Remote Working In Hawai'i: 6 Takeaways

The COVID-19 pandemic has clearly been the biggest disruptor this year and for all the bad things it's caused, it's also created some great opportunities to forever change the way we work…especially regarding remote working.

A little over five years ago, I was living and working in Chicago, IL. Chicago is a great city, but I found that I was growing tired of it and the monotony of working a clock-punching 9-to-5 corporate job where politics and pecking order mattered more than drive, ambition, and results. Don’t even get me started on the winters. At the time, I had one of my best friends living on Maui and she was regularly asking me to come to visit. While I’m not sure why I put it off for so long having never visited Hawai'i, I finally did in 2012…and not to sound banal but afterward, I reevaluated my life’s priorities and ended up moving in October of 2015 to Hawai'i Island (or the Big Island as it’s typically called).

Now, I’m obviously glossing over a lot of details here, but this article isn’t about my personal choice to move to Hawai'i, it’s about what it’s like to work in/from Hawai'i. It didn’t take more than a handful of months after I moved to start my business, Expected X, from my small ‘ohana (guest house) in the tiny, unincorporated village of Hawi (pronounced "ha-vee") where I first lived. What a far cry from living in the City of Chicago that was! Working in the data science and machine learning field, I had no preconceived notions that I’d be drumming up much business locally, so I began my journey working remotely (which I already had some experience with working at my previous role in Chicago).

Here are a few things you should know about working remotely in Hawai'i:

1.      It’s NOT all fun and games. What’s the first thing that comes to mind when you think about Hawai'i? I’d be willing to bet it isn’t business and industry! Unfortunately, the powers that be have essentially “sold” Hawai'i as a tourism destination to the masses with not much more to offer than sun, sand, and splendor. From my experience, this can have a detrimental effect on remote workers since many “mainlanders” tend to think you aren’t working as hard or as much as they are – instead, you are out surfing or drinking Mai Tai’s, or some other cliché activity. There is even outright jealousy. If you already have a remote-friendly job and have established relationships with your colleagues, clients, and co-workers you might be better off than trying to establish those after relocating.

2.      Be prepared for standard Q&A when someone finds out where you live. I’ve always tried to keep where I live under wraps as long as possible when meeting a new professional connection (obviously this article won't help). When you disclose where you live, expect “Oohs” and “Ahhs” and some additional questioning about what it’s like. You aren’t living on the moon, but it can feel that way sometimes. After five years, I’ve essentially crafted standard responses to these repeated questions and suggest you do as well so you can move on with the business discussion.

3.      You’ll probably have to work strange hours. This isn’t necessarily specific to Hawai'i as most remote workers have had to do this at some point. Yet, Hawai'i’s geographic isolation means that unless you’re working on a project in the state, you’ll always be working two to three hours behind the West Coast of the United States. For some “morning people” (myself included) this isn’t all that big of an issue. However, outside of that particular region of the country, it can get difficult. For example, I sometimes teach my machine learning classes to audiences located in Europe which typically means a 13-hour difference and working overnight.

4.      Local resources will vary depending on your industry. Outside of Hawai'i’s main industry, tourism, the state has a modest industry presence in agriculture, renewable energy, and of course U.S. military-oriented contractors. If you are in tech or finance or manufacturing, for example, you’ll be a little less likely to find the right resources at your disposal. Hawai'i, unfortunately, suffers from “talent decay” (or, colloquially “brain drain”) where most skilled individuals that move here at some point move back to the mainland for better opportunities and salaries. If you have long-term plans on working remotely from Hawai'i or intend to get into the startup game, while the state does have resources (e.g., Entrepreneur Sandbox, Hawai'i Technology Development Center, Blue Startups, TRUE, etc.) my recommendation would be to already have an established network before making the move. Today, I live in Honolulu and part of that decision to move from Big Island to O'ahu was to try and help build a local interest and educational resource for professionals in artificial intelligence, machine learning, and related disciplines. I even have started my own Meetup group, “Hawai'i AI!”

5.      Professionals: looking to do business in Hawai'i? It’s O'ahu or nothing. I think it’s an unspoken truth that if you have any aspirations of doing business in the state outside of tourism or service-oriented business, you need to live on O'ahu. I’ve had countless conversations with other local professionals that have been working in Hawai'i much longer than myself and when I ask them if this is true, I typically get an uncomfortable head nod. I’d say it is still true that the local culture embraces face-to-face professional relationship building much more than other places in the U.S. Although the pandemic has made remote working more widespread, I suspect that people will return to the office setting much more quickly here than in other parts of the world when remote working will become the norm.

6.      Live Aloha, Share Aloha, Be Aloha. If anyone knows anything about Hawai'i at a minimum it’s usually “Aloha,” but what does that really mean? Sadly, the word has been overwhelmingly used to the point where most visitors (and even some residents) don’t understand its complexity or depth…I feel I fall short sometimes even. Being from a smaller town in the Midwest originally, I think I may have gotten a leg up in the manners and courtesy department and I think that has gone a long way for me here where community, compassion, and a sense of “we’re all in this together” trumps the hustle/bustle, self-first, sensibilities you may get in other parts of the U.S. It is fairly easy for local residents to spot someone from the mainland by their attitude and behavior and that usually isn’t a mark of distinction someone wants. Hawai'i is very much a place where people take time to help each other out, share gifts of gratitude, and think more about the group as a whole than the individual. While this does have some negative side effects, one thing I was told about fitting into the local culture having not been born and raised here was to not try and change the way things are. I suggest you do the same if you chose to work remotely from Hawai'i.

Hawai'i recently introduced a program to incentivize remote workers called “Movers and Shakas” while we try and revitalize our economy. While I’m not certain it will have long-lasting benefits to the state, I think it’s at least a start to welcoming remote work culture to the state and diversifying our “eggs-in-one-basket” economy. A hui hou koke iā 'oe! See you soon!

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John Sukup is the founder and Principal Consultant at Expected X, a machine learning and data strategy consultancy working with businesses seeking "hypergrowth" and investment. John has spent his entire career extracting insights and building solutions with data across several industries both public and private. John resides in Honolulu on the beautiful island of O'ahu.