Aloha, Mahalo: On Settling Into Island Life on Maui

LAHAINA, MAUI—When I first began this little life adventure of mine, I started a blog that chronicled my day-to-day experiences—what I did, how I felt about it, and little willy-nilly observations about the eccentricities of the backpacking lifestyle. Over the years, what I like to write about (or at least share publicly) has evolved, and it’s been a while since I’ve sat down and done anything like chronicling my experience for anyone who might be interested in what I’m doing with my life.

For a number of reasons, all of which I’ll surely digress into throughout the course of whatever I decide to type here, I think it’s appropriate for me to give a little recap as to what I’ve been up to. 

Sunset from the Valley Isle

Sunset from the Valley Isle

Two weeks ago, I moved to Maui for the winter to work on a whale-watching sailing boat. The first question anyone ever asks me when I tell them that is “how did you find your way down here??”, and it’s a reasonable thing to wonder. The short answer is that I have a dozen friends I worked with this past summer (in Alaska) who all spend their winters here in Maui. While it might seem like a super-crazy abstract destination to anyone not in my shoes, it’s an idea that I’ve been conditioned to for some time…any of you who knew me five years ago when I was working in New York might remember that I was always yapping off about moving to Hawaii. Welp, here I am. 

Because I already know so many people coming here I had a pretty good idea of what to expect: what the housing & car market would be like, what companies I should and shouldn’t work for, and what everyone did in their spare time. I also have a built-in network of people that I’m already friends with, which obviously makes any “big transition” far easier to handle.

Moving to Maui wasn’t as much of a leap of faith as some of the other destinations I’ve found myself in, but that doesn’t mean it hasn’t been without its challenges and eccentricities once I found myself here.

A few things to know about Maui if you’ve never been here: it’s an island, but it’s a pretty big island. You can definitely get by without a car here, but there’s definitely a difference between surviving and thriving. When I move somewhere new and have to spend a lot of time and energy getting myself settled, it’s easy to think about what I need to be able to accomplish on a weekly basis: getting myself to work on time, bringing groceries back home, having a reasonably comfortable place to sleep, and access to some sort of leisure activities in my spare time. Those are the basics, what I need to get by. 

Yet I’ve done this whole moving-to-an-exotic-destination thing a few times, and I’ve found that getting by is fine; I can do that. But it’s easy to get caught up in what you need to accomplish on a weekly basis, and not think about the big-picture things that you came here for in the first place—the big-picture things that anyone back home (those of you that are reading this) want to hear about when I tell you all about my time in Maui.

In the end, everything that I’m doing takes place in Hawaii—that means there are palm trees growing everywhere, the weather is nice all the time, and the scenery is like something from a storybook. I’ll give you all that. But it also means that living here is extremely expensive. Groceries are ~20% more expensive than they are on the mainland (which is what everyone calls the continental US), and rent is as high as any place I’ve lived since I was a two-block walk from Gramercy Park. It makes the getting-set-up-to-get-by-on-a-weekly-basis part of moving here fairly difficult. Keeping costs low until I’m settled in with a place to live, a car, and a stable work environment means that I’m not really doing anything “worth coming to Maui for”. Sure, I can watch the sunset from the beach—it’s one of the perks of this lifestyle—but it doesn’t mean that I’m treating myself to fancy meals or lounging around sunning myself all day.

My life here has been a hustle, just like it is for you at home. It’s just in a different place with a different set of people who have a different idea of how to spend their free time.

At work, I’m still very much the new guy, and that means I need to prove myself all over again. 

Do you remember when you started at work and no one knew you on a professional level, let alone a personal level? That first month or two is spent establishing yourself as you want to be seen by your co-workers—and if you’re smart, it means that you get there early, do what you’re told without complaint, watch how everyone else solves problems and following their lead, and in general being someone who can be counted on as a reliable co-worker. It doesn’t really matter what your inter-personal job performance was like in the past, it matters what you are doing now

I came down here to “follow the whales”, as people call it, and work on the whale watching excursions. But the whales aren’t here yet, and they won’t be for another few weeks, meaning that I’ve spent the past few weeks at work training on snorkeling trips. Sorting equipment, lifeguarding, and scrubbing the decks have been an integral part of my Hawaiian experience so far, which is just how it is when you’re new somewhere. You’ve got to start somewhere. Once I’m familiar with my co-workers, my job duties, and the flow of work out of Lahaina Harbor, things will be different…but for now, it’s a grind. The view from my new office is beautiful, but that doesn’t mean that I can take the time to enjoy it whenever I want to.

Maui is a cool place, obviously, but I am living and working in Lahaina, which is a tourist MECCA. I’ve spent the past few years living in destination-places that hundreds of thousands of people visit every year because there are things worth doing and seeing there. Yet the tourist cultures of Steamboat and Juneau have absolutely NOTHING on the entrenched industry here in Maui, and in Lahaina particularly. This place is absolutely overrun with vacationers, many of whom have clearly been coming here for a long time. In theory, this is obvious—I am after all coming here to work at a job that only exists because people travel to Hawaii as tourists—but in practice, it is somewhat startling. 

I rented a car for my first two weeks on Maui to make the logistical hassles of getting to work, lifeguard training, looking for places to live, initial grocery shopping, etc, easier. I’ve spent a good deal of time driving around the island running start-up errands, and the traffic here can be mind-bogglingly awful. On one of my first few days, there was an accident on the one-lane highway coming into Lahaina, and I sat in a virtual stand-still for three hours before making it back home. A drive that should have taken 25 minutes took me three hours. Sure, I could spend that time gazing out the window at the gorgeous ‘Au’au channel, looking for whale spouts…but it’s not the same when you’re just trying to get from A to B. That single traffic experience made me certain that I wanted to live as close as possible to where I was working because many of my check-in times are well before dawn. I want to minimize commuting time as much as possible.

I get the feeling that the infrastructure of this island was designed for about half the people that currently live here. Everything works fine—there’s water that comes out of my tap, and the power doesn’t go out. The supermarket shelves are full, and there are places on the beach to lay out a towel and sunbathe. But I just get the sense that there are far more people here than there should be, and the crazy-ass traffic is just one indicator of that. It makes me feel a little bit guilty, because I am the one moving here and trying to get a slice of the Maui pie when everyone else already lives here, and likely sees ME as the problem, overruling their home. I can only imagine what the people who have lived on Maui for generations think about the rampant development of the tourist industry here, and all the people coming to visit. I can imagine that they’re a little bit resentful that their piece of paradise is being overrun by tourists who come here year-round. There are slow periods in Maui, but I get the sense that this is a town that never really gets a chance to breathe from the pressure of having two million people visit every year, each seeking their own idyllic tropical experience.

I bike around town because I haven’t purchased a car just yet…it’s just not a sensible financial decision to spend SO MUCH MONEY all at once. Finding an apartment means laying out for first and last month’s rent, furnishing it with the little knickknacks that make it feel like home—lotions and other toiletries, a case of beer, cheerios, a yoga mat. That sort of thing. I like having cash flow before I really start investing in anything meaningful, and while I have paychecks coming soon enough, I like to feel the clink of money hitting my bank account before I buy a car. But that’s just me. 

Biking also means that I can take the time to explore my new home, and avoid the crazy-ass traffic all over the place, but I’ve found Lahaina to be a particularly unfriendly bike town. While there are other people that bike, it feels like EVERYONE drives, and everyone drives like a maniac…especially considering how small the roads are. There aren’t any bike paths, so I find myself biking on the shoulders of side streets. It’s totally fine, and it’s good exercise (which I always need), but it’s not a particularly pleasant experience to bike around Lahaina when you’re doing it to get from A to B. 

This has been a relatively random smattering of thoughts about my short life here in Maui thus far, and I know it seems like I’m just listing things that are annoying about Hawaii, the paradise of our mind’s eye….but that’s kind of the point of what I set out to do. Don’t get me wrong, I’ve greatly enjoyed my time here. Getting a suntan is FANTASTIC, and having the chance to sit on the beach and read a book as the sun sets is also FANTASTIC, but a lot of you back home only get a chance to see the glamorous parts of my life, and don’t get a chance to see the pain-in-the-ass parts of it.

Just because I’m living my life somewhere different doesn’t mean that I haven’t worked hard for it, and just because I’m living in a place where others go on vacation doesn’t mean that I’m on vacation all the time. Life has its challenges—its mundane, daily, small, annoying, surmountable challenges, and it’s very difficult to get away without attending to them regardless of where you live.

Yesterday, I was biking (up a very, very steep hill I might add) to a Friendsgiving celebration when my slipper (flip-flop) broke. A nice, reliable pair of Rainbows just broke…which was bound to happen eventually. It’s not a big deal—slippers are bound to break, and they’re relatively easy to replace. However it’s now another thing that I need to do, on top of all the other things I need to do. Most of my issues with moving to Maui have been of the broken slipper variety…none of them are particularly awful to deal with on their own, but there are just a lot of broken slippers to fix when I want to spend my time living the life you imagine here on Maui. 

I’ll get there, but I need to handle business first.

I once read a quote attributed to Jack Kerouac that I’ve since printed out and displayed prominently wherever I live: “In the end, you won’t remember the time you spent working in the office or mowing your lawn. Climb that goddamn mountain.” Simple yet powerful, it provides much of the motivation for putting myself in a position to have experiences that I’ll remember long after I’ve moved on from my time on Maui.

Life anywhere is not without its challenges, and that goes for life on Maui as well. I have to deal with innumerable broken slippers every time that I move somewhere new, so I’m familiar with the flow of it—but I’m looking forward to finally getting settled, buying a new pair of Rainbows, and climbing a goddamn mountain.