What Englishteacheralex says.
We've lived on Oahu for over 30 years (more than half my life). I've lived at my current address for over 19 years, which is eight years longer than I've lived at our previous Oahu address and many years longer than anywhere else I've ever lived. Our daughter was born & raised here. There's a good chance that she (and her spouse) will return to Oahu in a couple years to raise their family here.
I'll never be kama'aina like my daughter, but I know that I'm slowly getting to be local because people around me will talk about haoles... and then they suddenly realize that technically I'm one too. I'm not offended by the stereotype and we have a good laugh when they start to backtrack or even apologize.
Are there any others who have moved to an island and/or across the country?
The Navy brought us to Oahu and we've moved 13 times over our careers, from Spain & Scotland through the Mainland to Hawaii. We enjoy traveling and living local, and we've learned how to acculturate. If you don't already know how to do that then it's possible for you to learn it too.
I'm scared to death but also fear that I would regret not taking the leap.
You have to try this, or you'll spend the rest of your life asking "What if...?"
What about non-monetary concerns?
The most important point: nobody cares about where you're from or how you did stuff there.
You're embarking on an integration process that will take 3-4 years. After two years people will trust that you're not going to give up and return to the Mainland. By the third year you'll feel more accepted.
By the fourth year you'll be writing long posts on Internet forums telling people how to acculturate.
The best way to integrate is to adapt your style to the local rhythms and practices.
For example, "Hawaii time" is more about casual tardiness because you're enjoying the day, not keeping to a strict schedule. You're not watching your... watch... or your phone or the clock. This behavior has no relation to indolence or to power games.
15 minutes late could occasionally be an "island rush hour" traffic jam from a bad stop light or a lane-blocking accident, especially on two-lane roads. But frequently it's because you stopped to chat with someone else, and the talk story went a little long.
"Talk story" is a common culture around the world and sadly lacking on the Mainland. It's about taking time to check in with each other before the meeting starts. It's getting to know your coworkers and neighbors by spending 15 minutes aimlessly chatting about the weather, the surf, and family. Your part of talking story would be asking people questions about the local events, places, food, and surfing. You can talk about your family, and even your Mainland family.
But nobody (I mean
nobody) cares about how you did things on the Mainland. You could ask a question like "How would you do it here?" or "What was that word again?" or "What would happen if you tried <different technique>?" If you lead with "Well, here's what I've seen before..." then the entire room politely shuts down.
I'd suggest subscribing to local newspapers (now, online, and before you move) and reading a book or two. Try the links at the bottoms of these posts:
https://the-military-guide.com/good-reasons-not-to-live-in-hawaii/https://the-military-guide.com/lifestyles-in-military-retirement-living-in-hawaii/and search for your Maui equivalents.
You'll know you've really integrated when one of your friends suddenly asks you to backpack Haleakala Crater for four days and sleep in the cabins for three nights. The cabins berth 12 and reservations fill up a year in advance, so if someone drops out of a group then you'll get a last-minute invitation.
Is there an "ex-pat" community on the island?
Yes, but consider the implications of what you're asking.
Do you really want to hang out with people who identify as "expat" and not as a "new member of the community"? Do you really want to perpetuate Mainland culture? Do you really want to spend your time listening to complaints about Maui and why they're here instead of where they want to be?
... what should we be looking out for?
It's possible that your new coworkers thought they were going to be promoted to the job you've just usurped. They may think you got hired by fooling the bosses with your Mainland college and Mainland companies and parachuting in like some Mainland bigshot, and they're sure you have no idea what you're doing on Maui. They know they'll outlast your attempt to stay for the long term and that you'll soon give up to go back to the Mainland.
Hopefully you'll be able to make those coworkers feel like a more valuable member of the team by asking them what you can do for them, and by learning your job from their experience. But that's probably common wherever you start a new job.
Learn about the people and the community around you, and try to figure out how you'll fit in.
Here's another cautionary tale about not fitting in.
My parents-in-law lived on Oahu from 2001-07 to watch their only granddaughter grow up. When she became a teenager, they realized that they had no other life here.
They were born in the 1930s and they're retired. They spent most of their careers with the Washington DC bureau of CBS News. Living in that political bubble may have perpetuated an attitude.
My FIL turned out to be casually racist about "Japs" and "Orientals". He kept saying "Back in the states..." instead of "Back on the Mainland" and "You people" instead of "us". I explained this offensive vocabulary to him many times but he couldn't (or wouldn't) stop using it.
He endlessly name-dropped his stories about reporting the news from 1964-95. The issue is that Washington DC is the center of his universe and he assumed that Hawaii residents cared to hear about people who they only knew from Mainland TV-- or history books. He made fun of Hawaii politics by comparing the local legislature to the news of Congress or NYC or other Mainland places he'd been. He was a union steward at his CBS career, and he used to make many unflattering comparisons to unions on Oahu... without ever asking his acquaintances about their union experience. He was constantly telling us (and his neighbors, and our friends) how politics are done on the Mainland and how we should do things differently here.
I think he hit rock bottom one day when he was reminiscing about growing up during WWII and rationing... without realizing that the people with whom he was speaking had either been interned or had childhood friends in the camps. It had never occurred to him that he was living in the middle of something he'd only read about.
My MIL would hear people using pidgin, and she'd assume that their vocabulary equated to lower intelligence. She'd put on her loud, slow, American-tourist voice and eee-nun-seee-ate every word "in propah English". After about two minutes of that, the other person would give up on her and try to escape. This accounted for most of her interactions with bank tellers, gas station attendants, store clerks, and cashiers. It was a mystery to her why she could never get help from anyone on the island for anything. She complained perpetually for over six years.
When she heard her granddaughter speaking pidgin, I thought Grandma was going to burst a blood vessel. My daughter is in her late 20s and still has to listen to that story.
My parents-in-law were self-isolating, but they eventually found some friends: other Mainland snowbird retirees who lived on Oahu for part of the year and were deeply interested in the history of the Civil War. My PILs spent more of their Hawaii days reminiscing about Gettysburg than learning about Oahu history.
There was no talk of learning how to surf or kayak or even swim in the ocean. You were supposed to sit on the beach or walk along the shore. They completely missed out on that phase of their granddaughter's life.
In 2001 when my parents-in-law moved to Oahu, they sold their Mainland home (4BR on a half-acre) and parked the money in short-term Treasuries... for over six years. (That money had to be "absolutely safe.") By 2007 when they moved back to the same Mainland ZIP code, they were priced out of the real-estate market and had to downsize to a 2BR condo. With a mortgage.
