A Practical Guide to Vagabonding and Long Term Travel (Part 1): Taking the Leap
How would you like to take the plunge into an exotic life of long-term travel? To stand at the edge of the chasm of life, dipping your toe into the waters of adventure, culture, new experiences, strange foods, interesting people, unanticipated challenges, and the abyss of the unknown? To push your boundaries far beyond what you thought possible? To shed your life of routine in favor of experiences you can’t even contemplate or imagine?
Vagabondish is reader-supported. When you buy through links on our site, we may earn a small affiliate commission. Read our disclosure.
You can do it.
Really. You can.
I have frequently encountered people (readers and friends alike) who are enamored with the life my boyfriend and I lead. They wish they could do it themselves: quit their jobs, sell off everything, and travel the world in a financially sustainable manner for as long as they wish.
But there is a fine line between becoming a vagabond at the expense of your future, and doing so responsibly. Bills and loans need to be paid off (or money set aside to make the payments), and investments for the future are always a good idea (because the only person who will plan for your future and take care of you is you). Paperwork needs to be filled out, logistics addressed, and a support network of people to help you from home put in place. Add to that the daunting prospect of selling everything, figuring out what to take, earning money on the road, and stepping outside the social norms, and many people are paralyzed before they even get to square one.
This article is the first in a series of step-by-step instructions on how to become a vagabond. From logistics to emotions, there is a lot to think about. So let’s get started.
Get a Travel Journal
This will become your bible for the duration of your travels, starting with the preparation phases at home. In it you will record motivations and ideas, resources people give you on the fly as you formulate and discuss your plans, and to-do lists. As with any journal, use it to record your feelings around the emotional journey of your transition — this is something you will want to revisit once you make it over the hump — believe me.
The Mental Stuff
Here are a few questions to ask. Do yourself a favor — answer them as completely as possible, and write your ideas and thoughts for each of these questions in your travel journal.
Why Are You Traveling?
What prompted this change in life? Did you burn out? Are you sick (yes, people will ask you this)? Did you get laid off or quit your job and decide that now is better than never? Or is long-term travel a dream you’ve been shooting towards for years?
No matter what brought you to the pivotal moment of wanting to shed the routine life for one of travel (if even for a gap year or career break), you must define for yourself why you are traveling. It doesn’t have to be a reason you stick with forever (because motivations change as life’s journey does) — but there has to be a reason to begin with; this will help in the further steps of setting goals and taking care of the finances.
Where Will You Go?
You don’t by any means need an itinerary right off the bat. But a general idea of where you want to go will shed a lot of light on why you are traveling and what the nature of your trip will be.
I was originally headed for Costa Rica to be an outdoor adventure guide, when a family wedding took me across Canada, then an opportunity I couldn’t pass up to go to Hawaii came my way. I was going to be on my way to South America after that, when another opportunity I couldn’t pass up to go to Australia came my way. In between, Southeast Asia called my name. I still haven’t made it to Central or South America, but I know I will.
Knowing where to start gives you something to hang onto in the absence of “opportunities you can’t pass up” taking you on detours.
What Will You Do?
Do you plan to earn money on the road? Volunteer? Camp? Wwoof? Teach English? Drive a bio-diesel vehicle across a country? Climb the highest mountain on every continent? Travel through hostels, or even hotels? Do you have friends to stay with along the way, or to travel with for all or part of your journey?
Will you stay in one place, or see many cities and countries in a short period of time? Are you hoping to relocate entirely, pass through, or visit for a few months?
How Long Will You Be Gone?
For some people, this is easy. The incidences of gap years and mid-career breaks are on the increase. Some school teachers have the ability to work a “four over five”, where they are paid an even salary over five years, but only have to work for four of them.
If you don’t have a set time frame, that’s okay too. You probably have a general idea though, if you will be gone for six months, a year, three years, or forever (whatever “forever” means). Be sure to define, at least for yourself and at least for now, how long you plan to be away for.
The next step is a tricky one. It’s the first full step to traveling after talking a big game to your friends and family. Now it’s go time.
Make an appointment with your boss at work. This is not a passing-by-the-water-cooler-and-thought-I’d-tell-you-I’m-leaving-this-world-to-be-a-vagabond kind of conversation. It’s stranger than simply giving your notice that you are leaving this job for another, because many people won’t entirely understand why you are leaving the comforts of a secure job and career for the unknowns of life on the road.
My regional manager tried to convince me to just leave for six months. He promised to take care of my client base (I ran a financial planning practice) in my absence and pave the way for my return. He was convinced that this was just something I needed to get out of my system. I love him for being so understanding and leaving the door open, but I knew this was going to be an adventure that would take way longer than six months, and that I would likely not end up in the same place (career-wise or geographically) by the end.
But it does bring to light an important factor to quitting your job: if you can manage it, do not burn any bridges. To have the opportunity to step right back into your “old life” is a wonderful security blanket to have just in case your travels don’t prove to be as illuminating as you had hoped them to be. And for some, taking the six month leave of absence to travel, knowing you have something to go back to, will alleviate some of the stress that might impede your enjoyment on the road.
Either way, as you announce your travel plans to your boss, co-workers, colleagues, friends, and family, you’ll have some explaining to do. Luckily though, you’ll already have done some of the mental groundwork above and will have defined for yourself why you are traveling, where you are going, what you’ll do, and how long you’ll be gone.
Stay tuned to learn how much money you need to be a vagabond, how to sell all your belongings and get the logistical stuff out of the way, and the finances of life on the road among other golden tips.