This is a photo of the West Maui Mountains. There always seems to be rain clouds above them, and it makes for some consistent rainbows. Maui is, to me, the best place to live in the Hawaiian Islands.

Brian wrote me below, and told me just about everything I would have asked, so I’ll be able to give him a good response. I think this will help others in a similar position see what their chances of success are if considering a move to Hawaii.

Because the email is long, I’ll comment within the body of his email, that way I don’t miss anything. I’ll answer in italics.

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Hi Vern,

I hope you don’t mind me reaching out directly to you. I recently read the most current version of your ebook, and it sounds as though you welcome questions.

Peter – yep!

I can only imagine that you probably find yourself on the receiving end of some very long winded emails, so I’ll try to stick to the key details.

Peter – Occasionally, yeah I do. But, usually I prefer those because I get a lot of information that I can use to formulate a response. It does take a while to respond to the long emails, but they help others a lot more because they are jam-packed with information. Like yours!

My wife and I are entertaining the idea of moving to Maui. We have two kids – a 4 year old and an 8 month old. We currently live in Orange County, CA. I’m a brit. My wife grew up in Connecticut, but has been in California for 15 years. I have been here for 10. We have no family here in CA, only in the UK, NY, OK and HI.

My wife is an elementary school teacher, with 10 years of experience, including a Masters in Education.

Peter – Would you consider moving to Thailand? Your wife could make $3,000-3,500 per month teaching in Bangkok or Chiang Mai. You could continue your online efforts. Aesthetically, it’s as beautiful as Hawaii. Not quite the same feeling, but sometimes it’s better, sometimes worse. An amazing place to consider if you ever want to move overseas internationally. Plus there are decent international schools and you’d save thousands per month if you wanted to. Ok, sorry, moving on…

I manage all paid digital advertising SEM, display, rich media, mobile, social etc for a small (15 people) agency. I have done so for 4 years. I have also crossed over into TV, print and radio at times. Prior to that I produced video and broadcast commercials as an independent contractor, for 5 years. I have also written copy for a global brand in that time.

You clearly have a lot more to [credibly] offer on the topic of moving to Hawaii than most. I have really enjoyed what I have read [so far – not including all the articles on your site]. I appreciate how much you love the islands, but even more so, how honest you are about the realities of living in Hawaii. You mentioned that you, personally, wouldn’t recommend moving young kids to Hawaii – for various reasons. I wanted to present our particular scenario and see whether you would maintain that advice.

We have family living on Maui. My wife’s brother, his wife, and her parents all live in Kihei. His wife and her parents are mainlanders but have lived on various Hawaiian islands for a couple of decades. We have visited a couple of times, staying with them.

My wife has a potential opportunity to teach at a charter school in Maui. The conversation hasn’t got as far as salary. She is connected to another employee at the school and it is somewhat of an ongoing opportunity. It has been suggested that she could make roughly what she is currently earning in Orange County. Right now she is on the higher end of the teacher pay scale. Some of teaching would be in an e-learning environment, with my wife working from home.

Depending on my work situation, it is possible that she could work part time, and/or home school the kids [when they are old enough]. It’s probably also safe to assume that if she is teaching at a school then our kids will be able to attend also. Lots of ‘what ifs’ and mostly hypothetical at this point. It’s also possible that she could get a job at another school.

Peter – in your case, since you’ll likely be educating your kids at a good private school, or homeschooling, I think there’s no real issue except leaving the friends they have made where you are now. They’re still young, so that’s no problem. Drugs are rampant on the islands, maybe less so on Maui than Oahu, but it isn’t like there isn’t that same problem in most places in the USA and every other country in the world. My main problem with Hawaii public schools is that one just doesn’t know how their children will come out of it. It’s a crapshoot. Some will turn out very well adjusted and go on to have brilliant lives. Others will get stuck with poor teachers, poor school, poor support system, choose friends that influence them the wrong way… I think by sending them to private schools, and/or homeschooling, you’re doing the best you possibly can and it shouldn’t be an issue in deciding to move there. Not saying your kids will grow up as you wish, but, maybe there is a better chance.

Knowing that you have extensive online marketing experience, I suppose the bigger question is; is there work for online marketers, or should I be thinking about operating as a consultant from home? A lot of my experience is within a specific industry [automotive aftermarket] – working with a host of industry leading brands. I am hopeful that this experience would make me an attractive prospect to similar companies in the same industry. On a couple of occasions competitive companies have attempted to head hunt me. I don’t say this to brag, only that it suggests [to me] that my particular experience may have enough appeal to allow me to go at it alone [working remotely on a contract basis] and generate sufficient income. Of course, I can also apply my digital marketing skills outside of the industry I am currently working within.

If we made the move, it would be with very little debt [student loans], and with $25k+ in savings.

As mentioned, we live in SoCal, so we are very used to a higher cost of living. We currently rent a small 3 bedroom house for $2200 per month.

Sorry – I have only really asked one small question and have given you a ton of detail, as well as the long winded email I was trying to avoid.

I would very much appreciate any insight that you may have, as it would apply to our situation. Please fire away if you have any questions.

Many, many thanks.

Brian M.

Peter – You have a couple of great things going for you… One, your wife’s teaching credentials are excellent and I don’t think she will have a tough time of finding a good job on Maui. However, it is not Oahu, and there are far less jobs on Maui. Two, you have your wife’s family there, which makes it VERY nice. You can have every question answered before you move, and while you’re there. Nice to have that opportunity. Most don’t.

I think you’re writing me to get some idea what the market might be for your talents. Back in 1984 I remember co-workers talking about there being a “brain-drain” of Hawaii. The smart kids moved away and got great jobs in California, or over on the east coast. Hawaii couldn’t offer much for them. I think that is still the case, but, I know that some smart folks are staying right there in Hawaii because it doesn’t matter where they live, and they choose to stay in the most incredible place in the world… any of the islands qualify as that, maybe even Oahu.

You might have read about my first couple jobs in Hawaii at the Hawaii Articles link at the top of the page (click here to see the list).

I found jobs easily. Problem was, Hawaii was still so far behind the times that there were few people to network with and get my own company started. I had an impossible time finding people that were current with the skills you now have. Today there are more of us, but, I see the same ads in Craigslist for “Internet Marketing Managers” that I saw 8 years ago. The positions open up repeatedly, probably because those that apply and get the job, cannot do the job. The job needs filled by people in California, east coast, that have done it for years. It’s not entry-level stuff, but some Hawaii corporations (Big Hotels and property management firms) try to treat the jobs that way. So, it’s a mis-match and they both end up losing, employer as well as employee.

Selling, coordinating, ads on sites is a very valuable skill to have. Whether you can find a good company doing that in Hawaii or not is an unknown. I don’t personally know of any. I’ve not been looking though. My guess is that you will be able to find a job very similar to, or exactly, the job you are doing presently – on Oahu. On Maui, it isn’t likely, but who knows until you really investigate? The need for online ads is global. Hawaii is a little microcosm to itself, there are likely some local companies that are trying to get a network of good Hawaii sites together to sell ad-space for. If you cannot find one, you might consider starting your own. Not sure if you’re entrepreneurial or not, but with the right idea – you can still make a killing in Hawaii. Problem is, so few come up with the right idea!

You have enough savings to really give it a go and see what happens. I don’t think you’re going to have any problem at all with moving and making it on Maui. If you can swing consulting for your present gig for a while, I’d strongly recommend that. No sense spending your savings while you and your wife scout for jobs.

Hope that helps Brian, if you have anything else to run by me, feel free. Do let me know how it works out for you, I think you should definitely go give it a try after a lot of research into existing ad networks that might be there on Oahu. Not that you’d have to work there, they might be OK with you working on Maui by cyber-commute. 

Best of luck and life, ALOHA!