10 Things Freelance Life on a Remote Tropical Island Has Taught Me So Far
By: Desiree Gamotin
Tags: Remote Work, Freelance, Purpose, Career Advice, Travel

Photo by: Matias Olivieri

Almost exactly two years ago I decided to leave the city life in pursuit of a simpler island lifestyle. And when I say city life, I mean deep city life.

Born in Manila, Philippines (one of the most populated metropolises in the world), my family migrated to New York when I was 2-years-old and then to Jersey City, New Jersey, while both my parents continued to commute daily to Manhattan for work. Even as kids, my older brother, younger sister and I would frolic the streets, taking the subway from JC to NYC, dodging the crowds of people and taxi cabs, to visit my mom at the pharmacy right by World Trade Center where she worked. Then in my high school years, we moved to Canada — Mississauga at first, and then naturally, I moved to downtown Toronto, post-university. So city life was the only life I knew.

The past seven years of my career before I moved to a tropical island — so my work life in Toronto, and then moving back to NYC in 2015 for a job opportunity — was pretty much a blur. I don’t want to get into detail, but in sum, think months of unpaid 40-hour work week internships in the beginning, learning (and then fully DIVING) into Twitter world and social media for brands (so more like 60-hour work weeks, underpaid), agency politics, client drama, business flights and remote work from hotels, startup cultures and pitches galore, burnouts, layoffs, meltdowns — the works.

Don’t get me wrong — I LOVED being busy, even if it meant no time for a love life (strictly situationships for me), cancelling plans with friends over a client deadline or a last minute work trip. But then you just get to a point. You know, the POINT. When your boss notices you staring out the high-rise building window during a team meeting, fully knowing your head is just not there. When you start walking around barefoot in the office like a mad woman, imagining your toes curling onto the warm sand, instead of cold hard slabs of tile. When you literally start “mind-surfing” on a packed train on your way home from work, daydreaming of a life outside of this work grind. That POINT — when you truly take a step back and think, why are we doing all this? What is our purpose?

As a big-time lover of travel (after university I also moved to Seoul, South Korea for a year, then travelled solo to Japan, India and Nepal for months), I knew I had to leave the city and move somewhere completely opposite. I just wanted nothing but to spend my days surfing, doing yoga and just chilling tf out. Cliché, I know — but I was actually surprised to learn it wasn’t as common as I thought it was.

When I decided on Siargao Island in the Philippines, I got this a lot from my city friends: “You’re so brave for doing this.” While flattering to hear that people saw me as this brave, free-spirited, ‘galloping into the sunset to pursue my dreams’ kind of person (the Leo inside me was getting a bit of an ego boost), I didn’t feel that way at all. I wasn’t afraid, and I think ‘bravery’ connotes that showing of mental strength in the face of danger, fear or difficulty — in fact, I never felt more at peace and aligned with this decision in my whole life. So I don’t think it was bravery that got me to decide to pick up, move to a remote island in the Philippines and completely change my life — it was a necessity. Not only was my mental health suffering, but my physical health as well — my herniated disc injury was aggravated even further from sitting at a desk chair for 8–9 hours a day and the severe psoriasis on my face and neck only worsened from the stress, air pollution and, according to my dermatologist, lack of sun. But it took taking the time to dive inward and truly listen to what my heart needed at the time, trust it, follow my intuition and then surrender to its calling. I had to decide to put myself first for a higher purpose and a higher self.

From high-rise buildings to coconut trees.

So in October 2018, I left everything and moved to an idyllic surfing island called Siargao — and I never looked back.

It was exactly how I thought it would be — but also not. I work around the tides and the best times to surf. Even typing that line right now, I sometimes feel like I’m still dreaming.

It’s a global pandemic, so I know it’s easier said than done now to just pick up and leave for a tropical paradise. Country bans, travel restrictions, flight changes and unpredictable lockdowns across the world make it so hard, and obviously home and family situations are prioritised. That said, I wake up feeling immense gratitude every day for the privilege and opportunity to be able to choose the lifestyle I lead now.

For those thinking about (one day) taking the leap into full-time freelance work on a remote island, JUST DO IT. Or at least start planning now. Take the leap off the plane and figure out how to work the parachute after.

Since my full-time freelance journey began in Siargao two years ago, I’ve gained a few insights and gathered some tips on how to live and thrive on a tropical island as a freelancer. The local surfers have a saying here: “Share waves to share happiness.” I hope these tips help or at least inspire you to find your happy island home in the future.

1. But First… Meditate (and Journal)

Confession: I didn’t just decide one day to pick up and leave for Siargao — it was planned years in advance. Well, not so much planned as it was me planting the seed. Before I decided to leave my Toronto job in 2015, it was already ingrained in my mind — I am moving to an island. That’s it. No questions asked. Then my oldest friend offered me a marketing job in Manhattan that I couldn’t pass up. That wasn’t the kind of island I was talking about, LOL, but I couldn’t resist the offer and thought I had one more ounce of youth energy in me to frolic in the Big Apple one last time. But over those years in NYC, I came up with my game plan — once my last big city “hit” was over, it’s onto tropical island life for me, for real.

It may sound a bit unconventional to some, but before finally deciding to pull the trigger on Project: Island Life, meditating was a game changer for me. The clarity and inner peace I felt through simple breathwork in the morning or whenever I was stressed in the city allowed me to gain deep personal insight and discover what it is my heart truly desired. I put all those thoughts on paper in my journal. What is it that you truly want? What are your hopes and dreams? What have you always wanted to do, but were too afraid to do it? And what are the steps I need to take right now to get to that place?

Now more than ever, there is a plethora of available (and free!) resources, meditation apps (my personal fave is Insight Timer), guides and journal prompts to give you a head start. Get inspired. Read my BIBLE, Women Who Run with the Wolves by Clarissa Pinkola Estes, to help you connect with your inner wild, creativity and intuition. Go to workshops and sessions to help you on this new journey (I can’t forget that time I fan-girled over wellness writer and self-care advocate, Alex Elle, when she came for a workshop in Brooklyn). And I honestly believe solitude is the greatest source of knowledge and inspiration — don’t be afraid of that alone time to just think and reconnect with yourself. To help you get into that flow and just ride the wave.

Strength in solitude.

2. Build a Foundation (or Discover It)

Yes, the initial million-hours-a-week work grind was BRUTAL — but I am grateful beyond words for every single boss, client and colleague that helped get me where I am today. Good or awful, every person I have encountered and every experience I had was a lesson, which served as a catalyst for my next new endeavour. And although I now have close to a decade of marketing and content writing experience under my belt, the biggest and best secret is you may already have a solid foundation of experiences and the skills that you need to get the gig you want — you might just not know it.

I once had a friend ask me how he can start a freelance career when all he had was mostly restaurant industry experience. I later found out he managed one of my favourite restaurant Instagram accounts in Toronto “just for fun,” and the humour and approachability of the posts and captions actually helped to generate foot traffic to the restaurant. This was HUGE.

When I started my first agency gig in 2011, I had ZERO marketing and advertising experience. But what I did have was a bit of writing experience at my university student newspaper, creative ideas I wasn’t afraid to share, high energy and a bit of charm. (Also, a ‘fake it until you make it’ mentality that they didn’t have to know about, hehe.)

What I’m saying is to literally list down all your past career and personal experiences, accomplishments, big or small, and all of your present and transferable skills, both hard and soft (and if you need to learn how to do something asap, just Google it!). Ask yourself what was your career like up until now? Do you want to keep at it and grow, or completely switch careers/industries? Discover what it is you are (or can be) good at and find the confidence to sell yourself.

3. Do Your Research

Once you kind of have an idea of the type of freelance career you want to pursue, hit the web. Research a ton and find resources, recruiting agencies, remote work job boards and Facebook Groups (FlexJobs, Workew and Remote Work and Jobs for Digital Nomads on Facebook were good sources of inspo for me), and find out what works for you and where you get the most response from. And don’t feel intimidated! The Interwebs can be overwhelming af, but just think of it as your playground of discovery. See what job descriptions catch your eye, the type of companies you want to work for and which resources benefit you over others.

4. Beef Up Your LinkedIn and Network

Once you get an idea of the direction you want to take, use your connections — online and in-person (socially-distanced or virtually). Another confession: About 80% of the jobs (and the best jobs) I got was through LinkedIn or from a personal connection. LinkedIn is an amazing source, and if you use specific keywords that make you searchable for recruiters and hiring managers, eventually you wouldn’t have to lift a finger — the offers and opportunities come to you. Add a high-res professional profile photo, any featured media, portfolios, accomplishments, personal blog posts and list your services and offerings to get found. Here’s a decent list of LinkedIn profile optimization tips to get found if you don’t know where to start.

And P.S. all this can be done while you’re already on the island, so don’t feel the need to stay locked in the city or wherever you are now to “build your network” (unless you really can’t travel yet because COVID). The future (actually, the present) is REMOTE WORK, so I truly believe you can do this from anywhere and everywhere, now more than ever.

Views from the office.

5. That Said… Island WiFi — Be Prepared

I’ll be perfectly honest with you — as a freelancer, good WiFi is the biggest, if not only, true source of stress in my usually stress-free island existence. Make sure the island you’re moving to has GOOD WIFI. Admittedly, it was a struggle for me in the beginning — as a small island in the Philippines, Siargao does not have the greatest Internet service. BUT, there are specific areas on the island with the best, fastest, Western-world signal — I just had to find it.

As we speak, I’m writing from my new home in the backroads of the main town, General Luna — and I live right next to the cell towers. Best Internet ever. It only took me two years to finally learn how to “load” my phone data and home WiFi service (without having to go to the local sari-sari store), download the right Philippines-based apps for easy tracking and payments, know which Internet provider is best for which area, and know the best spots or cafes with generators for Internet if/when there’s an island brownout (which happens A LOT). Worth it, tho.

So when you make the move, be sure to research the island’s Internet connections or simply ask the locals or residents there who know about the WiFi struggle and how to deal with it.

6. Work With People You Want to Work With

When I left the startup world in Toronto, I promised myself three things moving forward: 1) I will only work for a female founder/women-owned business and women-led teams, 2) the company I choose to work with must have a mission and values that align with my own, and 3) I will only work with people who understand my lifestyle and will allow me the freedom to work wherever and whenever I want. I made a pact with myself to devote my time, energy and brain power to people who will actually listen to me (I just can’t with bro culture in the workplace) and appreciate my hard work ethic, talent and ideas. And I’m happy to say that five years and counting, I was able to uphold those three promises to myself!

The two regular freelance clients I work for now I truly LOVE — which helps when you’re in a tropical paradise, constantly distracted by surf and sunshine. Essentially, what motivates me to choose WORK over surf most days is my passion to help their small businesses succeed. I get excited about the projects I’m working on, the people I’m working with and what I’m helping to grow and achieve for them. And especially if you left your 9-to-5 because of a toxic workplace environment, you don’t want to fall into the same old patterns, working the same hard grind but from afar. Work with humans who care about your well-being, pay you on time and will help you progress further (without stressing you out).

Hard to focus when even the barista is telling me to GO SURF.

So think about and reach out to the people you loved working with in the past. Whether it be a co-editor from that college paper you used to work at, an old boss you always looked up to, even that one bar manager you got along with that one summer — try and reconnect with them. You never know if they know someone who needs help with this thing, or if they’re working on a cool project they could use your help with — it doesn’t hurt to reach out.

7. Don’t Hesitate to Ask for Help

Ever heard of having a personal Board of Directors for your life? Don’t hesitate to ask for advice or just a listening ear from the people you trust, near or far. For example, my sister-in-law is my go-to freelance mentor warrior woman when I need any advice on rates, payments, invoicing, even design tips — whatever! My Capricorn bestie from Atlanta (who I met during my NYC stint) is secretly my life coach — she asks me the deep, tough questions about myself, my reactions to things, the decisions I make and other personal and professional aspects of my life. And my sister is my overall life rock, wellness motivator, no-filter soundboard and therapeutic laugh factory. Seriously, every person needs someone like her in their lives. Find them, keep them and treat them with the same attention and love as they do you.

8. Motivate Yourself (Even If It’s Excruciatingly Hard)

Living on an island has its perks, but it’s no vacation. I still want to (need to) work hard and produce the same level of results as if I was living in the city. So I create a solid routine and a bit of a reward system for myself to keep me accountable. If the surf is good at sunrise, I’ll go but I’ll make sure I’m back at a certain time to check in with my clients via Slack or email (it’s a 13-hour difference in time zones for me). Or some days, if I wake up really early and work my ass off for 5 hours straight, I get to surf at sunset. And if I don’t meet my deadlines, I’m not allowed. This is the mom/boss inside telling me to stop procrastinating, or you can’t have fun. Work hard, surf hard.

Never late to a board meeting.

9. But Also Find the Perfect Balance

For some reason (and this is my own personal opinion), the term “digital nomad” doesn’t sit well with me. I once had someone on the island introduce herself to me, saying, “Hi, I’m Becky, and I’m a digital nomad.” Cringe.

Maybe it’s the ‘digital’ part, mixed in with the ‘nomad’? I don’t know. It just sounds a bit too Black Mirror-y for my liking. My career is in digital marketing and online stuff, yes — but I don’t define myself as a digital person. I’m in the human world. I like to touch and feel things, experience and bask in the glory of nature, and try and be as far away from the digital world if and whenever I can in my free time. Island living is a no burnout zone. So don’t lose sight of why you came here in the first place. Live simply. Enjoy the freedom (it’s awesome). Catch yourself when you’re working a bit too hard, always on your phone or laptop, and take a digital detox for a couple days to reset. Be a part of the community and learn the local language. Volunteer with local organizations and give back to the island more than you take.

The first time someone called me a “local,” I nearly cried with joy. I AM a local. Proud and dark-skinned Filipina with sun-drenched blond-ish hair. I’m part of this island community now and it feels so good.

The local kids inspire me to be a better human.

10. Last But Not Least, Practice Manifest-action

Be the energy you want to attract and the opportunities will come. Of course, you do have to work for it (I know I put my time in). But it’s all about manifest-action. And going back to the question, “What is my purpose?” Find that out, first and foremost, and every decision you make afterwards will just come easier. Stay true to yourself, stay humble and be kind — and the universe will back you up.