This Month, 11 Years Ago, I Quit My Full-Time Job to Travel.

Are you going to quit? My boss asked, intuitive as ever.

I hesitated for a moment. It wasn’t so much the organization I felt indebted to, as this man sitting in front of me who wasn’t just my supervisor but a mentor, friend and idol.

Yes, I somehow mumbled. I’m sorry.

What are you going to do then?

Move back to India, try to work with a non-profit, maybe travel.

We had big plans for you here.

I know… In my head: I hope the universe does too.

Also read: Insider Tips: How to Get Paid to Travel the World in 2024!

vaeroy island view point
A journey that began way before “quit job to travel the world” became the trend it is today!

Quitting my job to travel: The dream vs reality

Exactly 11 years later, here I am. Typing these words on a breezy afternoon, from a minimalistic house in a lush Goan neighborhood. Gazing at the surrounding greenery from my work desk, I spot a furry mongoose scurrying away into the wilderness. After a morning of wild swimming in an abandoned quarry, I’m tempted to tuck in for an afternoon siesta.

As peacock cries echo in the far distance, I wonder if these were the big plans I had dreamt about when I quit my corporate job in Singapore all those years ago.

When Facebook reminded me of this 11 year quit-o-versary, it simultaneously showed me a glimpse of the life I had left behind. As I scrolled through my feed, I saw pictures of university friends who have risen the ranks in their corporate careers, purchased or rented fancy condos, acquired the coveted Singapore citizenship, and popped a baby or two!

11 years later, would I swap my life with the one I left behind?

Also read: The Story of How I Quit My Job to Travel

Life is a great adventure or nothing

robinson crusoe island images
Always in search of life’s great adventures.

The previous afternoon, while on a long bicycle ride along a sleepy Goan village, we came to a particularly challenging uphill.

As I huffed and puffed up on low gear, I simultaneously tried to take in the changing landscape around me – rolling grasslands, ancient mangroves, and paddies flooded by the relentless rain. Finally emerging at the top of the hill, I felt both exhilarated and exhausted, and psyched to continue the ride.

That bicycle ride sort of sums up the past decade.

Since I quit my job as a social media strategist at the Singapore Tourism Board, life has been quite an adventure. I’ve been on a financial rollercoaster, while simultaneously savoring epic experiences around the world. It’s been a mostly exhilarating and sometimes exhausting journey. While I’m psyched to continue the ride, I feel like I’m at a crossroads and this time, I’m eyeing a different path.

Also read: 10 Life Lessons from 2 Years of Travelling

I fear falling, but what if I fly?

patagonia scenic road view
How to quit your job and travel? Know that beyond fear, there’s freedom waiting for you.

I always thought it was the fear of failure that would drive me to make my life choices work. I dreaded pleasing the ones waiting to say, I told you so.

But in reality, it was the taste of freedom that pushed me to persevere.

I first tasted it while volunteer travelling with Spiti Ecosphere. Here was an organization based in the breathtaking Trans-Himalayan region, rooted in environmental and social impact, while financially sustaining their work.

It was everything I wanted to do too. Pursue work that gave me a sense of purpose, allowed me to travel far and wide, and meet my expenses. I dreamt about becoming my own boss, so I could spend Mondays hiking up mountains and happily burn the midnight oil on Fridays.

Turned out, on this quest for freedom, I needed to become a tough boss! I had to prove to myself that I had the discipline to make it – as a freelance writer, blogger, social media consultant, Instagrammer, speaker, author, and most recently, sustainable tourism consultant. I learnt to hustle, accept rejection, compromise, compete, collaborate and fight back.

Each time I tried something new and feared I was falling, I found refuge in poetess Erin Hansons’s words:

“There is freedom waiting for you,

On the breezes of the sky,

And you ask “What if I fall?”

Oh but my darling,

What if you fly?”

Also read: How I Managed to Pay of 26000$ of Student Loan: Candid Tips for Freelancers and Travel Bloggers

Feeling “not rich enough”

kashmir breakfast by the river
Forever grateful for the experiences this life of travel has afforded me.

At first, I was naïve enough to work for free for large companies, in exchange for the promise of ‘exposure.’ I learnt the hard way that exposure would never pay my bills or help me build the kind of future I wanted.

So even though I dropped out of the corporate rat race, I adapted my learnings from my past life. Gradually, as my income grew, so did my expenses and ambitions. I hired my first employee, then the second, and soon, I began dreaming of building up a content empire. That’s when I happened to hear a talk by Nomadic Matt – the envy of all travel bloggers – who runs such an empire. In a candid revelation, he confessed that he’s become the very thing he walked away from! With tens of employees and targets every month, his empire functions very much like a corporate.

That jolted me back to my drawing board. Am I too becoming what I walked away from? I began asking myself.

In the years that followed, I tried to make just enough money to travel comfortably, while also being able to support local businesses, work on meaningful projects, and pay more for sustainable experiences and products.

I’ve long lost the aspiration to be rich, but for the first time in a long time, the pandemic has made me feel ‘not rich enough.’ If I had the kind of money many of my peers do, I would’ve liked to buy land, plant a native forest, grow my own food, and build an upcycled house powered by renewables!

But who knows, maybe if I did have that kind of money, I’d be a totally different me with totally different dreams.

Also read: How I’m Funding My Adventures Around the World Through Travel Blogging

Reimagining the next decade

south goa ocean cliff
Contemplating life and this decade.

Over the years, I found some sort of purpose in the transient high of the feeling of freedom and the joy of pursuing work I loved, while sustaining myself financially.

But when the pandemic crushed both, fulfilment began to elude me.

After many months of introspection, I’m slowly beginning to reimagine what this decade might look like for me.

I foresee delegating a lot more to a small team of brilliant people who can continue the work I began 11 years ago (no content empire though, thank you).

I’ve begun to invest in expanding my knowledge and skills, so I can work with tourism businesses and destinations to achieve much-needed sustainability, animal welfare and climate action goals.

While the internal pursuit continues at its own pace, I hope to chase fulfilment by pursuing impactful work of a different kind.

Also read: Why Long Term Travel is Less Like Instagram and More Like Real Life

Is it worth taking a year off work to travel, or altogether quitting your job to travel?

quit job to travel
In the age of Instagram, travel feels more like a performance than a deeply personal act.

I often receive Instagram DMs and emails from folks who’ve read my book or follow my blog. Should they quit their job to travel the world? They want to know.

I have mixed feelings.

On the one hand, I feel like I owe everything – from my journey towards minimalism to my choice to go vegan – to the road. If there’s a better teacher, we haven’t yet crossed paths.

But on the other, travel today is so different from 11, or 5, or even 3 years ago. Revenge travel, overtourism and climate change are realities we must face. And as my friend over at BreatheDreamGo recently pointed out, in the age of Instagram, travel feels more like a performance than a deeply personal act.

Ultimately, the question we must ask instead is, can we bend the Instagram trend, eke out a living travelling in a way that truly fulfills us, and leave a positive impact on the places and people we meet along the way?

What’s your current status of freedom, financial sustenance and fulfilment like?

Also read:

How to Quit Your Job and Travel the World?

How I Manage Visas on My Indian Passport As I Travel Around the Globe

How to Earn Money While Travelling

Get Paid To Travel

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  1. I realized early on to spend as little as possible on a car and try to invest in property so I could have the life style I wanted that, like you, involved travel (as you can see from my blog). It took me until my mid-thirties to find a profession that I enjoyed and kept me challenged, though didn’t pay a lot. Freedom for me is being satisfied with my life.

  2. Still trying to pursue a lifestyle like you! Thanks for sharing your experience and thoughts. It really helps.

  3. Its been twelve years now, took voluntary retirement, enjoying both the family life and freedom to travel.

  4. Rishikesh D Vaidya says:

    Extremely thoughtful reflections, shivya. Questions concerning jobs and careers are the hardest ones, for they define our souls. It may sound like an interesting exercise to rethink our past decisions with the hindsight of experience but I am sceptical of its real utility. One, we cannot revisit the past; and two, it does not make the future any more fail-proof. This is not to suggest that we should not evaluate our past in the hindsight. Only that the insight it offers may not necessarily be the template for the future. Our gut feeling on the other hand is not only informed by the wisdom of experience but can also look at the fears of “what-if-I-fall?” in the eye, giving the hope of flight a chance. Your trajectory surely seems gut inspired. That is why you have the guts to reimagine the new decade. Trust, you can only grow and fly higher from where you are.

    As for my career, I am lucky that I get paid to do that, which I would any day pay to do. I get to teach some of the brightest students in the country. On the other hand, I have not given in to the pulls and pressures of promotion. I am “married” to Physics, but savour “live-in relationships” with philosophy, prose, poetry, and photography with equal zest. The only purpose of the destination is to fool us into a journey that is beautiful in its own right. At the risk of sounding immodest I will quote a maqta from my ghazal:

    रूह नहीं क़ाइल ‘ऋषि’ जानिब-ए-मंज़िल कोई
    रवाँ है बनकर दरिया कोई सफ़र में जब से जहां है।

  5. You are so brave, it s not easy to leave something comfortable behind and go for adventures. I have always found something that behind that would attach me back.

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