If You Can Make It In Hawaii You Can Make It Anywhere

If you can make it in Hawaii, you can make it anywhere. Hawaii is one of the best places to live, but it's expensive and the pay is low. The median home price in Honolulu, for example, is roughly $780,000 in 2024.

My grandparents came to Hawaii in 1906. My father is Chinese Hawaiian and I've been going back to Oahu for 46 years. I love Hawaii and plan to relocate my family back to Hawaii once both my children are over age 6.

As a resident of San Francisco since 2001, it's been a good run. I've made enough money to achieve financial independence. However, leaving San Francisco now in the middle of the artificial intelligence boom is hard given so many fortunes will be made. But I promise to make it back to Hawaii and retire in Hawaii in my 50s and beyond.

However, living in Hawaii can be hard if you don't adopt the slower-pace, aloha lifestyle.

Borrowing A Phrase From Living In New York

Making it in Hawaii is a play on an old saying, “If you can make it in New York, you can make it anywhere.

The idea is that with New York City being so competitive, only the strongest survive. I worked on the trading floor at one of the most hardcore investment banks around and I can unequivocally tell you that making it in NYC is brutal.

The weather beats you up for at least six months a year, the work hours are long, and your money doesn't go very far.

Two years and 15 pounds heavier I left NYC in 2001 for an easier life out in San Francisco where I didn't know a soul. I thoroughly admit I didn't make it in NYC.

Perhaps I could have stayed on as a third year financial analyst, but surely Goldman would have made me go back to business school afterward rather than promote me directly to Associate. The thought of returning to school at the time and spending all that money wasn't appealing.

By spring 2001 it was clear the economy was not in good shape one year after the NASDAQ collapsed. I decided to take matters into my own hands and jump to a competitor for that Associate promotion and raise instead.

Waiting to get let go is like waiting to die.

The “Difficult” Hawaiian Life

I've been coming back to Hawaii for over 45 years because that's where half the side of my family is from.

Ever since college graduation in 1999, Oahu has been tempting me to hurry up and quit the stressful finance life so I can kick back on the beach and live off mother nature. Every year I resisted because I knew that once I moved to Hawaii, there was no going back.

I wanted to make as much money as possible in New York City and San Francisco and then relocate back once I was burned out. Frankly, I'm getting really close after working non-stop since 1999 in banking or with my online website, Financial Samurai.

During Joe Biden's presidency, I plan to re-retire and move back to Hawaii. The pandemic has really just zapped away all my energy as a father of two stay at home kids. With taxes going up and the stepped-up basis potentially going away, it's time to take it easier post-pandemic.

But I have some concerns.

Kahala Resort & Hotel View - If You Can Make It In Hawaii You Can Make It Anywhere

Concerns About Living In Hawaii

I noticed several childhood friends attend the University of Hawaii and never leave. They'd find stable jobs as accountants, dentists, telecom operators, realtors, car salesmen, and public servants making a healthy $35,000 – $90,000 a year.

Instead of living on their own, they'd continue living with their parents, saving lots of money in the process to one day buy a place if they ever meet someone special.

Family (Ohana) is the foundation of Hawaiian culture and having three generations live under one household is not uncommon. Even at our weekly Friday night poker game, a grandma comes to wipe us out ever single time.

Unfortunately, the pay in Hawaii is 30% – 70% lower than the pay for similar jobs on the mainland. As a result, many generations shack up under one roof giving housing expenses are high.

How To Make A Living In Hawaii

Here are the main potential ways to make a living in Hawaii:

  1. Tourism Industry: Hawaii is a major tourist destination, and jobs in the tourism sector are plentiful. Opportunities range from working in hotels, resorts, restaurants, tour companies, and more.
  2. Hospitality and Service Sector: With a growing population and tourism, there's a demand for services. Jobs in retail, customer service, and hospitality are common.
  3. Healthcare Professions: The healthcare industry is often in demand, and Hawaii is no exception. Nursing, medical practitioners, and other healthcare-related jobs are needed.
  4. Education: If you have the necessary qualifications, you could explore opportunities in education. Teaching positions in schools or colleges are available.
  5. Technology and Remote Work: With the rise of remote work, especially in technology-related fields, you might find opportunities to work for mainland or international companies while living in Hawaii.
  6. Local Agriculture: Agriculture and farming businesses are vital in Hawaii. You might consider working in or starting a business related to local produce or other agricultural products.
  7. Real Estate: Real estate, including property management or real estate sales, can be a lucrative field, especially given the demand for housing.
  8. Creative Arts and Culture: If you have skills in art, music, dance, or other creative pursuits, you might find opportunities in Hawaii's vibrant cultural scene.
  9. Environmental and Conservation Work: Given Hawaii's unique ecosystems, there are opportunities for work in environmental conservation and sustainability.
  10. Entrepreneurship: Starting your own business can be a fulfilling option. Whether it's a local restaurant, a small shop, or an online venture, entrepreneurship allows you to create your own path.

How I'd Make Money In Hawaii

If I were to go back to Honolulu, I would work on my online business with Financial Samurai. I can make money online from anywhere, so that's convenient.

I'd also probably become a real estate agent because I love real estate, my favorite asset class to build wealth. I speak Mandarin so maybe I could focus on selling real estate to foreigners from China and other Chinese-speaking countries.

The tourism industry is back to full force now that COVID is long over. As a result, the Japanese have returned to Hawaii as well. I'd probably also brush up on my Japanese and work as a scuba diving instructor. What a great way to make money in Hawaii by doing something fun.

Can Always Return To Hawaii

In the back of my mind I always knew Oahu would forever be waiting for me. As a result, I didn't want to permanently return until I could thoroughly see what I could do on my own on the mainland or in a foreign country.

If your first car is a Ferrari, your car driving experience is ruined for the rest of your life. Besides, the speed limit on the H-1 highway is only 50 mph! That's when you know you've literally got to slow down for island living.

I wanted my first car to be a beater with electrical gremlins and funny screeching sounds so I decided to start my career on the East Coast and gradually move my way West as my energy for work faded. The hope was that by the time I could move back to Hawaii, my finances would make up for my lost enthusiasm to be somebody's whipping boy.

Motivation To Become Financially Independent Is Hard

When it costs nothing to surf or hike, it's really hard to get motivated to make a lot of money. As a local, you get Kama'aiana rates which gives you further discounts on hotels, services, and golf rates.

There are loads of parks all around the islands where you can play tennis, soccer, and basketball for free. Best of all, every beach is open to the public, even the ones with multi-million dollar mansions behind them.

There is a strong feeling that everyone in Hawaii is on vacation because of the large tourism industry that dominates the economy. If every other person you meet is from Japan, Europe, or the mainland hanging loose for a week or two, you're going to feel mighty compelled to also get into vacation mode.

Hawaii Feels Like A Permanent Vacation

You start thinking, If they are enjoying life on vacation, why can't I? Hawaii's biggest import product is other people's leisure!

When it's 70-88 degrees every single day, it's hard to motivate yourself to work inside a cubicle for 8+ hours for a better life when a better life is waiting for you right outside. There's no point saving for retirement!

New York City's grey skies, muggy summers, and frigid winters made it EASY for me to work 14 hour days at 1 New York Plaza. We had computers, free internet, a small shopping arcade, a gym, and free food. What more do you need?

Saving money and working like a dog came naturally on the East Coast because all I could think about during the winter was buying a plane ticket to somewhere warm and never working another day again.

Related post: The Pros And Cons Of Living In Hawaii

Hawaii Makes You Easily Satisfied With Life

I remember vomiting junior year of high school after an intense training session in track. My teammates and I were practicing for the 4X200 meter relay for Districts and we pushed ourselves to the max because we were never satisfied.

As I was barfing my lungs out my coach told me, “That a boy. You haven't really tried your hardest until you start vomiting all over the place!” She sounded cruel at the time, especially since she was extremely out of shape. But I took her words to heart and aimed to vomit all over her shoes every single day!

Less Desire To Grind For More Money

Major cities in the mainland propel you to want more, more, more. There's never an end to the amount of money you can make in New York City or the number of startups you want to kill yourself over in San Francisco. Hawaii gives you the entirely opposite effect of making you slowdown and appreciate all that you have.

I knew if I returned to Hawaii early I'd be absolutely satisfied with a $50,000 a year job working 9-5. Of course there's nothing wrong with a $50K a year job and regular work hours, I just wanted to test my limits.

The only way I could thoroughly enjoy Hawaii was to make my fortune elsewhere and come back without having the need to work 40+ hours a week. The temptation to slack off would be just too great.

I'm keenly aware that locals hate it when non-locals go away and come back to the island with their flashy cars and fancy homes, making things more expensive in the process.

This is why I'm happy to just live in an old home I've been coming back to since I was a kid and drive an old car. It's all about rolling in a hatchback or old truck to blend in.

Hawaii Is Expensive Once You're On Your Own

The median home price is about $780,000 in Honolulu according to online estimates in 2024. Based on my conservative 30/30/3 rule of home buying, this means you need to make roughly $260,000 a year (house max price is 3X annual salary) and have $234,000 on hand in cash (30% of house in cash for 20% downpayment and 10% cash buffer) to be able to buy a home.

To get a home in a desirable area, you probably have to spend at least $1,000,000 nowadays.

With the median household income of around $85,000, Honolulu households are making good money compared to the national median of $76,000.

But when the median house is 9X the median salary, the income isn't that great if you're looking to buy. So how does the typical Hawaiian buy a median priced home? The answer is with a lot of help from family.

Multiple Generations Living Under One Roof Is Common

The majority of my Hawaiian friends end up living at home with their parents after college until marriage. As a result, decent sized nest eggs should grow over a five-to-eight year period when the children typically tend to move out to start their own family.

But even with $50,000 – $70,000 saved up during this time period, that's still short of the $115,000 downpayment on a median $575,000 house. In every case I know their parents pitch in to cover the rest of the downpayment or more.

Given the finances, most households will stretch to buy a home equal to 5X their household income. However, that still means earning a $200,000 median household income if you want to now buy the median $780,000 home.

Stories From Friends About Living In Hawaii

To corroborate my anecdotes, I sat down for lunch with a Prudential partner one day. He mentioned at least 50% of his friends before they were 30 lived with their parents. 25% of his friends still live with their parents over 30.

In other words, generational wealth plays a huge part in the home buying process. For real estate investors out there, the partner sees houses on the Waialae Nue Ridge as good relative value.

Food And Gas Are Expensive

Gas prices are on the high end at $4.70 for normal, $4.80 for premium, and $5 for super. But food prices is what really stings. Because over 80% of the food consumed in Hawaii is imported, prices are regularly 10-30% higher than the mainland.

You may want to change your diet to something more locally oriented. Example includes eating papayas, mangos, poke, laulau, and poi to save money.

If you come to Hawaii from foodie havens such as New York City or San Francisco, you may be disappointed with the cuisine. It would be one thing if the comparable cuisines were the same price. But if food costs 10-30% more than the mainland, your expectations are for 10-30% tastier food. When you don't get that, it's disappointing.

The main cuisines revolve around Korean BBQ, Chinese, Japanese, Hawaiian, and fast food. It's the same five things over and over again. If any entrepreneur wants to open up an incredible Mexican or Malaysian restaurant, the opportunity is wide open. Some good restaurant choices in Honolulu include: Ono's, Salt, Yakiniku Camelia, Doraku, Morimoto's, and Uncle Bo's.

Due to high living costs, Hawaii makes it much harder to leave your parents as an adult. If you become overly dependent on your parents then it becomes very difficult to stretch to do other things because you're already stretching to survive.

If You Can Make It In Hawaii You Can Make It Anywhere

Hawaii Life Will Test Your Resolve

Everywhere you go in Honolulu, the city is booming with people. Tourists are flocking back to the islands in droves now that world economies are back. Even with all the tech, internet, and artificial intelligence fever in San Francisco, San Francisco sometimes doesn't feel as busy.

To give you an example of how strong the economy is, pre-pandemic, we hosted a team building offsite at The Kahala Hotel & Resort during off peak season in November and the standard rooms with only partial views were going for $600 a night! Post-pandemic, the hotel prices are 20% more expensive.

The hotels in Waikiki were also packed with average room rates of over $250 a night. The Kahala Hotel & Resort is my favorite resort in Oahu due to its location and very tranquil setting (top picture). I just can't afford to stay there for very long! Shout out to Shane Lani, the manager from the Seaside Grill for taking care of us for lunch. The service is always fantastic.

A booming economy does make doing business theoretically easier due to higher demand. But Hawaii is still tiny compared to the immediate publicity you might get from starting a business in New York City with 10X the population.

Just open a BBQ joint and you could easily see lines around the block if it gets profiled by a major food blog like Eater. If you want to start a tech company in San Francisco, you've got unlimited resources to do so.

Selling Property During The Tech IPO Boom And Retiring Early To Hawaii

Enjoy A Better Life In Hawaii

Hawaii is a magical place that promises to make you happier. The people are friendly if you respect the culture. There is also a tremendous amount of diversity. Diversity is great if you hate racism, bigotry, and all types of other hate that's going on the world.

Most importantly, the life expectancy in Hawaii is the highest in the country! Hence, if you value living longer, living in Hawaii makes sense. Its state policies and social influences are conducive to a longer life.

But be careful. Hawaii might make you soft. If you can avoid the temptation of good weather, amazing scenery, and pristine beaches to focus on your career and earn enough to afford a house on your own, you can make it anywhere.

All the glory goes to someone who doesn't succumb to temptation when temptation is all around!

Family Life In Hawaii Is Great

As a father now, I do find the massive appeal of relocating to Hawaii. The family culture in Honolulu is one of the best. Hawaii has one of the highest kids per capita in the entire country. If we can get our kids into one of the great private schools like Punahou or I'olani, that would be fantastic too.

I just fear that once my kids know what paradise is like, they won't have motivation to go anywhere else or do much of anything again. It is the hardship that I experienced as minority growing up in Virginia that helped make me the gritty person that I am today.

Finally, I do want to say that retiring in Hawaii is a good idea. If you are seriously OK with no longer climbing the corporate ladder Hawaii could be the ideal place for you!

Wealth-Building Recommendations

In order to optimize your finances, you’ve first got to track your finances. I recommend signing up for Empower’s free financial tools so you can track your net worth, analyze your investment portfolios for excessive fees, and run your financials through their fantastic Retirement Planning Calculator.

Those who are on top of their finances build much greater wealth longer term than those who don’t. I’ve used Empower since 2012. It’s the best free financial app out there to manage your money.

Planning for retirement when paying for private grade school

Are you on the right retirement path? There is no rewind button.

Invest In Venture Capital The Easy Way

Did you know the richest people in Hawaii are mostly entrepreneurs or their heirs? Taking a leap of faith to become an entrepreneur is hard though. Instead, you may want to keep your day job and invest in private growth businesses. This way, you get to have brilliant entrepreneurs work for you. Or you can do both! I certainly am.

Companies are staying private for longer, as a result, more gains are accruing to private company investors. Finding the next Google or Apple before going public can be a life-changing investment. But that's hard to do without already having a lot of capital, the right connections, and a lot of luck. 

Fortunately, Fundrise created the Innovation Fund which makes it easy to invest in tomorrow's great tech companies today. Plus, you can get started with as little as $10.

The Innovation Fund invests in the following five sectors:

  • Artificial Intelligence & Machine Learning
  • Modern Data Infrastructure
  • Development Operations (DevOps)
  • Financial Technology (FinTech)
  • Real Estate & Property Technology (PropTech)

Artificial Intelligence Is The Future

Roughly 35% of the Innovation Fund is invested in artificial intelligence, which I'm extremely bullish about. In 20 years, I don't want my kids wondering why I didn't invest in AI or work in AI!

Most venture capital funds have a $250,000+ minimum, which is why the Innovation Fund's $10 minimum is groundbreaking. You can also see what the Innovation Fund is holding before deciding to invest.

If you enjoyed this post, join 60,000+ others and subscribe to my free newsletter where I discuss investing, real estate in Hawaii, retirement, career planning, and everything financial independence.

95 thoughts on “If You Can Make It In Hawaii You Can Make It Anywhere”

  1. Matt Cornell

    Sam –

    My wife and I relocated and moved to Maui five years ago. We live in Wailuku in a house that we own that we bought six years ago, and then two years ago we also bought an oceanfront condo in Lahaina that is a vacation rental property for us. We don’t have kids so obviously that makes everything easier. We both still do work – my wife is a teacher here at a small private Catholic school, and I work remotely from home – I am an enterprise software salesman for a small software company in Texas. My wife is a local native Hawaiian and most of her family lives here on Maui. I would be happy to answer any questions you have about living here and our finances if you’re interested. I have also bought and read your book which is fantastic. Please feel free to email me at mcornell_56@hotmail.com .

    Matt Cornell


        Hi Sam –

        I don’t think that I have island fever, not yet anyways. We’ve been here 5 years now. I actually do miss the seasons – there is no fall or winter here at all whatsoever. Any travel out of Hawaii is obviously more expensive and just more difficult and time consuming since it’s a minimum 5 hour flight to get anywhere on the mainland and a minimum 3 hour time difference. And I do miss the selection, variety, and quality of restaurants as you talked about. Otherwise I am happy here and it’s very beautiful and I love the beach. If you don’t really like beaches, then I probably wouldn’t live here.


  2. This article looks current, but I cannot tell. I really wanted to brainstorm ideas about moving to the big island. Much like yourself I am not new to the islands as my moms side is still there. My grandmother (who is Hawaiian) actually met my ha’ole grandfather during Pearl Harbor there. In my mid 40’s the cold of Seattle is draining my Aloha. My mom just lost her brother who passed away at home on the big island. I had never been so close to cancer as in the zoom from my raining little house in Snohomish. The family, the ohana all the keki’s running around. They are barely blue collar but rich in Aloha and that, that is where my heart, my soul is telling me to be.

  3. I can relate! My parents and I moved to Oregon when I was 8 in ’96 and I have been wanting to move back ever since. My dad’s side of the family is all there but most importantly I miss everything about Hawaii. Sometimes I feel guilty though for thinking about moving back after the sacrifices my parents made to get me here but I know I’d be happier there. The only caveat is money and there isn’t much IT jobs there. I just bought a condo here in Oregon so when you said real estate was a good investment, makes me feel like I’m on the right track for now. I can’t imagine being here forever so hopefully in the future my dream will come true. Thank you for this article.

  4. Tracey Baysden

    I was born in Honolulu, before it was a State. I graduated High School in Wahiawa. Both of my
    grown adult children were born in Hawaii. I currently live on the East coast, but Iam seriously
    considering transferring my VA job to Honolulu. I would greatly appreciate any and all information
    you can give me re: the cheapest/reasonable rental properties/areas on Oahu. Preferably, apt.,
    townhouse, condo,etc. No yard maintenance. So, I guess, no house. (?) I don’t have much $.
    No family to help out financially. Just me.
    Please see what you can e-mail me.
    Thank you so much,and Mahalo.

  5. Great read. I moved to Oahu in January 2019. I was in Maui on vacation exactly one year ago and I knew I had to start looking for a new job when I got back mainland since my company was having financial hardship. I have been coming to the islands for 20 years and always wondered what it would be like to live here. I went on indeed and just for fun decided to apply for some jobs. Crazy enough I heard back. I interviewed in November, got an offer in December and started my new job as the Director of IT for Hawaii Health Systems in January. It’s been crazy. When I tell locals my story most find it hard to be true. I certainly do. It’s was a great cushy state job with amazing perks but I was bored. So I reached out to a company I knew that was a vendor of ours at a previous position and now I work remote for a company in Oregon. I’m ready to move back mainland as the company will relocate me back but I will be on island for another 6 months (avoid moving in winter). If this opportunity would have happened in 10 years I would have stuck it out but at 45 I still want some career growth and I found that difficult to find on island.

  6. Bert Gilbert

    Just came across this article, have to say after 12 years of living and working in New York City, the title of this article is perfect. I work remotely and live in Kailua and I’ve probably thought that same thought about one million times at this point. Having said that, it’s definitely been worth it.

  7. Angela White

    I don’t know if I’ve read an article so spot on!!!! I live in Kahala just around the corner from the resort, totally my favorite. Always walk to the beach park and sneak on to the resort and hang out. I have a son here who is a pastor, so pretty much self employed and he travels around the world. His wife is from here and teaches and is very dedicated. I decided to join them and moved out here from Texas, where I just jammed at work all the time. It’s just what we do. I have gone through like 5 jobs in the last year. I can’t get settled and I just don’t want to work and I haven’t been able to figure out what in the world is wrong with me. I read your article because I literally googled, I live in Hawaii and don’t want to work. This article came up and I was like WOW!!!! This is it. I’m gonna have to go back to the mainland and just come visit.

    1. Nice to have you! Glad Google worked. Do you enjoy the lifestyle and how are you though? We’re thinking about moving better in a couple years now that we have a 14-month-old son. It seems so family-friendly.

  8. Mike Martinsen

    For a family of four with a 150,000 cash and that’s it. No 401k, no nothing. Such is how it is when you fish for a living. A love of the ocean and a life’s work on the water. At age 46 we’re thinking of leaving NY to struggle in paradise. Noticing real estate in Waianae that seems to be in our range. Will have one child entering 9th grade as the others go off to college. Heading out in two weeks to take the Honolulu Police entrance exam. My girl is a personal trainer. Is Waianae ok for a family? Any other areas we should look into. Would be prefer to be away from the city. Maybe windward side?

    1. Waianae is gorgeous, but the overall vibe has gotten quite sketchy – more meth-fueled crime, such as a colleague’s 2×4’s stolen right out of their pickup while at a stoplight, in broad daylight. Things have gotten much worse all over the islands in the past decade or so (wife & I moved here in 2010, left in 2014, returned in 2017 & things are so different). I attribute this to the fast growing disparity, largely thanks to “over tourism” & many mainlanders w/ pipe dreams (like ourselves). All this being said, it’s still paradise in most ways – especially if you’re an ocean person (this area is also extremely overfished – shorecast & deep sea). Pro’s & cons, as the rest of the world continues to change as well.

  9. It’s interesting how you posted this so long ago, people are still commenting, and you’re still responding!

    So did you end up moving back to Hawaii? I’m going through this thought process of moving back. I was born in Hawaii and left after my freshman year. I’ve been hustling in the mainland and realize my home will always be in Hawaii.

    I’m also in SF and have decided that it’s time to create a game plan to move back. My goal is in 5 years I will own a business there after I’ve saved up enough money to buy one.

    What are your thoughts on the finance industry out there? I imagine booming with all the retirees out there! My current salary is almost 6 figs and not sure if I can ever find something comparable out there to hold me over until I’ve bought my business.

    Wondering what your thoughts are on this!

  10. Hi! I found this website through Mr. Money Mustache. Have been binge reading all morning on my day off and was just surprised to discover the Hawaii connection.

    I’m from NY and moved to Hawaii in 2003 right after college to become a teacher for the DOE. I never left. Found a husband here and purchased a condo in Salt Lake a year ago. We are very frugal and pretty good about optimizing the financially advantageous stuff about living here while minimizing the high cost of living.

    I don’t think we’ll ever leave, unless something unforeseen happens. We have no family out here and both of us are from the East Coast, so it’s a little rough at this point with two toddlers. But we have a strong network of close friends and our entire professional networks are here (husband is a social worker).

    Nice blog! Also, fwiw: both of our cars were purchased for around 2% of our gross yearly income. 10% is insane for a depreciating asset! Especially on an island, where we never average more than 6000 miles/year. :)

    1. I’ve lived in Oahu my entire life. I commute from Pearl City to downtown Honolulu, 5 days a week and easily put 10k miles a year on my car. AND it’s traffic miles. So about 35 minutes going to work and 1.5 hours going home, Monday thru Friday.

      1. Thoughts on if you didn’t have to commute to work and could work from home? Where would the ideal place you would like to live in Oahu? My family is really considering relocating there this year.

  11. I’ve lived on Maui alone for the past 6 months. I moved here after a lifetime in NYC. I’m 28, single and have a full time job with the government making 40 k per year. I absolutely love it here but there times when I miss my parents and brother and sister very much. That being said they are all living their own lives and we rarely saw eachother when I lived there, brother is in Delware, sister in Pennsylvania, Father in Jersey, Mother in Manhattan. I haven’t made any friends in 6 months outside of work. I also haven’t been looking, i’m generally an intorvert and do my own thing most of the time. I don’t know how long I can hack it here due to the prices. As beitiful as it is here unless you’re a regade individualist you should come here with someone.

  12. I can understand your love for Hawaii since it is your home, half your family is here, and of course the environment is just unique and perfect. However, it is very different for outsiders, people who come to try the life here. I have been in Oahu for 3 years and as funny as it may seem, I have never worked so hard. The hourly pay is very low compared to other cities in the mainland, house is expensive and not having family around makes it even harder to stay. Don’t get me wrong, I love Hawaii.. but it isn’t where I want to live forever and raise my kids. I miss my family a lot and it is very expensive to travel to see them as much as I want. HI will be forever in my heart. I believe that home is where our heart is, and we can live the life we want anywhere. I share the same philosophy of simplicity with you and know that it doesn’t matter where I am that will keep that way.

    1. Thanks for sharing you perspective. It certainly is hard to make a lot of money in Hawaii. This is why I think everybody should start their own website. You don’t face a domestic local demand curve, you face global Internet English-speaking demand curve. as a result you can live wherever you want but has Internet access. This is how I planned my life and I wish more people would consider harnessing the Internet to plan theirs.

      Check out this post;https://www.financialsamurai.com/why-you-need-to-start-your-own-website-today/

  13. I made the opposite move! After 13 years living in Oahu, I moved to the Bay Area, Silicon Valley, to pursue a job offer in Telecom I’d never get in Hawaii.
    I had a great time in Hawaii, made some lifelong friendships but in my opinion, if you are in the productive years of your life, Hawaii is not the best choice of place to make a career. If you can invest in your own business you may be very successful but, speaking from a perspective of someone that wasn’t born there and have to actually pay rent and finance my own living, it’s hard.
    I was after “work-life ballance” more yhan I was after money. It doesn’t matter to live in Paradise if you gotta work for 8-10 hours straight and by the weekend you may have to do extra work to complement your income, or just to tired to actually go hike Koko Head! Lol
    I am happy I made the move, plan to visit every year, but I feel so much happier being done with work at 3:00pm or if I’m not feeling like going to the office, i just connect into the VPN (the Internet in Hawaii is too slow for VPN) of my company and work remotely half the day. My boss couldn’t care less where I’m workjng from and I get paid more for doing that.
    Depending on what your life goals are, the main thing is to find balance. Not all work, not all play.

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  19. I am considering moving to Oahu. My only concern is I am a single 30 year old white male. I wonder if it will be difficult to find a decent girlfriend.

    1. There are a lot of amazing looking women in Hawaii because there’s so much mixing of races. I think you’ll be fine, well, I guess it depends on how smooth of a character you are!

  20. I lived on Oahu, just for a year and a half and I have to say you are so right about the work ethic going down hill due to the lovely surroundings. There’s no sense of urgency to move ahead because everything’s already great. Hiking, kayaking, bbq’s, eating at delicious shrimp trucks was a lot of fun.

    I obviously never bought a home there but the prices seemed prohibitively expensive. If I worked in Honolulu I would want to live in Hawaii Kai for the traffic problems alone. But it’s culture is too bougie. And I totally understand why the locals are bothered by all these wealthy foreigners buying property that they themselves are having difficulty affording. It’s their home and it is becoming increasingly difficult to afford thanks to outsiders or ‘haoles’ hiking up the prices.

    Ultimately, I wouldn’t want to stay in HI for life as I feel too isolated on a rock in the middle of the ocean and island fever is REAL. Coming from the east coast I just couldn’t handle being on an island that I’ve thoroughly explored. I love road trips and exploring new places and after a while I became *gasp* bored of Oahu. I’d island hop too but after a while it all seemed to be pretty beaches and greenery. I also missed the 4 seasons which I know you didn’t love so much in the east coast but without them it’s almost as though you don’t notice time passing by, which I think also reduces any sense of urgency.

    Ok that’s my rant thanks so much for your blog, it’s a goldmine of great info!

  21. Wow you make it really sound like paradise but as a kamaina most people here do struggle making ends meet. Kamaina rates are few and far between and not that great anyway, cost of living is so high that a family of four with 100k income per yr would be living modestly at best. Strong feeling that everyone is on vacation here is probably how tourists and transplants feel, not locals. A lot of mainlanders try to move here thinking its paradise but soon find out it’s really difficult adjusting to the local customs and culture and end up moving back after a year or so.

  22. i first went to hawaii in 1996, working as a computer consultant back when no indian competition was around. honolulu was love at first sight for me. i loved walking around waikiki at night and watched the japanese tourists passing by.
    the white consultant i worked with made comments that hawaiian police would never dared touch japanese tourist. he called it “reverse racism”.
    i was borned in saigon south vietnam where at night before 1975 i could walk around the city and watched people for fun. waikiki reminded me of that old saigon i loved and missed.
    i have several attempts to buy waikiki condotel since 2010 but no luck.
    i have been to all 50 states in the united states and hawaii is by far my favorite.

  23. You’re definitely moving the right direction. I constantly hear about how expensive everything in Hawaii is, especially the food. Honestly, compared to the Bay area and dealing with the high prices here, Hawaii doesn’t seem so bad.

    Personally, I don’t like humidity. So while Hawaii is wonderful in the winter, the humidity in the summer is uncomfortable.

    Great place to visit, but I don’t think I’d want to live there.

    1. Everything in Hawaii is cheaper than San Francisco except for the food due to importation. But I love their papayas, pumelos, white puree mangoes, and Hawaiian food so that’s what I’ll be focusing on eating the most.

      Summers are hot indeed. Got to pray for the tradewinds.

  24. I haven’t been to Hawaii for many years, but what I remember it’s a very laid back atmosphere. I loved visiting Kauai – it was my favorite island – and remember talking to a young girl (my age at the time). I mentioned that we were staying at Princeville but were in Poipu (I think) that day. She was flabbergasted that we were trekking all over the island. To her, Princeville was so far away. She had never traveled much farther than Poipu. Coming from Los Angeles, I thought nothing of the distance and had trouble understanding her perspective. The Hawaiian Islands offer a different lifestyle than the mainland, especially the large metros. But I think I could get used to a slower and more content lifestyle.

  25. “Is there a correlation with weather, effort, motivation, and work ethic?” I definitely think so. Reminds me of the spring quarters in college when the weather turned nice. Nobody wanted to be in classes or hanging out in the library. You wanted to get outside and go play. Blowing off studies became too easy.

    I’ll second the shout-out to the Kahala…beautiful resort. And I’ll confirm the traffic issues around Honolulu. Thought I was back home in Atlanta’s rush hour traffic. My favorite parts of visiting Hawaii were seeing a large group of dolphins swim next to our boat on a sunset cruise and then flying over and hiking out to the volcano lava flows on the Big Island. Spectacular!

    1. Bingo on the school example!

      I wonder if Hawaii will have to go the way of Singapore and charge huge fees during rush hour and importation taxes. That’s really the only way to curb traffic as Honolulu isn’t building public transportation fast enough.

  26. Ben @ The Wealth Gospel

    Loved the article, Sam! I lived in Fiji for a couple of months and then vacationed in Hawaii a year later and the island life has drawn me like a magnet ever since. One day maybe we’ll make it out there to stay. We’ll be on Maui for Thanksgiving next year, though! Baby steps, right? :)

    I agree wholeheartedly that living in Hawaii would make me a little more content with a slower-paced life and therefore a slower-paced income. Why spend so much time working when you are surrounded by so much?

      1. Ben @ The Wealth Gospel

        I was working with a non-profit organization doing a number of different things like teaching business classes, square foot gardening, health, etc.

      2. Ben @ The Wealth Gospel

        And it was a really cool experience. We got to work in the villages during the week and play on the weekends.

  27. My husband and I relocated to Kauai in May of this year. We work for ourselves (web development) and are renting. Yes, gas is higher BUT we drive about 10-20% of what we used to drive back on the mainland, so overall, we’re saving money on gas. We eat a whole foods type diet so we’ve found that while food prices are marginally higher for meats, veggies, fruits — overall, it’s not enough to really cause us any worry. Plus, we quit eating out when we moved here so food-wise, we’re coming out way ahead. Another thing we quit doing was going to the movies. There are no mega theaters here (the only kind we like) so we just wait for the movie to come out on Redbox and watch it on our large tv. Right there we’re saving somewhere in the neighborhood of $30-40 per movie (tickets, snacks, etc).

    We’ve found that the only thing to really complain about (if one wanted to complain – I mean, we’re in Hawaii now… what’s there to complain about? lol) is the cost of electricity. We don’t have an AC unit or any central air/heating of any kind but our average utility bill is $280/mo. That’s for just 600kwh per month. Really outrageous. Our way of dealing with this is to turn off the hot water most of the time. We turn it on 30 mins or so before we want to use it and off again an hour or so later. This has cut our bill down considerably and we haven’t had to really adjust how we live (hot showers are not needed here…).

    We love it here and wish we’d relocated sooner. Prior to our move, we were “nomads” traveling the country in a travel trailer (as long as we have internet, we can work anywhere). After being put out of commission but a freak hail storm in northern TX, we made the decision to go to Plan B – Hawaii. We chose Kauai as we wanted a more laid back lifestyle w/out all the tourism and traffic that is so prevalent on Oahu.

    Re: our work — I don’t know that it has really changed since we moved here. I know we’re both more relaxes and less stressed so we get more done and any issues that come up as a result of being stressed out have pretty much died off. Since moving here, we’ve started walking every night – that’s new – so we both feel healthier and sleep better.

    We love the island life. We love the roosters (even those that crow outside the window at 4am). We don’t miss anything that we used to have in the larger cities we’ve lived in. But most of all, we feel like we’ve finally found home. After 22 years of marriage, this is the first place that we both feel is IT. There are no plans to ever leave this paradise. When work gets on our nerves, it’s a delight to hit the local beach and not see a million people there. It’s sometimes just us and the waves and in the end, that’s really what it’s all about to us. Peaceful tranquility, lush foliage, the scent of flowers on the daily breeze, the torrential downpours that come at a moment’s notice. This is home.

    1. Love the feedback! Moving from N Texas to Kauai must be the best move ever! Are you not shell shocked over property prices though? You can buy a nice house for $200k in TX but not so much in Kauai. Did you domicile your Internet biz in TX to avoid paying HI state taxes too? If so, that is a sweet move.

      I’m also curious to know if/when you’ll start getting island fever. I’ve got this 6months in Oahu, 3 months SF/Tahoe and 3 months traveling notion in my head for the future.

      1. We didn’t live in TX – we were just there for a month as we traveled the US. That being said, we were looking to make that our domicile later in the year – but with the travel trailer out, that changed. We’re actually AZ state residents and everything is registered there. We’ll be switching it all to HI now since we’ve made the decision to live here full-time.

        I have had gypsy fever most of my life. Thus our decision to move into the trailer and travel. That way we could go anywhere as the mood struck. Surprisingly, this is the first time EVER that I can recall being somewhere over 6 months and not feeling the move to go elsewhere. We made plans to go to WA state for Christmas (family there) but now that we’re on the eve of leaving, we’re both feeling saddened to be leaving. We were really looking forward to Christmas under the palm trees.

        It’s like where we’re at is what we were unconsciously looking for our entire marriage. I’m not saying we’ll *never* get island fever — but certainly not as quickly as others have thought we would. We love our life here. It’s simple and basic and we’re super duper content. That being said… we have plans to go to New Zealand for a month or so sometime in 2014. We have this burning desire to visit there and experience a few weeks in Kiwiland! Travel is always a great idea ;) Your plan sounds good to me.

    2. Hello,

      Thank you for your comments. Can you give me an idea of housing costs in your area for renting?


  28. Mele Kalikimaka, and Don Ho Ho Ho!

    “No matter what religion you are, have a Merry Christmas!” – Steve Martin

  29. Yes, nice article! And oh so true. The gas, among other things, is expensive but on a positive note, we don’t have very far to go. Maybe the occasional trip to the other side of the island, but it’s not very far–not compared to the mainland, at least.

    The issue for us is that my children do not know another season besides summer. It’s Christmas week and they are at the beach with friends. Their goal is to get to the east coast to see “the leaves change color.” My daughter spent this fall in Europe and can’t stop talking about the beauty of ‘leaves’ — but once the temperature dropped into the low 40’s, she couldn’t take the cold and had to come home!

    I guess the grass is always greener elsewhere, but even with the high prices, I’m happy where I am. If I want to see “leaves” or culture or go shopping, I can always go on vacation. Wherever you may be, life is truly what you make of it! Here’s wishing happiness to all! Peace.

  30. I think you can become complacent no matter where you are, but worse in nicer/expensive places. I don’t have much experience with Hawaii, but we’ve had people with a master’s degrees in business, biochemistry, and health care administration apply for receptionist jobs there. You live with three or four roommates, make enough to eat, pay rent, and go out to the bars. Find a way to get Pro deals on all your gear and work enough hours at an employer who offers a ski pass and you’re set. However, most people grow up and move on to somewhere more affordable when they actually want to have a family and settle down.

    1. Hard to move anywhere else though once you’ve been accustomed.

      Seems like the lesson from your anecdotes is to NOT move to Hawaii if you’ve got graduate+ degrees because they have a lower chance of being fully utilized.

  31. Sounds like a dream Chuck! What is it that you do exactly in Maui?

    I wonder if Maui Jim’s is hiring?

    To my thesis, given it’s hard to start a business in Maui, if you can start a successful business in Maui you can start a successful business anywhere!

  32. This is a great post Sam. I was in the exact same situation – and although I wish I could say I packed up my bags and moved to my dream city, I can’t. I did change fields after the market crash in 2008 from investment planning to corporate communications, but I think a part of me will always wonder – What if I moved away and started over? Where would I be and would I be happier?

  33. It is definitely harder to continue chasing the “almighty dollar” if you live in a fantastic environment!! But is that such a bad thing? At what point should you “slow down” (whatever the heck that really means), breathe deeply, and enjoy life to the fullest?! I am always fascinated with the question of, “enough”… I have met with several millionaire entrepreneurs (50s) on the east coast who wish they had exited the “accumulation phase” sooner in order to figure our what makes them (and their families) happy.

    It’s interesting that in the end – the things that make us most happy don’t cost that much: good food, peace of mind, exercise, challenging work and quality relationships… :-)

    I really loved your “tone” in this post Sam. I am very encouraged that you are continuing to discover what the “good life” means for you!! Cheers!!

    1. Living in a fantastic environment is certainly great. I just wouldn’t want to START living in paradise. Starting at the opposite end will allow for a longer lasting appreciation of what we have. It’s really the journey that’s most rewarding because all we know is what we experience.

      It’s so easy to take things for granted. Better to have more perspective.

      Thanks Nate!

  34. Vivek Gupta


    I started reading your blog very recently & wanted to congratulate you for maintaining such a useful blog. Each of your blog entries are very well researched, useful & entertaining.

    Keeping writing such useful stuff.

    Vivek Gupta

  35. Hawaii is awesome. I love NYC too but I’d pick Hawaii over Manhattan in a heart beat. I can totally understand the distraction element of living somewhere warm and beautiful and wanting to be outside all day instead of inside at work. I guess finding a job that allows you to be outside in Hawaii would be ideal. But it can get super hot too in the middle of the day so being outside isn’t always better.

  36. Living in southern California, I just do not understand the fascination with Hawaii. We went with friends years ago to Maui for a week in August. We enjoyed it, but not enough to return. I guess it is because we get enough hot weather and beautiful scenery. Almost all our vacations have been to Europe, if I exclude our summers at the beach in southern California.

    I definitely agree there are many obstacles t the good life in Hawaii. Insufficient pay, high housing prices (similar to California) and food prices (groceries & restaurants). I even saw ads for teachers with salaries of $100k. Not enough to live well!

  37. Done by Forty


    I hadn’t thought of it in that way, but I had similar experiences when I lived in San Diego for a decade during my twenties. I was all too content to make $40k or so at my government job, hang out on the beach, play kickball, and drink. It was a great life. Only when I moved to Arizona did I find the drive to get ahead financially.

    Like you said, the glory goes to he who fights temptation. But I wouldn’t mind moving back to SoCal someday.

    1. Must have been nice down there! But were you itching to leave after a while? I’ve got to imagine SD is much nicer than anywhere in Arizona no? The good thing about AZ are housing prices though.

      I experienced Laguna Beach and Newport Beach for the first time last year. Amazing. Exactly what you think about when people refer to California. Might have to go explore over there more. But I like the diversity of Hawaii better. It feels like home because that’s where my family is.

      1. Done by Forty

        My wife is pursuing her PhD in Arizona, so that brought us here from San Diego. On the plus side, AZ has been fantastic to us financially and I’ve grown to really like it. But I’m not picky. I think I’d be pretty happy regardless of which city we end up living in.

        We visited Oahu last year and had a great time. Took Da Bus up to the north shore to check out the wave and ate some Thai at Opal’s…one of the better dining experiences we had. We’re going to the Big Island in February and can’t wait. Hawaii’s a pretty awesome place — glad you get to be with family there.

  38. thepursuitofriches

    I moved to NYC 2 years ago, and coming from a small town and a tiny European country, I completely agree: brutal city, trying to knock you down daily. And although it gets too hot in summer and too cold in winter, I see resemblances with what you state about Hawai: this city is distractive. Yes, the workload is heavy and the hours are long, but there’s always a party, always a free event, always someone inviting you for brunch and so, so much to see! I think everyone eventually finds his or her place on this planet, whether it’s NYC after a painful battle, or Hawai after enjoying the weather to the max.

    1. Great point about lots of distractions in NYC as well! What a great place to be. Love your last line about everyone eventually finding his or her place on this planet, even if such a place is in the MidWest or Canada during winter.

  39. charles@gettingarichlife.com

    Sam it’s a myth that people who live at home are saving a lot of money. Majority of them have some saved up but usually have lifestyle inflation. No one puts down 20%, usually 10 as a first time homebuyer.
    By 2018 or 2019 the median house price is projected to be $1 million dollars, at that point I don’t know how people starting out will afford a place.
    You also missed about how people are more genuine here and really do watch out for each other. In the Bay Area I had such a different vibe.

    1. You sure about that? Did you not save up to put 20% down or was it less?

      Seems to be easy to save money if you live with your parents.

      If the median house price is projected to be $1 million in HI, shouldn’t we all be buying and getting rich? Why would anybody rent then if they could buy?

      Hard to get everything from a 2,200 word article, but I did emphasize family. And when I think family I think people watching over each other. Each person’s experience is different?

      1. Charles@gettingarichlife

        Sam I got in my first property at 5%, second 6%, my current house was over 20 but we borrowed against other properties for that. The wife’s unit was over 20 thanks to help from her parents.
        Most of the people I know save maybe 5-10% to get into a home as there is a lot of first time home buyer programs that required 5 to 10%.
        We just had a friend buy a 400K townhouse with only $15,000 down. What happens is the money they save living at home they spend some of it going out and enjoying life. Very few people I now that bought houses put 20% down, and the few that did parents gave them half

        1. Hmmm, I guess on the one hand it’s good to hear banks are lending with only 5-10% down. In the mainland, 20% or more is required, well at least here in the Bay Area. It has always seemed a little backwards to me that those with the least amount of financial reserves get to leverage up the most.

          I definitely believe in plenty of help from the parents in buying a home in Hawaii. It’s generational wealth and buyers need to know they are competing not only against one person.

  40. harry @ 4HWD

    Well as you know, I just got back from Kauai and you’re right on. Food is definitely more expensive but I love Hawaiian food: fish, poke, katsu, etc In fact, my whole trip kind of revolved around where we were going to eat haha. I actually forgot how expensive food was/is but there are so many free activities on HI like you mention. I try to avoid the helicopter rides and fancy tours in favor of snorkeling, hiking and exploring.

  41. Okay, first things first. Nobody anywhere in North America is ever entitled to complain about high gas prices!

    Now that’s out of the way … the lifestyle is a lot slower paced in Hawaii though right? In the Cook Islands life is sweet and anything that’s not produced locally costs a bomb (which is almost everything) but it’s so slow – island time. It’s all about leisure.

    1. Funny that is the one thing you pointed out that consisted of one line in this 2,200 word article! There wasn’t even a complaint just a comparison to mainland prices! Are high gas prices a sore spot for Kiwis? :)

      Yes, the lifestyle is slower, even the speed limit of 50mph on the highway. Takes time getting used to, but not so much for me anymore.

  42. Great article Sam; I’m hoping to make it to Hawaii sometime in the next two years.

    I also started my career at Goldman. You missed the new 200W building, which was awesome, and now I’m at the Blackstone Group. I’m curious to know which bank in San Francisco you went to after GS. Can you divulge?

    I definitely agree with you though that it’s expected to be working long hours in NYC. Between the free food and your employer’s expectations, you often find yourself leaving the office past 9pm. I’m hoping when I move out of NYC, I’ll have an easy time finding a job since it’s the center of the US financial markets.

    Enjoy Hawaii!

    1. I have definitely heard some amazing things about 200W! You’ll never have to leave the building again with those facilities yeah?

      I think you’ll get one shot at leveraging NYC on your resume. As soon as I’m done receiving all my deferred comp I’ll be more open to discussing my previous employer. Never quit Blackstone Group OK?

      1. Sam – you should do a post on defferred comp. This allows you to trickle income over years to dodge the higher tax rates? Wow u must have cleaned house, just read another post where u are pulling 36k in CD income, I’m in the wrong business!

        1. It took 13 years of aggressive saving to accumulate a 36K/year CD income. And after all this time, the income will go down as the 7-year CDs come off. Rates are currently only around 2.5% at best for a similar long term CD, so I’m looking to reinvest elsewhere.

          If one can smooth out their compensation, all the better due to taxes. I think the ultimate income is roughly $200,000 for tax purposes and lifestyle combination.

          What business are you in?

        2. >> What business are you in?

          Im in tech, in my mid 30’s and earn just over 100k/yr. Currently socking away 50% of that income (401k, IRA, HSA, taxable- CDs/savings). I guess grass always seems greener on the other side. Tech there is plenty of chances to make it big (get lucky with startup IPO I suppose), I feel finance, esp wall st., bonus money paid out is huge. GS avg bonus tends to be twice what the average american makes in a year. Im just a line worker must go into management to earn 150-200 and beyond. It will probably take me at least another 10 years to obtain your level… I suppose if I really want it I could go management route or gamble with an IPO…

          1. Joe,

            If you can sock away 50% of your income, that’s really all the matters. You’ll be financially independent in no time.

            Yes, Wall St. compensation is large relative to other industries. The good thing is that America is a free country and if they wanted larger compensations, they can always apply to join a financial services firm.

            I’d shoot for the management track. Nothing to lose!

        3. Thanks Sam for the vote of confidence. I will however respectfully disagree with you about anyone joining financial services, at least earning incomes you obtained. I recently obtained a master degree in my technical field. Before hand I highly considered the management track, that is going with a MBA program. What I found is MBA’s are dime a dozen unless its a top 10 school and Wall St. seems to only hire from top 10. I’m certain my undergrad GPA and GMAT wouldn’t be enough for a top 10 school acceptance. Sure maybe this is just a detail that the MBA could still enable someone to eventually earn $200k+ at a regional bank, non-wall st firm, etc. But even those positions are still highly competitive, require 10+ years exp on top of the MBA credential, etc. IMO only doctor is only a sure bet, but after factoring school debt 200k is not 200k.

          1. I think anybody who has enough drive can get into a top MBA program to join a Wall St. firm. Don’t sell yourself short. You’ve got to believe to make it happen.

            I went to a non-target state school and got into Goldman Sachs in their WHQ in the Equities department. It was a front office job as opposed to back office. Anything is possible. But it starts with self belief.

      2. Sorry for making this thread so long! Thanks again Sam always good view points. In a piece of irony, yesterday, I read Jim Cramer’s book Confessions of a Street Addict. Jim made 1 million per year in his forth year at GS — this back in the mid 80’s, impressive. During the interview process they made him wait hours before eventually telling him to leave because the building would be locked up for the night. I don’t know if it was you or some other source, but I heard GS does that even today. See who is that dedicated or something.

  43. We love Hawaii. I guess everyone does. Can I get on the list for the offsite team building? The housing price is high, but we can probably swing it. I’m more concern about the higher cost of food and fuel. We’ll keep our option open, but we’re leaning toward Santa Barbara at this point for our retirement destination.

    1. I really think you need to spend at least $800,000 in Oahu to get a house you’d enjoy in a location that’s not too far away even though the median says $575,000.

      Everybody who works for over 500 hours for my company a year will get on the list for the next offsite for sure!

      1. We’d probably go for a more rural place in Hawaii. Honolulu area is pretty busy. Far away would be fine as long as we have good internet connection.

  44. Money Beagle

    I’ve been to Hawaii once, for our honeymoon back in 2007. We spent a few days in Maui, then a few days in Waikiki right in the center of it all. The thing that blew my mind was the existence of an ABC Shop on every block, sometimes more than one.

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