Last Updated: 7/8/23 | July 8th, 2023
I make a lot of mistakes. Despite years of constant travel to over 100 countries, I can’t believe how often I still make rookie mistakes when I should know better.
For example, over the years years, I have:
- Almost gone to the wrong airport – twice
- Mistakenly booked two plane tickets for the wrong day (yay, cancelation fees!)
- Overpaid for a taxi when I knew I was being ripped off
- Forgot to haggle for market goods (thus overpaying)
- Forgot to buy travel insurance until three days into my trip
- Didn’t pack shorts on a trip to a tropical destination
- Forgot to pre-book accommodation during Christmas
- Didn’t rent a car in Curaçao (despite knowing I should) because I am cheap, and I ended up missing a lot of the island because the bus didn’t go there
- Messed up the bus times in Iceland and had to hitchhike because I was in a remote area.
- Tried to move abroad to Sweden, only to have to change my plans when I couldn’t find a place to live.
- Flashed my phone while walking in Colombia and got knifed.
Those are just the ones I remember off the top of my head. There are countless other instances in which I break my 27 cardinal travel rules (hence why rule #27 is the most important).
After all these years on the road, I still mess up.
Every day, I receive a lot of emails from new travelers that are filled with worry, fear, and concern.
For example, I once had a woman email me was preparing to study abroad. She told me she thought she was making the biggest mistake of her young adult life. Looking at her two suitcases filled her with dread. Another guy worried that he wouldn’t ever really be “ready” to travel. And another reader was concerned about her lack of worldliness would only lead her to screw up.
And like many, many other people, they emailed me asking for help.
How can they avoid mistakes? How can they ensure that everything is going to go smoothly?
It’s easy to look around and see travel writers as “experts” and “gurus” who seem to travel through the world with seamless effort. We glide through airports, make instant friends with locals, and blend seamlessly into new and unknown cultures. We’re like ninjas.
But I don’t know anyone like that. All my “expert” friends make plenty of mistakes. I’ve witnessed many first-hand, obvious mistakes from people who should have known better.
But we are all human and humans make mistakes. Even the “superhuman travel experts.”
It’s natural to worry about problems that might happen on the road. It’s easy to let that worry and fear cripple you and cause panic.
Before I went traveling, the worst-case “what if” scenarios consumed my thoughts.
How would I deal with this or that situation?
What if I got on the wrong train, booked the wrong flight, or made the wrong hostel choice?
I have done all three of those things (and more). It’s easy to beat yourself up over silly mistakes. Hell, how could I have been so stupid as to leave my passport on a plane?!
But, with time, one comes to realize that if you don’t occasionally make mistakes on your travels, you aren’t pushing yourself enough. Mistakes happen to confused people in unfamiliar places, people who don’t take preapproved tours and deviate from their guidebooks. Going to unfamiliar places and getting a bit lost was exactly the elsewhere I was looking for, even if that meant taking on some risks.
Mistakes keep you growing.
So you can’t let them get to you.
All you can do is move past them.
I long ago stopped beating myself up over my travel mistakes. Humans make mistakes. Experts make mistakes. I learn from them and hope I don’t make them again (but I probably will).
So the next time you book the wrong flight, catch the wrong bus, or screw something up, know that you are not alone and that others, even the experts, have made far worse mistakes…and we survived and continued on.
Just take a deep breath and move on.
Because you are going to make a lot of mistakes on the road.
But that’s OK — no one is a perfect traveler.
You’re only going to stress yourself out if you try to be one.
As they say, to err is human but to forgive divine.
Learn to forgive yourself.
You’ll get to where you need to go eventually.
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.