How to Quit Your Job and Move to Hawaii (In Less Than Two Months)

By Sean Ogle •  Updated: 07/17/18 •  22 min read

How to Quit Your Job and Move to HawaiiQuit your job, move to Hawaii.

That’s the dream.

How many times have you sat in your day job and dreamt about white sand beaches, crystal clear waters and sipping mai-tais day in and day out?

Sounds pretty good, doesn’t it?

Well way back in 2009, my best friend Ryan did just that.

While I was writing blog posts on this site about daydreaming and not knowing what to do with my lifehe actually was going out and doing things.

How Ryan Helped Me Leave My Job

In February of 2009, Ryan and I both saved up all of our vacation time to go to Brazil for Carnival. We had the time of our lives exploring Iguazu Falls, hang gliding over Rio, and even dancing in the Carnival parade in these ridiculous outfits:

Outfits for Carnival in Rio de Janeiro

Why I’m sharing this publicly, I have no idea….

On our last day as we sat on Copacabana Beach drinking out of coconuts, we made the agreement that we should be able to do this whenever we wanted. It was time to take life back into our own hands.

Well, one of us followed through on this faster than the other one.

Less than 2 months after we got back, Ryan was on a one-way flight to Hawaii.


This is the very coconut we were drinking

I, on the other hand, was not.

Yet, as it turns out, Ryan moving to Hawaii was one of the best things that ever happened to me.

While he was working as a lotion boy at a resort hotel, I was wasting away behind spreadsheets and feeling totally stuck.

But I used to talk to him on my lunch breaks, often as much as three times a week, where he’d tell me about how great the island life was in Hawaii.

Sunset helicopter tours…

Mid-day surf breaks…

Unbelievable hiking…

And sun!

Sunset helicopter tour on Maui

I wasn’t joking about those sunset helicopter tours…

But that wasn’t it. This whole Hawaii thing wasn’t permanent. He was doing it through the end of that year to tread water and have an adventure until he began an even bigger adventure in the form of a world trip.

His world trip became my deadline.

January 2010, that’s when I had to figure something out. Because if he was partying in the islands of Thailand, and I still didn’t know what to do with my life…well, I might have gone insane.

This video details some of the rest of the story and how things went down:

How to Quit Your Job and Move to Hawaii

Way back in 2009, when this blog began, I was desperate for content. I was still wasting away in my cubicle and wasn’t yet doing all of the things I said I was going to do. 

Ryan was.

And as part of that, he agreed to write a 4 part series on Location Rebel all about how he quit his job and moved to Hawaii, if expectations lived up to reality, and if it was the right move in retrospect.

Today, I’ve combined those posts into what you’ll see below.

What was it really like to live on a tropical island?

Note: Two years later I ended up moving to Bali for two months. You can see more from that experience in these YouTube videos.

These posts have been updated for readability and such, but what you’re getting is a first-hand account from someone who actually did the thing so many of us have thought about doing.

Note: The following was written by Ryan, and edited to be updated in 2019. There are also occasional notes and links to relevant posts that have been written over the past 10 years.

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Moving to Hawaii: The Pre-Amble

As I sat on Hawaiian Airlines flight 39 bound for Maui, I pondered, how did I get to this point?

How on Earth did I gather the courage to pack up shop and buy a one-way flight to literally one of the most isolated places in the world? The answer is complex and convoluted, but in short, it was one part fate and two parts ambition.

Let’s back up a few months and the answer will become more clear.

My life in the months before my departure was pretty rough.

I’d come home every day bitching to friends and family about how I dislike my job.

I was a conveyer belt salesman, for a mining supply company.  Let that sink in for a second…

Many people would love my job. I had the freedom to do whatever I wanted and pursue potential customers in whatever way I saw fit. However, there was one problem.  There’s no way I could care less about the product that I was selling.

That’s the problem with sales. If you’re not passionate about your product, the job becomes boring, monotonous, and unfulfilling.

So there I sat in my truck on my way to the next customer, thinking how to get out of this “rut” in my life.

Then my phone rang from a good friend in living on Maui.

“Hey man, I know you really hate your job. You should move to Hawaii and live with me. It’s great over here and we would have so much fun. Plus, I need a wingman.”

That’s all it took. I was in. What better way to make an exit from rainy Oregon than to get a one-way ticket to America’s paradise.

Sometimes in life, opportunities present themselves and you have to be ready to act. And I know it’s not for everyone, but if you’re like me and have an adventurous spirit:

Ryan Martin After Quitting His Job to move to Hawaii

Ryan, just a couple days after living on the island.

Be ready to act.

You only live life once and what’s life without the experiences you gain from it, right?

Now some people may say, “Come on, it had to take more than that. You can’t just make a life-altering decision with one phone call.”

And honestly, that’s all it took. Obviously, I had to get a few things in order before I took off. I needed to get my finances straight, pack up, end my lease at a house in Portland, and quit my job. But literally, once that phone call ended, I was brainstorming on how I could make it work.

What I’m really trying to point out is please, please, please don’t let yourself be stuck in a rut.. And if you are, DO something about it. Be proactive, research, use your networks, get out there.

Life is way too damn short to be living life unfulfilled and unhappy.

And one other thing I forgot to mention. Don’t worry about the details.

Think about the times in your life when the absolute worst case scenario came to pass? For most of us, it probably never has.

As long as you keep your head level and your spirits lifted, it will work out, I promise. (Looking back on these words now a decade later, I can say this is still completely true).

For me, everything came together in a nick of time.

Three days before I was going to put in my two weeks notice at my job, I was laid off. It was a godsend, really. My head was already on the chopping block and I’m sure I wouldn’t have been granted the two weeks I was giving, anyway.

As I sat in my bosses office being told he was going to have to let me go, I tried not to crack a smile. He’d just given me the greatest gift he could offer. Unemployment, an extra two weeks to get my life together before leaving the mainland, and the guilt was on him for letting me go.

It was a huge weight lifted off my shoulders and to this day, I still don’t think my boss knows the favor he did for me. Cause now I’m sitting in paradise listening to Margaritaville, drinking a coffee, and listening to the waves crash on the shore next to me.

Just remember, if you want it, go out and get it. The world is yours to discover.

Grab our free book that shows you exactly what to do before, during, and after quitting your job.

Move to Hawaii: What It’s Like After You Move

Flying fish, humpback whales, spinner dolphins, shipwrecks…this definitely ain’t (insert the state you currently reside in here) anymore! File this under things employees can’t do!

Humpback whale in Hawaii

Yes, less than 48 hours after moving to Hawaii, I saw this. Good decisions for a 1,000 please Alex.

This is how I spent my first full day in Hawaii. I’m quickly learning that on Maui, it’s not what you know, but WHO you know. Fortunately for me, my roommate is a hotel concierge and one of the perks of the job is getting to do any activity on the island for free with one guest.

Insert me, the pesky roommate who wants to do everything possible, and you’ve got the “golden ticket” to nearly limitless fun (as cheesy as that sounds, it has proved to be true)

My roommate also works on Safari Boat Excursions (highly recommended) in Lahaina. So for my first day we decided to take a snorkel trip to the neighboring island of Lanai.

Somebody or something must be looking out for me because it was a banner day. I’m told only a handful of them happen a year. The 5 mile channel we crossed to get to Lanai was uncharacteristically calm, which allowed us to visit spots usually inaccessible to visitors.

As I looked up at our first snorkel stop, I could hear the creaks and groans of rusting steel and rebar. We had dropped anchor next to an old shipwreck where the captain purposely ran the ship aground to save the crew on board during rough seas. Today, it’s a haven for turtles, tropical fish, and tourists who are lucky enough to swim around it on a calm day.

Humpback whale in Hawaii

Not a bad snorkel spot!

It was an eerie feeling to be snorkeling while hearing the ship groan nearby. If you’re adventurous enough, you can even climb up the side of the ship and jump off on the other side (not recommended).

The problem with it is that the ship is not structurally sound and if one were to fall through, let’s says a rusty hole, there would be nobody to save you.

However, if you knew anything about my roommate, this just encouraged him to do it more. I opted out as I’d like to spend more than just one day in paradise.

As I sat there watching him climb up the rope on the hull of the ship, I wondered, what would it feel like to be impaled by rebar? Thankfully, I heard the gentle splash of his dive over the side of the ship as I meandered back to the boat while gazing at exotic fish.

On the backside of the island, we came across a pod of spinner dolphins. If you didn’t already know, dolphins are highly intelligent creatures (I mean, come on, any animal that has sex for pleasure must be smart) and they catch the waves of boats passing by for a free ride. The boat sped up towards the pod of the dolphins and as everyone looked back, we could see the sleek torpedoes riding the waves and acrobatically jumping out of the water.

It truly is majestic on these islands.

The wide-open blue sky melts together with crystal clear water and you know you are someplace special. This is in direct contrast with what I am used to in Oregon. The green Pacific set against typical gray skies.

Also, the fact that the water itself doesn’t put you into hypothermic shock is something I am getting used to. Some people call this island paradise, others call it the perfect getaway, I am beginning to call it home.

So I’ve been told that the site has been getting several hits on “quitting your job and moving to Hawaii” so I thought I might add some actionable steps to making a dream become your reality.

Set Attainable Goals

I’m probably beating a dead horse here, but I can’t stress enough how important it is to make goals. If you need to write them down, go ahead. Sometimes that helps people actually attain them.

If you have goals, you not only have something to look forward to and work towards but something tangible to attain. For instance, in regards to moving to Hawaii, I made a timetable with a realistic amount of money I needed to have saved up before moving in case I couldn’t find a job and needed to live off of savings.

Resources for this:

Create a Support Group

What I mean by this is surround yourself around those who encourage you to follow your dream. I can’t tell you how important it is to have people “get your back” cause, believe me, there will be times where you doubt yourself.

Just be sure to stick to your goals and in times of need, fall back on those who understand you and encourage you to move forward.

Resources for this:

Read Books That Will Inspire You to Pursue Your Goals

Believe me, you’re not the first or last person to take a leap of faith and go into the world of the unknown.

There are countless blogs and books out there that help with, and encourage following your dreams whether it regards travel or not. Obviously, these are other peoples lives so don’t follow their life verbatim, but it is comforting to know and read about other people going through the same trials and tribulations as you.

Resources for This:

Move to Hawaii: The Reality of Island Life Sets In

So far I’ve been writing about how awesome Hawaii is and how it’s pretty much been all fun and games. Now here comes the dark side…or so it was for me.

After the honeymoon stage ended for me on Maui, I decided I needed to get a J-O-B. I mean, half the reason I came to Hawaii was to pursue a job in the hospitality/tourism industry.

Home in Maui

It’s nothing fancy, but this was Ryan’s place on Maui.

So I set out on a quest to find a way to continue to fund the limitless fun that I’ve been enjoying on Maui. I literally made it four blocks down the street to the closest business to my residence (a coffee shop), walked in, and asked if they had heard of any job openings after ordering a cup of coffee.

The sweet, kind middle-aged lady replied, “Well, as a matter of fact, we’re hiring.” Hot damn, this is going to be easier than I thought. I handed her a resume, she interviewed me on the spot, and 5 minutes later I had a job.

I started the next day and soon learned that what I thought was going to be an easy, laid-back job at a coffee shop was turning into a concentration camp of sorts.

My first hint of this was when I brought up a casual conversation with a customer about travel.

Boy, did I get an earful when they left.

The nice, middle-aged lady instantly turned into a she-beast and ripped me a new one. “In this coffee shop, we educate customers about coffee and bring all conversations back to coffee. DO NOT talk to customers about anything other than coffee. Do you understand me?”

Oh, I understood loud and clear.  Most of all, I understood that this was going to be a big mistake.

After being verbally reprimanded, I put my tail between my legs and cowered back behind the counter in anticipation of the next customer.

Before the next customer arrived, a co-worker asked me about the surf that morning. I responded like any social human being would, and was quickly ssshhh’ed by my boss.


“Ryan, what did I tell you?” I replied, “Yes, mother.” Ok well, I really didn’t say that, but I was thinking it in my head.

Two weeks of social oppression followed and I finally couldn’t take it any longer.

I called the “Coffee Nazi” out on her outrageous demands and we agreed that my employment there was not going to work. She wanted complete control over my existence in the coffee shop and I apparently couldn’t keep my mouth shut. So after two arduous weeks of slavery, I was free once again to pursue a job more so related to tourism and such.

Three days later, I sniffed out a lead on a job selling suntan lotion and Maui Jim sunglasses.

I went in for the interview and met with the Big Wig there (or so I was told).

“I can already tell you look good for the job. When can you start?”

That was literally my interview.

Somewhere in the U.S. jobs are suppose to be hard to come by, but apparently not here. A few days later I became a member of an elite society of oil boy experts.

Home in Maui

The resort where he became an “oil boy expert”

As I write this, I’m about to start my first day on my own as an Oil Boy Specialist, as I like to call it.

I would say it’s a step up from my former job. They pay me to talk at this one and even encourage it (who would have thought talking while at work could turn into a privilege).

Now, I wander the pool deck and look at the gorgeous azure seas to my right and perfectly fitted Brazilian cut bikinis to my left. I have the best office view in the world, get to work on my tan, and best of all, get paid all at the same time.

This is the first time in awhile that I have worked at a job I enjoy, rather than a job that was convenient or paid well. So for those of you out there that can’t take it anymore at that crappy job, don’t.

Follow your passions, keep looking, and don’t give up because if you keep an optimistic outlook on life and your career, everything will work out in the end.

Move to Hawaii: Some Final Thoughts

So it’s been a few months since I’ve written for Sean.

As a recap, I’ve been on Maui for almost 5 months now. I moved here with no job and no real expectations except to try something new and have an adventure.

Now, I work at a hotel in sales, make decent money, and am basically living the stereotypical island lifestyle. Every day I’m reminded of how lucky I am to be living in such a gorgeous place, but that isn’t to say it comes without a price.

Island Life Isn’t Always Easy

Although Hawaii is considered by most to be an island paradise, it does have obstacles to overcome when living here.

The most apparent of which is the fact that “Howlies” (white foreigners), are often treated differently than the locals. In some cases, this can be good (employment), while in others it can be bad (state licensure, service).

Now, I don’t want to come across as if I dislike Hawaii, because the fact is, I love it here. However, it’s taken some getting used to the fact that as a Howlie, I frequently get dirty looks and at times have been harassed by the locals.

I’m sure this is rooted in the fact that 50 years ago the island was not nearly the tourist hot spot it is today; hell if I were them, I would be mad about that too! Yet I suppose this can be a lesson for all of us who strive to become location independent and see exotic and foreign places. By dealing with this type of adversity one can learn more about themselves and other cultures, and in the end, peacefully coexist.

Hawaii Can Be Really Lonely

Something else that one must consider when moving to a new place, is the fact that it can get lonely on the road.

I’m certainly not trying to throw a pity party for myself, but I’ve learned that many times I have to be able to entertain myself.

By working in the hotel industry I’m constantly meeting people from all over the world, yet they always leave just as quickly as they arrived. This has made it really difficult to maintain a core group of friends.

Maui has proven to me that it’s a haven for both tourists and vagabonds alike. When you factor those people out, there’s a very small percentage of people I have met that are here for good and an even smaller percentage that are of similar age and interests.

Because of this, I’ve found it imperative to be open-minded when meeting new people, as well as being OK with being alone, because it definitely gets lonely at times.

Many people who move to Maui get “Island fever” at one point or another.  Essentially, this is getting the feeling of claustrophobia from being stuck on this rock 3,000 miles out in the middle of open ocean.

I’d be lying if I said I haven’t felt it myself.  Sometimes it feels as though there’s only so much you can do here, and only so far you can go.

This is when creativity is vital.  Instead of dwelling on the fact that you’re on a desolate piece of rock, you go out and explore.  Finding new places, hobbies and meeting new people has become a way of life for me.

I’ve talked to many people from various backgrounds, and there always seems to be one common thread to their thinking:

“When life is all said and done, what else do you have other than your experiences? You can’t take that nice car or house with you to the grave, but your memories and stories will live on forever.”

I consider myself very lucky to be living in Hawaii.

It’s natural beauty is fabulous and the recreational opportunities are endless.  I just hope this opens your eyes to the fact that although it’s great here, there are certainly some tough obstacles to overcome.

Things aren’t always fun and games, but I certainly hope that more often than not it is.

Scooters in Maui

The preferred mode of transport on the island.

So, What Happened Next?

Ok, Sean again.

These posts were originally published between April and September of 2009.

A month later, I left my job and got an offer to work with Dan at the Tropical MBA in Thailand.

My original plan after leaving was to travel through Central America with Ryan.

But with my new Thailand plans, I convinced Ryan to start his trip in Asia.

Less than a year after Ryan and I tool our life changing trip to Brazil, we’re both finally living out the lives we’d been dreaming about for so long.

Here’s us in Railay, Thailand the following January:

Swimming in Railay Beach

Hanging in Railay less than a year after promising to make a change.

And the best part of this story?

Nearly a decade later, we’re still doing it.

Last year while my wife Tate and I were on a two month sabbatical, we were able to spend time with Ryan and his girlfriend Annika in Germany and the Dolomites of Italy:


BluffworksatOktoberfest e1507538575297 1

Ryan and I with other friends at Oktoberfest in Munich

And honestly? It would never have happened had he not been the first one to make a leap and make a move.

On this site, I talk a lot about the importance of a community and a support system. Ryan was the one person I could turn to in the early days of starting my business because he got it. He was going through the exact same thing as me.

It was seeing first hand just how valuable that accountability and support was, that was part of the impetus for creating the Location Rebel Academy community.

We’ve now helped hundreds of people build lifestyle businesses that have allowed them to travel, spend more time with friends and family, live happier lives, and frankly, just do more of the stuff that they like most in life.

If you’ve been thinking about making a change, but you’re not sure how, don’t have any ideas, or are lacking that support system, then I invite you to join us.

There’s a reason that 10 years later, our community is still so active, while so many others are not 🙂

Or if you just want some help quitting your job so you can move to someplace a little more exotic (or just work from home.

Check this out.

Sean Ogle

Sean Ogle is the Founder of Location Rebel where he has spent the last 12+ years teaching people how to build online businesses that give them the freedom to do more of the things they like to do in life. When he's not in the coffee shops of Portland, or the beaches of Bali, he's probably sneaking into some other high-class establishment where he most certainly doesn't belong.
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3 comments on "How to Quit Your Job and Move to Hawaii (In Less Than Two Months)"

  1. Steve says:

    I was stationed at Pearl Harbor for three years. I loved it. I had a working vacation in a spot people pay thousands of dollars just to spend a week there. I never once got Island Fever. I always found enough to do to keep me busy.

    I’d *LOVE* to go back.

  2. SI Hopper says:

    After doing some research myself: it appears that East Hawaii on the Big Island is the least expensive area to buy. I entered “Puna” into sites like Zillow and Trulia and found tons of nice homes between 200k and 250k, some even come fully furnished, so the moving part is easy! What’s neat is that it’s still only a max 90 min drive to the touristy resort areas on the Kona side, though I’m attracted to the wilder coasts of Puna myself. I’ve also read that the population on Big Island is much less dense than on the other islands and they say that people really live with Aloha in Puna: open, friendly, no rush, respectful to all cultures, even seniors and us regular, not-wealthy folks. Sigh. I’m still working on the dream.

  3. Josh says:

    I love the article, and I’ll be reading more of your stuff from now on! It was nice fresh breath of air and all, the only thing that brought me back down to reality was the fact that he knew somebody that lived there already and was invited to stay. I have a bachelors, lots of debt, live in Kansas, and basically day dream of escaping every moment I’m awake, and hate it. Very inspiring read, though!

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