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Why Hawaii: How I Uprooted My Life

6 min


The date was August 14th. I was supposed to fly back to the mainland on August 31st.

I did what any overthinking analytical professional does: a decision tree.

I needed to rationalize the reasons in order to stay. I listed out pros and cons as bubbles attached to “stay in Hawaii ”. I was creating proof on paper that I didn’t just want to stay but I needed to stay. 

It was foolish to do. My decision tree only grew a few branches before I realized no matter what I wrote on that tree, I was not getting on that plane back to the mainland. Spending two months in one of the most unique places I’ve ever lived was not enough. My gut told me the answer. I chose to listen.

After the last year or so with Covid-19, the world hasn’t stopped going bananas. l started to craft my own path as a solopreneur, and I needed a break to gain clarity. I felt like I was always “on” and I didn’t know how to flip the switch “off”. Organizational psychologist, Adam Grant would describe what I was feeling in my little shoe box apartment in dreary Chicago as languishing. “It just feels like you’re muddling through your days, looking at your life through a foggy windshield.” I felt a sense of hopelessness in life despite not necessarily being unhappy or burnt out or depressed or lonely. 

On the surface, life looked fine. I wanted more than that though, especially after turning twenty five and feeling simultaneously too mature for my age but also wishing I was still in kindergarten. 

Just as I had reached the peak of “languishing”, an email popped up about a program. I jumped and felt my heart race a little faster. I couldn’t help but inquire. One of my mantras this year is: “Ask or you will never receive.”

The previous year, I had already been rejected by this company. I figured I had nothing to lose and I still kept in touch with the recruiter. The security of a job and support with relocating would be just enough to encourage me to take the plunge. 


When I got offered the position, it took awhile for this to all sink in. I wrote in my journal at the start of this year that I wanted to leave the comfort of my home in the MidWest. I wrote that I wanted to move out west. I didn’t know how that would manifest. It sure as hell was not in the cards to fly as far west as an American citizen could possibly go on the other side of the world. 

I still wake up every day and cannot believe that I live here. I’ve never lived so close to a beach on a huge body of salt water with barrel waves rolling in from Asia. I grew up where the only “mountain” was five hours north as a landfill and the only elevated surface in my town was called “The Hill”.  These strides in my life have been intentional in designing a life that I am more proud of despite the obstacles I faced getting here. To list a few of them, my loved ones told me it was too far away and Hawaii was only nice for a vacation. I was afraid to begin a role as a community and operations manager because I didn’t feel qualified. I’d be taking a pay cut. The cost of living is horrendous, where I bought eggs and milk for $10. I didn’t know a single person on this island.

I told myself that the risk is the reward, signed the contract, bought the 14 hour plane ticket and the decision was made. I convinced myself that it was merely a two month experiment and that I would determine what success meant later. I knew all I needed was to equip myself with an open mind and to come with a toolbox full of questions. 

Since deciding to stay in Hawaii, I feel like I’ve been intentionally getting lost in order to get found. To trace the stories I tell myself. To see which ones to prioritize, which to still write and which to eliminate. I recognize this means abandoning pieces of my identity though any reinvention requires this. I want to invest in myself and learn the things that I have been curious about. This environment is the most ideal one yet for me to focus on what I care about. 

I felt for the longest time that I needed permission to do something like this. That uprooting one’s life was a decision that needed justification along with a decision tree. In reality, to figure out how to expand my worldview, I need to shake what I think I know about the world. 

I’ve been asking more questions than I ever had and getting connected with people I would’ve never met. I’ve been reflecting on stories and how they are changing and where my next chapter can be. I’ve been sitting in my liminality transition phase to reflect, process and learn. 

It’s so easy to get caught up in the social norms of the traditional linear life of going from being a student to a worker to a parent. I question where they came from and why I felt I had to follow them.

I’ve been actually living and I don’t plan on stopping any time soon. 

I’m a beginner again and it’s humiliating. I learned how to cut an onion last week and that there are ones that don’t make you cry. My vegetarian roommate taught me how to cook tofu. I learned my first chords on the guitar and that E minor chord sounds sad and that the E major chord sounds happy. I went on an awful first date and learned more about what I value in a partner. I spontaneously bought a firetruck red moped without ever knowing how to drive one. I named him Ciao and he makes me feel alive. I signed up to run a half-marathon before realizing it was actually on a different island. I’ve nearly drowned in a tidepool and learned that no matter the confidence I have as a swimmer, not to mess around with Mother Nature. I’ve gone rock climbing for the first time in my life and learned to turn off my brain and trust my body. I’ve looked eye to eye with an eight foot Galapagos shark and felt calm rather than terror. I’ve jumped out of a perfectly good plane at 13,000 feet to feel like a bird flying for 90 seconds in the air. 

I’ve been taking risks to get the reward. I’ve been updating what it means to be a friend and how to have emotional intelligence about my own self. I’ve been more emotional and trying to understand those more intelligently. I’ve been doubling down on my personal finance and figuring out how to wheel and deal in one of the most expensive places in the nation to live and received a kamaʻāina locals discount. 

I refuse to wait until retirement to learn how to surf or how to scuba dive or to do the hikes on AllTrails that are only for challengers. It’s definitely not comfortable to live an adventurous life, but I know my future self will thank me for it. 

Living by the expectations of society is suffocating. In order to uncover more of what I want in life, Hawaii has offered me the environment to focus on what it means to be human. Even though I feel lost some days, I wake up in paradise and I feel courageous for that.

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