you've booked your flight, make a list of everything you need to do before you leave (it won't be as long as you think):

That's for the most part – and most of these things can be done months before you leave.

Go down your list.




Buy a book or two to gain general knowledge about how to travel and prepare for your trip.

Read the guidebook and get a good idea of ​​where to go.

Develop a general plan and then fill in the details along the way.



Everything will work out by itself.

And, when it does, you'll wonder why you were so stressed out in the first place.

Book Your Trip: Logistics Tips and Tricks

Book Your Flight
Find cheap flights using Skyscanner. This is my favorite search engine because it searches websites and airlines around the world so you always know there's no stone unturned.

Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, go for it because it consistently returns the cheapest rates for guest houses and hotels.

Don't Forget Travel Insurance
Travel insurance will protect you from illness, injury, theft and cancellation. It's comprehensive protection in case something goes wrong. I never travel without it as I've had to use it many times in the past. My favorite companies that offer the best service and value are:

Want Free Travel?
A travel credit card lets you earn points that can be redeemed for free flights and accommodations — all at no extra cost. Check out my guide to choosing the right card and my current favorites to get started and see the latest best deals.

Ready to Book Your Trip?
Check out my resource page for the best companies to work with when you're on the move. I list everything that I use when I travel. They are the best in class and you can't go wrong with them on your travels.