The Truth About Working on Sail Boat and Why I Left
From Cruise Director to Yacht Sales Broker: A Career Shift Anchored in Real Life
Let’s rewind a bit. For most of my adult life, I was a cruise director sailing across Indonesia, curating dream holidays, dodging storm systems, fixing dive masks mid-snorkel briefings, and troubleshooting everything from leaking tenders to confused charter guests ("Is Komodo a day trip from Bali?").
It was wild, fulfilling, and ridiculously beautiful. But somewhere between the manta rays and the midnight wake-up calls to check on the generator, something shifted.
In November 2024, I made the biggest pivot of my career: I stepped off the boat and into a new role as Yacht Sales Broker and Marketing Manager. Yes, I went from guiding barefoot luxury expeditions to juggling CRM platforms, Google Analytics, and boat listings.
But trust me, it wasn’t just about switching careers. It was about reclaiming my life.
It’s true, being a cruise director sounds like a dream job. And for many years, it really was. But here’s what the job description doesn’t show.
At first glance, it might seem strange to walk away from a job that involves sailing through paradise, hosting incredible people, and living out what many would consider “the dream.” But behind the photo-worthy sunsets and curated itineraries, there were some very real, very human reasons I knew I needed to change course.
1. I Was Physically Exhausted, All the Time
Cruise directing isn’t just giving cheerful announcements and leading beach barbecues. It’s non-stop physical work, day in and day out. My days regularly stretched 14 to 16 hours, with barely a moment to myself. Wake guests at 6 AM. Snorkel briefing. Gear logistics. Shore excursions. Guest feedback. Crew issues. Dinner hosting. Navigation planning. Repeat.
Even on calmer days, I had to be alert and ready for anything: weather delays, engine hiccups, seasick guests, last-minute food allergies. The emotional and physical toll quietly accumulated like salt on skin.
There’s a unique kind of tired that settles into your bones when you’re “on” all the time: cheerful, composed, competent, even when all you want is ten uninterrupted minutes to lie down without someone asking, “Can we snorkel just one more time before lunch?”
I loved the ocean. But I also love my spine. And it was starting to feel like I couldn’t keep this up forever without something breaking.
2. I Was Tired of Constantly Having My Heart Broken
There’s a unique kind of loneliness that comes from always being away. I don’t mean the romanticized version where you're sipping tea on a remote deck watching the stars, feeling wistful. I mean the kind where you’re quietly nursing another broken heart while welcoming guests with a smile so polished it could win an Oscar.
Over the years, I kept trying to make relationships work, squeezing in video calls between charter turnarounds, planning visits that got canceled due to sudden trip extensions, sending good morning texts from time zones no one could keep track of.
But despite my best efforts, nearly every relationship ended the same way: with me having to explain (again) that I’d be gone for another two months. That I’d miss yet another anniversary. That I couldn’t be reached for the weekend. Again.
It was exhausting. And it was heartbreaking.
Smiling through the pain while giving safety briefings or leading sunset hikes became a weird kind of emotional gymnastics. I got good at it, too good. But the toll it took was real.
My most recent relationship was the wake-up call. It started with hope, like they always do, but eventually it began to feel more like a chore than a connection. Every interaction felt strained. Every conversation felt like a negotiation. There was no joy left in it, and eventually, no “us” either.
And this time, the breakup didn’t just sting, it wrecked me. I realized I wasn’t just tired of being heartbroken. I was tired of navigating heartbreak while pretending everything was fine.
So I made a quiet promise to myself: I want to be around. For my partner. For my friends. For myself. I want a life where love doesn’t have to fit into Wi-Fi windows or between guest briefings. I want real intimacy, not just WhatsApp voice notes sent from a crew cabin with bad signal and worse timing.
3. Losing My Dad Changed Everything
This one’s hard to write, but it’s the truth: when my dad passed away, I wasn’t there. I was at sea, hundreds of miles from cell service, unreachable in his final days. And that reality hit me harder than any storm I’d weathered on the job.
Grief is a strange thing. It breaks you open and rearranges your priorities in ways that feel permanent. After losing him, the thought of something similar happening with my mom, or anyone I love, was unbearable.
That was the tipping point.
I realized I didn’t want a career that took me so far from the people I care about. Not just physically, but emotionally too. I wanted to be reachable. Present. Available to show up when it matters most, not just when the charter season allowed it.
Enter Land Life: Still Nautical, Just Less Nomadic
When the opportunity came to join a yacht brokerage and marketing team, I jumped on it. It wasn’t a retreat from the maritime world, it was a recalibration.
Now, I get to stay connected to yachting, still working with boats, owners, and charters but without being physically gone for weeks or months at a time.
And wow, do I sleep better in a bed that doesn’t move.
How My Skills at Sea Translated to Sales & Marketing
The Sales Part
Turns out, walking someone through a 7-figure yacht purchase isn’t that different from managing charter guests. Both require:
Listening
Patience
Understanding unspoken fears
Explaining things clearly and kindly (without making anyone feel stupid)
Being on the water for years gave me firsthand insight into what buyers are really looking for, not just specs and layouts, but lifestyle fit. It’s less about square footage and more about, “Will I feel at peace here?”
The Marketing Part
Onboard, I was already writing daily briefs, planning activities, and creating experiences. Now, I just do that on-screen.
From social media posts to blog content (meta moment: like this one), I tell stories that connect people to the idea of yacht ownership, chartering, and the lifestyle that comes with it.
The audience may be different, but the essence is the same: help people see what's possible.
What I Gained (and What I Let Go)
Gained:
A sense of normalcy
Nights off
Time to reconnect with family
The ability to build a home, not just a bunk
The energy to explore creativity in new ways (hello, Canva addiction)
Let Go Of:
Waking up in a new island every day
The unbeatable bond of living with a crew at sea
The thrill of winging an itinerary when the weather ruins Plan A
That inexplicable joy of dancing barefoot on deck after a successful trip
Was It Easy? Nope. Was It Worth It? Absolutely.
Identity Shifts Are Hard
For so long, I was the cruise director. The marine-life nerd. The go-to person for all guest dramas and champagne requests.
Letting go of that version of me felt like grief and liberation in equal measure. But it also gave me the space to grow in a way I hadn’t imagined possible.
Now, I’m learning the intricacies of brokerage deals, SEO strategy, Google Analytics, client nurture funnels and slowly falling in love with this side of the industry, too.
For Anyone Out There Craving Change...
You don’t have to stay somewhere just because you're good at it.
You don’t have to sacrifice your personal life to feel successful.
And no, it’s not too late to reinvent yourself, even if your identity has been “that ocean girl” for the last decade.
The sea will always be there. You can still love it without living on it 24/7.
Still Me, Just Slightly More Moisturized
In a way, I’m still doing what I’ve always done:
Helping people get closer to the water, just without sand in my ears or sunburn in strange places.
So here I am:
Part yacht sales broker.
Part marketing manager.
Still deeply ocean-obsessed.
Just… with better Wi-Fi.
Want to chat boats, charters, or career pivots?
Slide into my inbox or connect with me on Instagram @happilyroaming
Thank you for reading and now back to happily roaming!