25 Years of Wandering Lessons

This week marked a big milestone. Travel and I hit our big 25 year-silver anniversary of being inseparable. I know you’re wondering how is it biologically possible that Stephanie has been traveling for 25 years and could write 25 years of wandering lessons since she’s barely even that old? Let’s just say that travel keeps you young. Maybe it’s odd to you that I celebrate my travel anniversary every year. Perhaps it’s because I don’t really have another anniversary taking up calendar real-estate. More likely it is because travel has changed me and shaped me so much over the years, and I’m a pretty big fan of reflecting and growing. Throughout the years, I’ve celebrated this day by writing about all kinds of memories and lessons like the addictive sound of my first passport stamp, how my sense of travel fashion has improved, and how I eventually realized that traveling more than half of my life didn’t help me find myself. The truth of the matter is that travel and I have learned a lot together. And really, wouldn’t all those misadventures have been a waste if I hadn’t learned anything? To celebrate all that she’s taught me, I decided to write down 25 wandering lessons I’ve learned–one for every year that we’ve been together. And yes, we are aware that some of these lessons contradict other lessons on the list- but hey, that’s travel, isn’t it?

25 Years of Wandering Lessons:

1. When in doubt buy a plane ticket

Start with the basics. If you’re thinking about going somewhere, the answer should always be yes, unless you already know that it’s no. There are plenty of trips I regret not taking, but none that I wished I hadn’t gone on.

2.The confirm button never disappoints

Just buy the damn ticket already or make the hotel reservation. There are so many options when traveling and there is never ever a perfect decision. The best decision is the one that you have already made. Seriously, you won’t regret it, press buys now. (And repeat this to yourself every time you spend days researching plane tickets even after 25 years of travel)

3.You can’t do everything

The world is full, full, full of stuff to see and do. Even if you never travel you’ll never do everything in your own home town. How could you possible to see everything in the places that you visit? Slow your roll, decide what’s important to you (not what’s important to a guide book writer) and let go of everything else.

4. There aren’t wrong choices about where you should go

Everywhere is a new adventure, and since you can’t see everything (see above), you really can’t go wrong seeing whatever it is you like exactly where you’re at. Don’t listen to unsolicited advice about where you should go. There really are no wrong choices. And if you really don’t like a place, guess what– you can leave.

5. The world is not nearly as scary as CNN and FOX news would have you believe

Your mom wasn’t lying: Things on television are not as they are in real life. Most of the places that you fear based on what you’ve seen in the news are 99.9% occupied by regular old people worrying about their families, cooking dinner, washing the dishes, and picking their kids up from school. (You should still probably stay away from places with active wars though unless you’re being paid to go there as military or a humanitarian. War zones aren’t great travel destinations.) 

6. Don’t get stressed over dimes and dollars

Money stresses me out, but on the road, you can’t be stressed over small change, because you’ll literally be stressed all the time. If you get overcharged by a dollar and can’t get the rock bottom price you want at the market don’t sweat it. Your joy is worth a lot more. Be thrifty, but not cheap. If some small expense is going to make your travel experience remarkably better, get over your budget and just do it. 25 years of wandering lessons have taught me - It’s a cost of living.

7. A bathing suit is never (and will never be) appropriate airplane attire

No one wants to sit next to you in your bikini top, plus airplanes are cold. Keep your clothes on. (Note: This lesson was not learned by experience. It was learned by over-exposure to backpackers in bathing suits at 30,000 feet).

8. Travel styles change over time- and that’s perfectly okay

If you travel as long as I have your tastes are going to grow up on the road. You might eventually feel like a sell-out because you now prefer to stay at the fancy beach resort instead of the 4$ hostel dorm that you always loved in your youth. Own the season you’re in and whatever experience you like. And don’t forget to be nice to yourself.

9. Your experience is more important than your Instagram feed

If you spend all your time caring what other people think about your trip, you’re creating an image for others rather than an experience for yourself. Take pictures to capture the memories that you’re making, and for the love of God, put your phone into your pocket every now and then and use your eyes to look at the view instead of your screen.

10. When in doubt stay

If you are feeling overwhelmed, can’t decide where to go next, and are failing at implementing lessons 1 & 2 for inexplicable reasons, walk yourself to the reception desk of your hotel or hostel and book yourself in for another night. There is usually a reason for indecisiveness–channel your inner wise friend, and chill the F out. Then make your decision after you eat food and take a nap.

11. You never need to carry any more than you can lift into an overhead bin

You never need a giant suitcase. Unless you’re going somewhere long term, traveling for an occasion that requires lots of special equipment or hauling multiple children along, you can get by- and even look good- with a modest amount of clothing. Mastering packing may take years of practice, (25 years! lol) but you should start practicing today. And even if you can lift your case into the overhead bin by yourself, it’s definitely appropriate to let the kind gentlemen from the aisle seat lift if up there for you.

12. Always take one thing out of your suitcase before you leave for the airport

Even when you become a zen master of packing, you’ll still overpack. To keep this at minimum, always take one item out of your suitcase right before you leave for the airport. There is always one thing that you won’t need or could at least live without. The worst case is that you really do need it- and that’s what shops are markets are for. See if you can make under packing your new goal.

13. Not all clothes can be dried safely with a hotel hairdryer

Packing masters eventually also become masters of doing piecemeal laundry in hotel sinks and bathtubs. While learning this art it is important to note that some clothing will actually melt when you attempt to dry them with a hairdryer. Due to the laws of the universe, the clothes that you melt will inevitably be your favorite shirt, socks, and underwear. You will eventually learn to batch your washing in locations where you have ample time to air dry.

14. Solo-traveler honeymoons should be a thing

Don’t put off going to your dream destination because you’re waiting for the perfect person to take you there. Take yourself to Bora Bora. I felt awkward the first time I holidayed solo on honeymoon island, and now it’s one of my favorite things. Tahiti- check. The Maldives- check. Mauritius- check. If everyone owned up to their awkward and just did this, you’d all help increase the odds of meeting other amazing people in these romantic places. (commercial interruption for couples: If you are actually planning a honeymoon, have you checked out The Honeymoon Hack?)

15. There is always another way off the island

If you happen to miss your flight out of Seychelles, or just decide that you really want to stay another day in Maui, there is almost always an alternative option to your plans. This may cost money (consider indecision as a travel tax–see #2) but it’s always cheaper to figure out how to stay than it is to go all the way home and then pay for another trip to come back. (note: leaving Seychelles by boat is not a viable option thanks to actual pirates. It is recommended to enjoy another day on the beach while waiting for tomorrow’s flight.) 

16. Bad things will happen and prove your resilience

Bad things–some even worse than being stranded on an island–will eventually happen. These will suck. Some of them will suck at the moment, some will suck bad enough to ruin your trip, and some of them may suck so bad that you may consider going home and never traveling again. But when you eventually recover and find your wings again, you will recognize you are a resilient badass.

17. Excuses are always readily available

The world is full of reasons to not travel, or do not travel now. Fear (see #5) is a big one of these, and so is missing out on other parts of life that the people in your community will be experiencing while you are away. The problem with excuses is that they have no expiration. Excuses will keep showing up as long as you pay attention to them. Ignoring them is the only way out the door. (Note: this truth applies to both life and travel.)

18. There is always a way to make your dream trip happen

International travel doesn’t have to be a once in a lifetime opportunity. Creativity and ingenuity can really take you a long way to dreaming bigger than you have before and figuring out a way to pay for experiences that are larger than your budget. Learning this for myself took lots of trial and error. Lucky for you, if you really want a dream trip and aren’t sure how to do that, I taught a whole course on it. Seriously, you can go anywhere.

19. You’ll never get what you don’t ask for

I hate asking strangers for things, but after 25 years I’ve gotten a lot better. You know what– sometimes people actually want to help you with upgrades, information, cups of tea and rooms with views. While asking has no guarantee, not asking has a 100% rate of failure.

20. There are always trains going the opposite way

I’m always in a hurry, and I jump onto the wrong train all of the time. Even though I get very frustrated with myself every time I do this, I’ve also learned that this isn’t the end of the world. Nine times out of ten you can get off at the next stop and get on a train that will take you back the opposite way. Going backward sucks, but most travel mistakes are reversible like this. In the 1 out of 10 situations where you can’t simply turn around to reverse course see #15. Or who knows, maybe the destination you’re going to wind up at will be the place you’re supposed to be (see #4). 

21. Contribute where you visit

I’ve come to dislike the phrase “give-back” when you travel. A wise traveler should be acting in a way that isn’t taking anything away from a place. Figure out how you can let a place transform you for the better when you visit and be cognizant of the effects of your interactions. It’s way more important to travel well than to “do good”. An ethical traveler often does more good than many well-intentioned volunteers.

22. Your own culture is just as weird as every other culture you encounter

After you visit a lot of different places, you will eventually realize that all cultures are super weird and your own traditions seem as strange to an outsider as theirs do to you. Stretching your culture perspective will eventually help you become more open-minded and grant you the ability to see your own life from an outsider's perspective.

23. Plans are sometimes good, but uncertainty can be awesome too

No one lives their regular days with a minute by a minute operating plan, and the best travel doesn’t need to be conducted with this type of rigorous activity schedule either. The more comfortable you become with uncertainty, the more open you will become to adventure. You might miss something on the “best sites to see before you die list” but you’ll nearly be guaranteed to have an experience that isn’t in any book.

24. No one tells you that you will get tired of traveling

Living in a perpetual state of motion is awesome. It’s also tiring AF. There should be a chapter in every “How to Become a Digital Nomad Course” that is entitled “What the hell do I do when I get really exhausted from traveling?” One day you will wake up and the thing that you’ll desire is to eat your dinner off of your own plates and not to have to decide where you are going to maybe live next. This is absolutely normal. It does not mean that you don’t want to be a traveler anymore. You may just need a year-long nap, or maybe a small home base to anchor yourself between trips and cook dinner every once in a while.

25. The best travel stories will never be all about you

We are each just a small part of the big picture of what is happening across the globe. Your very best stories will be about how this world welcomes you, the beauty you find in unexpected people and places, and the misadventures you encounter when that same world spins you in circles and spits you out and you still find the meaning in it. Learn these lessons and let these interactions become your narrative. Make sure you speak them loudly and broadly so everyone hears them and recognizes that our incredible world is still a good place. There are so many more lessons that travel has taught me, and I’m pretty sure she’ll keep teaching me more as we continue our journey. Learning, like travel, is never complete. Happy Wanderings Friends. Here’s to 25 more years. If you enjoyed 25 Years of Wandering Lessons, check out more of Stephanie's posts here.