30 August 2026

Aloha, Hawai'i


I had a new job starting in Japan in nine days, and I'd been instructed to land with a minimum of $1200 cash to pay my first month's rent and to cover expenses through the month. I only had $900, which was dwindling fast, and a one-way ticket to Osaka for a departing flight on my 28th birthday.

I could have been at the Maui Hilton and still been restless, but in the reclined driver's seat of the rented Pontiac Sunbird, flannel shirt on backwards for warmth, I didn't stand a chance of sleeping. My mind was racing.

I was single, broke, and directionless. I was heading to Japan to teach English -- on a whim, basically: I'd made the decision on a phone call with a friend one coffee-and-Bailey's-soaked Sunday morning when I called her so I wouldn't be drinking alone. She and her husband were moving to Japan to teach English, she'd said; the money was good, and they hired anyone. I was bored in my college admissions career and ready for a change, so I flew to Boston for an interview, got an offer, and here I was. I spoke no Japanese (I had thought "sayonara" was Spanish - and I only knew "sayonara" from a Debbie Harry song) and I was completely unprepared for the plunge I was taking.

What was most unsettling, though, wasn't this impending move and career change - I wasn't that anxious about the job or the move because, incredibly naively, I thought those were no big deal. What was most unsettling was Hawaiʻi. I was completely overwhelmed: by the sheer breadth and depth and scale of the natural beauty -- you simply couldn't open your eyes wide enough to encompass all of the green -- by the graciousness of the culture, by the beauty of the locals. I'd been so focused on moving to Japan that I'd never seen it coming.

I gave up on sleep, popped up the driver's seat and cranked down the window to hear the muffled surf from far below. From that scenic overlook on that parking area above that cliff in west Maui I could see the hump of Lānaʻi to the left, looking so close I felt I could touch it, the bulk of Molokaʻi dead ahead in the middle distance, and between and above them over the channel a crescent moon leaving its reflection on the ocean below. It was somehow chilly, with a breeze from the mountain behind me, but my shivers weren't all from the breeze. It was the most beautiful place I'd ever been. 

I wanted to stay.  More than I'd wanted anything in a long time. 
 
Restless, I punched the cassette into the tape deck, out of habit, not really listening until I heard this lyric: "He was born in the summer of his 27th year, coming home to a place he'd never been before." Yup, pretty much. I was 27, and I got it.

It was the middle of the night but I didn't go back to sleep. What was propelling me forward to my next step? What was keeping me from staying? It felt like an impossibly juvenile, impulsive, Romantic thing to consider -- giving up a job to stay someplace I'd been for less than a week because it was pretty. For sure it was impractical: there was just no way I could afford it, I was already broke. What would I do for work? I'd accepted an offer for decent money in Japan. I had a job in hand. I had student loans (so many student loans). Didn't Japan have the potential to be awesome, too? Was I really someone who could quit a job without having another one? 

I watched the moon on the waves and listened to the surf from far below until the sky lightened, and then drove back down the hill towards Lāhainā town. I showered at a beach park just after dawn, using a sliver of soap left by a previous user, and I listened to the cadence of the lyrically spoken language around me. I looked at the beautiful men just back from surfing dawn patrol, all lats and tans and teeth. I noted the poverty of those who, from appearances, were living rough, permanently, as opposed to me who was there in a career interregnum. I tried to take in everything, every last bit of it. And I thought. 

I didn't realize at the time that I was one in a long line of Westerners who had come to these islands and felt the same things, that I was a colonizer, unbidden and by many unwelcome. I am embarrassed to say I knew nothing of the history of these islands, of the illegal overthrow in 1893 of a sovereign nation, of the illegal annexation by an imperial power (us) in 1898, of the successive waves of people from the North American continent who came here to cavort and convert, spread disease and steal land, and impoverish the indigenous people. My education about these islands would come later. Right now, I was part of the problem.
 
I was in the islands to cover some college fairs for the admissions job I'd resigned from a few months earlier - god knows I was profligate but not so much so that I'd take a Hawaiʻi vacation between jobs. The college wasn't paying me but they covered the airfare to Honolulu and around to the neighbor islands, and I could expense hotels and meals and get reimbursed in a couple of months. I could just barely afford to front the cost for meals; there was no way I could afford to front the money for a hotel every night - hence the restive night in the car. I agreed to the trip to save on airfare (one way to Osaka from Honolulu was way cheaper than from Chicago) and of course to see Hawaiʻi as well. 
 
I'd been fascinated by these islands since looking at my parents' photos and slides from when my dad was stationed at Schofield Barracks after being drafted during the Korean War. I'd thought about moving to Hawaiʻi before - I even considered Chaminade for college (one of three vetoes my mom exercised, along with enlisting in the Navy and Notre Dame) -- but I'd never even visited before. And now here I was. The fascination was only growing.

I inexpertly changed into my khakis and a new $7.99 aloha shirt from T.J. Maxx there in the beach parking lot and then drove to McDonald's for breakfast. I savored my pancakes and waited for other diners to finish their copies of the Honolulu Advertiser so I could read the news - and the classifieds - before I had to head to the college fair. Scanning the help wanted ads wasn't too helpful - the realization that I had no real skills was painful, but really, what could I do? -- and there weren't many apartments listed in that morning's edition.

Could I make this work? It was expensive, but why not try it? What did I have to lose? I had quit a job I hadn't liked to go to another I knew nothing about, so it wasn't like I was on a high powered career track. I had a shit ton of student debt to pay back, which had been a primary motivation to go to Japan, but... so?  I could defer that, right?

I was down to eight days in the islands before before my birthday, before Japan (if I was going), before I had to decide.

I wasn't super focused on work that week. I don't even remember all of the venues. 
 
What I remember from those eight days is rain -- every day, rain, and the few extant pictures from the trip corroborate that: after Maui there were no sunny days -- and the kindness of strangers. The bartender at Hamburger Mary's who told me where to park overnight to sleep in my car safely where I wouldn't be hounded by the cops. The off-duty HPD officer I met at Queen's Surf Beach, then the gay beach in town, who showed me around Kapiʻolani Park. The man sitting under the banyan tree at the old Hula's who shared his spliff and gave me ideas for where to find work. Lawrence, the local guy who worked at a Waikīkī hotel who let me use an un-booked room for a few hours. 
 
And all the while I wondered: could I make this work? Could I get the money back from my plane ticket and -- together with my meager savings -- find a place to crash while I looked for work? Could I build a life here? 
 
I didn't, in the end. I didn't stay. Not then. On my 28th birthday I returned the rental car to the Honolulu airport and got my stuff out of long term storage and checked it in for Osaka. In the United terminal in Honolulu you an still see the bays under an escalator where there used to be pay phones and where I sat for a couple of hours calling friends and family (using a friend's calling card number) to say, well, "Sayonara" for a while.
 
How do you know if a decision like that was the "right" one? Financially, it was. Undoubtedly. The yen-to-dollar exchange rate then hovered around 115 and I was able to pay down my student debt over my two years in Japan. I made some amazing friends there, three of whom I've kept in close touch with despite the years and the miles. I got to explore Japan (a little) and Thailand (a little more) and developed a cultural literacy that I had been sorely lacking before my departure, and that made me a much better resident of Hawaiʻi when I did first settle here in 2000. 
 
But what if I'd stayed? I have no regrets, only curiosity. If there were a "Sliding Doors" -esque movie made of my life, that week in November of 1996 is the moment I'd choose. 

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