This was a great email I got a couple weeks ago from a couple living in the mainland USA that were going to make a run of moving to Hawaii and that had a lot of questions. I’ll do my best to answer below. Maybe your situation is similar?


Hi and thanks for you videos. (i wish i knew your name)

me: Peter!

Aaron: My Name is Aaron I am 23 my wife is 22. We live in Marietta, Georgia and we hate it. We have decided to move to Hawaii and we’ve done just about all the research you can do in preparation for it minus visiting there first. I know the most popular suggestion from people is to visit HI. first before moving, but honestly that’s in a world where we have enough money to visit, come back, and leave again to move there. Yeah…not gonna happen. So we’re just gonna bite the bullet and move there without seeing it first hand.

me: In a way it is scary to know that people that don’t have enough money to go visit Hawaii first, and then decide if it’s worth spending a lot more money, say they don’t have money to visit first. That means, probably, you don’t enough money to move there in the first place. On the other hand, this might be me writing this email to a Hawaii-site 20 years ago because I was also full of optimism and confidence in myself. I was sure I could do anything, move anywhere, do anything. There was no doubt. Aaron and his wife probably have a bit of this in them too. Can they do it? Sure, they could.

Moving to HI without enough money saved requires:

1. Busting your butt to get a job once you arrive and ignoring the hundreds of other activities you would rather be doing. It means working on your resume in your hotel room when you could be out surfing 3-4 foot surf at Makapu’u. It means going to interviews for jobs you don’t even care about – just so you can get it for a few weeks or months and forestall spending all your cash while you look for the “ultimate job” – which probably doesn’t exist at all in HI.

2. Having realistic expectations. Like mentioned above, you might need to take on a job that is below you. You might need to wait tables. You might need to hand out brochures. You might need to eat ramen noodles for a couple weeks. Realistic expectations means steadying yourself for what might be a less than ideal first few months. Expect the worst – and know that you’re going to power-through that and come out on top. Or else – don’t go to Hawaii at all.

3. Resources. Your resources could be in the form of cash on hand, skills that could get you a job quickly, or family or friends you already know in the islands that can help out in whatever way. The most important resource for a move to Hawaii isn’t money. You need a minimal amount – for sure. The best resource is your set of job skills that will enable you to get a job quickly and a job that pays enough to support your lifestyle – whatever that is.

Aaron: I of course have no qualms about the people, the danger, the wild life, the highly possible meager living, or the culture shock (if any). My wife feels the same way about a lot of those things.

me: If you’re great, the people are great. The wild life is as wild as you make it, my last time there I lived almost like a monk. The meager living is a very real possibility and sounds like you’re ready to face it. The culture shock – there is some I guess.

Aaron: We just have unnerving feelings about how to establish employment. She is a Dental Assistant and I do contract IT work for PriceWaterhouseCoopers (PwC). I have been programming and troubleshooting their laptop’s in an Win XP and Win 7 environment for them for about a year now, and I’m am very close to attaining my A+ certification (of course achieving this before we move). I appreciated the info in your videos about jobs, that was very helpful. Thank you.

me: I’ve had a number of dental assistants write me to say they are moving to Hawaii. I don’t know whether there is an overabundance of people with this skill now, or what the answer is. However, I’m inclined to start wondering if there will be enough dental assistant jobs in the islands in the near future. Start cold-calling dentists while you’re still in GA. It won’t hurt. Find out what the employment market is for dental assistants in Hawaii, whichever island you’re considering – you didn’t say.

Aaron: I don’t think that trying to apply for a position before we move would work for either of us, would it? I don’t know. Should we try to get a service job (waiter, food delivery, retail, etc.) to start with as soon as we get there?

me: I’d say call places directly that are looking for employees. It cannot hurt. Will you secure a job before going, having never lived in HI in your life? No. Very unlikely. But, calling will give you new information – current info you can use in your decision. Should you try to get ANY job as soon as you arrive? Maybe. Sounds like you don’t have the money saved to do it right, so maybe you should. I cannot say – I don’t know your finances.

Aaron: We of course are going to have our money ready to live off of for a few months (rent, food, transpo) But we want to have jobs before that runs out obviously. We are young, no kids (yet) and no huge obligations to anyone or anything except our car payment that we’ll have for the next 5 yrs. Love to be outdoors, love to explore, love to snorkel/scuba, very active and we are going to do our fair share (and more) of surfing. lol We just wanna feel better about landing jobs. Any suggestions? Know of any IT jobs my skill set would match?

me: Sounds like you are the kind to love the Hawaiian islands. Most of us are! Jobs are the main problem for most people. I have the certifications you have and in 2002 I found jobs easily. I also was an SEO expert and internet marketing consultant for some years. I had no problems finding jobs. You know there are awesome government jobs available in the computer field. Possibly for dental asst. too – not sure about that. Check out the National, State of Hawaii, and County of Honolulu job sites online. Make sure you visit the state of Hawaii jobs center in downtown (on Oahu) too.

Aaron: How would you suggest negotiating a place to live before we move, without being able to meet anyone face to face first? If you cant answer any of these that’s fine. lol I just wanted to let you know of our plan and update you along the way because we don’t have anyone else to talk to who has done this before.

me: Contact a lot of people through Craigslist. I have also contacted people using Twitter search. One woman said I could stay with her at her large house for minimal rent until I found a place. There are some amazing people living in Hawaii. You’ll find some if you are also an amazing person.

Best of luck to you and your wife Aaron, it is possible to make it – but, it will probably be a struggle. I’d encourage you to either add some more skills to your repertoire (spelling?) to make you easily employable, or save more money. Or both.