Where should you begin?

What is the first step? What’s the second step? Will it all work out? What is the best way to proceed? What should I do? What should you book first when booking a holiday?

You have a lot of things to consider, especially if your trip is going to be extended.

You quickly feel overwhelmed when you decide to take time off from work and travel worldwide. It takes work to plan a multi-month trip. To make your dream come true, you’ll need to do a lot of planning.

Sometimes, the endless list of things to do can be overwhelming.

How can you stop feeling overwhelmed?

You’re more stuck than you think. I have developed a unique four-step system (patent pending).

Buy your first plane ticket. Still, trying to figure out where to begin? Simple. Choose the lowest-priced flight to start. You only need the first flight.

You should also turn off your computer and stop browsing 93,754,302,948,320 travel websites (except mine, which you should read!). If you don’t, then you’ll be overwhelmed by information.

Celebrate the beginning of your vacation with friends.

Fourth, smile.

That’s all there is to it. You’ve bought your ticket. You’re going. You can’t turn back. You don’t need to worry anymore. The rest of the planning comes second.

At an industry event, I heard that people would look at 20 websites in 40 hours to plan a vacation of two weeks. That’s unbelievable. You don’t have to do so much research.

It’s no wonder I receive many emails saying, “Matt, I feel over my head.”

Our information-overloaded society leaves us powerless and confused by too much information.

Understandably, you may be anxious about planning your trip, as you want everything to go smoothly. When I planned my first trip, I can remember how it felt. In my room, I had all the guidebooks you could imagine. I made spreadsheets. I did all the research. I had multiple itineraries drawn up. I made lists and lists. I was always worried about “the perfect trip.”

You will feel more anxious the more you plan. I know this from experience. You will overwhelm yourself with information and stress.

You will feel more in control of your trip if you plan. It’s a great feeling. Travel is one of the most enjoyable parts.

I’m sure that overplanning can lead to stress, and once you get on the road, your plans are likely to change.

You’ll be told about a new place and rush there instead of going to Amsterdam.

You will wander through the streets and stumble upon unexpected restaurants.

You will meet people who convince you to stay with them on the tropical island just a bit longer.

It would help if you only had a rough idea of where you want to travel and your first few stops planned before you depart. Then, let the wind carry you.

This rule is applicable even if it’s a quick trip. You can plan a few sights you’d like to see every day and let the rest fill in itself. Let the day flow!)

My first trip through Europe in 2006 was to be like this:

Oslo -> Prague > Milan > Florence > Rome > Naples -> Corfu

It ended up looking like this:

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

It didn’t go as planned. It turned out much better. I was pulled in a new direction by people and cooler, more exciting things.

My recent trip to Southeast Asia changed utterly when a friend asked, “Want to meet me in Chiang Mai?”

I was supposed to fly to Bangkok but ended up in Chiang Mai instead. Then, on to Laos.

I rarely keep my original plans. There are few people I know who do.

After booking your flight, Please make a list of all the things you need to get done before you leave (it will not be as long as you think).

  • Buy your backpack
  • Buy travel insurance
  • Get your visas (if needed)
  • Get New Bank Cards
  • Book your hostel
  • Cancel cable and other bills

This is the majority of what you need to do. Most of it can be completed a few weeks before your trip.

Continue to the end of your list.




Purchase a few books to learn how to travel and prepare for your trip.

Get a feel for your destination by reading a guidebook.

Plan your general strategy and fill in details as you go.



It will all work out.

When it happens, you will wonder why you worried so much initially.

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