Originally Posted: 8/8/2011 | August 8th, 2011
Updated with new links: 2/20/22 | February 20th, 2022
Five years is a long time to be on the road. Five years spent living out of a backpack, with no permanent home or address.
I never thought I was going to travel this long. It was only going to be a year, maybe 18 months tops, and then I’d go back home, find a “real” job, settle into life, and by now, I’d be married, have a house, 2.5 children, and be complaining about my retirement fund to my friends.
I celebrated five years of travel by giving away all my frequent flier miles and reflecting on what this journey has taught me.
Here are 18 lessons I’ve learned from the past 1,825 days of travel:
1. It’s not that hard
Every day, people get up and go out the door to travel the world. And they survive and thrive. In fact, it’s never been easier to travel the world on a budget. Sure, long-term travel is a privilege but with a little planning, you can make your next trip a reality. Do your research, make a budget, save your money, and sooner rather than later you’ll be getting on that bus or train or plane.
It can be a bit scary to take the plunge and head out into the world on an extended trip, but I learned quickly that all the worrying and fear I had was for naught. Traveling is a lot easier than you think. It’s not like you are the first person to ever do this. There are people out there who can help — both at home and on the road. You just have to take that first step.
2. You learn a lot of good skills
Traveling around the world has taught me to how to be more social, how to adapt and be more flexible, and, most importantly, understand nonverbal communication a lot better. It has made me be more independent, more open, and, overall, just a better person. While I’ve certainly had some frustrating and challenging experiences on the road, there’s no reason to be scared that you might not have “it” in you. We’re all a lot tougher than we think.
3. You make a lot of friends
It may seem scary just throwing yourself out into the world and talking to strangers, but we are all strangers in a strange land. At the end of the day, most people are very friendly. It took me a while to get used to just saying “hello” to strangers, but now it seems like second nature. Most everyone you meet — locals and travelers alike — is friendly and welcoming on the road that even when you travel solo, you are never really alone.
4. You meet some of your closest friends traveling
Those times I just want to relax and do nothing were the times I made my closest friends. Whether it was in a hostel in Vietnam, on a boat in Thailand, or walking into a hostel in Spain, when I least expected (or wanted) to meet people was often when I met the best people — people who shaped my travels, and my life.
And even though you may not see them for years, you still end up at their wedding, Christmas dinner, or family celebration. Distance and time cannot break the bonds you formed.
5. Relationships come and go on the road
I’ve met lots of people on the road, including members of the opposite sex I’ve found attractive. But the nature of travel doesn’t always lend to a lot of long-term relationships. It’s hard to make something last when everyone moves in different directions and holidays end. If you get too attached too often, you’ll have nothing but heartache as people come and go. But I’ve realized you need to simply enjoy your time together for what it is and stay on good terms when it ends. Just because something doesn’t last doesn’t mean it isn’t valuable or worthwhile.
6. But chase the ones you like
Yet once in a while, you’ll find someone you really connect with. Meaningful romance on the road does happen. And when you have nowhere to be and no place to go other than where you want, sometimes there is no reason not to follow. Don’t force yourself to say another goodbye if you don’t have to. Pursue it even if the distance seems too vast because you never know where it could lead or how long it might last. Sometimes you only get one chance, and when it is gone, you’re filled with nothing but regret.
7. It’s good to try new things
I used to be a very rigid person, but traveling has helped me expand my worldview. I’ve pushed myself to the limit, eaten new food, taken cooking classes, learned magic tricks and new languages, tried to conquer my fear of heights, and challenged my views on people, politics, and perspectives. I’ve learned that the more you try new things, the more enjoyable life becomes.
8. Be adventurous
Doing the canyon swing was tough. So was jumping off the boat in the Galápagos. As was eating the maggots in Thailand. And getting my butt kicked in Thai boxing. And, while I won’t do either of those last two things again, I don’t regret stepping out of my comfort zone and trying new things. Even if you only try things once, it’s good to challenge yourself and be adventurous. We only grow when we are outside of our comfort zone, so even if you’re not an adrenaline junkie (I’m certainly not!) it’s good to scare yourself once in a while. You never know what you’ll learn in the process.
9. There is no such thing as a mistake
No matter what happens on the road, it’s never a mistake. As was once said, “your choices are half chance, and so are everybody else’s.” Make your plans and then just go with the flow. The road will unfold ahead of you so there’s no reason to have regrets or think you made a mistake if things don’t work out exactly the way you wanted them to. Remember, every obstacle is a learning experience — especially the frustrating ones! Embrace the fact that the journey is the destination.
10. Don’t be cheap
When you travel on a budget and need to make your money last, it’s easy to be cheap. But why live like a pauper for so long while you were home so you could not eat the food in Italy, drink the wine in France, or have fresh sushi in Japan?
While it is good to be frugal, it’s also important to splurge and not miss out on doing once-in-a-lifetime things. Who knows, for example, when you will get another chance to dive in Fiji?! Don’t be penny-wise but pound-foolish.
11. That being said, don’t be wasteful
But remember you aren’t made of money, so don’t always feel like you need to party with your new friends every night or do every activity in a new place. Sometimes it’s ok just to sit around and relax, watch Netflix, cook your own meals, and be boring. In short, be frugal, but not cheap.
12. Go with the flow (and take it slow)
Sometimes it is great to have a plan. When there is limited time, you want to try to see as much as possible and stay on track. But stop being hemmed in by that plan. Traveling is about opening yourself up to change and letting life take you where you want to go. In the end, you throw the plan away anyway, so why even bother getting caught up in one? Have a rough idea of what you want to do, and just fill in the details along the way. The best experiences I’ve had are always the serendipitous ones!
13. Drop the guidebook
Don’t be glued to your guidebook. Sure, they are helpful at the start of your trip, but you can travel fine without it. Use it to plan an outline and learn about your destination, but don’t rigidly follow its suggestions. Get off the beaten path. Get lost. Ask locals and travelers for tips and information. You’ll make more connections and deepen your travels that way.
14. It’s never too late to change
Even if you aren’t the traveler or person you want to be in your head, it’s never too late to change. Travel is all about change. The more you say “tomorrow,” the less likely it is that tomorrow will ever come. Traveling has shown me aspects of my personality I wish I didn’t have and also shown me that I can be really lazy. I’ve always sworn by the phrase “Carpe Diem” but sometimes I don’t really do it. It’s never too late though, and realizing that has made being more proactive a lot easier.
Life on the road is no more dangerous than life at home (and in many places, it’s less dangerous!). Sure, you should be vigilant when you need to be (and you should never leave home without travel insurance) but that doesn’t mean you need to avoid “scary” countries just because the news says so. Take the precautions you need to but don’t stress out and miss out on opportunities because you can’t relax. The world is far less scary than you think!
16. Learn more languages (seriously)
Learning the local language when you travel opens so many new doors. It not only deepens your travels but you’ll be able to talk to more locals, avoid scams, better navigate the places you visit, and find better deals. It shows the locals that you appreciate their culture because you took the time to learn a few words and phrases.
By learning some of the local language, you become more than just a bystander — you become a participant in the places you visit. It’s the best way to have a more unique, authentic travel experience.
17. Wear more sunscreen
Seriously. Science has proven it helps, and with all that beach time you do when you travel, you could always use a little more. Being tan is great. Having skin cancer is not. SPF up!
18. People are good
All over the world, I have encountered amazing people who have not only changed my life but have gone out of their way to help me. It’s taught me that the old saying is true: you can always depend on the kindness of strangers.
Sure, bad things can happen — but they are the exception to the rule. We grow up in this culture of fear in America but 99.9999% of the people in the world aren’t murders, rapists, or thieves. There’s no reason to assume someone is one. Sometimes, people are just trying to be friendly. The more I travel, the more this is proven true.
I’ve learned more about the world and myself in the last five years of travel than I have in the previous 25 years of my life. Travel, after all, is the ultimate personal development tool.
So, no matter what happens in the future, I know that I am very blessed to have these last five years. And I’m a better person because of them.
Book Your Trip: Logistical Tips and Tricks
Book Your Flight
Find a cheap flight by using Skyscanner. It’s my favorite search engine because it searches websites and airlines around the globe so you always know no stone is being left unturned.
Book Your Accommodation
You can book your hostel with Hostelworld. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and 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. My favorite companies that offer the best service and value are:
- SafetyWing (best for everyone)
- Insure My Trip (for those 70 and over)
- Medjet (for additional evacuation coverage)
Want to Travel for Free?
Travel credit cards allow you to earn points that can be redeemed for free flights and accommodation — all without any extra spending. Check out my guide to picking the right card and my current favorites to get started and see the latest best deals.
Need Help Finding Activities for Your Trip?
Get Your Guide is a huge online marketplace where you can find cool walking tours, fun excursions, skip-the-line tickets, private guides, and more.
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.