How I Eventually Came To Call Hawaii My Home

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A Dream Deferred

I first fell in love with Hawaii as a teenager, when I made my first trip to Oahu with my parents and sister. We stayed at one of the Outrigger hotels (knowing my dad, I’m sure it was the cheapest one!) near Waikiki Beach and did what many first-time visitors do: We swam in the ocean, people-watched on Kalakaua Avenue, snorkeled in Hanauma Bay, ate Dole Whip cones at the Dole pineapple plantation, marveled at the kamikaze surfers tackling the ginormous waves off the North Shore, scored free shell necklaces at Hilo Hattie, tried the free hula lesson at the Royal Hawaiian Shopping Center, and watched the Friday evening fireworks at the Hilton Hawaiian Village.

My parents didn’t seem overly impressed. My mom found Waikiki too crowded, and my dad — our rental-car driver — complained that all the street names were unpronounceable and looked alike to him. But for me, I had found my slice of heaven. Here was a place where it was summertime all year long, fragrant flowers grew everywhere like weeds, tropical fruit was the cheapest produce in the market, and the ocean was actually warm enough to swim in! I, the girl who grew up in San Jose, California, and deemed it “too cold,” had found my balmy paradise.

And so my dream of one day moving to Hawaii began and continued for the next 20 years. First I had some growing up to do back in California. I had college to finish, careers to try, boyfriends to date, and parents to become independent from.

Then in 2006, my friends Andrew and Masae invited me to their wedding on Kauai, where Andrew’s parents lived. I jumped at the opportunity to go back to Hawaii, and to experience a different island. Those four days I spent on Kauai revived my dormant dream, and I started to think more seriously about moving to Hawaii. I realized that I was now in a place in my life, financially and emotionally, where I could make this dream a reality if I truly wanted to.

A nice gig, If you can get it

I knew my biggest obstacle in moving to Hawaii would be finding a job there that paid well enough so I could afford the high cost of living. At the time, I was working as a copyeditor for Yahoo! in Sunnyvale, California. After briefly surveying the job listings on Craigslist Hawaii, I was shocked to discover how low the posted salaries were. I quickly realized that, while the cost of living between the San Francisco Bay Area and Honolulu is about the same (among the highest in the U.S.), I would not be earning nearly as much doing the same type of work for a company in Honolulu as I was in Sunnyvale.

How the heck do people survive there? I wondered. Do entire families live in studio apartments? Are there slums I don’t know about? Does everyone work two or three jobs just to make ends meet? Are there better-paying jobs that only the locals know about? The only jobs I saw on Craigslist that seemed to pay a decent wage were for military personnel and techie people., and I was neither.

Then I had an idea: If I could somehow convince my employer to let me work remotely from Hawaii, then I would have the best of both worlds: A California salary and a Hawaii home. I was already working one day a week from home, and all my copyediting work was done online. My idea made perfect sense to me, but would I be able to convince my manager to let me do it? I had serious doubts.

What’s the worst thing that could happen if I asked? I wondered.

I could be told “no.”

I concluded that I had nothing to lose (except maybe a little pride) and a lot to gain, potentially.

However, before I approached my manager with my proposal and risked becoming known as “that crazy woman who had the gall to ask if she could work from Hawaii,” I wanted to make one more visit to Hawaii to be absolutely sure that I could see myself living there as a resident, and not just vacationing there as a tourist.

I knew from my last visit that, as glorious as it was in all its natural beauty, the island of Kauai was too rural and quiet for me to live there long-term. I wanted to be in a big city with lots going on, where I wouldn’t suffer a huge culture shock after living all my life in Silicon Valley suburbia. There was never really any question in my mind that Honolulu (by far Hawaii’s largest city), on the island of Oahu, was where I wanted to live.

So in January 2010, I took a week off from work to revisit Oahu. I was concerned that maybe Honolulu had changed (for the worse) in the 20 years since my last visit, or that my grown-up self wouldn’t like it nearly as much as my teenage self did. Or maybe I would find that the “real” neighborhoods — where the residents lived — were not what I had in mind and that what I really liked about Honolulu was being a tourist in a Waikiki hotel.

To test the validity of these concerns, I made sure I stayed out of the Waikiki area during my daily explorations of Honolulu so I could see where the locals lived. I rode the public bus and walked through different areas of Honolulu, all the time asking myself if I could picture myself happily living there. I noted which neighborhoods I liked, and which I didn’t.

As I explored various residential areas of Honolulu, I mentally went through my typical daily and weekly routines: If I were living in this neighborhood, where would I buy groceries? Where would I work out? Is there a library nearby? Is there a theater that shows the indie movies I like? Does this place cheer me up, or depress me? Would I likely meet people here, or would I feel socially isolated?

When I returned from that trip, I felt confident that I had identified several neighborhoods where I could see myself living the life I’d dreamed of. I could also foresee some of the sacrifices I would need to make to live in Hawaii (no Trader Joe’s!), and the challenges I’d have to accept (making new friends), and I felt ready to do that.

When I went back to work, I worked up some courage, pulled my manager aside, and made my proposal about working remotely from Hawaii. To my pleasant surprise, she didn’t laugh in my face, and in fact, gave me some hope that it might be possible. Of course, she had to ask her boss next, and then he had to ask his boss, all the way up the chain of command. I didn’t get my hopes up while I waited for the final decision to be handed down.

The answer came about a week or two later. I was in the middle of my regular weekly meeting with my manager, when she casually mentioned, “Oh, by the way, upper management gave you the green light to work from Hawaii.”

And with that one sentence, an ordinary Wednesday afternoon turned into a life-changing moment.

If It’s too good to be true

After being granted permission to work remotely from Hawaii, I spent the next few days in a state of bliss. And then the reality of the situation dawned on me: I was moving. In a few short months. Across the ocean. And I had a house to pack, a new rental home to find, two cats to prepare for entry into a rabies-free state (more on that later!), flights to book, moving services to research … aack!

The next few months were very busy ones, indeed. My first priority was getting my cats, Alice and Amy, vaccinated and tested for rabies — a detailed process requiring several months to complete — so they wouldn’t have to be quarantined for four months upon entering Hawaii.

My next task was to find a rental home — not an easy feat when you live 2,394 miles away. Plus I had a couple other factors working against me: (1) I had pets, one of whom refused to stay indoors; and (2) I wanted to try living without a car in Honolulu.

I dug through the rental listings on Craigslist Hawaii every day, looking for a place that allowed outdoor cats, was in a location I could walk to without too much difficulty, and was priced within my budget. Oh, and it also had to be in one of the neighborhoods I had liked during my last scouting trip. Um, sure, no problem!

Well, except that more than half the listings specifically stated “no pets.” And half of those did not allow them to go outside off-leash. And wouldn’t you know it: Many of the homes in the neighborhoods I liked were located on hills that required a long, hard hike to reach on foot. D’oh!

I was starting to lose hope that I would ever be able to find a place to live. And then I spotted a listing for a house that shocked me — in a good way. It was located in the upscale Kahala area, where rental homes are typically way beyond my budget ($3,000+ per month), so I was shocked to see that this listing was asking for only $1,200.

What’s the catch? I wondered. The photos showed a beautiful, well-kept home. It was located just a couple blocks from the beach. Pets were OK. Hmmm.

Maybe $1,200 referred to a weekly rent? I wondered. Yeah, that had to be it.

But just to be sure I wasn’t missing out on a ridiculously great deal, I emailed the owner to ask.

I soon got a reply from a “Mr. Philip,” who stipulated that he was looking for a “God-fearing” person who would take good care of the house while he was on a job assignment for four years in Buffalo, New York.

OK, I thought, so maybe this guy is one of those rich eccentrics, and he doesn’t care about making money off the rental. He just wants someone whom he can trust to live in the property while he’s far away in New York.

In his reply email, Mr. Philip had also asked me to tell him more about myself, and to fill out an attached rental application. I eagerly did so, hardly believing my good fortune in finding this listing.

The next day I received another email from Mr. Philip, telling me that he and his wife had discussed it, and had agreed to take me on as their tenant. They would send me the house keys via courier as soon as I had paid them the typical deposit of first and last month’s rent.

I was beside myself. I could already envision my friends and family visiting me in my beautiful new home — we would play in the pool, stroll a couple blocks to the beach…

Without giving it a second thought, I dashed off to Western Union to wire the deposit to Mr. and Mrs. Philip in Buffalo, New York. I was already mentally planning ahead: As soon as I got back home, I was going to book a flight back to Honolulu to go see my new house first-hand.

But when I returned from the Western Union office, I first decided to do a quick Web search on this Mr. Philip, just out of curiosity. I found only one brief mention of his name — apparently he and his wife were on a donor’s list for a hospital-related charity in Honolulu.

Then I took a look at the website of the courier service that Mr. Philip had told me he’d be using. He had emailed me a link to a site where I’d be able to track the delivery of the house keys. But when I saw the site, it looked surprisingly amateurish. I clicked around, trying to find the section where users could track their deliveries. I found no such function. In fact, the site didn’t appear to have very much information at all on it, although it did list a phone number at the very bottom of the homepage. With a sinking feeling in my stomach, I immediately did a Web search on the phone number.

I felt sick when I saw the search results. All of them were warnings of a scam operating out of the U.K. and Africa. The phone number I had entered was one of several that the scam artists used.

I immediately got on the phone with Western Union to see if there was any way I could put a stop on the money wire I had just sent. I was told there was, as long as the recipient hadn’t already picked up the deposit.

I held my breath while the phone rep checked on the status of the wire, mentally berating myself for being so gullible and allowing my emotions (namely greed) to cloud my judgment. Why on earth would I wire money to someone I knew only through a couple of emails? How could I be so stupid? I had ignored all the warning signs so I could continue believing what I wanted to believe. Never before had these words rung truer: If it’s too good to be true, it probably is.

When the phone rep returned on the line, he told me that the money had not yet been picked up and he was able to cancel the wire. I was flooded with relief, realizing what a narrow escape I’d just had. I would never have guessed that I would fall victim to an online scam.

But I did. I had underestimated the power emotions can have over judgment, and the cunning of Internet scam artists.

I later discovered that the description, address, and photos of the Kahala home in the fictitious listing were copied directly from a legit real estate site, where the house was listed not for rent, but for sale.

The actual asking price? $2 million.

hawaii my home

House hunt take 2

After my close call with the rental-ad scam artists, I learned it was critical that I view prospective rentals and meet with the owners in person. So I booked a flight back to Honolulu, made a reservation for a week’s stay at a cheap Waikiki hotel, and set off on a mission to find my new home.

Armed with my laptop, I positioned myself every morning on a couch in the breezy hotel lobby, pouring through the rental listings on Craigslist Hawaii. I made phone calls and email inquiries, set up viewing appointments with owners and leasing agents, and rode the bus to check out various properties.

After a few viewings, I felt discouraged. Although the rental prices were comparable to those in the San Francisco Bay Area, the properties were not in as good of condition. I realized that if I were to stay within my budget, I would need to accept the wear-and-tear that seemed to be common in the older homes that fell within my price range.

I was particularly interested in the Kaimuki neighborhood, which had a main street full of mom-and-pop stores and restaurants and was very walkable. But I noticed that the small houses in that older neighborhood tended to be packed tightly together. It was typical to see two, three, or even four cottages sharing a single lot. Privacy certainly commanded a premium price in Honolulu.

If it weren’t for my cat Amy, who goes nuts when forced to stay inside (we’re talking literally climbing the walls, scratching holes in window screens), I probably would have opted to rent a condo instead of continuing my search for a home with a yard. But I couldn’t imagine Amy living in a high-rise apartment (except maybe flinging herself off the balcony!), so I kept looking.

Toward the end of my week’s stay, I decided to revisit the very first property I had looked at. At the time, I hadn’t been very impressed by it. Although it was a large, detached house and had its own backyard, it was very run-down: The flooring buckled in places due to extensive termite damage, the sliding glass doors leading to the balcony and the backyard were very difficult to open and close, the kitchen had no refrigerator or oven…

And the location was on a steep hill.

But having seeing several other similarly delapidated homes during the week, this house’s advantages now stood out more clearly: It had lots of privacy, with no other houses on its lot. It was located in the upscale neighborhood of Waialae Iki, which I could never afford if the house were in better condition. And it had a view of the ocean that made my draw drop the first time I walked through the front door.

Also important, the owner/landlord and I had instantly “clicked” when we met. He was friendly and down-to-earth, and was willing to install the appliances that were missing in the kitchen. I went back to the house to visit a second time, and even though I was out of breath and dripping with sweat after hiking up the hill to get to it, the place felt “right” to me.

Of all the homes I had seen that week, this was the one that I could actually picture myself happily living in, and its flaws were ones I could live with. It met my most important criteria: in-and-out privileges for my bratty cat, privacy, a safe neighborhood, a landlord I could work with, and within my budget. The only major downside was the steep hill.

I could foresee the purchase of a moped or small car in my near future.

I left Hawaii at the end of that week with a lease agreement in hand, and with a move-in date just a month away.

Rolling up my sleeves

Even though my new lease’s move-in date was one month away, I wouldn’t be able to bring my cats into Hawaii for another two months (to avoid the quarantine), but I figured it would be good for me to get the house set up first before bringing them over. And now that I had my new address, I would be able to start shipping stuff to Hawaii.

Fortunately, my landlord was currently living in my new house, and he was amenable to bringing in any packages I shipped over there before my official move-in date. Initially, I planned on taking few belongings with me to Hawaii, because I had heard how expensive it was ship things there. Plus, my new rental came furnished, and I’ve always subscribed to the “less is more” philosophy.

But then I found out that I could ship boxes via FedEx at work, using the company’s hugely discounted rate. So I decided to ship more stuff than I had originally planned, because it would be cheaper to do that than buy new replacements once I got to Hawaii.

Thus began the long, tiring, and tedious process of boxing up and shipping my household overseas. Every night after work, I would come home and pack a few boxes and bring them to work the next day so I could ship them from the company’s mailing room.

Each item I packed had to meet three criteria:

  • I truly needed or wanted it.
  • It could fit inside a box that I was able to haul to and from my car.
  • It would cost more time and money to replace it in Hawaii, rather than ship it right then and there.

I decided I would donate whatever didn’t meet these qualifications (like my car, large furniture, and winter clothes) to friends, family members, and charities. I was just too tired and overwhelmed to hold a garage sale or sell a bunch of stuff on Craigslist or eBay.

A month later, when my move-in date arrived, I took my third trip that year to Hawaii (it’s a good thing I’d saved up a lot of vacation time at work!). This time my mission was to unpack the boxes I’d already shipped over to the new house, and buy whatever else I’d still need once the rest arrived.

Because I knew I’d be doing some serious shopping, this time I rented a car for the week. When I arrived at the house, my house keys were hidden in the secret spot where my landlord told me they’d be. I opened the front door, excited that my dream of a home in Hawaii was finally coming true.

But within a few minutes after entering, my enthusiasm started to wilt. The house was hot and stuffy from all the windows having been shut. I started to worry that I was going to seriously regret not having air conditioning. When I tried to open all the windows, some of them wouldn’t open all the way because their old-fashioned cranks were so aged and rusty.

Suddenly the house looked exceedingly old and decrepid, like everything was about to fall apart. I wandered from room to room, looking at all the furnishings that the house came with, much of it clutter that I didn’t want. I had a huge amount of work ahead of me to get this house set up the way I wanted, but I was so hot inside the house that I just wanted to flop down and cry.

What did I get myself into? I lamented. Did I make a terrible mistake in renting this huge old house that requires so much work? Should I just cut my losses, call my landlord, and tell him I changed my mind?

I sank down on the second-hand sofa, feeling completely overwhelmed. I allowed myself a minute to shed a few tears and feel sorry for myself. Then the stern grownup in me took over.

Buck up, I told myself. You got yourself into this situation, and now you just have to make the best of it.

I remembered my mom’s advice on how to tackle an enormous task: “How do you eat an elephant? One bite at a time.”

And with that in mind, I got off the couch, changed into some shorts and an old T-shirt, and started getting my house in order.

After spending some time cranking open as many of the levered windows as I could and strategically placing portable fans in different rooms, the house began to feel a little cooler, I started to relax and feel better about my situation. It was already getting late in the afternoon, so I made up my bed, took a shower, bought some groceries to make dinner, and determined that I would start fresh the next day, taking one “bite” out of the elephant at a time.

By the end of the week, I had unpacked everything, stored away all the clutter, bought all the odds and ends I still needed, and set up each room the way I wanted. There was food in the fridge, cable TV installed, wireless Internet set up, a new state ID in my wallet, and even a litter box waiting for Alice and Amy in the laundry room.

Mission accomplished. The most labor-intensive part of my move was over.

Now I had just one more trip to make to the Bay Area so I could pack up the rest of my house and prepare my cats for their first airplane ride.

Aloha alice and amy

One of the hurdles I faced in moving to Hawaii was completing the set of requirements outlined by the Department of Agriculture so my cats would not be quarantined upon arrival in Hawaii. It took me eight months to complete all the requirements: two rabies vaccines administered months apart, a blood test submission, a health certification, and a vet-administered tick treatment.

Once I submitted Alice’s and Amy’s blood tests, Hawaii’s Department of Agriculture was able to calculate the date on which they would become eligible to enter the state without being quarantined: August 4. So that became our official moving day.

Next I had to decide how to transport my cats. I dreaded the thought of them traveling in a commercial jet’s baggage hold, but because there’s a quarantine checkpoint that all animals must go through when they arrive in Hawaii from the mainland, pets are not allowed to fly in the cabin of any commercial airline (except for service animals). This way, as soon as the plane lands, the baggage handlers can take your animals directly to the airport’s quarantine holding station for processing.

On moving day, despite my best efforts to make the trip as comfortable as possible for Alice and Amy, they were terrified during the whole air-travel ordeal. I think all the unfamiliar people and noises in the airport frightened them more than anything. I remember holding Alice while a TSA agent inspected inside her pet carrier for any hidden bombs and such. I could feel her shaking, something she’d never done before, even during vet visits.

But at least my careful preparation in completing all the Department of Agriculture’s requirements paid off. When we arrived at Honolulu Airport, I had to wait only a few minutes to get my cats back from the quarantine holding station. When they were brought out, Amy and Alice were hunkered down in their carriers, looking shell-shocked and quite displeased.

After a 15-minute taxi ride to our new house, I brought them inside and was finally able to let them out of their carriers. I immediately saw (and smelled) that Alice had soiled herself, so off to the laundry sink we went to give her a bath — the first (and hopefully last) she’s had. She was not a happy camper, and after several claw-bearing escape attempts, neither was I!

In the meantime, Amy had gone straight downstairs and hid under the first bed she could find. As soon as Alice was done with her bath, she followed suit. I left them alone for a while, so they could get used to their surroundings. With some coaxing, they eventually came out from under the bed and, creeping low to the ground, sniffed all over the house.

They soon became interested in looking out the windows that faced the backyard (and beyond that, the Pacific Ocean). This view was certainly different from our last house, which was a single-story home whose view didn’t extend beyond the fruit trees in the backyard. I can only imagine what my cats thought when they first saw that big blue swath of ocean on the horizon…

Amy goes AWOL

Three days after my cats arrived at our new home, Amy (the outdoorsy one) got too adventurous in her exploration of the new neighborhood and went missing.

At first I wasn’t too worried — she had wandered off before at previous places we’d lived at, but always returned within four days. So after a week had gone by and there was still no sign of her, I became concerned.

I wandered up and down the hills of my neighborhood, calling for her. I printed out flyers and put them on my neighbor’s doorsteps, asked anyone I met along the way if they’d seen her. I called up the microchip-tracking service to report her missing, and filed a missing pet report with the local Humane Society.

After seven weeks, I decided to make a last-ditch effort to find Amy. I knew if I were able to show a photo of her to the vast majority of residents in my neighborhood, someone was bound to recognize her (assuming she was still alive).

However, my previous canvassing of the neighborhood had proved difficult, due to the hilly terrain and steep driveways in my neighborhood. Distributing flyers to just a dozen houses left me exhausted. So decided to enlist the help of the U.S. Postal Service.

I went online and ordered postcards from a direct-mail service with Amy’s photo and my phone number printed on each. I then had the postcards sent to all addresses within a one-mile radius of my house.

About a week later, my “Lost Cat” postcards began arriving in my neighbor’s mailboxes. Or at least that’s when I started getting phone calls, many from people who had not seen Amy, but wanted to express their sympathy.

After four days of well-intentioned but ultimately fruitless phone calls, I got a voicemail from a woman named Bonnie, who said that a cat that looked just like the one the postcard had been hanging around her backyard every evening for the past month. When I called her back, I discovered she lived only a quarter of a mile away from me.

Within two days, Amy and I were reunited. She was a little thinner and sans collar, but not too shabby for having been on the lam for seven weeks! Having learned my lesson, I promptly bought a tracking device to attach to Amy’s collar so I wouldn’t have to go through this experience again the next time she decided to “go on walkabout.”

As harrowing as the experience was, it did prove to be a good way to meet my neighbors. Bonnie and I still keep in touch — in fact, I recently helped her with a fundraiser at her son’s school.

I count myself fortunate to not only have found my cat, but also a new friend.


I’ve now been living here in Honolulu for eight months. During that time, I’ve:

Tried traditional Hawaiian foods: lomi lomi salmon, poi, haupia, kalua pork, lau lau, chicken long rice, and poke

  • Tried less-traditional Hawaiian foods: Spam musubi, Leonard’s malasadas covered in li hing sugar (not as good as the plain sugar ones), nearly all the flavors of Bubbies mochi ice cream, pink guava bread (meh), shave ice covered in green tea powder and azuki beans (to die for), and acai bowls from four different establishments
  • Hiked to the top of Diamond Head Crater
  • Learned to pronounce “Kalaniana’ole Highway”
  • Seen some crazy-looking, giant-pod-bearing trees at the Ho’omaluhia Botanical Garden in Kaneohe
  • Checked out the fledgling standup comedy scene in Chinatown
  • Was introduced to one of the most awesome supermarket/department store chains ever: Don Quijote
  • Been to the most awesome farmer’s market ever: KCC Farmer’s Market
  • Tried sea kayaking for the first time (and spent most of the time capsized)
  • Learned not to go swimming at Waikiki Beach 10 days after a full moon
  • Attended the series premiere of “Hawaii Five-o” on Waikiki Beach (mainly to see Daniel Dae Kim)
  • Surrendered to the hill I live on and bought a little car
  • Hosted 11 houseguests
  • Hiked for four hours through thick mud on the Laie Falls Trail (thanks, Vera!)
  • Taken an introductory hula class
  • Visited the USS Arizona Memorial at Pearl Harbor
  • Spotted migrating humpback whales from my living room window
  • Rescued numerous geckos from Alice’s clutches
  • Been eaten alive by mosquitos in Waimea Valley
  • Become immune to the sight of flying cockroaches
  • Thoroughly enjoyed wearing “slippers” (flip-flop sandals) all day, every day
  • Experienced my first tsunami warning (and learned to appreciate living on a hill)
  • Visited a gazillion beaches: Waikiki, Ala Moana, Sandy, Wailupe, Hanauma, Kahala, Diamond Head,
  • Kailua, Lanikai, Waimea…
  • Ended my six-year stint as a copyeditor at Yahoo!
  • Launched How To Live In Hawaii

Regarding those last two points: A couple months ago, I decided I needed a change in the type of work I was doing. I wanted to try doing some of my own writing, rather than editing other people’s writing. I’ve always wanted to work for myself, so when I found out that there are people who write blogs for a living, that sounded like exactly what I wanted to do. Soon after that, How To Live In Hawaii was born.

Despite the long list above, there are still many new things I want to experience in Hawaii. I still want to learn to surf, and I’m determined to give kayaking another go (this time in calmer waters!).

When I moved to Hawaii, my friend Nancy gave me ukelele as a farewell gift, which I want to learn to play. And I know I won’t feel like a full-fledged Hawaii resident until I can properly pronounce the name of Hawaii’s famous triggerfish, humuhumunukunukuapua’a. And believe it or not, I haven’t done any island hopping since I moved here, so I’m itching to hop on a plane and continue exploring the rest of the Hawaiian Islands.

So although this concludes my story of coming to Hawaii, my story of living in Hawaii is to be continued…hopefully for a long time!

Written by Elizabeth.

My name is Elizabeth. I had a dream to live in Hawaii when I was young, and I was able to make my dream come true! I write for How To Live In Hawaii and share my stories!

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