After taking my family on a nine-day vacation to Honolulu, Hawaii, my plan to relocate there is back in the cards! Since 2014, two years after retiring from my finance job, I've been contemplating moving back to Honolulu to spend more time with my parents. However, actually making the move has been much harder than expected.
Just as financially insecure people often tell themselves “just one more year” before retiring, I've been saying “maybe next year” about moving to Honolulu for the past 10 years!
The thing is, life keeps getting in the way. First, we had a son in 2017, then a daughter in 2019, and the pandemic made us crave stability and familiarity. Our son got into a school he enjoys immensely, and now our daughter has joined the same school, which we believe she'll also enjoy. As a result, the inertia of life has kept us in San Francisco.
However, with my parents now in their mid-70s, the time to spend more time with them is now. Our kids also handled their longest time away from home well. Although, they complained about the heat, they missed it once we returned. My concerns about them adjusting to a new environment have diminished.
For background, my grandparents were born and raised in Honolulu, so was my dad. My grandmother is half native Hawaiian as well. Both my parents are retired in Honolulu.
The Challenges of Living in Honolulu, Hawaii
There are three main challenges of living in Honolulu: housing, food, and work. If you plan to send your children to private school, affording the tuition and getting accepted are also significant challenges.
Let's discuss each challenge if you're considering living and working in Honolulu. If you have ever lived and worked in Honolulu or currently do, I'd love your insights as well.
Honolulu's High Home Prices
Honolulu boasts one of the highest median home prices in the nation at roughly $1,050,000. Meanwhile, Zillow has the median Honolulu home price around $800,000, but I don't trust Zillow. When house hunting, it often seems that homes cost much more than the median price, no matter the city. Funny how that is.
To afford a median-priced home using my 30/30/3-5 home buying rule, you'd need to make between $210,000 and $350,000, have a $210,000 down payment, and maintain a $105,000 liquid buffer post-purchase.
If you come from high-priced housing markets like San Jose, San Francisco, Los Angeles, San Diego, Seattle, New York, or Boston, you might not be as shocked by Honolulu's high home prices. However, if you're coming from everywhere else in America, prepare to feel the pain.
Owning Real Estate in San Francisco Makes Moving To Honolulu Easier
The median home price in San Francisco is around $1,800,000, which is about 75% higher than in Honolulu. Therefore, moving to Honolulu could save us around 40% if we buy a median-priced home.
However, we don't want a median-priced home; we want a fantastic home with ocean views or one that is remodeled and close to the beach. Unfortunately, these homes cost over $4 million, with really no upper limit.
To pay for such a home with cash, we'd need to sell several rental properties. This would simplify our lives as we age, but it would also hurt our passive income again. After cutting our passive income by ~29% in 2023 due to a cash home purchase, we don't want to make such a drastic move again.
Luxury homes in Honolulu often take 3 – 6 months to sell, unlike in San Francisco, where selling in one month is common. Given the fewer high-paying jobs in Honolulu, there's a greater investment risk associated with buying luxury real estate there.
If you buy property in Honolulu it's best to think of the house more as a consumption expense than as an investment.
Honolulu's High Food Costs
Produce in Honolulu is the most expensive in America due to the extra shipping costs. For example, a bag of cotton candy grapes I bought costs $18 at Safeway in Honolulu, compared to $14 in San Francisco.
Expect to pay $20 – $25 for a plate lunch, making it easy for a family of four to spend $80 – $100 for lunch, including tax, tip, and drinks. However, portion sizes are relatively large when dining out, including food trucks.
Below highlights a variety of food costs in Honolulu, updated at least once a year by a community of travelers. No matter where you come from, you will definitely feel the burden of high food costs in Honolulu.
We Grow Our Own Fruit in Honolulu
In Hawaiian culture, there's a saying: “If you take care of the land, the land will take care of you.” Thanks to the trees my grandparents and parents planted decades ago, we have plenty of fruit in our backyards.
We have several mango trees that produce over 500 mangoes a year. By relocating to Honolulu, my family of four will ensure these mangoes don't go to waste. We also have guava, orange, and pomelo trees, which means we won't need to spend much on breakfast if we keep to a mostly fruit morning diet.
During our trip, our family of four mostly shared two plate lunches and had leftovers. Most of the reason is because our children are still young. However, my wife and I have always been moderate eaters and are only about 5% heavier than we were since college.
Honolulu's Relatively Low Pay
The most common feedback from locals is the lower pay compared to the mainland. We're talking 40%-60% lower pay for the same jobs. There are also fewer six-figure jobs available, especially compared to San Francisco's tech sector. The main industries in Honolulu are tourism, defense, agriculture, fishing, and manufacturing, which aren't known to be high-paying industries.
According to the 2020 Census, the median household income in Honolulu was $96,580. The St. Louis Fed data shows it was $96,304 in 2022. For 2024, the household income is likely closer to $105,000 – $110,000.
While not bad in a vacuum, it's not great compared to the median home price of $1,050,000. Consequently, it's common for two or three generations to live together. If a household consists of two-to-four working individuals, a median household income of $100,000 isn't high.
As of May 2024, ZipRecruiter reports the average salary in Honolulu is $61,247. To own a median-priced house and raise a family in Honolulu, you need to earn far above average or cohabitate with multiple working individuals. The financial support of parents is also quite common.
We Have Enough Passive Income For Living In Hawaii
After saving and investing since 1999, we have enough passive income to support a middle-class lifestyle for a family of four in Honolulu since it's cheaper than San Francisco. The key is to keep our housing costs lower than they are in San Francisco. If we want to buy a luxury property, we may need to work part-time or full-time.
However, going back to work is something I look forward to because I want to be a teacher at my children's school. Relocating to a new city means making new friends and meeting new people, and diving headfirst into my children's school community is an ideal way to do that.
As a teacher, I'll get to know many other teachers and administrators, as well as plenty of new parents. I'd love to teach personal finance, entrepreneurship, marketing, branding, and communications to middle or high school students. I spent three years coaching high school tennis and enjoyed it for the most part.
If I can't get a job teaching at my children's schools, I'll continue to write from home. But instead of slowly going crazy writing in a dark room, I'll get to write outside on a lanai overlooking the water!
If my next two books do well (scheduled for 2025 and 2028), maybe I'll get another book deal that keeps me writing until both kids graduate high school. The pay isn't high as an author, but writing books will show them their old man takes academics seriously.
Honolulu's Independent Grade Schools
Honolulu has some excellent independent and public schools. Since our kids already attend a Mandarin immersion independent school, we plan to continue with independent education initially.
My parents live near two of Honolulu's best independent grade schools: ‘Iolani and Punahou. We toured ‘Iolani and Punahou with our children, and found both schools to be amazing incredible facilities. Maryknoll also offers a Mandarin immersion program, which is attractive if we relocate while our kids are still young. We highly value learning a second language.
As a bonus, the annual tuition at ‘Iolani and Punahou is about $13,500 less than what we pay in San Francisco, and Maryknoll is $23,000 cheaper. The tuition is also the same from K-12, so if we move when our kids are older, we'd pay about 50% less since prices go up by grade in San Francisco.
The combination of better facilities and lower costs is hard to beat. I'm sure the teachers are wonderful too. However, getting into these schools will be challenging without a local network to support us.
Iolani's main entry points are Kindergarten and 6th grade, while Punahou has entry points at K, 4, 6, 7, and 9.
The difficulty will be in getting into schools
If our experience with applying to preschool in San Francisco is any indication, getting both kids into such independent schools will also be difficult. Demand is always high, and we are coming from San Francisco, where we don't have a local Honolulu network to support us.
It's possible that one of our kids gets in and the other doesn't. Logistically, having two kids go to different schools is suboptimal. Punahou has more accommodative entry points with K, 4, 6, 7, and 9. Given our kids are three years apart, entry for grades 4 and 7 or 6 and 9 would work.
We hope my background now as an author provides variety from other families who are mostly in medicine, law, and finance. We also don't need tuition assistance for two kids and can regularly donate.
Based on the ages of our kids and the schools' main entry points, we would apply in the Fall of 2029 for our daughter to enter as a 4th grader and our son to enter as a 7th grader at Punahou in 2030. Or we can apply in the Fall of 2031 for 6th grade and 9th grade in 2032.
Relocating to Honolulu in 2032 is probably best because our children will learn more Mandarin at their school, which goes until the 8th grade. We'll get to enjoy our San Francisco home we just bought in 2023 for nine years.
The Fear Of Being A Stranger In A New City Is Overblown
You might fear relocating because you'll have to start over making friends. The stronger your friendships and family connections back home, the harder it is to move.
However, as a school parent, I've realized how easy it is to meet new people and make friends if you want to. There are endless social functions to meet other parents, including playdates, birthdays, school events, parents' nights out, and fundraisers.
In addition, you can join meetups or clubs related to your hobbies. My private sports club in San Francisco has provided the biggest lifestyle boost for only $175 a month. It’s been a great way to meet fellow tennis and pickleball players.
So don't be afraid of loneliness when relocating. Honolulu has warm and welcoming residents. Just make sure to understand the culture, familiarize yourself with Hawaiian language, and respect island traditions. As a new resident, try to give more than you take.
As for the kids, it’s better if they relocate to a new city when they were younger. It will be tough to leave their friends in SF, but they will make new friends. Besides, their school only goes to the eighth grade, which means they eventually have to reapply anyway.
Selling Property Before Relocating To Honolulu
We've been accumulating properties in San Francisco since 2003. We now have four rental properties and one primary residence in San Francisco, plus a vacation property in Palisades Lake Tahoe. Our net worth is getting complicated and we wouldn't mind simplifying.
Given we need capital to buy a new home and don't want to deal with tenant and maintenance issues, we probably need to sell at least two properties before we relocate. Currently, I manage all properties in San Francisco, which is easy and gives me something to do.
With real estate commissions coming down after the NAR price-fixing settlement, selling now has become more palatable. I just can't get myself to pay more than a 4.5% selling commission rate when technology has lowered commissions in every other industry.
At the same time, with the tech and artificial intelligence boom, selling now is hard. I expect AI to boost housing prices in the San Francisco Bay Area decades to come. Besides investing in private AI companies, the next best way to participate in AI is by owning real estate in cities with the leading AI companies.
In 20 years, I'm sure I will look back with regret having sold a prime west side San Francisco property today. Therefore, I would like to maintain at least two investment properties in San Francisco if we relocate. Maybe a property manager is the solution, but I’m not sure.
It's Worth Living In The Best Place Possible
I've lived abroad for 13 years in five countries, worked in international equities for 13 years, and traveled all over America for the past 47 years. Honolulu is one of the best places to live in the second half of your life.
There's a reason why Hawaii residents have the longest life expectancy in America: a better, more relaxing lifestyle. Once you've accumulated enough wealth, having a long and healthy life becomes a priority.
Yes, there are downsides to living in Honolulu, such as traffic, higher prices, relatively high state income taxes, and island fever. It will also be tougher “making it in Hawaii” unless you’re in medicine, law, or an entrepreneur. Even then, it's tough to grind so hard when island life is so relaxing. Finally, the pace of life is much slower, which can also be hard to adjust to.
However, I believe the positives far outweigh the negatives. Once you've built enough wealth, your goal should be to live as long and as healthy a life as possible.
Winding Down In Honolulu In The Second Half Of Life
I want to wear shorts and t-shirts year-round. It would be nice to swim in the ocean in the mornings and play tennis in the evenings. Living in a medium-sized city also provides enough work opportunities to stay productive, but not so much that you feel overwhelmed by competition. Most of all, I want my family to be safe and happy.
Honolulu provides all these things. However, we won't know until we try to relocate in 2030 at the earliest. Ideally, we relocate in 2032 when our son is in 9th grade and our daughter is in 6th grade. This timeline will maximize our time in our new house, benefit from the AI boom, and give us time to space out the sale of our properties.
In the meantime, we will be sending our kids to summer school in Honolulu for at least a month so we can try before we buy!
If you live and work in Honolulu, I'd love to hear your thoughts! What are some other negatives and positives we should know about before relocating?
Don't Quit Your Job To Relocate To Honolulu
If you're planning to leave your job for a new one in Honolulu, I'd try and negotiate a severance package instead of quitting. You will appreciate the financial runway given pay is often lower in Honolulu.
Check out How To Engineer Your Layoff, the best resource to teach you how to negotiate a severance package. Use “saveten” at checkout to save $10. I've updated the book six times with new strategies and insights since 2012.
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Have you looked into summer school for your kids?
One way to ease the transition for your kids, especially if you’re not going to move soon, is to send them to summer school here every summer. It’s a lot easier to get your kids into Punahou or ‘Iolani for summer school than as regular students (except for HS, when summer school is only for full-time students).
I’m not familiar with Kamehameha’s summer school, but given your kanaka ancestry, perhaps you should look into that. Even if you don’t end up moving, your kids will have a chance to learn about their heritage.
Hi Rob, we are definitely considering it starting next year, summer school in Honolulu. Might as well try before you buy especially if we can do so, right?
I’m from the Bay Area and have a second house in Hawaii Kai (east honolulu). Great public schools K-12 including Kaiser High (the only IB – international baccalaureate on the island). Why pay 6 figures for private school at Punahou or Iolani when you can get a great public school education? Hawaii Kai and Mililani (and Kahala) have arguably the best K-12 public schools.
Also I disagree on the need for a high end luxury home. We have a nice house on a cul de sac, it’s older but safe. I think safety/privacy, quiet and friendly neighbors are far more important. You can always upgrade remodel the house, and remember Hawaii has the lowest property tax rate in the United States at 0.35% of assessed value (as opposed to California’s 1.25% rate) and massive homeowner exemptions at $140k (as opposed to California’s $7k exemption). Happy to chat more if/when you are serious in getting a place in Honolulu.
Good to know! I will seriously consider these public schools. Hawaii Kai is a nice and safe area for families.
Besides Kaiser High, what are the other public elementary through high schools?
How much would a remodeled 4-5 bedroom, 4 bathroom, 3,500+ sqft home on a 10,000 sqft lot cost in Hawaii Kai?
Kamiloiki or Koko Head elementary and Niu Valley middle schools.
For that size, you’re taking $2.5-8M in Hawaii Kai. Here’s one I found on Redfin not far from my place. But it’s on a busy road, which explains the lower price: https://redf.in/ArH6yu
If I wanted that dozen I would just build a second level to expand our current 1700 sqft ft 4/2 to get the size. A second floor would also get the 120-150 degree ocean views. And it’d be way more economical than buying a $3-7M mansion and the property assessments for that high value.
Thanks for the school info. $2.5 million is not bad for that house, but that is a busy road, so I’d probably pass. I wanted to be on a quiet road that’s nested inside.
Is it easy and affordable to build a second floor and another 1,000+ sqft in Honolulu? In San Francisco, it would probably take 2-3 years to get permits and approval, and then cost about $1 million.
Here’s the thing, if you can afford a $5-8M house, then why not spend $30,000 a year to send your kids to Punahou or Iolani? Seems quite affordable.
What is it you do for work and what do you think is a very comfortable household income for a family of four in Honolulu?
I’m like you – semi-retired and mostly doing personal investing and some real estate. Comfortable household income is probably $100-150K in Honolulu/Oahu, although may family households of 4-6 are perfectly fine making far less than that.
Like you said – wages are far lower so cost of living is 50% of the SF Bay Area. It would be even less, but housing is still relatively expensive. Don’t believe the hype on food prices – yes eggs milk etc are far more expensive in local grocery stores but Costco is the great equalizer. And gas prices are about $1 buck cheaper than the Bay area per gallon.
On the house – I never said I could afford a $5-8M house lol. I bought mine as an older house in one of those inner quiet private residential streets you mentioned that are away from busy Lunalillo Road. I’d say whereas the Bay Area may be $500-1000 per sqft, it’d be maybe half that – $250-500/sqft to add the second level. The great thing about Hawaii Kai is most of the homes are on concrete slab (as opposed to post & pier) so you have a solid foundation. So maybe $250-500k to get another 1000 sqft with a panoramic ocean view.
One note – many of the transplants to Hawaii Kai (and Kailua further north) are from California and Washington state. Especially from the SF Bay area and Seattle – massive desire to escape the decline of society from homeless encampments, meth/fentanyl druggies, smash and grab theft, and cost of living affordability that is the worst in the country (Hawaii is bad adjusted for population income, but the Bay area and NYC are the worst in absolute terms). SF is relatively modest at $1.8M for an average home but the Peninsula at $2.15M and south bay at $2M are insane! Honolulu in comparison is a dream – and most critically you have aloha culturally and neighbors care (ohana). Unlike big urban concrete jungles like SF that can be very tech and money driven where you don’t have the level of wide-scale friendly aloha spirit and making nice with neighbors is the standard (not the exception).
My question to you is why wait? Depending on the Nov 5 election results, we may see a massive surge in demand for Honolulu real estate lol :)
Cool. I haven’t found the cost of living to be 50% lower than the bay area. Maybe 25%, which includes like-for-like housing.
There’s just so much excitement here in San Francisco that it’s hard to leave. With technology and artificial intelligence, there’s always something going on and then of course, there is great sports, temperate weather, lake Tahoe, Napa, Valley, Sonoma, and more.
If you can comfortably afford to live in San Francisco, I think it’s the best place for lifestyle and wealth building opportunities. So I think maybe once I hit my 50s, Hawaii will be perfect.
Before then, I’ll just visit for a month spread through the year.
How old are you? To me, Hawaii gets better as I get older bc I naturally slow down.
So that’s the thing on the initial assumption. If you can afford to pay $5 to $8 million cash for a house, then you might as well pay for private grade school tuition don’t you think?
I believe Mid-Pac also has an IB program.
Just saw this report on the news about a lot of protesters in Barcelona shooting water Guns at tourists and telling them to get out and go home.
Oh, there seems to be an undeniable resentment, and even hate for anybody moving anywhere.m, definitely including Hawaii.
https://www.yahoo.com/news/protesters-barcelona-tell-tourists-home-224139896.html
https://realhawaii.co/blog/who-owns-hawaii#:~:text=Who%20owns%20Maui%3F,landowner%20at%20over%2033%2C000%20acres.
That woman, Kamalani, has a lot of nerve. If you are buying a home (not taking) the home a native family can’t afford anyway, what’s the problem? Indigenous people keep themselves poor with this kind of thinking. I suppose it makes them feel important or even noble. After ten generations it’s time to knock the chip off their shoulder. Despite their delusion the Hawaiians, Polynesians and native Americans were not a peaceable people. Their culture was backward and often barbaric. Intertribal warfare was the standard.
It’s amazing how quickly & succinctly you showed how racist you truly are while also announcing you know nothing about Native Hawaiian culture…at all. You *are* taking away from Natives when you are the direct force behind the demand for extreme development that caters to capitalist foreigners & tourists while ignoring the locals basic needs such as….housing that is affordable for locals.
Oahu has been declared the extinction capital of the world because of foreigners & their destructive unsustainable norms. Hawaii has more flora & fauna that are endemic disappearing that any other US state. *Multiple* scientific disciplines from marine biologists to environmentalists to dendrologists keep talking about the degradation of Hawaii’s nature due to human expansion which, amazingly, isn’t due to Native Hawaiians activity on the islands.
Native Hawaiians who champion stewardship of the land, you know, keeping what makes Hawaii a paradise intact – are being pushed out of their homeland by the same people & apologists (you) who benefited from the history of overthrowing Hawaii’s government & Queen for American White capitalistic exploitation & you’re sitting here acting like you aren’t the bad guy for defending that.
The worst thing Native Hawaiians ever did was show you people Aloha since the concept went utterly over your heads & you instead are content to sit here on the internet defending your inherently violent culture & the *excessive historical proof* that your culture is & has been terrible to Hawaii & terrible to other cultures, other races, minorities, lower classes, low income individuals & humanity as a whole.
You possess a total lack of compassion & you fully deserve all the ire Native Hawaiians throw your way for being complacent in the destruction of their home & having the audacity to act like they have no reason to be upset.
How about you? What’s your backstory Noah? How are people like Larry Ellison and Mark Zuckerberg able to buy so much of Hawaii? Someone must’ve willingly sold the land to them.
“How are people like Larry Ellison and Mark Zuckerberg able to buy so much of Hawaii?”
You know for someone whose claiming Hawaiian ancestry you sure don’t know anything about Hawaii or Native Hawaiian resistance.
Huh, lets see. Larry Ellison bought Castle & Cooke’s 98 percent share of the island of Lanai for $300 million.
But who are Castle & Cooke? They were one of the “Big Five” companies in Hawaii that helped overthrow the Hawaiian Monarchy.
Castle & Cooke was started by Amos Cooke & Sam Castle – Amo’s son Charles Montague Cooke personally traveled to Washington D.C. on February 1, just thirteen days after the overthrow of the monarchy, to try to persuade the U.S. to annex the Hawaiian Islands. Castle and Cooke driver Ed Benner was the one who drove the coach that contained arms meant to overthrow the queen in a violent coup dʻetat because, oh yeah, they didnt actually plan for it to be a “bloodless” overthrow. Isn’t it interesting how a neo-colonizer had no problem buying land from the entity that stole it in the first place in an act of violence that was illegal under international law. It’s telling you’re using two really morally corrupted individuals here to highlight.
Ah, Larry Ellison – the guy in control of most of Lanai’s land, buildings, & businesses who runs a holding company called Pulama who has been caught ending rental contracts with no explanation or kicking out businesses when locals complain about Ellison’s influence on the community? The guy where locals are now afraid to complain publicly & then cite nondisclosure agreements in their leases? The guy who has been forcing out the local mom & pop shops like the longtime grocery store? Of buying companies & then changing the employees terms to be more predatory & pay them less? Whose in control of the entire local rental car industry of Lanai? The guy who has a 30-day lease policy for commercial tenants when no bank that serves Lanai will lend startup capital to a business with a 30-day lease? The guy who Solomon Pili Kaho’ohalahala, a native Hawaiian & seventh-generation Lanaian has said on record he has been waiting 10 years for Larry Ellison to respond to his requests to talk about the conservation of Lanai’s humpback whales & the increasing erosion of the beaches? The guy whose company Pulama promised locals a 150-unit housing project that would include homes for purchase, but then Pulama abruptly announced they’d all be rentals instead? Or stated 8 years ago they would build a tennis academy, a desalination plant, a university, and a film studio for the community which has never materialized & they have never brought up since? Who tore down a local beloved landmark, the Purple Church?
Or Mark Zuckerberg – The guy caught running a shell company, Northshore Kalo LLC who was exposed for pursing lawsuits against small landowners who had parcels of land that were surrounded by his already enormous 700-acre Kauai estate? Yeah, I wonder how he managed to get all that land – certainly not by strongarming the locals or throwing around his excessive wealth as leverage – it’s almost like nobody should have enough money to buy upo huge swaths of land people already live on or something.
Where the landowners he sued had the choice of selling their partial shares or try to outbid a billionaire in a public auction? Where if they lost, they could be forced to pay a billionaires legal fees? Where he only addressed what he was doing because everybody & their brother dragged him publicly for it once it was exposed what he was doing? Where one of the people he sued for their land is quoted as saying about the 2.25 acre parcel he owned a share in that Zuckerberg’s company sued him for ““Even if we lose, this has to be fought,” Rapozo continued. “I want my nieces and descendants to know that someone thought it was wrong … I want it to be known that it was resisted.” The guy who now owns more of Kauai (1500 acres) than the government of Kauai itself (975 acres)? Or maybe we should get into the environmental impact of his new venture – raising premier beef cattle in Hawaii & how that substantial amount of land, water, and feed required for cattle farming contributes significantly to deforestation, habitat loss, and greenhouse gas emissions….in a place that is already being decimated by an influx of human activity.
This is great. How about people just not sell so much land to these people and just say no to the money?
Please share something about your background. It’s always good to get some color from passionate commenters. Thanks.
It’s weird how the history of Hawaii very clearly shows a through line of white American foreigners illegally overthrowing Queen Lili’uokalani’s rule specifically to control & exploit Hawaii’s resources for their own economic gain & in order to annex Hawaii & you are somehow unsure how that relates to thieves being in total control of stolen land who then sell that to more foreigners who are displacing Native Hawaiians into the now.
Take a look at Hawaiian politics or history – few if any Native Hawaiians from the moment Hawaii’s monarchy was overthrown were allowed into positions of power to decide what happens to Hawaii or it’s people. Six years earlier before the overthrow, in 1887, a group of sugar barons & other businessmen forced King Kalākaua at gunpoint to sign the so-called Bayonet Constitution, dissolving his power & disenfranchising Native Hawaiians because, Native Hawaiians, who previously had the right to vote & run for office – now were required to own property valuing at least $3,000 dollars, or have an annual income of no less than $600 meanwhile – Americans were allowed to vote in Hawaiian elections without ever becoming naturalized citizens.
When Hawaii was annexed by the US 38,000 Native individuals out of 40,000 across the Hawaiian Islands (95%) collectively signed two Kū’e petitions that rejected annexation & called to restore the monarchy.
Hawaii’s state vote happened in 1959, of 600,000 people 140,000 votes were cast 93% of which voted in favor of statehood: the population of Native Hawaiians was around 102,403 & the population of foreigners was over 500,000.
James Keauiluna Kaulia declared that “consenting for our nation to be subsumed within America is like agreeing that we…be buried alive.”
It’s almost like Native Hawaiians have been systematically suppressed in their own homeland.
Foreigners had been imposing their rules on a land they are not part of beginning with the arrival of Christian missionaries banning the Hula in 1830 because they saw it as “pagan” & then those same people starting the “Big Five” companies that participated in the overthrow of the Kingdom.
Meanwhile, modern foreigners are happy to destroy Hawaii, push out its Indigenous people & encourage yet more inward migration in a fragile ecosystem by selling more property to aimed at them & refusing to build affordable housing for locals. You continue to march on, joyfu,l to be part of the reason Hawaii’s natural resources are being decimated. Every piece of Native Hawaiian culture has been fought for & many acts of resistance to the rampant development that is destroying the ecosystem have continued to this day.
The US has a long well documented history of committing violence & Hawaii is no stranger to that. In 1959, when the U.S. legislature voted to make Hawaii America’s 50th state – they allowed colonizers to confiscated lands and militarized parts of the island. They further suppressed traditional cultural & spiritual practices as well banning the Hawaiian language in schools and government. resistance leader
Thanks for the history lesson Noah. I love your passion. Tell me about yourself and your background? Are you native Hawaiian? I’d love to know where all your passion comes from and what type of solutions you can offer.
Keep up the fire!
Thanks!
Sam,
The comment from the supposed “local “ is not fair. People like him need to “get over it” and quit thinking Hawaii only belongs to those who were born there.
My daughter graduated from UH-Manoa and was constantly reminded by “locals” that she wasn’t from the islands. After finishing her Masters degree she left and told me recently it was the “right decision” because of the attitude these islands only belong to “them”.
They should count their blessings and be grateful for what they have.
You have the right to buy what you want and “where” you want. Just saying.
Respectfully,
MT
Your children will probably prefer to move earlier than that as they will be reluctant to leave the friends they have made the older they get…
I’m not sure where you are looking to live. If you want your kids to go to private school I wouldn’t count out Kamehameha Schools- Kapalama. You and your kids are Hawaiian and as such can get a quality education at a much cheaper price than Iolani or Punahou (granted KS is a notch down from those in my opinion). I think you have a good handle on the costs generally, if you are working to generate income the taxes are pretty high but it appears you are banking on passive income that won’t be generated from In-State activities so it appears you might be side-stepping this. Hawaii is a great place to live if you have money already or don’t need to actively work in-state for money (like you said low pay, high income taxes). Being part Hawaiian is helpful, but it really just boils down to what you look like. I’m 1/8 Hawaiian but otherwise am very fair and as such get called Haole boy, et al. You /your family will be viewed by the Asian lens and as the majority will probably be welcomed and seen as local (until you speak). You and your kids will make friends easy, I think its a slam dunk decision.
Thanks for sharing your thoughts. Thanks for also making me feel welcome. Kamehameha Schools website says I need to get verification, which can be done through my grandmother’s death certificate.
Thoughts on the quality of Kamehameha Schools?
Kamehameha Schools have the best facilities of any schools in Hawai’i.
TMK, students there have as large a variety of opportunities as any school in Hawai’i.
One thing you won’t find there that you will find and Punahou and ‘Iolani is the opportunity to be in classes and activities surrounded by NMSF level kids. But many alums get into JABSOM and other med schools.
But it’s the only school that offers Hawaiian kids the level of education in their culture that they do.
It’s not uncommon for kids to transfer out of Punahou when they get accepted to Kamehameha.
Cool, I need to get my grandmothers death certificate that shows she was born in for proof.
Not a true statement. We still have many full blooded Hawaiians.
What’s the statement? Who are you responding to? This article is about the challenges of living and working in Hawaii.
Sorry I replied to the statement someone made that we don’t have any full blooded Hawaiians or that his/her family was the last. I’m not sure why it didn’t track properly.
You mentioned may be getting a property management company to oversee your rentals. I have seven paid for rentals in Houston Texas that are keeping me from relocating to either another state or overseas. How about doing a blog on property management companies, explaining what they actually do, referring to maintainace, releasing, etc. How much do you think they would charge percent wise, repairing, releasing, etc. My parents lived and I visited the Marshal Island of Kwajalein back in the seventies and I was quite impressed with island life. I hope you get your wishes for the future.
As folks living in an English speaking environment, what are the motivation for the parents to enroll the kids in a second language immersion program? Many multinational companies have English as the working language. Many folks are dying to learn English around the world so that they could go to schools in an English-speaking post-secondary schools.
I’m convinced that learning a second language has many benefits in the cognitive development of a person. I picked up English as a second language out of necessity, so I fail to see why English speaking parents enroll their kids in another language immersion program.
To understand and preserve one’s culture and history. I think it’s important to understand and appreciate our history. I also find it easier to connect to others when I can speak their language.
Perhaps because you speak a second language you take for granted knowing one? What is your first one?
I speak one of the Chinese languages as the first one. I got laughed at in school for speaking it. Indeed, kids laughed at others who spoke languages foreign to them! Many dragged going to Chinese school on Saturdays because we didn’t see a point getting proficient in Chinese. Many kids spoke English during recess anyway.
I live in an English-speaking part of Canada. Many parents are dying to get their kids in the French immersion programs in the publicly funded school near them: Some move to a more desirable neighbourhood for the school. (House price went up for those areas!) The immersion programs have better test scores in general. Many have recognized the value of second language learning. Some parents exercise their francophone rights.
Not every parent can get their kids to the immersion program. There aren’t enough qualified teachers because the previous generation didn’t emphasized in second language learning. The only very dedicated kids in the generation ended up to be qualified to teach in the French immersion system.
Gotcha, so maybe being made fun of for speaking Chinese has made you not appreciate your ability to speak Chinese? Kids often just want to fit in and shed anything of theirs that makes them seem abnormal.
But I say be proud of your language abilities and culture! That’s what I will teach my children. To be proud of who they are and learn about their ancestry.
If you have kids, are you not introducing them to a Chinese language?
That’s right. The kids and the adults back in those days despised people who didn’t speak English. The mentality back in the days were so different. Well, many could not predict what will be desirable a generation later.
I’d introduce my kids and my partners to the language and the food. I have no way going back to the old days when displaying language and culture was downplayed.
Some of my Canadian-born Chinese friends could not order what their parents used to eat because they don’t know what they’re called. When I ordered those foods in a restaurant without problems, they were visibly moved because their parents have died.
Thanks Sam for reinforcing that investing in the kids is not only about money!
Moved to Honolulu in 2017 from North Carolina. Was previously in nyc for quite some time. Kids were pretty much babies at the time of our move, so uprooting their social scene really wasn’t a concern. I feel they’ve integrated fairly well, was able to find a cheaper private school with quality education, so atleast have bought some time until 8th grade. Don’t really feel like shelling out $30K+ for punahoe or Iolani.
I do miss the mainland however. I miss seasons, friends, road tripping, so there definitely is some give and take.
Also one big perk of living in HI: proximity to Asia. 5 ~ 6 hour flights to Japan were pretty awesome.
Yeah, if I relocate to Hawaii, I would go to Taiwan and Japan all the time. And my kids to go to Taiwan for summer camp in Taiwan or China as well.
Better than 13 hours flying.
Sorry, it’s more like 7-8 hours to Japan from HNL. I was thinking HNL to SEA which is more like 5-6 hours.
I moved to Oahu for a job at age 28 after living mostly in WA state. I stayed there for 14 months before moving back to WA. Living in HI was awesome, but I didn’t like the job, which is why I went back.
As far as I am concerned, HI is pretty much a different country compared to the rest of the US from a cultural perspective.
IMO the older your kids are, the harder it will be for them to adapt. Even something as basic as the pidgin could be hard to deal with. Sometimes it was hard to understand what people were saying. The more time they spend growing up on the mainland, the less local they will be. And they will probably want to move back to the Bay Area (my guess), leaving you in HI.
Cost of living wasn’t something I really noticed coming from Seattle.
Thanks for the feedback. Would you have stayed if you enjoyed your job?
I agree on the kids and the adjustment. Which is why we plan to go back to Hawaii one or two times a year or years before they do relocate.
I’m thinking one month of summer school and then one week during the winter’s house a good cadence.
I never lived in Hawaii for longer than two months. But because I went back every year for decades, I always feel comfortable going back.
Sam,
Yes, I would have stayed if I liked the job. Sometimes I think I should have stayed regardless, it was not a bad situation in retrospect and my overall QOL would probably have been better especially as an Asian-American.
Sam,
Our family has been struggling with the same thoughts. We have a house in Kailua on Oahu where we spend most of our summers. I just returned (had to work for a few weeks) after spending 5 weeks there. I actually thought I saw you at The Pig and the Lady in Honolulu. Haha. Not sure if you ate there during your trip. I have friends who’s kids went to Punahou who got into very good colleges. Le Jardin Academy in Kailua also seems like a great school. We have toured it and were impressed. It’s 25 min or less from Honolulu (depending on where you live), but I know plenty of people who commute to town from Kailua, so it could be done in reverse!
We haven’t made the move yet because I’m still working part-time and my wife doesn’t want me to have to commute for a week a month back to the mainland and I’m not quite ready to pull the plug on full-retirement yet. My kids are young (1st-6th grade), but even they already have apprehension of moving and leaving their school and friends in Austin. Waiting until 8th grade may be tough from that perspective as another commenter mentioned.
Our kids have been going to the Ikaika Waterman Academy the last couple of summers and love it. If your kids like outdoor water activities, its a good program.
Ah, you’re more than halfway to Hawaii given you have a house there!
Have your kids gone back to Hawaii every year since preschool? I’m wondering if my plan to do so 1 to 2 times a year for one month total will help in the transition as they will be used to everything by then.
But yeah, moving in middle school is tough. I did that in the eighth grade, and I was heartbroken. But it forced me to adapt and make new friends.
In addition to many other good pros already mentioned there’s one more – low property taxes for full-time residents. In fact, one of the lowest in US. Tax for 1.5M home is roughly 3 times less than in CA.
That’s right! The lowest property tax in the nation is in Hawaii!
Ah… but I’m looking for more negative, not positive, because I’m already sold on living and working in Hawaii.
Pros
Best weather on the planet all year rd.
Free entertainment with world class hiking, beaching, SUP/surfing and open play pickleball.
$8 Foodland spicy AHI poke bowls
Cons
Mainland friends and family relationships have suffered.
Expensive to travel abroad from here/bad jet lag.
Kiss the music/concert scene goodbye.
Moving to the islands 12+ years ago was one of the better decisions I’ve ever made.
Everyone’s circumstances will be different though.
A top earner salary from your ZipRecruiter chart above would be a minimum requirement for me to move here from the mainland.
Thanks for sharing. Why did you move to Hawaii in the first place? And what do you do for a living now?
Tamara’s and Fresh Catch poke are amazing. So are the local mangoes.
On the cons, they are actually some positive for me as my parents and relatives live in Honolulu and flying to Taiwan or anywhere in Asia is quicker. I will go to Japan, much more often, which is an incredible country. So incredible that I took inspiration and named this site Financial Samurai.
Job opp/construction industry brought me here, still in same position.
Yeah, if you stick to Asia it’s not as bad.
Japan ski trips to Niseko have become the highlight of the year.
Very cool! Good to know. Were you able to meet someone in Hawaii and start a family? I hear it’s hot and cold for those who did not grow up in Hawaii.
However, I also know there are incredible nonstop networking events once your kids are in school. It’s actually pretty exhausting here in San Francisco how many activities there are.
Yes, we’ve been together 10 years now.
All networking now can be done at pickleball open play, ha.
No kids, so I can’t comment on the stresses that brings to the table. Friends of mine have had mixed success getting their kids into Punahou/Iolani.
Good stuff with Pickle Ball! I play twice a week and you open playing with a group of 4.0-4.75 players. I probably met over 60 people playing so far. And can easily say hi to 30 or so.
Good variety of people.
I would highly suggest moving earlier. Having kids, do you really think at 9th and 6th grade after being esconsed in the same place for years they will want to move and leave their friends? This is not the situation for a kid who has been moved from place to place for say military or foreign service. This is a kid who might have had the same friend all through elementary and middle schools. Because of the age of my kids a lot of people I know won’t even move out of district in the same state at the ages you are proposing.
Second, you want to spend time with your parents why wouldn’t you move now and let them grow up with your kids now? What is the point of waiting till later? Sounds more like SF is your home especially when you bought a home in SF instead of taking that leap and buying in Hawaii?
Truth is being from hawaii you know that Iolani and Punahou are more comparable to public schools in the mainland than top private schools. I know people who’ve worked at both and would agree. So is it the potential education miss? I don’t think you went to school in hawaii like so many of us who can discern the educational differences and it’s substantial.
We plan to spend the summers and winters there more often now that they’ve gone. Perhaps every summer and/or winter forever. So by the time they do relocate to Honolulu, they will be highly familiar and perhaps make new friends.
My parents are private and independent people. They’re interesting in that they enjoy their solitude more. I think if I was blessed to be a grandparent, I would move right next door to my grandkids! But my Provider’s Clock ticks differently.
In 8th grade, our school ends and we have to apply to high school (all over, with scattered friends). So we figure, might as well have our oldest apply to high school in Honolulu and see if he gets in. And if so does our daughter, then 6th grade it will be for her.
I’ve never heard of Punahou and Iolani as more run of the mill private schools on the mainland. Can you elaborate? As far as I could tell from our two visits, they had incredible facilities. Did you attend one? If so, what did you end up doing?
Lots of people both on the admissions board and teaching in the schools have said Hawaii privates aren’t better than good mainland public schools.
It’s no lakeside (Seattle) or Harvard Westlake (ca) or Phillips Andover (ma) or any other top tier private or public schools. Hawaii schools are not great and you have to be joking if you think so.
Also going to Hawaii for summers and winters is not the same as going there. They aren’t developing friendships they way they are and Hawaii is insular.
You aren’t local which makes a big difference. You have family and you go, I’ve gone 6 times in the past year for family. Born and raised until college. And my kids go on average 2-3x a year for extended periods and we’ve spent months there and went during COVID.
But I would never claim them to be local or to adapt. Or want to go now at 9th and 7th grade to Hawaii to start school. Besides them missing their friends. The kids in 9th and 7th grade have to want to be their friends too. Works both ways.
I just think if you are going to do it the sooner the better. I think you’ll find much like your early retirement and wanting more money after kids, at 9th and 6th grade you might be surprised at how much your kids want to stay put with their community, especially since unlike you they aren’t used to moving around.
Fwiw i too am part native Hawaii and am curious what’s the quorum? I’m an 1/8. My great grandmother was one of the last pure blooded natives and we can trace our ancestry back generations.
Sounds good. After going to back so often and so many times, that’s a bummer you don’t seem to feel as welcome?
Maybe I just haven’t encountered such people, but I always feel welcome going back. Maybe because I can blend in well or because I’m with family or go to places that are in hospitality?
Fascinating how different people have different views and experiences of the same place. It’s like people reading an article and coming away with completely different takeaways.
No I’m just back again from 3 weeks in Hawaii. And I am welcome and my kids enjoy it. But i can tell they aren’t the same as local kids and the interaction isn’t the same. And a large part is that they are older. Perhaps if we had moved when the kids were young then it would be different.
My suggestion still stands if you want to relocate go earlier than later.
Another factor to consider is that with the more laid back atmosphere in Hawaii, if your kids are pretty competitive, it may be advantageous for them to get into better colleges? However, if you move to Hawaii, there is no high ranking colleges in state, either. If your kids could get into in state UC systems, the tuition and fee saving would be huge? But it is also very hard to predict what the kids would do despite best efforts of the parents. Also would you consider climate change factors? Would Hawaii or California be affected by climate (i.e. recent wild fire, earth quakes, drought etc.)?
Yes, great points. And laid back atmosphere may also encourage my children to take it easier too. It’s hard to make it in Hawaii b/c the alternatives of going to the beach, hiking, and relaxing are all around.
I certainly was more laid back and stopped responding to e-mails, requests, etc while I was there. But, I am also very disciplined and continued to publish 5 posts and a newsletter while there.
So it all depends on the individual.
I’m more interested in the concerns of the erosion of beachfront property. Climate changes may be helping SF, as it seems to have gotten warmer and sunnier since I first arrived in 2001.
Good article Sam; I think whether Hawaii or some other Idyllic location there is always the “weighted” yes versus no columns. Yours sounded heavily weighted to Hawaii! Good luck with any and all your moves as I just draw Inspiration from your columns.
Well, whatever I think of doing, I’m ALWAYS enthusiastic about doing it. Hence, I often need throttling as I have a lot of optimism and adventure in my spirit.
Something to think about… you’re talking about moving at ages that the kids are going to be leaving all their friends behind. That’s going to be a challenge.
Indeed. I did so every 2-to-4 years growing up as a son to foreign service officers. Leaving in the 8th grade was the most brutal b/c I left my friends and new girlfriend behind in Kuala Lumpur, Malaysia. I was so sad. To then come to boring McLean, Virginia, the suburbs of DC was not great.
Leaving younger is better. The thing is, my son has to reapply to high school anyway since his school only goes to the 8th grade.
My two cents worth:
Definitely easier & better to make this big move when your kids are younger, especially since getting into good schools can be difficult and not automatic on your first try. Although the private schools talk about intakes at different years, the reality is that few spots are available and there’s lots of competition, especially at Punahou. We have multiple friends like you – smart, well-off; doing their homework etc who assumed that their equally bright kids could simply get into whatever school they preferred … they didn’t always and its not always straightforward. Likewise, being accepted locally has as much to do with where you went to HS (or where your kids go) as it does with whether or not an ancestor has Hawaiian blood. If you didn’t go to HS here, some people will still think of you as an outsider even decades later. Compared to the Bay Area, Honolulu is really a small town. Especially for kids, the first year can be tough. For both you and your kids, the sooner everyone gets immersed in the local lifestyle the easier it becomes.
Great article and you touch on all the major issues if you want to move to Hawaii. A few other things to consider:
1. Consider moving to an area with good public elementary and high school (like Hawaii Kai). Housing will cost more, but Iolani and Punahou don’t have to be your only options. And yes, some catholic schools are cheaper.
2. Food can be comparable to the Bay Area if you shop at Costco.
3. While logistically more difficult, you might consider renting in an area to test out the schools, commute (if you have one), amenities, etc. Remember not every area is “laid back,” and as open and accepting as you might want.
4. Don’t downplay the difficulty of making new friends. It will be easier if you connect through your kids at school, but remember that families/clans in Hawaii often have multi-generation connections and sometimes these can be hard to penetrate for close relationships. Often the first friends you will make will be mainland “expats” who are experiencing the same transition issues as you are.
5. Be prepared for your kids to move back to the mainland for college, especially if you go to Punahou or Iolani. That may seem like far in the future, but it will happen quickly. We eventually moved back to the Bay Area to be closer to kids and grandkids, and, while I miss Hawaii, I have no regrets being back in the Bay Area.
6. We are very glad we did not sell our house in the Bay Area. For the 10 years we were in Hawaii, the Bay Area housing cost rose higher and more quickly than in Hawaii. Keep a foothold somewhere in the Bay Area so you can return if you want to
7. Hawaii, even Honolulu, is very much small town.
8. You will not regret taking on this adventure even if it’s not your final family move. Hawaii is a great place to raise kids, enjoy being outside, and importantly, avoid mainland politics.
Wonderful advice, thank you! Hawaii Kai is nice. And much cheaper than the homes I’ve been looking at in Kahala and Blackpoint.
Where did your kids go to school in Honolulu and for college? What are they doing now?
I totally hear you on the potential difficulty of making friends due to the imbedded multi-generations living there, also under one household.
My plan is to teach, be a highly involved dad, and join Oahu or Waianae Country Club if they’ll let me in. Then I plan to play pickleball, tennis, and golf a lot. I’m a relatively sociable person with a lot of interests, so I’m hoping making new friends will be easy.
Also, I forgot, but I have several readers in Honolulu too, whom I’ve met up with. They said they’d intro me to a lot of people. I also know I will be viewed by some as an outsider and not welcome, despite my grandparents being born in Honolulu in 1906, and my grandmother being half native Hawaiian.
It’s just the way the world is. Gotta stay positive. The good thing, as a minority growing up for HS and college in Virginia, I’m used to being and feeling excluded. So living in Honolulu as part of the majority feels pretty good.
Sam,
I am a huge fan of Hawaii and often thought of having an investment property in Kauai but the leasehold land issue was a deterrent, at least where I was looking. For now my investments are in California where I currently reside.
I did live on the north shore of Oahu for a few years in the 80’s and we had one hurricane which meant power loss and other temporary challenges. I guess what one might consider for a move is climate impact to oceans, homeowners insurance and infrastructure for disasters. Perhaps your father has that information. We will all deal with climate impacts wherever we are but it would be good to look at models for the pacific.
Finally, I could see you teaching at business schools there – U of H, etc.
Can’t wait to hear about the planning! For now I will continue to vacation there. I get the lure!
Valerie Janssens
Sam,
I am a huge fan of Hawaii and often thought of having an investment property in Kauai but the leasehold land issue was a deterrent, at least where I was looking. For now my investments are in California where I currently reside.
I did live on the north shore of Oahu for a few years in the 80’s and we had one hurricane which meant power loss and other temporary challenges. I guess what one might consider for a move is climate impact to oceans, homeowners insurance and infrastructure for disasters. Perhaps your father has that information. We will all deal with climate impacts wherever we are but it would be good to look at models for the pacific.
Finally, I could see you teaching a business schools there – U of H, etc.
Can’t wait to hear about the planning! For now I will continue to vacation there. I get the lure!
Valerie Janssens
Would love to know what summer school options you’re considering in Honolulu!