How to Quit Your Job and Travel: 6 Easiest Pathways

The way we work has evolved. Offices are dying and remote teams are thriving. Workers are happier and more efficient, companies are leaner and cheaper to run. It’s a trend that’s only going to continue.

If you’re sitting in an office counting down the days until your next vacation, rest assured that there are ways out.

If you’re wondering how to quit your job and travel, there are three proven paths to getting there.

Let’s dive in and explore them!

Pathways for Quitting Your Job To Travel

When Tim Ferriss dubbed them the New Rich, they were merely a quiet underground culture—a small group of entrepreneurs who chose to value time and mobility over money. But in the past decade, the nomadic subculture has become a movement. Now there’s a new wave of freedom-seekers 30 million+ strong who know their options, refusing to be defined by a job title or refined by a zip code.

These travelers have escaped their cubicles and created a new type of freedom for themselves. It’s a digital freedom that allows them to travel the world as they work from their laptops.

The main pathways to getting there are:

• The Direct Route
• The Indirect Route

Here’s how to quit your job and travel the world.

The Direct Route

Escape Pathway #1: The Remote Job

The direct route to digital freedom is finding a remote job or becoming a digital nomad.

Get a job offer, hand in your two weeks notice, and you’re out the door.

Remote work is a booming trend that continues to grow as companies are waking up and realizing the benefits including bigger talent pools to choose from, lower costs, and happier employees. 

This is a great option if you want to maintain your career and just want more flexibility. 

You can even use your new location independence as a launchpad for your own side projects. 

No boss looking over your shoulder. Less paper ruffling. More efficiency. 

If your current company is forward thinking and you have the skills that lend themselves to remote work, don’t rule out trying to negotiate remote working terms with your employer (see The 4-Hour Workweek for effective scripts to use for talking to your boss).  

Remote Job Search Resources

Dynamite Jobs | dynamitejobs.co

Remotive | remotive.io

We Work Remotely | weworkremotely.com

Jobspresso | jobspresso.co

Escape Pathway #2: The Negotiated Freedom

Convince your company to let you work remotely. Not an option for everybody, but if you’re a programmer, developer or designer, then this could be an option for you.

Or get transferred overseas

Escape Pathway #3: The Work-As-You-Go Model

The allure of globe-trotting is undeniable. Consider fusing travel with work to add depth to the experience. There are plenty of opportunites, each allowing you to immerse yourself in different cultures while earning a living.

Here are some on-the-road jobs you can consider:

• Seasonal Work in Tourism/Hospitality. Tourist destinations constantly seek vibrant personalities during their high seasons. Whether it’s a sun-kissed beach resort or a quaint mountain lodge, there’s always room for someone looking to serve with a smile.
• Teaching English and Other Languages. English, the universal tongue, can be your ticket to almost anywhere in the world. Countries in Asia and Latin America, in particular, are hotspots for English teachers, with no requirement for prior teaching experience or knowledge of the local language. Europe offers similar prospects, albeit with the expectation that you’d know the destination’s language.
• Farming or Community-based Opportunities. With platforms like WWOOF, travelers can find themselves tilling the soil one day and sharing tales by the fireside the next. It’s hard work, but the cultural exchange is priceless.
• Volunteer Across Continents. By joining volunteer organizations, be it NGOs or the likes of the Peace Corps, you’re not only lending a hand but also enriching your soul. Often, you’ll find yourself in developing nations, each presenting its unique charm and challenges. But the beauty of it? In these locations, hopping between countries is usually dirt cheap.
• Barter Skills for Board. In certain countries, it’s not unusual to find travelers tending to a hostel bar or serving at a local café. It’s hands-on, and while the going can get tough, the stories and friendships forged make it all worthwhile.
• Sail the High Seas or Take to the Skies. Ever considered working on a cruise or for an airline? The world becomes your oyster. Cruise staff, in particular, get to explore a myriad of destinations. For those less sea-inclined, working for an airline can be equally rewarding, albeit with a bit more jet lag.
• Forge a Career Abroad. If the corporate world beckons, why not answer its call from a high-rise in Hong Kong or a boardroom in Brazil? Many developing countries are on the hunt for Western-educated individuals for lucrative managerial roles. Your money usually goes further, so even if you get paid a lesser salary, the value exchange plus freedom can make it worth it.

With the world as your potential workplace, the only question that remains is: Where will you go first?

The Indirect Route

The direct path can be a great option if you have a skillset that lends itself to remote work, but for others it’s more likey we’ll need to take the scenic route.

Here are three alternative methods I’ve seen work time and time again.

Escape Pathway #1: The Online Side Project

In the modern day and age, entrepreneurship is the new job security. When you receive multiple paychecks from different sources, you are no longer dependent on a single income source or employer. More income means more options, and more options means more freedom—including the freedom to choose where you work from. 

The idea is simple: have a stable base of income coming in that allows you to be more speculative with your own projects. The eventual goal is that the side project becomes your primary income source.

The primary income source ideally:

• Is stable and secure (allowing you to be more aggressive with risk-taking)
• Involves work intellectually unrelated to your side project 
• Doesn’t come home with you

In other words, it’s a regular source of income that allows you to use your evenings, weekends and vacations to work on your side project undisturbed. Once the side project is able to generate enough passive income to replace the primary income, you can make the switchover.

This is the method I used to earn my freedom initially.

Related: Questions for Coming Up With Business Ideas

Escape Pathway #2: The Sabbatical

With the side project method, you simultaneously maintain a stable source of income and work on your entrepreneurial side project. With the sabbatical, you alternate.

You spend a period of time focusing on money accumulation, then switch to focus entirely on your side project. Pure money-making, then pure creation. 

It’s about banking money so that you can cover your living expenses while you’re not working, giving yourself the runway to get your project the initial traction it needs to start bringing in an income.

If the side project takes off, you’re in the clear. If you require more time, you repeat the cycle.

A lot of the people I’ve seen successful with this method extend their runway by taking advantage of geoarbitrage, working on their side projects in countries where there’s a cheaper cost of living. 

Related: How to Get F*ck You Money

Escape Pathway #3: The Level-Up

If you don’t have the skills that translate over to online business or remote work, you have to adapt. 

Focus on leveling up as a first step. 

A lot of the skills required to be a digital entrepreneur or get hired in a remote job are the same, and the basics can be learned in a short period of time.  

Read. Study. Learn. Do. 

The internet is your friend. 

A few of my most successful friends initially found a mentor doing what they wanted to do and went to apprentice for them. 

Don’t get stuck in this phase. Gain some skills, choose a method and start implementing. 

Trial and error is the name of the game.

Here are some of the most important skills that lend themselves to online business:

• SEO writing
• Copywriting
• Marketing (email, social media, lead generation) 
• Platform know-how (ex. WordPress)

Note: See the Recommended Resources for a list of tools to use.

Choosing How to Spend Your Newfound Freedom

These paths can be used even if you have no intention to travel. This post could have just as easily been called “How to Quit Your Job and Do Whatever the &%*# You Want” but you know, Google wouldn’t take very kindly to that.

It’s about knowing you have the ability to mix things up and change your location tomorrow—even if you don’t exercise it. 

There’s a freedom that comes with that.

You might not hate your job. You might not hate your boss. You might just hate being confined to locations and schedules. 

But if you’re always waiting for your next vacation or are constantly feeling like you’re wanting to escape, you’re incapable of doing your best work.

Removing this resistance can help bring out more of your brilliant ideas and open you up to new opportunities in lifestyle design, unlocking new options for the work you do and the places you do it in.

Key Considerations Regardless of Chosen Path

Addressing Your Current Job

Making the leap into full-time travel often means making significant changes to your current employment situation.

1. Considering the Possibility of a Leave of Absence or Sabbatical

Before resigning, explore if your current workplace offers sabbatical or long-term leave options. This path provides the security of returning to your position after your travels, offering both financial stability and peace of mind.

2. Preparing a Resignation Letter and Navigating Exit Interviews

If leaving permanently is the route for you, draft a professional and gracious resignation letter. Also, prepare for potential exit interviews by being ready to articulate your reasons for leaving without burning bridges. Remember, the world is smaller than you think, and maintaining professional relationships can be beneficial in the future.

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Preparing for the Emotional and Psychological Aspects

Traveling isn’t just a physical journey. It’s an emotional and psychological one as well.

1. Coping with Loneliness and Homesickness

While the thrill of new places is exhilarating, there may be moments of loneliness or homesickness. Developing coping strategies, such as journaling or establishing routines, can help anchor you during these times.

2. Adapting to New Cultures and Ways of Life

Every place has its rhythm, customs, and social norms. Approach each with an open mind, ready to learn and adapt. Respect local traditions and try to integrate rather than isolate.

Maintaining Connections with Loved Ones Back Home

Staying connected with family and friends is essential. Thanks to technology, it’s easier than ever to check in, share experiences, or simply have a chat. Regular communication can also alleviate feelings of distance.

Logistics and Preparations

The practicalities of long-term travel require meticulous planning.

1. Addressing Healthcare and Vaccinations

Ensure you’re covered health-wise. Look into international health insurance options and make sure you’re up to date on any necessary vaccinations for the regions you plan to visit.

2. Deciding on Long-term Storage or Disposition of Possessions

Evaluate your belongings and decide what to keep, sell, or donate. If storing items, research secure and affordable storage options.

3. Forwarding Mail and Handling Other Administrative Tasks

Consider setting up a digital mail service or having a trusted friend or family member manage your mail. Don’t forget about other administrative tasks like suspending utility services or setting up automatic payments for ongoing bills.

With these considerations in mind, you’ll be well-prepared to make the jump into the world of prolonged travel. Embrace the adventure ahead with both excitement and prudence.

Frequently Asked Questions About How to Quit Your Job and Travel

Parting Words

As we wrap up this exploration on how to quit your job and travel, remember that every journey is deeply personal and unique. Like a city stroller choosing which alley to venture down, the decisions you make in this endeavor are yours and yours alone.

To be honest, it doesn’t much matter which route you take in the beginning. In the end, they all lead to the same place. The beauty lies in the experience, the memories made, and the challenges overcome. Choose a direction and just start walking. Embrace the unknown, the unexpected, and the sheer thrill of pursuing your passion.

We’d love to hear from you: Which escape path would you ideally choose? Share your thoughts, experiences, and aspirations in the comments below.

Originally Published: August 9, 2019