Last Updated: 9/30/2020 | September 30th, 2020

Planning a trip can be stressful.

Where do you start?

What should you do first? What’s step two? Will everything work out? Is there a best route to take?

There’s a lot to think about!

Taking time off and traveling around the world is a big life change, and it’s easy to feel overwhelmed. Multi-month trips just don’t happen. There’s a lot to do to make your dream a reality.

And your list of things to do can seem endless.

So how do you manage to stop feeling overwhelmed? How do you get over the anxiety of not knowing where to begin?

It’s easy — and I’ve developed a unique four-step process to doing so (patent pending):

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

Second, turn off the computer and stop visiting 93,754,302,948,320 websites about travel (except for mine — you should always read mine!). You’ll 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 it. You bought your plane ticket. You’re going. There’s no turning back. There’s no need to worry anymore. All other planning is secondary.

I once heard at an industry event that people will look at up to 20 websites over the course of 40 hours while researching their trip.


That’s before they even book anything!!!

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 many resources leave us conflicted and powerless.

I understand you might be feeling a lot of anxiety planning your trip since you want to make sure everything goes right. I remember what it was like when I was planning my first trip. I had every guidebook under the sun in my room. I created spreadsheets. I researched everything. I had multiple itineraries drawn up. I had lists upon lists. I was constantly worried about having “the perfect trip.”

I’ve been there and I understand, but I can tell you from years of experience that the more you plan your trip, the more anxiety you will face. You’re going to overwhelm yourself with so much information that you’re going to do nothing but stress over it.

Planning gives you a sense of ownership over your trip. There’s joy in it. It’s one of the best parts about travel.

But overplanning will lead to stress, and I can tell you from past experience that your plans will change anyway.

Someone will tell you about a new destination and you’ll race off there instead of going to Amsterdam.

You’ll wander the streets and into unexpected restaurants.

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

In short, plans change, so don’t go overboard. Have a general idea of what direction you want to go, plan your first few stops, and then just let the wind take you.

Don’t make yourself a lengthy plan. You won’t follow it anyway.

In 2006, my first itinerary through Europe was supposed to look like this:

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

But it ended up like this:

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

Almost nothing worked out as I had planned. It worked out better. Cooler, more interesting things and people pulled me in a different direction.

My recent trip to Southeast Asia was completely changed when a friend said “Want to come meet me in Chiang Mai?”

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

I have rarely ever kept my original plans. I don’t know many travelers who have.

After you’ve booked your flight, come up with a list of everything you need to do before you go (it won’t be as long as you think):

  • Buy your backpack
  • Purchase travel insurance
  • Get your visas (if needed)
  • Get new bank cards
  • Book your hostel
  • Cancel your cable (and other bills)

That’s the bulk of it — and most of this stuff can be done a few months before you go.

Go down your list.




Buy a book or two to pick up some general knowledge on how to travel and prepare for your trip.

Read a guidebook and get a good idea about where you’re going.

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

You can’t really know what you are going to do in a destination before you get there. Read up the guidebook on your flight because that’s when it matters.

You can’t do or change anything until you start your trip and the pre-trip stuff takes far less time than you think.



Everything will work itself out.

And, when it does, you’ll wonder why you stressed so much in the beginning.

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Book Your Trip: Logistical Tips and Tricks

Book Your Flight
Find a cheap flight by using Skyscanner or Momondo. They are my two favorite search engines because they search websites and airlines around the globe so you always know no stone is left unturned.

Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use as they consistently return the cheapest rates for guesthouses and cheap hotels.

Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. I’ve been using World Nomads for ten years. My favorite companies that offer the best service and value are:

  • World Nomads (for everyone below 70)
  • Insure My Trip (for those over 70)
  • Medjet (for additional repatriation coverage)

Ready to Book Your Trip?
Check out my resource page for the best companies to use when you travel. I list all the ones I use when I travel. They are the best in class and you can’t go wrong using them on your trip.

Travel Advice
17.07.2018 / motivation / SHHLR / travel planning
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