Why Kauai is the Perfect Antidote to Big City Living

I thought I’d stop in for 2 months. Maybe 3 months, TOPS. Then I’d pack my bags and jetset to another exciting location.


Nine months later, I was BARELY able to tear myself away. I had friends and family who I needed to see on the mainland, but now it felt like I was abandoning family on the island!

Kauai had become more than just a quick stop along my travels. This tiny, gorgeous island had become home.

And more than that, it had become an antidote. A cure. To years of big city living.

See, I didn’t even realize it, but living in big, abbreviated cities (LA, SF, NYC) had worn me down. Life felt static. Disconnected. Routine. I was constantly plagued by something’s-missing-but-I’m-not-quite-sure-what. And it was slowly suffocating me.

Kauai was that desperate breath of fresh OXYGEN that I didn’t even know I needed.

That sense of magic, adventure, and deep connection came rushing back into my life. It felt like being in college again. Or summer camp. And I thought those days were long gone.

So, if you’ll indulge me, let me break down why Kauai was exactly what this city-dweller needed…

Small Town Life = COMMUNITY

Most of my twenties were spent in sprawling cities where you couldn’t help but feel like another nameless face amongst millions of others.

Kauai’s the first small town I’ve ever lived in. And holy shit, what a difference!

Anytime you leave the house, whether you’re going to a cafe, the grocery store, or the beach, you’re practically guaranteed to run into a friend. It sounds like a small thing but it really made you feel like you’re part of a cohesive, tight-knit community. I haven’t had these spontaneous, UN-PLANNED run-ins since the university days. And man, I’ve missed them!

And there’s really this sense of one SHARED community. Anytime you meet someone new, you can bet you’ll have at least a few mutual Facebook friends. Everyone’s only one degree of separation away from each other. And that makes every stranger feel more like a friend you haven’t met yet.

Plus, I finally got to achieve a lifelong dream. I’ve lived in a LOT of places and I’ve always wanted to become a “regular” at restaurants, bars, and cafe’s. It never really happened. Until Kauai.

Here, it seriously felt like Cheers. Not only did the baristas and bartenders know my name, they knew my drink, and they got to know me as a friend. Some of my favorite days were spent just hanging out and “talking story” while these guys were on the clock. I felt like family wherever I went. It was everything I dreamed of!

The last time I experienced that shared sense of TRUE community was back at UCLA. And I thought once I “grew up”, I’d never get to experience that again. Thank Jeebus I was wrong!

The Focus is on Living, Not Working!

I’m a digital nomad. A stereotypical disciple of the 4 Hour Workweek. Meaning, my business is specifically run to give me as much freedom as possible. Freedom to live wherever I want and freedom to do whatever I want (which usually isn’t work).

That being said, everywhere else I’ve lived, work was everyone’s main focus. The top priority. Life revolved around your career and you squeezed in everything else where you could. There’s nothing wrong with that, but it always felt out of sorts with my own approach to life.

Well, Kauai was a bit different.

Work is definitely NOT the focus here. If you’re attracted to this island, chances are you care more about “adventure” and “chilling out” than “climbing the career ladder.”

And you can really FEEL that difference. Life is slower here. Relaxed. People don’t seem like they’re in this constant rush to get to an imaginary future. To get ahead in an imaginary race. Which leaves more room to appreciate what really matters, to soak all in all that really exists: the present moment.

I fucking loved it. I was living and hanging out with my friends all the time. Life had that lackadaisical, flowing, what-are-we-doing-today-not-that-it-really-matters vibe. Again, I keep mentioning it, but it was a vibe I hadn’t consistently felt since college (or summer camp, for you non-university folks).

When life stops revolving around work, people start to relax. Schedules start to loosen up. You have more room to breathe. To laugh. To play. To have creative Vine challenges. Or weekly philosophy discussion nights. Or spontaneous ice cream dance parties.

Here, it’s opposite world. Life revolves around enjoying the present and you squeeze in work wherever you can.

Say Goodbye to Schedules and Static Routines

One thing about big city life that was really killing me was how static and CLOCKWORK everything felt. Monday to Friday, 9 to 5. Schedule dinner. Catch up over happy hour. Get caught in rush hour. Go out Friday. Go out Saturday. Bar. Restaurant. Show. Repeat. Repeat. Repeat.

The rigidity and routine-ness was slowly draining my soul. Suffocating me. I desperately needed some randomness, spontaneity, and FLOW in my life.

And in those areas, Kauai deliver in spades.

Nothing feels routine out here. Nothing’s clockwork. Here, things just FLOW. People are always coming and going. Situations shifting and evolving. Even any plans you do make will probably give way to the island’s unpredictable weather!

And something special happens when schedules relax and planning loosens: space opens up. Space for magic to happen. Space to spend the whole day exploring caves and trying to perfect your 6-person synchronized cartwheel. Space to enjoy a freshly-picked guava smoothie as you talk about life and watch the sun set. Space to make new friends at a beach cleanup, who’ll take you waterfall diving, then to a beach bonfire where you’ll meet your new family for the next 9 months.

It reminds me of that vibe I feel when traveling. Of wanting to say “YES!” to life. Of people being down for whatever. That feeling of “anything can happen” and “adventure is around the corner.”

I thought I could only experience that kind of flow at Burning Man or while traveling. In short bursts. Or temporarily. Definitely not for 9 straight months in one location. I didn’t think it was possible!

Bond with Friends Quicker, Deeper

Ever since I entered the “real world”, I’ve always lamented how difficult it was to connect with people.

It didn’t add up for me: I’m super social. I was in my twenties. I had plenty of free time. And I’m surrounded by millions of others who all want to connect. Yet it never felt as effortless and deep as it did back in school.

I thought this New York Times article summed it up pretty well:

“As people approach midlife, the days of youthful exploration, when life felt like one big blind date, are fading… No matter how many friends you make, a sense of fatalism can creep in: the period for making B.F.F.’s, the way you did in your teens or early 20s, is pretty much over. It’s time to resign yourself to situational friends: K.O.F.’s (kind of friends) — for now.”

I found myself surrounded by tons of KOF’s. And with life and our schedules taking us in different directions, even my BFF’s were starting to feel more and more like KOF’s.

I figured, “Hey, this must be an inevitable part of growing up.”

Boy, have I never been happier to be wrong.

Living on this island was like being back in the dorms. Connection became a priority in my life again. And it happened effortlessly, deeply, and on a fast track. It felt like I had gotten my YOUTH back. It felt like THIS is how it should always be.

But why did it feel so different in Kauai? Well, since the 1950’s, sociologists have been saying there are 3 conditions crucial to making close friends. Conditions that were easily found in Kauai and summer camp, but not so easily in big cities: proximity; repeated, unplanned interactions; and a setting that encourages vulnerability.

The small town-ness of Kauai, as previously mentioned, easily lends itself to “proximity” and “repeated, unplanned interactions.”

And as for “a setting that encourages vulnerability”, I chalk that up to the open schedules and focus on living, not working.

When you only have a few hours free each night, your hangouts need to be condensed. You have an hour or two to “catch up” on life. This often can feel less like a live, present exploration and more like a quick summary of past events.

When your friendships have more time and room to breathe, you get to move past “catching up on the past” and into “living together in the present”. You share all kinds of experiences together instead of just hearing about them. It feels more like you’re walking this journey of life hand-in-hand.

And with that, it becomes easier to see all different sides to a person. To open up to each other. Be vulnerable. Share tears as well as laughter. To keep each other afloat during the worst of times, and to fly together during the best.

And with those kinds of opportunities for intimacy, just try getting stuck in KOF land. I dare you.

Full Permission to Explore Creativity

I love that in a small town, it felt like you could try your hand at ANYTHING you wanted! Whatever you’re interested in, it feels like you have full permission to get into it, get good at it, and get props for it.

Wanna try acting in a play? I had zero stage experience and yet I auditioned, got cast, and performed for 3 weeks in a hilarious production set in 1970’s Texas (yup, this Asian dude had to learn a full on Southern drawl, y’all). Wanna give fire dancing a shot? Too many people would jump at the chance to show you the gasoline-soaked ropes. Aerial silks? Live improv? Adventure photography? Yes, yes, and yes!

Like making organic chocolates or handmade jewelry? Just set up a booth at one of the town’s monthly Art Walk’s, bring your creations, and you might just sell out of everything! My friend Lindsay just sold her homemade chocolates for the first time this past Saturday – it was her dream for a while – and she completely CLEANED up! And my other friend just started selling her own custom-made jewelry and made over $300 on her first outing!

There were even open mic nights every week and even though I haven’t played guitar in YEARS, I felt comfortable jumping in and messing around.

On this small island, you really feel like you can try new things artistically and even sell your work or perform for other people…and not feel UNWORTHY.

What a concept!

If I was in LA or SF, no way in hell I’d try out for a play. Or try to sell my own chocolates or jewelry. The abundance of competition and talent would intimidate me and add tons of pressure. I’d think, “I’m not good enough to try this. I have no experience. I don’t even have the right training…”

But in Kauai, it felt like, “Dude, who cares. Let me give this a shot!” Low barriers to entry. And the stakes don’t matter so much, so everything can be a little looser, a little more fun. That was a really awesome part of it.

Don’t get me wrong, I think the abundance of talent in big cities is a beautiful thing, but it can also make us forget that art isn’t just meant for those who EXCEL, but also for those who want to EXPLORE.

And when it comes to the creative arts, you should ALWAYS feel like you have full permission to explore. Always.

Forever Young

I turned 28 while in Kauai (and was blindfolded and kidnapped…twice!) and could no longer ignore the fact that I was firmly, unavoidably, in my very late twenties.

A few years ago, the thought of this would’ve freaked me the hell out. But after living in Kauai, my fear of aging has been obliterated.

Living on this crazy little island, you realize that age DOESN’T really matter!

Within any given hangout, I’d be kicking it with friends from the age of 19 to 52. And it wasn’t weird. At all.

Probably because I never knew their ages until well after we were good friends. Or probably because it never came up to ask. Or probably because it JUST DOESN’T MATTER.

In the city, age seems to be a pretty definite marker of “where you are in your life.” Someone in their early-twenties probably just got their first job and still drink like a freshman in the dorms (college reference #378 for those keeping count). Someone in their early thirties? Taking their career seriously and looking seriously for a serious relationship, seriously.

But in Kauai, the land of wayward adventurers and free spirited hippies, the phrase “age ain’t nothing but a number” really feels true!

I thought once you hit mid-life, you’d automatically become a boring ass “grown up”. You’d lose all sense of play, fun, and wonder. And also all sense of style and swag.

Honestly, a lot of my friends in their thirties and forties were some of the goofiest, most immature, hardest partying people I’d ever met!

And I don’t get why, but none of them LOOK like they’re in their 30’s or 40’s either. Seriously, everyone in Kauai looks like they found the freakin’ fountain of youth. (Or maybe the true fountain of youth is in how you live your life? Deeeeeeep.) And older babes are just as sexy as their twenty-something counterparts – actually, often more so!

Living in Kauai helped me realize how much of a social construct age really is. It’s assumed that at certain ages you’ll be locked into certain lifestyles. There’s this creeping sense of inevitability.

But I realized in Kauai, by example of those around me, that age has NOTHING to do with lifestyle. You can ALWAYS choose the lifestyle you want. At any age.

I’m 28 and living like I’m a 70 year old retiree (frolicking about on an island with all the free time I could want). My first Kauai roommate is in his 60’s and is flying around the world, playing sold out shows, and smoking a ton of weed. And I know 23 year olds who are locked down in serious careers, paying off mortgages, and providing for beautiful families.

Point is, there’s a million and one ways to live a life. And at no point does an imaginary number called “age” ever determine that for you. YOU determine that for you, always.

So, those are just a few of the reasons why Kauai was exactly what that doctor ordered. And why I now call it “home.”

Don’t get me wrong though, I’m not saying Kauai’s a perfect paradise. Just like any other place, it’s got it’s personality quirks. All of it’s greatest strengths (flow, spontaneity) can also be it’s greatest weaknesses (instability, chaos). And as always, wherever you go…there you are.

But for those of you who need a break from the city life. Who want to say goodbye to clockwork routine and overpacked schedules. Who want to say hello to flow, openness, and community. Who want to spend less time working and more time playing. And who want to join others who want the same…

Then you just might need to book a ticket to Kauai. And just in case, I’d make it a one way.


– – – – – – – – – – – – –

Man, it’s already been a month since I’ve left and I’m still missing Kauai like crazy. But as much as miss that island and my fam out there, it’s SO good to be back in the Bay Area. I can tell this is exactly where I need to be right now.

When I first felt the pull for Kauai, I desperately needed some flow, spontaneity, and excitement in my life. But now, I’m feeling a pull towards the opposite: less distraction, more stability, routine, and focus. I’m in a productive-ass mode right now and (buh duh buh buh buhhh) I’m lovin’ it!

I’m so grateful that my lifestyle gives me the freedom to follow my heart/gut and be where I want to be, WHEN I need it. And for this summer, Bay Area Productive Time (with some choice trips around the U.S.) is what I’m needing.

But come fall? I’m not sure. If I’m still in get-shit-done mode, I might live with one of my old college roomies (can you tell college has been on my mind??) in Boston as he finishes up law school. If I’m in adventure mode, Bali has been on my radar lately and I could continue with this whole island theme. And of course, Kauai will always be there for me.

Either way, I never really know until I know. But if anyone has suggestions of cool places to check out this fall, send ’em my way. Till then, time to put my head down and get back to the joys of handling-shit-like-a-boss! (HUH!)

  • Fong

    Jaemin! I actually read through your entire entry- you’re a great writer! My fiance and I are going to Kauai for our pre-honeymoon so you got me even more excited! hope all is well, and I would highly recommend Boston- lived there last year and really loved it.

    • Fong, you guys are gonna love it! Hope life’s been good and CONGRATS by the way, I’m so stoked for you! I’ll add another tally for Boston :)

  • Nicole

    Loved the article! Very well written and I have the same sentiment toward Kauai! I’ve never stayed for more than a week, and I’m jealous you were there for so long! Boston and Bali are both amazing places! Best of luck in all your soul searching travels!

    • Thanks dude! It’s a special place, huh? Best of luck to you too.

  • Adrian

    I really appreciated reading your journey, thank you for sharing. Some truly valid points on life and the quality we live it at on Kauai. I am glad I got to meet you and spend some time while you were here. Come back soon, we will hit the mountains once more !

    • Yeah man, you guys have something really special over there…don’t you forget it! I’ll be back soon, until then, keep reppin the mohawks for the island haha. See you soon brother.

  • PK

    Such a well-written article!! Thanks so much for doing this Jaemin! (And for the shout-out! ;) All of us feel so blessed to have come to know you in this amazing place. (Especially me. ;) You have been a huge inspiration for me as a fun-loving entrepreneur who can make it work in a place like this! I know it isn’t easy. And you rocked it.
    I’m so happy to hear that you are in the right place for you right now and where you need to be but I miss you like crazy just the same buddy! Kauai will always have a place for you Jaemin. And don’t get me wrong I am far from a home body… there’s no reason you and I can’t find ourselves in far-flung places in this world! ;) Until then man keep learning and discovering and creating and have a hell of a good time doing all of it! <3 -PK

    • PK, you know I don’t even need to say it, but if I hadn’t met you that fateful night at the bonfire (and challenged you to a hot dog cooking contest), my time in Kauai would’ve been SO different! Kauai didn’t feel like home until I met you and Merv that day, so thank you so much for that freakin awesome gift.

      I definitely can’t wait to come back soon – I feel like I want to hop to a new location next but then will probably come back afterwards. But the thought of us meeting somewhere else also sounds SWEEEEET! Thanks for your love and support and I’ll see you soon man!

  • Brad

    Excellent post. I will be travelling to Kauai this January and will be basing myself in my vehicle while camping around the island for about 6 months. Im very excited to make new friends and play as many open mic nights as I can! Don’t forget the surfing! ;) Your post was inspiring and gave me the shivers many times. Stoked for Kauai!

    • You’re gonna have an amazing time, I have no doubt about that. Give Ha Coffee Bar and Small Town Coffee some of that open mic love for me!

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