Organic to Urban: Moving to Honolulu

Organic to Urban: Moving this Musician from Hawaii Island to Honolulu

Making the jump from an outer island to Oahu is a unique transition. While you aren't leaving the state, moving from the expansive, volcanic landscapes of Moku o Keawe to the bustling urban core of Honolulu ("town") feels like entering an entirely different world. It was Kealii first, accepting a Vice Principal position on Oahu three years ago to be closer to his nonagenarian dad and I soon followed.  I LOVE my life on Oahu; comfortable with the relative anonymity of living in a culturally diverse metropolis.

On the outer islands, music is woven into the very fabric of daily life—intimate, organic, and deeply rooted in community. Life and business move at an intentional, slower pace. The music scene feels like an extended family; gigs often come about naturally through word-of-mouth at a backyard pā’ina or while chatting in the aisles of the local hardware store. I’ve enjoyed years as a resident musician at various hotel and resort venues on the island of Hawaii, making cherished friends and forging fruitful professional relationships that will last long past any of my gigs.

Moving to Honolulu shifted my concept of Hawaii's music industry landscape in interesting ways. Oahu, as the commercial engine of our state's entertainment industry, demands a quicker pace where turnover and transiency seem to be the norm. One of the first things I was told by a top booking agent here was sobering: “There are no residencies available.” They added that over the past year, 60 local musicians lost their residencies due to venues cancelling or pausing their live entertainment offerings.

A residency is a standing gig—be it daily, weekly, or monthly. It is a gig you can count on. It's a valuable asset not just for the financial stability it provides, but as a reliable vehicle through which artistic and professional development can be honed.

The reality of introducing myself into a highly saturated music industry arena—one currently dealing with tremendous statewide, national, and international economic pressures—is challenging. For me, this inter-island relocation isn’t just trading a country pace for a city rhythm. It is forcing me to contemplate what being a musical artist is at this juncture of my life:

• What professional direction and what artistic challenges do I actually want to take on?
• What compromises as an artist and an industry professional will I need to make, if any, in order to “gig” in the big city?

To Compromise or Not to Compromise

Earlier in my musical journey, I didn’t always get to play the kind of music I wanted to play. Those early challenges taught me to be self-sufficient, to persevere through tough times and tougher lessons. I had to make artistic compromises to stay in the game and finally obtain the kinds of gigs that allowed me to “play for pay”—feeding my mouth and my soul at the same time.

As an Oahu transplant I do not want to give that up. And so, my compromise is a literal one: I fly into Kona every week to work my residencies.

I consider myself blessed beyond measure to have survived and thrived as a full-time musician. I am also blessed to have a tremendously supportive life partner and a minimum of economic challenges, allowing me the luxury to pick and choose what and where I want to play on the island of Hawaii.

On Oahu, music is less of an organic pursuit and more of a highly competitive business in an oversaturated market. The sheer volume of venues—from Waikiki hotel lounges and Chinatown bars to corporate events—means there is technically work. But for every opening, there are dozens of musicians eager to do the job for less. It’s a musical mosh pit, and I am loath to jump into the fray. I want to enjoy music's sweetness, not battle my way down a crowded freeway, pay a mint for parking, and lug heavy sound equipment a mile just to play for tips.

My Strategy: Finding Balance on Oahu

When you are a new fish in a very crowded ocean, it is easy to feel invisible. Early on, I realized that relying on the same word-of-mouth networking that worked on the Big Island wouldn't cut it here. In a congested market, talent is only half the battle; the other half is visibility, consistency, and professional presentation.

Instead of fighting for space on the marquee, here is how I am cultivating balance on Oahu:

• Treating Jam Sessions as Job Interviews: Showing up to select open mics and local jam sessions isn't just about playing a few songs. I use these spaces to observe local etiquette, support other artists, and introduce myself to other music professionals and academics.
• Leaning into My Roots: In a crowded market, your unique story is your biggest asset. The grounded mix of Hawaiian and jazz stylings I cultivated both on the mainland and on the Big Island is a distinct point of difference in a city dominated by high-energy commercial gigs. I lean into that authenticity rather than trying to blend into the background noise.
• Supporting Before Seeking Support: The quickest way to make connections in a saturated scene is to be a fan first. I spend my off-nights going out to watch other Honolulu musicians play and genuinely supporting their craft. Real relationships always outlasts transactional networking.

So, instead of cold-submitting a press kit to that booking agent, I choose to wade gently into the waters of Oahu’s music scene. I will find those of like mind and ilk. I will befriend kind musicians and learners of every age who are excited to try new things and grow as professionals and artists. I will fill my community with those eager to pursue refined collaboration.

At this juncture of my life, it’s not about getting more gigs. It’s about pure artistic expression, connection, and the sheer joy of making beautiful music.