My Story, Pt. 2: 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 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 teenaged 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 forsee 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.