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What To Know Before Moving To Hawaii

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I know, I know. It seems like a dream, right? To live in Hawaii. It’s one of the most common questions I get asked. Especially since I was raised in North Carolina and I’m an East Coast girl through and through. I wanted to share with you the things that I wish I had known before I moved out here to Oahu 14 years ago.

what to know before moving to hawaii
With Rupa Wong

So, if you are contemplating moving out here to Hawaii- whichever island- I’m going to be sharing with you what it’s like to live here as a transplant. I think most of what I’m going to talk about today is applicable to any of the islands. I’m also married to a local whose family has been here for generations! So, I have a little bit of an inside look into both worlds, though I am certainly not a local and would never be considered as such. Maybe you’re contemplating a move out to Hawaii- you definitely want to read on. But maybe you just want to know what life is like in Hawaii- the good, bad and the ugly. Please join me! All are welcome here. Let’s get started. 


The idea for this post came about because I’m about to leave to go to California to speak at an ophthalmology conference. Every time I go out to the mainland, that’s what we call the rest of the country when you live out here in Hawaii, people find out I’ve been living in Hawaii for the past 14 years and tell me how amazing that sounds. Though we desperately need so many different kinds of doctors (though we do have a lot of ophthalmologists…), there’s a lot more that goes into moving out here than what people initially think. So, I wanted to review some things I wish somebody had told me. As I mentioned, my husband is local! He was born and raised here in Honolulu and his family has been here for generations- since the late 1800s. So he didn’t really have any idea how to prepare me for life in Hawaii. I thought I was so adaptable! I was raised in North Carolina but I lived in New York City for 8 years and Boston for 2 years, and I had absolutely no trouble diving deep into those communities and making a life for myself in those cities. But Hawaii is different. I want to talk about it and what it’s like to actually live here. If that’s interesting, let’s get to it. 


It’s Not a Year-Round Vacation


It is not a year-round vacation. I know so many people who come here for a week or two and think it’s so great and they picture themselves living here. Let me tell you something. When we moved out here in July 2008, quite honestly we were working so hard that I joked with my husband that all I saw was H1. That’s the interstate- yes, Hawaii has an interstate! It doesn’t connect to another state, but that’s what we call it. We were living with my mother-in-law to save money, and that was the route I took back and forth from there to our office. That’s it. We were not surfing everyday or hitting the beach often, even though we lived 2 blocks from the beach. We didn’t see the beach aside from maybe once a weekend. I think people envision that if they move to Hawaii it will replicate being on vacation and…it is not. Because I know! I remember that first feeling when you get off the plane and you’re escaping a muggy, east coast summer or freezing winter. There’s beautiful tradewinds and the airports are open-air. It feels so peaceful and relaxing. But, guess what? Life is life and work is work. No matter where you are, you’re going to be working hard and you might be working even harder living in Hawaii versus the rest of the country. You have to remember it’s not vacation and you’ll experience a lot of situations that are very different than being on vacation, like the cost of living and trying to make ends meet. All of that which I’m going to go into. So, don’t base your decision on coming out here for vacation. I think it’s a great start! You can tell if you love a place, community, and people and see if you’re einto the island lifestyle. But remember it’s not always vacation. I wish it was (that would be amazing!), but it’s not. 


Each Island is Different 


So I live in Honolulu, the capital, and that’s on Oahu. It’s the most “city-like” of any of the islands and has the best schools, shopping malls, stores, healthcare providers, etc. It has the most access to things because it’s a city with about a million residents on the island. So it’s a little bit different than the other islands. Each island has its own unique style and “thing” that would draw you in- they’re not all the same. You should decide on this if you’re contemplating a move. Maybe Oahu isn’t right for you because you want something much different than where you live on the mainland. Maybe you want to go to Maui, which is about a tenth of the residents, only 100,000 people. There are fewer jobs but the beaches are gorgeous! You’ve got Haleakalā, the Road to Hana, you can live up country or by the beach… I have so many friends who have moved out to Maui and love the slower pace of life. Oahu, Honolulu specifically, can replicate a faster pace of life, for better or worse. Some of the neighbor islands, used to be called outer islands, like Maui and Kauai have a different vibe. Kauai has even fewer residents than Maui. Only 72,000 people in the entire island. It gets a lot more rain and it’s called The Garden Island. It’s simply gorgeous. It’s my husband’s favorite island! The Nā Pali Coast, gorgeous hiking- there’s so much you can do there. One of my good friends from residency is an ophthalmologist there and she jokes that she can’t go to Costco on the weekends, because she runs into all of her patients. So she has to go at surreptitious times if she wants to be incognito. It is really life in a small town, except that you’re in a small town where everything has to be shipped. It can be hard for me to get things shipped to Oahu, and it’s even harder to get things out on Kauai. The other large, neighbor island is the Big Island. I love the Big Island so much. We only first went there back in 2021, and to me, I needed that space. It’s huge. It’s the largest island with the second largest population. There are a lot of transplants from the mainland there and a lot of people moved there during the pandemic, especially a lot of silicon valley people. So it definitely has a different vibe to it than it did 10 years ago. So, each island is different as you can see! Just do your research and see if you can visit and see if you can envision living there. 


Community Can be Hard (at first!)

Here’s the thing. Communities in Hawaii are very insular. I did not realize that before moving here and I think that’s where there’s a really big difference between here and the places I’d lived before like NYC or Boston. I knew I wasn’t moving to a huge city like those, but I didn’t realize how much of a small-town feel even Honolulu would have- and it’s a pretty decent sized city. The funniest thing that will happen when you come out to Hawaii is people will ask you where you went to school. I would answer that I went to Duke, because that’s where I went to college. That’s not what they meant. So, I’d think they’re asking about med school and I’d answer Cornell. That’s not what they meant either. What they mean is where did you go to high school. It is a big part of your identity and I think it helps people find out not only if you’re a local, but also which bucket to put you in. Each school has its own stereotypes. Barack Obama went to Punahou, one of the private schools here on the island. It is where my kids go and where my husband went to school. However, I went to public school. We’ll get back to that in a little bit. But it gets back to the fact that the community is very tight knit, and they’re used to people moving to the islands, staying for a year or two, then moving away. So they take their time with their friendships with people who have moved to the islands, because they want to make sure you’re going to stick around before they invest their time and energy into building a friendship with you. Which I understand a little bit now, being on the other side of it! But, it is a little bit harder to break into this community and I did not think that it would be. Like I said, I thought I made friends easily because I’m an extrovert. But, I didn’t grow up here and none of my husband’s good friends from school live here on the island because he went to college and med school on the mainland. We didn’t have an instant network of friends. We had family, which was amazing to be able to rely on! But, it took a couple years for me to find a group of friends on the island and that’s not something I could have envisioned. So you do need to be prepared about that. Especially if you’re not moving here as a family with the military because that’s a little different. Most of those families live on base and have community with other military families there. However, if you’re moving with a job in the private sector, the community can be a little challenging. BUT, it’s 100 percent worth it. I don’t know of a more warm, welcoming community in general. My patients are amazing. If you follow me on socials you’ve seen this- my patients bring us stuff, they bake things in their house, and they do this all the time. You should see the office at Christmas because it’s ridiculous with the amount of baked goods! I definitely think that triggered my gestational diabetes in my third trimester. It’s so overwhelming the support that you have from the community for taking care of the island’s patients. It can be a little harder to break into, but once you do, it’s 100 percent worth it because they are some of the nicest, kindest people. Now that I have found my group of people, I love living here.  


Change Your Mentality 


You really need to change your mentality when you move out here. I mean that in two different ways. First, people always joke about “island time” because things operate on a different schedule in terms of time. In general, it’s more relaxed and laid back; not the stereotypical Hawaii surfer boy necessarily, but it is not east coast. It’s not New York. It’s probably a little more “midwest” I would imagine. I’ve never lived in the Midwest but that’s what I would imagine. Coming from NYC and Boston, it was a big culture shock for me in that regard. Because you know how I operate (imagine me snapping my fingers fast here), quick, quick, quick, let’s go! If you know me at all you know this. And that doesn’t work here. I mean, I can be who I want to be, but that doesn’t mean anyone is joining me in my need to get stuff done ASAP. You’ve got to adjust your expectations in terms of timelines and due dates. Not that you can’t run a very successful, professional business- you totally can. But you have to adjust your mentality a little. 


The second way you have to adjust your mentality is- and I have seen people fail and not develop close ties here because of this- to not come in thinking you are amazing and where you come from is the best. Some people kind of look down on us out here in Hawaii, 3000 miles out in the pacific ocean! They think we’re not up to snuff. If you come in with that superior mentality where you feel like because you went to Harvard and you know business and this is the way we do things, it’s not going to work. If you’re constantly putting down the island and what current systems look like, you’re going to have a really tough time. I have seen business owners make that mistake and they are not able to be successful. They go out into the community to meet other business owners and promote their businesses and it falls flat. Because they can tell. You don’t have to talk local- because if you’re not from here you can’t do that. But you have to at least immerse yourself in the culture and show some respect for where you live and the amazing things that are here in this state. 


It’s Expensive


Okay, now let’s get to the nitty-gritty. It is expensive. I’ve alluded to that before. It is very expensive. Of course, everything needs to be shipped in- for example, housing materials. We renovated our house and it was 2 to 3 times more expensive than renovating on the mainland. The median sale price of a single-family home on Oahu is 1.1 million dollars. I’m gonna tell you- that 1.1 million dollars in a nice neighborhood will get you a tear-down. That’s where you’re at. It is a very expensive place to live. You’re so isolated that every single thing has to be shipped and there is a limited supply so that is going to drive up costs. Food is expensive, your grocery shopping is expensive, gas is expensive, it’s all expensive. My parents, when they come to visit from North Carolina, will put boxes of cereal and oatmeal in their suitcases and bring them here. This is also because they still have that immigrant mentality even though they’ve been here for 50 years and if you want to hear more from my mom be sure to listen to the interview I did with her here! I swear, I took a picture just last week at the grocery store of the cereal that my kids eat…10 dollars. Ten dollars for a box of cereal. So, you’ve got to accept that you’re going to have to scale back. You might not be able to afford the same amounts of things you were used to on the mainland. The amount you spend on entertainment and shopping might have to be scaled back. People in Hawaii tend to spend less on these things than people on the mainland and that’s just because we have to spend that money on necessities. 


Included in this cost, if you have kids, is schooling. There’s a big dichotomy between the private and public school systems here. I mentioned before that I’m a public school girl and I really believe in the public school system. I went to a gifted and talented program in North Carolina, but I think my public school had a lot of offerings in AP classes, dance, and drama. I took a ton of education classes and almost got my education certification in college, so I really do believe in the public school systems. There are some good public schools on Oahu and the neighbor islands. But you will find that most people, not just the wealthy professionals, send their kids to private school. The cost of private school is less than, say, San Francisco or New York, but it is about 22,000-28,000 dollars a year per kid. So, that’s where you stand if you have kids and are not just moving for a few years. If you really want to invest in their education, this is something you will likely have to factor into your finances. Just in making sure it could all work. When I interview people who want a job at my clinic I tell them to look online, think about if they will rent or buy, consider the cost of living here, and, if they have kids, make sure they look into the price of schooling here. 




Alright, this next one drives me nuts. Traffic. The traffic, especially on Oahu, is horrible. Like really, really, bad. It’s much better on the neighbor islands- they’re much less populous. It almost borders on… well, I don’t want to say LA traffic. We live about 3.5 miles, that’s it, from the office. Typically, it takes about 40-45 minutes to get there in traffic. There’s a lot of traffic, especially in Honolulu. If you’re trying to get out to the North Shore (where Jack Johnson lives and where you’ve probably visited) there’s one road that goes in and out. For me, we only visit out there when there’s no tourists- like during the shutdown time. Because it takes so long to get out there because of the traffic! Recognize there’s a lot of traffic. I know there’s been some quality of life studies that say you need to live close to your work to avoid traffic. Therefore, if you want to live close to your work, you probably need to live in town where most of the jobs are and you’re going to pay more. There are some beautiful places to live on the east side of the island, but you will be sitting in an hour of traffic to get to work. Some of my staff do this too- it’s less expensive and you can live on the beach for a more affordable price, but you will hit that traffic. So, that’s a thought. 


You Need to Have Patience 


Everything here also takes longer. There’s no FedEx overnight. Everything is ground shipping. You can’t get something overnight- FedEx and UPS just don’t do it. Amazon Prime takes about 10 days. That’s nuts, right? When I was in Texas for Pinnacle, I was on Amazon Prime and was shocked to see that what I was ordering could be delivered by midnight that same night! It was crazy to me! Also, a lot of things just don’t even ship here. On Amazon or other websites there are some things that only ship to the continental United States. Again, these are first-world problems. There are a lot of things you can get. There’s no Ikea, but there’s a Target! There are a lot of things that can get shipped out here, as well as a lot of things that can’t. So, just be mindful of that if you’re thinking of moving to Hawaii. 


Relaxed Dress Code


This one’s a fun one- the dress code is different! No, we’re not wearing what people call Mumus. Well, okay, maybe we kind of are! It’s called Aloha Attire. This is what everyone else calls Hawaiin shirts. That’s actually counted as business wear here. The first thing my husband did when we moved out here was get rid of all of his ties. Gone. Nobody wears a tie- not even lawyers. The most dressed-up he’ll get is putting on a long-sleeved button down shirt. Otherwise, wearing an aloha shirt is it. Now, it’s gotta be good quality. There’s a range of quality you can get- like that one you got at a little tourist shop in Waikiki, that is not great quality. That’s not going to pass muster if you actually live here. You’ll know the kind of brands that look higher end and find out what suffices. 


Coming from the East Coast, I was used to wearing close-toed shoes. High heels, pumps, you know. I would never wear sandals to work, it just to me seemed inappropriate. But people do that all the time here. Open toed shoes like strappy sandals are considered business attire here. So it’s much more casual and relaxed. You can get rid of half of your wardrobe, which is really fun! I guess I would not have bought as many other clothes before I moved out here if I’d known that! 


Basically, in summary, you have to have a reason to live here. Think of it like a marriage. If you want to move out here and not move after year two, you have to truly commit to being out here. If you want to commit, then do your research! Decide what things you can sacrifice in order to make this move. It is expensive to live here and the cost of living is very high. Though the cost of living in cities like San Francisco, San Diego, and Manhattan is higher, the amount of money you make here is less than you make in those cities. I know physician and attorney salaries are typically taking a big pay cut here- they could maybe make double on the mainland. Then you’re paying more. I know most starting lawyers make under 100,000 dollars here. I know that seems like a lot but, after taxes and the high cost of living is factored in, it’s very difficult. Especially if you have a lot of law school or college loans. Same thing with medicine. Do your research and figure out what you can afford- do those spreadsheets! Because, yes, you can always move back. But it would be nice to be able to make a decision and commit to it. I think that’s the thing- if you commit to living out here and you can make it happen financially, then you’re going to be more invested in the community and people respond to that. I have seen people that succeed in staying out here because they’ve got an additional reason to be here. Whether it be a love of the ocean, being outdoors year-round, or finding a really good social group. Our optometrist is originally from Pennsylvania and she’s been on the island significantly longer than me- like 30 or 35 years! She found a great group of friends, she paddles, she’s high up in the outrigger canoe club, and that is her social group. She loves doing those outdoor activities with them. So if you’re like her and have that love of the outdoors or if you move for family like I did, having that reason to be here makes you want to stay. It helps you work through those harder parts. Because otherwise, who knows? Maybe I would have moved back after a year or two because it was challenging. I was having a difficult time making friends, we weren’t making as much money, and we were facing a high cost of living. But, if you have a reason to stay here then you’ll make it work. It is an absolutely beautiful place to live and I cannot imagine living anywhere else. I adore it. Even though I hate the traffic! For me, the sacrifice of living away from family is not easy, but the life that I have here makes it worth it. My parents and brother all live on the east coast, 6,000 miles and a 6 hour time difference away. But being able to go outdoors and ride bikes with my kids year round and going to the ocean make it worth it for me. We sacrifice some of those other things and that’s fine. For us, having that work-life balance and feeling like we’re part of a community is really important to use and we don’t need those other things. You just have to look deep and see if that’s you as well. We could always use more of whatever you are- doctors, lawyers, accountants, etc. They call it a brain drain here because a lot of people move away because it’s challenging to live here. A lot of people I know have moved away because it’s so difficult to make their private practices work. But, if you’re committed and are buying into this life, I think it certainly possible and very possible to be extremely happy. You’re going to live in a smaller house but, who cares? You’re going to spend all your time outdoors anyway, right? So, that’s what I think about living in Hawaii and what I wish I would have known before moving out here. I most definitely wouldn’t trade it for anything- I adore it. Though I still like to hold it over my husband’s head that I sacrificed a lot to move out here for him… I gotta have a little something! Overall, I really love it but I think it helps to go into it with open eyes so you know what the challenges will be and you can plan accordingly. 

I hope this was helpful because it’s something that I get asked all the time! Be sure to pass this post on to anyone you know that is interested in life in Hawaii or thinking of a move. I’d love to hear from you and to show you more of what day-to-day life looks like in Hawaii so be sure to come find me on Instagram! Until next time, it was good to see you.


I'm Rupa Wong.

Hi! I'm Dr. Rupa Wong. Physician. Private Practice Owner. Mama to 3 kids. Managing Partner. Educator. Textbook Author. Conference Co-Founder. Mentor. I am more than just one thing, even as a doctor and I bet you are too. I would love to help you envision the life you want, and then get after it. What are you waiting for?


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