A Tale of 2 Pairs of Shoes

Have you ever been too scared to take your shoes off, because you thought that the bottoms of your feet were going to peel off with them?

Now that I have your attention, I’d like to tell you the tale of 2 pairs of shoes.

Once upon a time, a long time ago (well, 2015…but since 2020 has lasted for a few years…), there was a new traveler who wanted to make the most of her first trip to Hawaii.

It was her first big trip across the Pacific Ocean and her first trip with her coworker friend. She was desirous to prove to this friend that she could be a good traveler, and better yet, demonstrate that she was down for adventure.

Although she never really enjoyed hiking, the girl agreed to hike the tallest sea cliffs in the world, again, wanting to prove that she was down for adventure. And wasn’t scared. That was key.

Since she didn’t really hike back home, the girl didn’t have proper foot attire for the trip to Hawaii. Nevertheless, she followed the example of those more outdoorsy and purchased a pair of Chacos.

damaged feet wearing yellow chacos with tall sea cliffs in the distance - tale of 2 pairs of shoes
Kalaupapa Sea Cliffs, Molokai, Hawaii

Surely, the Chacos would be ideal for tropical hiking, no?

Well, in a perfect world, they would be.

But the girl was a new traveler and novice hiker, so the first time she actually wore the Chacos was on the day of the hike.

Little did she know how much pain she would be in throughout the hike, and how it would affect her later in life.

To read about the hike, check out THIS ARTICLE.

lush mountains with a palm tree - tale of 2 pairs of shoes
Stunning Molokai – a view few travelers get to witness

Fast forward to November 2020, and the girl ventured to the island of St. Thomas for the second time.

Although travel has changed over the last few years (2020 in particular), she was excited to return to an island she fell in love with on her first trip in 2016.

Before the trip, the girl made sure to purchase a pair of appropriate hiking/water shoes, and managed to snag a pair of Tevas right before the trip.

You see, she found out about a magical hike to Mermaid’s Chair and wanted to check it out.

But experience taught her to break in the new shoes ahead of the hike. So, she used coarse sandpaper to smooth out the seams and a few other tricks…which proved to be a game-changer.

Not only did she enjoy wearing the Tevas more than for just the hike, she didn’t lose any skin after the hike.

All in all, it was a happy ending to the tale of 2 pairs of shoes.

black and orange Tevas on a bench next to a basket of sea shells - a tale of 2 pairs of shoes
Smooth Tevas = happy feet!

Now I know it will come as a big surprise to everyone reading that I am the girl in the story.

And although they feature in the first part of the article, this isn’t a story about 2 pairs of shoes. It’s about what they represent.

Stop the presses, let it all sink in.

During my latest trip to St. Thomas, I took some time to think about how far I’ve come since that trip to Hawaii.

The now-experienced traveler in me wanted to compare my travel styles over the last four years and see how much I had (hopefully) grown and learned.

The easiest way for me to do that was to use the 2 pairs of shoes as an allegory to introduce my thoughts.

selfie wearing a hot pink shirt, lowepro black backpack, yellow sunglasses on my head, sweaty - tale of 2 pairs of shoes
Exhausted after hiking Mermaid’s Chair, St. Thomas, USVI

How do you measure growth in something that isn’t necessarily tangible, like knowledge and experience?

Without consciously realizing it, I created the ideal measure of my travel growth: I purchased a pair of Tevas for my trip to St. Thomas in November 2020.

To be completely honest, I had some rather painful flashbacks when I was at REI, trying the Tevas on. My feet seemed to remember the similar feeling of wearing my old Chacos, and instantly started to throb.

But instead of ignoring the memory or opting to wear a trusty pair of Vans, my experience spoke up and built my confidence back up.

As long as I could wear the Tevas for a few days before I left for St. Thomas and find a way to smooth out the harsh seams on the heels and toes, there wasn’t a reason why I couldn’t bring them along.

sandy feet wearing Tevas on concrete - tale of 2 pairs of shoes
Successful hike to Mermaid’s Chair – and my feet weren’t killing me the way they did in Hawaii!

Looking back now to my trip to Hawaii, I can’t believe how inexperienced I was. 5 years later, however, the change is calculable.

So what does this all mean?

Experience, even if it’s not measurable on the day-to-day, builds up within us and guides our actions. We can’t always see it, but it’s there.

And makes adventuring so much better than we could ever imagine!


How do you measure success when dealing with things that aren’t tangible?

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