Millennial Travel Podcast

Challenge Yourself: 4 Ways to Find Flow and Crush Your Comfort Zone

Matt Wilson
January 16, 2024

Tamarindo, Costa Rica July 2012

I was officially homeless.  

My apartment in New York was packed up, my stuff was thrown out, donated, or put in various friend’s attics. I was free.

I had nothing but my Marmot climbing pack on my back. Minimalism had been achieved.  

Now it was time to see some shit.

My plane landed in the eco-capital of the world - Costa Rica, where 5% of all the world’s biodiversity lives.  

Did I break out my bucket hat and birdwatching pants and head into the jungle?  

Nope. I went to the most gringo town Costa Rica has to offer and took up surfing.


Goal #1: Learn a new skill

While I wasn’t exactly on an eco-lodge in the jungle growing my own food, hear me out…Tamarindo’s mix of surfing, partying, and people patient enough to listen to my broken Spanish was just what I needed.

Little did I know, surfing would actually be a great way to get in touch with nature and even develop a little more understanding of the zen philosophy I had been studying.

If you are looking to get rid of bad habits, or negative patterns in your life, finding a new hobby or a new skill is a great way to focus your efforts in a new direction. It’s why they give alcoholics the same advice when they put down the bottle; they are in need of a new best friend.

Speaking of new friends, developing new skills are a great way to meet people who you actually have something in common with. And yes, this works for romantic encounters as well. 

Surfing never worked out for me (it’s all dudes), but yoga has been a great decision (it’s all chicks). Figure out what you are into and get involved in a community of like minded people.


Goal #2: Do something physically challenging

Travel has a magical way of pulling you into the present moment, as your senses are immediately overwhelmed with new sights, sounds, smells, etc. Surfing, and any extreme sport for that matter, can do the same.  

I love strenuous physical activities because when you do things that are physically and mentally exhausting like climbing Dead Woman’s Pass or Rainbow Mountain at high altitudes in Peru, there’s no chance your mind is wandering.

Some days the waves were so big I could barely even paddle out. By the time I even got out there was I was too fatigued to try and catch a wave. This is the place where you really start learning to be present; when you are questioning your life choices.

When a huge wave is about to crush you, you aren’t thinking about your inbox or to-do list.  

If you are interested in this subject, I recommend the book The Rise of Superman: Decoding the Science of Ultimate Human Performance.  

Goal #3: Do something mentally challenging

The waves in Tamarindo can be fucking huge.

Intimidated or not, I had no choice but to paddle out into the lineup, learn the rules of the road, and try to catch my share of waves amongst the overly-aggressive locals. 

Learning a new skill, and one that can be extremely dangerous, was the perfect way to get myself out of my comfort zone and shock my system. I was literally developing new neural pathways by learning to do new things with my body.

Everyone says do something that scares you. It sounds cliche, but when I see people who are afraid of heights do things like zip-line in Costa Rica, or go paragliding in Lima, they have breakthroughs. 

If you can jump out of a plane, you can also quit your job, end that toxic relationship, or start that business you’ve been hesitating to start.

Exercise your courage muscle!


Goal #4: Do something in conjunction with the planet

Most of us are just so damn disconnected these days.

It’s said that if you live in Hong Kong, you can go the entire year without actually touching your bare feet to the ground. We now live in not-so-healthy, climate controlled environments where it’s possible never to get sunshine, fresh air, or water that is truly clean, as I described in my previous post on nature.  

Get yourself in the water and immediately you are getting exercise, absorbing nutrients from the salt water, producing Vitamin D by getting in the sun, and taking in beneficial ions and electrons from the sea. The health benefits are immense.  

You don’t have to go surfing, you can pick something else as your gateway to nature. But for me, it’s pretty cool when I start to think about waves and tides…

You literally sit out there and wait for the earth to move, so you can ride it. Talk about being in conjunction with the planet!

And to think the tides are dramatically affected by the moon...that’s some interstellar shit right there.

Even when I paddle out and don’t catch a single wave, the meditative effect of watching wave after wave come in rhythmically while listening to the sound of the ocean, puts me into a good mood for hours after I get out of the water.

Find something that helps you go with the flow. You won’t regret it.

Check out the podcast episode here:


Listen in Now, and start challenging yourself today!

You can get this episode directly to your iPhone on iTunes, your Android on Stitcher, or on Soundcloud.

Matt Wilson
Matt Wilson is Co-founder of Under30Experiences and Author of The Millennial Travel Guidebook: Escape More, Spend Less, & Make Travel a Priority in Your Life. He is host of the Live Different Podcast, Millennial Travel Podcast, and formerly Co-founder of He is committed to helping people live more adventurous lives.


last minute deals


As Seen In...