How to Quit Your Job and Travel: Well-Beaten Escape Paths

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 15 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.

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

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. 

Choose a direction and just start walking. 

1) THE DIRECT ROUTE

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

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 launching pad 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 Four 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

2) 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 best 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 replace the primary income, you can make the switchover.

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

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. 

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, unlocking new options for the work you do and the places you do it in.

Which escape path would you ideally choose?