Why a One-Way Ticket to Hawaii Changed the Rest of My Life

I’ve always intended to write more here — to share stories, memories, and lessons from the many places life has taken me. And today feels like a good place to start.

Seven years ago today, I flew to Hawaii with a one-way ticket.

That move didn’t just change where I lived — it fundamentally changed how I think about life, risk, purpose, and what it means to lean into a dream.

Why Hawaii?

I was in Maui in October 2018 and thought, “Why not see if there’s a job here?”
I’d been visiting the islands for years. I loved the place — the culture, the pace, the light — and I’d always wondered what it would be like to actually live there.

So I applied for a Director of IT position with Hawaii Health Systems.
I interviewed in November, got an offer in December, and by January 13th, I was on a flight to Oahu with no return date on the ticket.

In hindsight, it feels both impulsive and inevitable.

The Reality Behind the Fantasy

Moving to Hawaii wasn’t easy. I assumed that — and it didn’t disappoint.

The first week, my wife and I stayed in Waikiki while we sorted ourselves out. We didn’t have much; a blow-up mattress was my bed for a while. She had to return to the mainland to pack up our house and get it rented. For almost three months, I lived on the island alone — starting a new job, learning the lay of the land, trying to make sense of routine life while also absorbing all the magic around me.

A lot of it wasn’t fun.
A lot of it was.

And almost all of it was a first for me — the first time I’d taken a leap so big, from Los Angeles where I was born and raised, to somewhere fundamentally different, somewhere beautiful and unfamiliar and full of possibility.

14 Months That Last a Lifetime

Ultimately, I lived in Hawaii for 14 months.
I moved back to the mainland in March 2020 — just two weeks before the world shut down.

The time wasn’t long in the grand scheme of life. But the imprint feels deep.

Hawaii didn’t just influence what I did — it influenced who I am.

• The way I think about work

• The way I approach risk

• The way I eat and dress

• How I talk about culture and belonging

All of these carry echoes of the islands.

Since moving back, I’ve been back to Hawaii three times — and every time, the island pulls a little stronger. I miss it more than I expect.

What That Leap Taught Me

Thinking back over the years and reading some of my old posts from that time, a few themes come through:

Possibility isn’t a promise — it’s a decision.
You choose to look for it, and then you follow it. I didn’t know how it would turn out. I just did it anyway.

Life is as much about what you experience as what you accomplish.
There were challenging days — days when I questioned why I’d made that move. But the mix of struggle and beauty is precisely what made it meaningful.

Home isn’t a place — it’s the story you carry with you.
Hawaii is a part of me now. Everything I do carries a trace of that time — even when I’m back in California.

Is There a Return in My Future?

I’m not sure. Maybe someday I’ll make my way back to Oahu — perhaps even to retire there. But I do know this:

I am grateful for every moment I spent living in Hawaii, for every lesson learned there, and for every opportunity that brings me back.

Mahalo nui loa — thank you, Hawaii — for everything you gave me, and everything you continue to inspire.