There is a REALITY we don’t wish to face sometimes…The acceptance of LEAVING HAWAII.

I can’t count on my hands how many friends and acquaintances have left the islands over the years…some had been here only a year or two…but other had been here 20-30 years or even all their life!

When you make such a BIG CHANGE in your life to move across the Earth more than likely the hope and dream is to make it your final resting spot…Unfortunately sometimes dreams and hopes can be shattered…and when that happens you need to make the choice to do what is best for yourself and your family.

To live in Hawaii for 10 or 20 or more years it can be an ABSOLUTE CULTURE SHOCK when returning to the mainland…and for some…people who return after a long time in Hawaii can NEVER RECOVER!

For many…they feel they have failed…perhaps that they even have let themselves down…BUT…as long as you know HAWAII itself and the SOCIAL SYSTEM in place was BUILT for you to FAIL…you’ll have a GOOD HEAD START to make every effort to not allow that to happen.

JUST BE WARNED…Hawaii may be Paradise for some, but for way more it’s a system that is built to allow you to FAIL! As long as you know this you can put things in place to safeguard yourself as much as possible so you DON’T end up like the THOUSANDS of people who leave Hawaii every year because they just can’t make ends meet.


15 thoughts on “ACCEPTING the REALITY of LEAVING Hawaii

  1. Great show guys, thanks for the doom and gloom, and I see what the hell ya’ll are doing. Get ppl to believe how bad it is in Hawaii, so their dreams of moving to Hawaii are crushed. Only way I’m moving to Hawaii, is if I hit the lotto…and I’ll buy a 7 bedroom 7 bath house in Kailua. And we will drink obscenely expensive scotch, and party with Asian hookers every night. Kinda like Bruce’s weekends, minus the scotch. I know tours are the main job that takes up most of you guys time. But what are the things you guys do to reset and relax? And also, do you get the so called “Island Fever”? There are a lot of native Hawaiians that have made the move here to Houston for whatever reason. Keep it up guys, awesome job and see you guys soon. Peace out from H-town.
    P.S. Wade if you’re look for Mexicans?!, just drive buy HomeDepot there the ones standing in the parking like deer in headlights.

  2. Great show guys, thanks for the Doom and Gloom! I see what’s going on, discouraging the people who are thinking of moving to Hawaii. And I hope it works. Hawaii doesn’t need more people moving there, clogging the fucking roads. So true Lovers of Hawaii’s beauty, can have a nice relaxing Vacation in a place they love and respect. Hell I see enough Douche Bags here every fucking day driving in gridlock in Houston. I don’t need to look at fucking Howlie that just move there, giving me the stank-eye cause I’m ruining his daily commute.
    So, guy’s what is your routine when you want to reset, or relax and get away from the tours and crowds? and do you ever get the so called “Island Fever”?!
    There are a lot of people from the Island that have moved here for one reason or another. I always thought it was because of the Island Fever. But I think its really what you guys spoke of ” the cost of living” on the Island. Thanks again love you guys.
    And Wade, if you’re looking for a Mexican? just drive by Home Depot, their the ones standing in the parking lot with the Deer in the Headlights look.

  3. Hi Bruce and Wayde!

    This is my first time commenting/donating to the show. I’ve been listening for over a year and absolutely love all that you share. Love the balance of positivity and reality as it feels like your listening to a close friend talk. My husband and I got married on Kauai last year. I am coming back in April and August. We have a chronic Hawaii problem.. I wanted to thank Wayde for the shout out to teachers and nurses. I teach 6th grade in San Diego, CA and my husband is about to start nursing school. We are absolutely passionate about what we do and feel so honored to hear others recognize it as well. We talk all the time about moving to Kauai but just can’t seem to get our shit together. Maybe one day when we can get it right. I am so inspired by all that you do for the island. We are hoping to visit Oahu and take a tour once he finishes school. Thanks for the awesomeness!


  4. Hey guys –

    I started listening in medical residency after my wife and I decided to move to HI; most often I’d put you guys on when trying to fall asleep in my call room in the middle of the ICU. Just the thoughts of Hawaii and friendly banter would calm me down. So Thank you.

    Your show is fantastic, but it’s rife with medical error over and over.

    I live on Oahu, work on outer islands. When I’m in town, if you need an anonymous medical consultant for the weekly show, count me in. No worries if not.


  5. Hey guys! I’ve been listening to your show for just over a year now and figured it was time I leave a comment – particularly after your call to arms about needing more audience participation. For starters, your show has helped me get through a fairly stressful period of my life. There were a lot of changes, moves, endings, and stressful new beginnings – but I had many, many hours of you guys arguing/debating/updating/loving to keep me going. So thank you for being part of my support system without even knowing it.

    I’m an American who’s been living abroad in Ireland for about ten years now. I’m 29 and I’m finishing up my final degree in grad school – I’m due to graduate in 2020 and by then I’ll be a Clinical Psychologist. I know you’ve said that healthcare is an area where you can be confident of finding a job, so I’m wondering whether you know much about the career prospects of a psychologist in Hawaii? I intend to move back to the states when I’m qualified and I’ve fallen in love with Hawaii from afar. Me and 90% of your listeners, but hey. A dream is a dream!

    I also wanted to ask if there were any tips for getting involved and meeting great people over the next couple of years and when I (hopefully!) eventually move there? Of course I’d be signing up for 808 Cleanups and taking a Jeep tour with Wayde and throwing a bottle of whiskey in Bruce’s direction (or if you can help me find cheap flights from Ireland, I’ll do that in addition to the airborne hootch) – but how else do you recommend meeting new people there? I expect I’ll be moving over solo and I understand the importance of having people to connect with, so any advice would be welcome.

    I’d love to be able to visit before I actually make the big move, but grad school isn’t quite as lucrative as I’d like! Any suggestions for how to visit Hawaii on a shoestring grad student budget, and what’s the absolute minimum amount I should be looking at to just arrive and survive there for two weeks?

    Thanks so much for all you do!


    • KIRBY! You are in SUPAH LUCK! I have a direct LINK into the PSYCHOLOGIST FIELD here in Hawaii…Please E-MAIL me Directly ( ) and I’ll do what I can for you when you have made the choice to make your dream come true and move to Hawaii! On one hand people who live in Hawaii don’t give the time of day to people who are not living here yet…it’s just something we do here…unless you’re on the ground, we don’t invest time in you…mainly because you’re not here…and if you are here we usually don’t invest time in you or even trust you until you get past the 1 1/2 itch of living in Hawaii…this is the time frame many go home and leave…People don’t want to invest in you, build trust and a friendship or relationship just to see you leave…so it will be hard…on the other hand reach out to those in IG, YOUTUBE etc who live in Hawaii…Follow lots of FACEBOOK HAWAII GROUP…start having conversations and talking to people, commenting…build up your love for Hawaii with others…join my FACEBOOK GROUP: and ALSO please join this Group to talk to like minded people: HAWAII OR BUST: ALSO focus on REDDIT on HAWAII

  6. Aloha guys, it’s been a while. I figured this would be an appropriate topic to weigh in on since it just recently touched me. For those that don’t know I was an early listener to the podcast and it helped me a lot in planning my move from Nebraska to Maui.
    My situation was a bit unique in the sense that I continued working remotely for my employer. A situation I highly recommend for those looking to move here as it is very hard to get a job here actually paying you what you are worth.

    Wayde is right when he says the system is almost designed for you to fail. Whether it is corruption or greed, whatever it is. People here can’t get ahead if they rely on the local economy because the laws in place in this state make it nearly impossible for people to succeed. Since moving here we knew many that had come and gone. Amazing just how many in a short period of time. I always thought I was safe. Working remotely gives you a sense of security.

    I write now to warn those that move here. If Hawaii stacks the chips against you, then those on the mainland are fully prepared to stab you in the back. I’ll explain.
    After 3 years of hard work, waking up and being available for every 3:30 am phone call my company called and offered me what they thought was a deal I couldn’t say no to. Last October my director called to “invite” me to move back to Nebraska. Or quite simply I wouldn’t have a job.

    It’s a conversation I never expected to have and yet, at the same time I think in the back of my mind I knew it would happen someday.

    What do you do? What would you do? I’d seen so many people give up. Swearing they hate this island and it’s challenges and pack up for the mainland. I have to admit for a brief moment I thought about it. Moving back to the midwest where my mortgage was a 3rd of what I pay for rent. Where I’d be able to slide right back into a familiar space and plot my next move. To be honest, the idea of packing up made me sick to my stomach. We have truly grown to love Maui. We didn’t just move here to see what happens. We put down roots. With local friends that are close to me as any family. Not only that but I had actual family members relocate here as well.
    Abandoning them was not an option.
    So we decided to stay and fight. I’m now working for a silicon valley VC firm and things are going well. Sure I’m dealing with problems like discovering just how terrible health insurance options are here on the island and I’m pretty sure my 401k is in shambles but we just weren’t ready to go back.

    I already know I would have been depressed and broken had we moved back to Nebraska against our will.

    Sorry for the long absence, but honestly the show has changed quite a bit and I’m just trying to keep myself surrounded with positive vibes. I still check in occasionally and enjoy hearing that you guys are still at it and expanding the tours and services available on Oahu. The Slingshot tours sound amazing. Keep fighting the fight.

    Have a good one, hopefully you were able to stay dry this weekend

  7. Hi, Guys.

    Another great show! Thanks for keeping it real, and covering the good and the not so good of living in Hawaii.

    Cost of living is going up everywhere it seems. Case in point, Nashville is one of the fastest growing cities in the Southeast. Builders are selling houses quicker than they can build them. Average cost in most areas of town is upwards of $500k. I know that’s no where near the cost of housing in Hawaii, but it’s high for this area.

    Also, just wanted to clarify my comments from last week. I work in insurance for a living. So I know a few things. When I stated that most insurances don’t cover helicopters between islands, I didn’t mean you could not include this service in your policy. It can be added, but it’ll cost you. Usually it’s not included in basic coverage. When I stated that life flight insurance can be purchased, I assure you it was not for an advertisement. This is a type of insurance, not a brand. I apologize for not being clear on that.

    Have a great week! Looking forward to the next podcast!

    Nashville, TN

  8. Hi there, I found your podcasts a few months ago and found them very interesting. I love drawing while listening to your podcasts whilst dreaming about one day going to Hawaii, keep up the good work!

  9. I lived on Oahu when I was 21 for a year in the mid 90’s, I’m now 44. I worked at Tower Records and made just enough to get by and was stoked. After that I moved back to Southern California near the beach. Hawaii is always calling me but I’m wondering if I’m just chasing my old memories and a time in my life that has already been done. I also realize we kind of change every 5 years or so and have different perspectives and wisdom. I might have a grass is greener mentality which I try to put in check because where I live isn’t so bad. I think about moving to Hawaii at this stage of my life and I’m just not quite sure I want to make the sacrifices it takes to exist there. I lived very minimal and light for at least 7 years after I moved back to So. Cal because I was always plotting a move back to Oahu. I’m just now starting to accept that maybe my Hawaii time and life there shouldn’t be attempted again and just live contently with the memories. If I had never moved there it would haunt me everyday but I think I scratched that itch and I’m at peace. Hawaii will always be the place you want to be after you leave but looking back with 20/20 vision helps put things in perspective. Aloha

  10.  I’d seen so many individuals surrender. Swearing they hate this island and it’s challenging and pack up for the mainland. I’ve to confess for a short second I thought of it. Shifting again to the midwest the place my mortgage was a third of what I pay for hire. The place I’d be capable to slide proper again into a well-known area and plot my subsequent transfer. To be sincere, the concept of packing up made me sick to my abdomen. We have now really grown to like Maui. We didn’t simply transfer right here to see what occurs. We put down roots. With native pals which can be near me as any household. Not solely that however I had precise relations relocate right here as effectively.
    Abandoning them was not a possibility.
    So we determined to remain and combat. I’m now working for a silicon valley VC agency and issues are going effectively. Certain I’m coping with issues like discovering simply how horrible medical health insurance choices are right here on the island and I’m fairly certain my 401okay is in shambles, however, we simply weren’t prepared to return.

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