Moving to Upcountry Maui and Selling Timeshares

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Here is a note from a guy currently living in Raleigh, North Carolina. He’s dreaming about Maui… and who isn’t? I certainly am.

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Peter – I have visited the Hawaiian Islands about 8 times, my favorite being upcountry Maui! I am 55, single, masters degree, excellent sales and sales management experience. I owned timeshares on Hilton Head island with Marriott for many years, and every time I visited ,thought… what a way to “retire”. My last visit to Maui in 2010 I went to a timeshare presentation and have not been able to shake the idea of moving to Hawaii and doing timeshare sales/management. I like to work, but have spent a lifetime of high stress positions and feel it might be great to work and live the next 30 years in paradise… I know that to live and enjoy you really need around $100K a year and figure only a sales position would enable that. I was never really fond of Honolulu , just seemed like a big city… Kona was nice. I, like you would be moving there to embrace and soak in the Hawaiian culture. As you can see by my email, I have a lot of other skills then “just” sales..I am a licensed/registered insurance and securities advisor, very tech savvy, masters in marketing, owned my own company for a few years. It is a bold move, but I don’t think I will have trouble supporting a “comfortable” lifestyle

Based on the above, what thoughts or concerns or advice comes to mind?

Thanks in advance,


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OK Mark, it sounds like a good plan. I met some people – husband and wife, in their mid-twenties, when I lived on Maui. They were selling timeshares and were absolutely killing it back in 2002. They were very upbeat people and obviously jazzed about making a couple hundred thousand dollars a year putting people into timeshares and condos on Maui. So, is it possible – yep, I’ve seen it. I knew a couple of other folks on Maui that did it, but that weren’t nearly as successful at it. If I’m remembering correctly, the husband-wife team were either from North Carolina or Tennessee. Memory fails me at the moment. They might still be there doing it for all I know. They were in our ohana before we moved in and they were good people to meet.

You are probably not going to have any problem at all transitioning into sales of any sort in the islands. I think there is probably always a need for timeshare salespersons. It isn’t something that is easy – but, when you have the right formula – you can cash right in.

You didn’t mention anything about savings, but I guess you’re fine there. If you’re single, I think just making $60,000 you will probably be happy enough. No sense moving into anything high-stress again if you have savings. Relax and enjoy life, tomorrow it could all change.

I would go for it, you have enough skills to do many things. Apparently you’re single and ready for an incredible change of life. Maui is that… all that and more. Let me know how it goes if you would!




About the Author:

I’ve lived Hawaii since the mid ‘80s when I moved here at the age of 21. I arrived site-unseen in Honolulu with zero contacts and about $5k in savings. I worked from nearly zero and today Hawaii has given me the greatest gifts in the world in all aspects: spiritually, financially, romantically (married since early ‘90s w/ 2 children), and most important, peace. My goal with this site is to share the magic of this Land of Aloha and help others who are on a similar quest.

One Comment

  1. Michele Muir White 03/02/2013 at 1:11 am - Reply

    Aloha Vern,

    Moving to upcountry Maui is like living a dream, whereas selling time shares may not. The Time Share business can be very cut throat and may not be suited for the faint of heart. Most time share companies are located in West Maui. Quite a commute from upcountry. Maui’s real estate market is recovering. We are currently experiencing a seller’s market and there are plenty of opportunities to earn a good living. Perhaps Mark should also research Maui’s residential real estate market. I am a realtor with Coldwell Banker Island Properties Wailea. We have a great team of owners and realtors. Aloha, Michele Muir White, Maui Real Estate Guru.

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