Hawaii 5-0: Crone in Paradise
What my epic birthday taught me about aging, friendship, and myself.
Like Saturday Night Live and the UPC code, I turned 50 this year.
I remember as a child being amazed at the prospect of turning 26 in the year 2000. Growing up, thinking about my future came with the belief that hitting milestones like buying a house, getting married, and having kids would set the stage for a “successful” life. In those days aging was something that happened in the background, so I admittedly never truly envisioned my life at 50.
When I turned 49 I began taking stock.
In a few short years I’d gone from being contentedly partnered and chasing a future informed by the endlessly slippery “American Dream”, to happily divorced, child-free, middle-aged and living solo in a Bay Area suburb. At its core, much of my journey in recent years has centered on reevaluating belief systems in which I was an active participant (monogamy and marriage come to mind) but had not thought about critically until 2022 when I blew my whole life up. It was messy at times but I was finally getting to know myself…outside of romantic relationships, beyond career aspirations and financial goals, and away from the beliefs of others and society at-large. And I liked what I was seeing and feeling.
Liberation is funny like that.
Within months of turning 49, I started thinking about the big birthday. How would I celebrate? Did I want to go all out, or keep it low-key and quiet? Whom did I want to be there? When a friend randomly threw out Maui as a potential destination, that’s when I knew…
Time to plan a party.
But why Maui?
An island known for its sandy beaches and breathtaking beauty certainly makes for an obvious choice. But Maui is also very special to my family. My dad’s older brother moved there sometime in the 1970s, met and married my aunt, and together they lived and raised 2 boys upcountry. In the 90s, my uncle passed away and in 2004 I lost my dad — both patriarchs were in their 50s. And this year marked 5 years since my cousin, who was born just 11 days before me, died at the age of 44.
My family has been through some shit, but so has Maui. Consider its history and the impact of last year’s wildfires is even more devastating. A check-in with my younger cousin a few months after the disaster revealed to me the cursed-blessing of tourism: needing travelers to come and spend money to support the economy while the locals mourn and try to rebuild.
“Just don’t be an asshole,” he told me, setting the tone.
Celebration of Life
My research led me to a hotel in Kihei located within walking distance to everything from the beach to local businesses, was not affiliated with the major chains, and offered a nice spot to eat and plenty to do onsite for those who prefer to stay on the property. In June, I emailed invitations with a booking link to the hotel to a group of friends and loved ones, which including spouses and children totaled more than 50 people. Then I let go of the outcome, figuring what mattered was that I’d be taking the trip whether I had company or not.
Before I knew it, twenty people had locked in their rooms and flights!
We all descended on the island the first weekend of October and other than a few partners and kids, our group was mostly comprised of women — some on their first solo trip in years, or ever. Though my birthday may have been the catalyst, we each had our own unique reasons for booking a getaway: from navigating personal losses, health challenges and divorce, to celebrating work promotions and succesful entreprenuership, to simply needing to rest. I loosely planned 2 activities — a breathtakingly luxe picnic as my official birthday celebration with everyone, and an optional group field trip to the Old Lahaina Luau — but otherwise had no intention of packing everyone’s itinerary.
Over the course of 6 days, alchemy guided us into a flow of eating, chilling, and being in community with each other. People who had met a mere 24-36 hours before were hanging out on the beach or by the pool, going on farm-to-table culinary excursions, booking massages, and driving the road to Hana together. Everything from coordinating rides to converging at a resaurant to opting out and going one’s own way felt easy and drama-free. And each night, a group of us would venture on a nightly beach sesh with the beautiful sun-grown herb my cousin had scored from a local farmer.
Friends expressed to me daily how blown away they were by the group’s synergy, but even though I was the common thread, I couldn’t take credit for any of it. The people who showed up represented several chapters in my life: former classmates from first grade school to college (though interestingly enough, not high school); people I met in workplaces, fitness spaces, and from when I spent 5 years finding myself in New York; connections solidified through years of deep conversations and creative collaborations; and even a dear friend of my sister’s who came all the way from the UK. I do take credit for enjoying humanity and being drawn to people that are brilliant, adventurous, creative, hilarious, and kind. Everywhere I turned, there was someone I adored and I got to spend dedicated time — away from work, social media, traffic, pre-election noise, and other life shit — catching up and feeling safe, supported, and seen. It was absolutely magical, and could only happen with that group of people together in that place, at that same time.
That trip was nearly 2 months ago, and I feel like a changed person.
In addition to doing my best to maintain the slower pace that on Maui made time feel like it was going backwards, I returned home with a renewed sense of curiosity and a desire to seek out connections and experiences that give life meaning. Instagram isn’t enhancing my life in any way, so I’ll be deleting my account soon.
Taking my first big trip in years then coming home to the reality of second incoming Trump presidency also leaves me evaluating whether America is where I belong after all. The mere prospect of spending 40 minutes a day writing, researching what life is like for Black expats, or literally anything else instead of doomscrolling is already soothing my nervous system. And now that my brain is rested, all kinds of ideas are flowing.
I’m not sure what’s next, or how this newsletter will evolve, but I’m glad you’re here.
