Play the fool

Howdy,

I hope all our readers in the US have bounced back from those Labor Day Weekend meat sweats.

This week, our team released a few articles on product round-ups for the best zipperless luggage, the best vegan leather luggage, and travel games for adults (we kept the classics and added a few new games you probably haven’t heard of before).

I’ve been diving deeper into the creative realm with SiteSee and gave some thought as to what it really means to be creative below.

Happy reading ✨

Hey, this is Kelsey, and you’re reading the SiteSee newsletter. Expect an email from me every Friday packed with personal travel stories, cutting-edge research from our team of globetrotting writers, and insights on embracing a location-independent lifestyle and the gear to get you there.

I spent most of my 20s hustling, working for various startups in Austin trying to make a name for myself in the marketing space. I read Meg Jay’s book, The Defining Decade: Why Your Twenties Matter--And How to Make the Most of Them Now, and took every principle to heart.

As I hit my 30s, I felt pretty accomplished by my own standards. I finally became my own boss, enjoying the freedom to set my own schedule and work from anywhere as a location-independent professional.

However, something didn't quite feel right.

After nearly a decade of constantly opening my laptop to tackle emails and rush to complete projects before deadlines, I found myself rather exhausted. And bored. Even though I was working from a new place almost every day, I still felt stuck in a hamster wheel.

During one of my late-night doom scrolls, I stumbled upon this short talk by Ethan Hawke about granting yourself the freedom to be creative. In his talk, he mentions how our job in life is to follow our passions and creativity. He points out that “there is no path until you walk it”…and the only way we can walk that path is by being willing to play the fool.

Like most millennials, every creative hobby I ever had eventually turned into a side hustle to make money. Looking back, I never really did anything just for the sake of doing it and being creative.

So I decided to switch things up.

When I arrived in Cape Town back in July, my partner surprised me with a pair of roller skates. Over the past couple of months, I've been making my way to the oceanfront promenade for some practice.

And let me tell you. The first week was hell.

I was so embarrassed to have other people see me. I could feel eyes burning in the back of my head when I’d hit a pebble and scramble to get my balance like a baby deer learning to walk. Homeless men were yelling at me to watch out as I came barreling down the path, causing them to leap out of my way.

But a funny thing happened. After the sting of embarrassment would wear off, I’d lose track of time — something I haven’t really felt since I was a kid. I’d hear a song and think of a way I could dance to it on my skates to it. On rainy days, I’d make obstacle courses in my Airbnb that I had to skate through. “…Now skate backward to the kitchen, do a turn, then glide on one foot to the living room…”

And the more fun I had skating, the more I noticed things starting to happen in other areas of my life. I’d get new clients seemingly out of nowhere. SiteSee experienced one of its best days yet traffic-wise. I’d get connected to the exact brand I wanted to work with through a friend of a friend.

I know there are dozens of variables at play here and that correlation does not necessarily imply causation. However, it's worth acknowledging that when you embrace your creativity, it seems to have a positive impact on other aspects of your life, making everything feel more effortless and carefree.

It took me 31 years to learn that being creative is not just a luxury. It’s vital to our being and humanness.

When we give ourselves permission to express our creativity in whatever way it needs to be expressed, everything else in our lives improves with it.

Don’t get me wrong, I still feel like a complete fool every time I slip on my skates. But that’s my job.

Be outrageous. Feel foolish. Play the fool.

Other Things I’m Mulling Over

• What I’m listening to: This Tim Ferriss episode, “The Man Who Studied 1,000 Deaths to Learn How to Live.” It’ll make you tear up — but in a good way.

• What I’m watching: This comedy special from Nate Bargatze. I find his jokes so clever.

• What’s on repeat: This Darius song. It has the perfect beat to skate to.

Thanks so much for reading and, as always, please let me know how I did by replying directly to this email. Which part of this email was your favorite? What do you want more or less of? Other suggestions?

​Have a wonderful weekend, all.

Onwards,

Kelsey

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