How to Work from Home in Hawaii

Lessons learned from five weeks in paradise.

If you like offbeat stories about money and business that inform and amuse, you’ve come to the right place. I write one to two columns a week, and you can receive them directly to your inbox by subscribing for free. And spread the word!

The last two years have taught many people they can work from anywhere. If you haven’t seen your desk since March 2020, why not spend March 2022 working somewhere fun, like Hawaii? This could be your last chance.

It may not be as expensive as you think. It will be different than you expect.

I experimented with “WFH” for five weeks over the holidays in Kona, on the Big Island. I loved it, but I learned a lot. I will do it differently next time. Perhaps my experience can help you decide whether you should give it a shot.

Mele Kalikimaka from my lanai.

First, let’s talk about the cost.

AIR FARE — $237

Round trip prices from LAX to Kona are as low as $237 right now on United, Hawaiian, and Southwest Airlines.

Southwest’s entry into the Hawaiian market has driven down prices. Southwest even gives you something more than peanuts on the flight. Still, bring your own food. (The Hawaiian Airlines sandwich thingy served in coach can best be described as tasteless doughy bread.)

HOUSING — AS LOW AS $3,010

My situation is a little different than most. In the fall of 2019, my husband and I scraped together enough money to buy an old condo in Kona. We’d been visiting for years. It needed a lot of work, but the location was perfect — right across the street from the beach.

Then Covid hit, and we had to remodel remotely from the mainland. It was a challenge; I could write a whole column just about that. Don’t get me started on the tale of the missing refrigerator. I hate that fridge. My advice for buying appliances and furniture on an island during a pandemic is to buy what’s on the floor of the store.

But I digress.

There are plenty of places to rent in Kona for an entire month. If all you need is a roof over your head, with a bed, bath, kitchen and “desk” — most likely a table on the lanai — there are a few spots in Kona this March renting for a little over $100 a day. It won’t be fancy, but then again, you don’t need fancy when you spend most of your time wearing shorts and flip flops (aka “rubbah slippahs”). Perhaps you could offset the cost of staying in Kona by renting out your regular home while you’re away. (Also, pets have to quarantine in Hawaii unless you jump through several hoops.)

A rental in Kona on Airbnb that costs $3,010 for the month of March.

Check this out if you’re really adventurous. For what I would call “glamping,” you can stay in an unfinished home called “The Crow’s Nest” for under $100/day, including cleaning and taxes. Remember, it’s always 80 degrees in Kona!

Described as “Not cold, no bugs, just pure inspiration.”

TRANSPORTATION — FROM $0–$72 PER DAY

Rental cars can be expensive, though I found a car available on Enterprise during March for about $54 a day if you rent the entire month. Locals rent out their cars on Turo for as low as $72 a day. (These prices may have changed by the time I publish.)

But how often do you need a car? Maybe you only need one for a few days to do some sightseeing, like a visit to Volcanoes National Park. The rest of the time there's Uber for quick trips. Instacart can deliver, even from Costco. You’ll find racks of bikes for rent along the beachfront drive in Kona, and you can also take the $2 trolley. Or just walk. I did that a lot (though not to the volcano!).

My photo of the volcano. I recommend the trip, along with the waterfalls near Hilo.

FOOD — EAT LIKE YOU’RE AT HOME

It took me a while to get out of the vacation mindset of going out to eat every day. Here’s a good rule of thumb while living and working in another city: Only eat out as often as you would at home.

To be honest — and this will make some people angry — there aren’t that many good restaurants in Kona. I know, right now you’re yelling at me, “Jane! Haven’t you tried this dish at that restaurant?” The answer is yes, I have. Probably twice. It was good, but not great.

I do have my favorites:

— Da Poke Shack, though the line has gotten so long it’s like waiting for Space Mountain. I discovered the poke at Costco is fresh and fantastic.

Da Poke Shack is one of the highest-reviewed restaurants in America.

— Kona Brewing has the best pizza on the island. It’s better than their beer.

— I like the Lilikoi Cheesecake at The Coffee Shack, the fish special at Jackie Rey’s, and the Hana Hou cocktail at Magic’s Beach Grill.

A surprise guest joins our table at Jackie Rey’s Ohana Grill.

— I like the mai tais at Lava Lava Beach Club and Don’s Mai Tai Bar at the Royal Kona.

We always stop by Don’s to kick things off.

— Merriman’s is great (the kalua pig quesadilla!) but it’s an hour away, and the meal there can cost more than plane fare.

Meanwhile, the beef, pork and fish are remarkably fresh at the grocery store, and the local produce is amazing! Creamy avocados, tomatoes right off the vine, juicy limes. That’s in addition to “the usual suspects” of fresh pineapple, papaya, and bananas. The Saturday morning Keauhou Farmer’s Market is truly farm-to-table.

WHAT’S THE DAY-TO-DAY LIKE?

So you’re moving to Kona for the month of March to work. What will it be like living there?

— THE CLOSER TO THE OCEAN, THE NOISIER IT GETS

To be clear, the neighborhoods where you can rent affordable rooms or condos are not inside resorts. You’re not staying at a timeshare in Waikoloa. You’re staying in a community comprised of locals who live there year-round, and off-island owners who stay for months at a time.

There’s a lot of daytime noise, and some at night. Locals have an affinity for revving motorcycles. Fireworks here are legal, but recreational marijuana is not — though you wouldn’t know it.

Reasonable noise in my complex includes Airbnb renters enjoying themselves down at the pool, while beachgoers across the street play music and party, sharing space with a couple of homeless folks.

My iPhone health app said my five weeks in Kona were “loud,” with the sound level reaching 119 decibels on December 15. Some of that noise may have been waves crashing, but that’s the kind of noise I like.

If you want quiet, you have to stay up in the hills.

But here’s what I‘ve learned: It’s Hawaii. It’s wonderful. You accept what it gives you. Everyone in Kona is very chill, and they are the friendliest people in the state.

— STICKING TO A SCHEDULE IS CHALLENGING

The toughest part of working from home in paradise is figuring out when to work and when to enjoy paradise.

A glamour shot of me at the office.

Most of my work in Hawaii was for this column. I researched and wrote nine articles, produced three live events on Facebook, and I conducted more than a dozen Zoom interviews for current or future stories.

A Facebook Live event with Virgie Tovar of BodyPositiveUniversity.Bulletin.com

I also covered a big winter storm for CNBC, though it wasn’t very big in Kona. Still, the storm was big enough that it snapped off the top of a beloved palm tree at the beach. The first video below shows the tree still intact, followed by another video shot a few minutes later with the treetop gone (and a homeless guy gathering coconuts).

As for my daily work schedule, here was the original plan:

6:30 a.m. — Rise and shine, pour some coffee, sit on the lanai and look at the ocean, run through emails, thank God for being alive.

8 a.m. — Work (research, write, conduct interviews)

10 a.m. — Workout or hike

Noon — Lunch

1:30 p.m. — Snorkel

4 p.m. — Cocktail hour/practice my ukelele (don’t laugh)

5:45 p.m. — Watch the sunset

6:30 p.m. — Dinner

7:30 p.m. — Stroll around the neighborhood and look at all the stars I can’t see at home because of light pollution.

To me, dear readers, this is the perfect day. The. Perfect. Day.

Sunset from Magic’s Beach Grill

It didn’t happen.

Here’s what my real day was like during the first week:

6:30 a.m. — Rise and shine, pour some coffee, sit on the lanai and look at the ocean, go through emails, thank God for being alive.

8 a.m. — I’m still going through emails, and tumbling down internet rabbit holes, and generally stalling.

10 a.m. — I finally start working.

3 p.m. — Oh wait, I’m still working. WHAT THE…

3:30 p.m. — Run down to the beach to get my feet wet.

4 p.m. — Cocktail hour, but I need to squeeze in a little more work.

5:50 p.m. — Wait, did I miss the sunset?

6:30 p.m. — Dinner

7:30 p.m. — Occasional nighttime stroll

This was not the WFH that I came for.

“These are not the mai tais you’re looking for… “

After week one, I changed my schedule. Instead of working a few hours every day, I’d work 40 hours one week, and then work zero hours the following week. Rinse and repeat.

This new plan worked. Mostly. After three days of all work and no play, I needed to play, because it’s sinful not to in Hawaii. So I took some time off in the middle of the work week to enjoy myself.

But even though my new plan worked better, work continued to pop up during “no-work” weeks. This is where I need to improve.

If you’re like me, you struggle with balance, because balance doesn’t really exist. “Balance” sounds like everything is in equal proportion. One thing I learned as a working mother is that there’s never going to be “balance” between the job, the kids, the husband, the house, and the occasional mani-pedi. Life’s a constant state of imbalance. Some things win the battle for your attention, while other things lose.

I just need to make sure Hawaii wins more. So next time I work from home in Hawaii (and there will be a next time), here’s my new new plan.

When it’s a work day, I’m going to set an alarm to go off one hour after I get up to signal that it’s time to start working. Then I will set another alarm for when the work day is supposed to end (just like Fred Flintstone!), and I will stop.

On days when I do not plan to work, I will not work. No work means no work. Put the phone down, Jane. Stop checking your emails.

What could go wrong?

— OH YEAH, DON’T FORGET TO LOOK PROFESSIONAL ON ZOOM

LOOK AWAY!!!

Every time I arrive in Hawaii, I deplane in full-face makeup. By day two, I’ve replaced my foundation with sunscreen. By day three, I’m just filling in my brows and stuffing my hair into a frayed old USC cap. By day four, I say the hell with it.

Man, I really let myself go for five weeks. It was wonderful. I mean, I did a Facebook Live looking like this.

Sadly, there were people who suffered through Zoom calls with me in Hawaii who must’ve wondered if I needed an intervention. So if you decide to WFH here, please remember that even though you can look your worst in Hawaii and no one cares — in fact, you might get a “kama‘aina discount” because they’ll think you’re local! — the rest of the country still suits up. At least from the waist up.

FINALLY, DON’T TAKE IT FOR GRANTED.

Hawaii is breathtaking. I swam with turtles. I snorkeled with parrot fish and eels and trumpet fish and unicorn fish. I saw dolphins spin and whales breach. Flowers were blooming in every color, with leaves as big as pillows.

I don’t even know what this is, but a friend decided it’s “the rare Cheeto Pineapple Flower.”

By the third week I took it all for granted. I would be driving somewhere and not even notice the most beautiful scenery on Earth right outside my car window.

I had to stop and mentally slap myself. When would I ever be here again, see this again, feel this again?

Soon, and with a better imbalance in Hawaii’s favor.

So what’s stopping you from going? Let me know in the comments, and follow me on Twitter, Facebook, Instagram, and LinkedIn.