Expert Travel Lessons Learned The Hard Way

In a recent post I wrote, Are You More Confident Now That You’re Older?, I touched on how a lot of times confidence comes from being okay with failing and getting rejected again and again.
Now that I’m 30, I’ve already accumulated piles and piles of messy, crazy mistakes I’ve made and lessons learned the hard way.

Before this blog, I used to have a travel blog called YouSomewhereElse (hence my wordpress handle LauraSomewhereElse). I don’t consider myself the absolute best expert on travel, per se, but I do travel more than 2/3 of the year for work, so I consider myself at least somewhat of an expert. And when you travel as much as I do, you rack up a whole lot of experience under your belt. Some of it is good, and some of it…not so much.

Right now I’m in the middle of a 5 city trip without hitting home between cities. I’m in city 4 out of 5. I’ve probably only spent about 10 days total at home in New York since the beginning of January. I’ve been traveling like this- at an ever increasing rate- for over 8 years, and have been on the road so much that I should be great at it, right? Well, sometimes even if you’re “great” at something, it just means that you do it so much that you’re bound to do a bunch of things wrong at least some of the time.

Just to prove that being a confident expert takes lots of failure, and to encourage you to not be afraid of the really bad experiences, here are just a few of the many mistakes I’ve made on the path to becoming a travel expert..

  1. I’ve gone to the wrong airport..twice. One time I completely missed the flight and they wouldn’t rebook it. I lost $550 buying a new last minute flight, and another $100 taking a cab from one airport to the other..only to miss that flight anyway.
  2. I’ve booked a flight on the right day,..but in the wrong month..and the $400 flight cost was non-refundable.
    3. I bought a cheap suitcase and had the entire handle come off on a hill in the middle of England.
    4. I bought a different cheap suitcase and had the handle come off in the middle of a staircase in Washington DC.
    5. I’ve exploded a bottle a seltzer all over my laptop and BROKE THE KEYS FOREVER in the middle of Philadelphia a month ago.
    6. I’ve been stuck in Charlotte airport for 3 days when the airport closed because of bad weather…and I had to sleep on a cardboard box because I was on the phone when they gave out cots.
    7. I’ve booked numerous bus tickets that ended up being at the wrong time..and they were nonrefundable.
    8. I let my phone fall off my lap while sleeping on a plane and it was stolen while I slept.
    9. I opened the back of a car where my suitcase was stored, only to find my suitcase gone! I thought it had been stolen and completely panicked, only to later realize that I was in the wrong car.
    10. I’ve accidentally tried to bring my permanent plastic Contigo water bottles filled with water through security…and have had them confiscated at least half a dozen times because I was in too much of a hurry to go back and dump them.

11. I recently dropped all my suitcases off at the wrong hotel. This was two days ago.

12. Today I went running in Fort Lauderdale, got completely lost, and had my phone’s GPS stop working on me. I had to continuously ask construction workers and random passerby directions for an extra half hour until my phone suddenly started working again. If it hadn’t finally worked, who knows when I would’ve made it back home.

So don’t worry about going out and failing. Failure probably means that you’re just putting yourself out there more…or at least I’d like to think so. Go ahead and make tons of crazy mistakes..and you’ll perhaps become a confident expert along the way 🙂

Other computer 1966

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