chapter 25: life at sea + under the sea⛵️🤿
one week of trying on a different lifestyle | the start of nonstop continuous travel
welcome to my digital travelogue – chronicles of how taking a career break to travel for a year shapes you as a person, because you are where you go. quick notes:
three weeks ago: said goodbye to my home in LA. one week ago: said goodbye to my family in NJ and friends in NYC, and hello to a nomadic life for the next year
join my group trip to Morocco on October 5-12! It’s first come, first served for the 10 adventurous people who put down a $500 deposit🐪
I’m adding a new section to the bottom of this newsletter about my efforts to live/plan intuitively — aka, doing what feels right, right now. I’m curious to have a written record of my intended upcoming travel plans for me (and you all) to see how it evolves over time.
This week, I’m writing to you while the room slightly rocks in my peripheral vision as I adjust back to life on non-moving land — I just spent the past week living on a boat while diving the sparkling turquoise waters of the Exumas in The Bahamas.
And no, I don’t mean a cruise ship. I mean a small, 65-foot sailboat full of 20 scuba divers and 4 crew members packed into cozy bunks.
The past week was a peek into a vastly different lifestyle. The people who work on this ship never had a desk job, never were tied down to a 9 to 5, never had the luxury of “working remotely” – just working hard, but working joyfully. For them, work involves the sun, the sea, the winds, and listening to Mother Nature rather than a middle manager.
This week at sea was an experiment. It was a taste of something new, something salty. It was entering life’s fitting room and trying on the lifestyle of a sailor to see how it might suit me.
It was hearing our British divemaster bellow “THIS IS YOUR TEN MINUTE WARNING TO THE DIVE BRIEFING” four times a day — which prompted everyone to double check their scuba tanks’ pressure, pull on damp wetsuits, and gather on the boat’s top deck to peer at a whiteboard drawing of our next new dive site before splashing into the ocean on a strike mission to hopefully see new underwater things we’d never seen before: a trio of loggerhead turtles! a feeding frenzy of reef sharks and groupers! a pair of squid! unparalleled masses of Christmas tree worms! a washing machine-esque drift dive of barreling currents!

It was completing my 100th dive – in just about 2 years since I first got scuba certified! – and realizing this was just one small milestone in the grand scheme of the scuba industry, where divemasters and instructors commonly have thousands of dives under their belt.

It was the ding ding ding of the mealtime bell turning us into a feeding frenzy of sharks ourselves, as we descended down into the main saloon three times a day to enjoy delicious home-cooked meals prepared by our talented chef in a galley the size of a broom closet. It was a week of eating steak with chimichurri, fried chicken sandwiches, spaghetti with homemade meatballs, smores brownies, pineapple rum cake, and a traditional South African dessert called malva pudding while we sunned ourselves in the middle of the ocean.
It was getting used to the constant rocking of the boat, acquiring sea legs so strong that we could balance going up and down the boat’s ladders hands free while holding our plates piled high with food.
It was the daily indulgence of our silly little human fixation with the sunset — everyone ooohing and aaahing while snapping a photo to capture the memory (despite every single one of us already having hundreds of sunset photos in our camera rolls).
It was a week of 24 people sharing one onboard shower. It was late night hours of banter and playing back GoPro videos of the day’s adventures while waiting our turns to bathe in saltwater (with a luxurious 30-second freshwater rinse at the end).
It was sitting on the top deck late into the midnight hours watching lightening strikes on the horizon, mesmerized by the striking visualization of danger in the distance.
It was lying down in the cradle of the ocean as it rocked us to sleep in our windowless cabins.
It was a taste of a life far, far removed from sitting behind a computer screen all day.
It was exactly the refreshing new perspective I was looking for to officially kick off my career break year of travel.
Although I’ve been "at sea” for weeks before on big cruise ships, this was dramatically different. Living on a small boat for a week helped me envision what life would be like in the maritime industry.
Even if becoming a full time sailor is not something I’m actively thinking about ever doing myself, I have developed a deeper understanding and empathy of what it’s like for the people around the world who do consider boat life just “life”.
And that’s one thing I’ve realized is my top priority in this upcoming year of nonstop travel and continuous exploration: to explore, to learn, to understand more of the world.
Especially in cities like New York and Los Angeles where I’ve spent most of my adult life, it is so easy to get caught up in a metropolitan mindset, where you can think that someone starting their own company is “going off the beaten path” in comparison to traditional careers.
But in the grand scheme of things, every laptop-oriented job is still pretty damn on the beaten path. I want to make the most of my career break not by learning how to build a business online, not by starting a digital side hustle to make a career pivot – but by taking time to try on different lives and understand more about the world outside of a laptop: in nature, at sea, in places where wifi doesn’t reach.
We often refer to things outside of the internet as IRL – and that’s where I want to be living this year: in real life.
👯♀️ join me on an upcoming group trip!
🇲🇦🐪 october 5-12 = sands of the sahara: a moroccan odyssey roadtrip
If riding a camel and sleeping under the stars in the Sahara desert is on your bucket list… come along with me!
Join me, 10 like-minded strangers (who will become your new friends!), a local guide, and a private driver on an epic roadtrip from Marrakech to Tangier, stopping for an overnight in the Sahara desert, Fes, Chefchaouen, and small villages in the Atlas Mountains. Check out the full itinerary, cost, and some inspiring photos of what we’ll see – and book your spot ASAP! Spots are first come, first served for up to 10 people.
Optional add-ons if you want to join me in traveling longer: I’ll be hitting the Moroccan coastline to surf the longest wave in Africa for a few days before October 5, and will be taking the ferry from Tangier across the Strait of Gibraltar to end my trip in Spain if you’d like to tag along for a little bit longer and a lot more adventure 🏄♂️🚢
📝 notes on living + planning intuitively
About 2 months ago, I wrote out my tentative travel plans for this upcoming year and shared them. I’ve already started to change this plan as I acquire new information and inspiration, so I thought it would be interested to jot down these learnings and new decisions for you to follow along in real time if you’re curious about the ever-evolving journey of intuitively planning a year-long sabbatical.
Originally, I assumed that Dec–Feb would be a great time to visit Australia since it’s summertime down under. But, upon further research and conversations with people more knowledgeable than myself, it actually is jellyfish season – and therefore not peak season for scuba diving the Great Barrier Reef. Back to the drawing board on when best to visit Australia, since my main priority for staying there a few months is to surf and dive…
Simultaneously, my good friend from South Africa who spent the last week diving and living on the boat with me invited our friends to come visit while she’s visiting family there this December… which compelled me to consider spending a chunk of December in Cape Town with her instead of in Australia. If I’m in the area, maybe I’ll also finally complete the Botswana-Namibia-South Africa overland safari that I was supposed to do in 2020 prior to COVID wrecking all my plans that spring/summer. It feels right… so I might do it and just stop overthinking everything else!
I also originally really wanted to visit the Maldives for scuba diving but have heard that February is usually the best time to visit. So now with re-arranging my Australia plans, the Maldives might actually fit in better… and I can still easily hop over to India in March to celebrate Holi there which is a non-negotiable bucket list experience I want to have next spring.
A lot of people ask me how I decide where to go, and honestly it really goes down just like I’m describing above – I google “best time to visit [country name]” and see if it aligns with gaps in my existing travel plans, or I follow opportunities to meet up with friends/locals for a unique and more fun experience, or sometimes simply follow an enthusiastic recommendation I’ve heard one time from one person – like the girl I spoke to recently who put me on to the idea of surfing the longest wave in Africa on the coast of Morocco! My lesson to anyone (including myself) deciding where to go is: don’t overthink it. If it sounds exciting, just fucking do it.
thanks for reading !
my goal is to inspire you to travel more as a tool for personal development – and, to live life in a way that feels right to you.
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if anyone you know loves to travel and is perhaps thinking about exploring an alternate life path/taking a sabbatical… send this their way!
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that’s all for now…
remember, you are where you go – never stop exploring the world and yourself! 🌎 🌍 🌏
if you enjoy my writing in this newsletter, you’d love my book called You Are Where You Go: A Traveler’s Coming of Age Journey Through 70 Countries and 7 Continents During College
Love it! I also just spent a week disconnected in Ireland in a campervan. I always feel so, so good when I disconnect.
Congrats on your 100th dive! Amazing!