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  1. Quick facts
  • Total days on the road: 586
  • Currently in: USA
  • Miles Driven: 36821
  • Countries Visited: 17
  • Days Camping: 389
  • Days Indoors: 202

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Questions to Ask Yourself Before Becoming Location Independent

Written by Jared on March 19, 2011

It is important to a bit of soul searching before you start planning your location independent lifestyle. Figure out what you want to do and define short and long term goals to achieve it. For us this process was a long time in the making.

We’ve always preferred to work remotely and keep our own schedule. We made the most of this and traveled as much as possible. Unfortunately it took us several years to realize that we needed a new lifestyle instead of different ways to live the same.

To get there faster than we did, ask yourself the following questions. Your answers will help you realize what you’re after and how much work you’re willing to put into it. There are no right or wrong answers. Our expectations and experiences should not be yours.

How many hours per week do you want to work?
At home we work 40+ hours per week. While traveling we try to work less than three days a week. And some weeks we choose not to work at all. The type of job you do will help define how often you need to work. How many hours you work will hopefully be up to you. See our article about balancing work and travel for more advice.

How much money can you save?
We save as much as possible and live as cheaply as possible while we’re at home. Savings usually finances the start up costs of a trip, which can be expensive. Money in the bank also extends your travels if your income is reduced, and acts a safety net in case of emergency. See our travel advice section about budgeting and money for more info.

How much effort are you willing to put into adapting your profession for life on the road?
We started this journey with jobs that could be done from home. It did not take us much time to transform our remote jobs into location independent jobs because of our experience. If your business is not service based, you may have an easier time than us. If your work currently requires you be at a desk 40 hours a week, the process will be longer and more difficult. Refer to our articles about adapting your profession and transitioning your 9 to 5 job for more info about our experiences.

What travel destinations interest you the most?
An easy question: where do you want to go? We’re researching a long trip to South America, and will probably check out Asia after that. Where you go is up to you. Just keep in mind that it’s more expensive to live in cities and developed first-world countries. A $15 day in Ho Chi Minh City, Vietnam easily translates to $50 in rural areas of the U.S.

How much time do you want to spend planning your trip?
We like planning our trips. It gives us a break from the daily grind of life at home. Some people prefer to plan as little as possible and make it up as they go along. Others like having detailed travel itineraries. We’re somewhere in the middle. We prefer to plan for flexibility and fun rather than a rigidly defined daily life or potential chaos. See our plan & prepare section for articles about researching and documenting destinations.

How much time do you want to spend updating your plans while you travel?
We spend less time planning once we’ve hit the road. We take care of critical stuff like reservations, buying tickets and updating our budget. Reading travel books or websites in our downtime and when we’re moving between locations tends to give us enough information. For the rest, we play it by ear.

How long do you want to spend at your favorite places?
In our experience, longer is better. It’s cheaper and you have more time to experience what local life is like. We’ve had trips where half of our time was spent moving from point A to point B. We’ve since made an effort to avoid that scenario. If you feel like you need a vacation from your travels, you’re doing it wrong. it's also a lot easier to get work done if you aren't constantly on the move.

How much time do you want to spend traveling between locations?
How much actual traveling do you want to do? Do you want to fly quickly between major cities? Or would you prefer to make your way slowly along the back roads? We’ve done both. What matters most is how many days are spent on the move. Travel days are always more stressful and tiring making it more difficult to get work done. It’s best to spread them out to keep from becoming exhausted.

How do you prefer to travel? Do you want to drive your own car, rent a car, fly, take public or private transportation?
How you get from A to B helps define how you’ll plan your trip. For shorter trips we either rent a car or take public transportation. Longer trips might involve buying and outfitting a vehicle, but there’s no reason to rule out public or hired transportation. When possible, we prefer the freedom and added comforts of having our own form of transportation. This also makes working easier.

What worldly possessions must accompany you on your travels?
Stuff. The bane of a life in constant motion. The more you have, the more restricted you will be. You need much less to survive on the road than you think you will need at home. Bring the minimum you need to live and work. Consider your ability to pick up what you’re missing on the road. See our gear section for more about packing advice and packing lists.

Will you maintain a house, car, storage etc. at your current residence while traveling?  
This was easy for us. We rent houses, own cheap cars, and have friends and family willing to borrow our stuff while we’re gone. Paying bills for things you don’t get to enjoy while you’re traveling is not much fun. If practical, rent or sell big stuff to avoid paying for storage.

What other monthly bills will you have?  For example: loan payments, insurance and medical expenses.
Monthly bills on the road can add up. We do our best to minimize these expenses. Credit cards and loans get paid off quickly. We make sure to budget for unavoidable bills like insurance and medical expenses.

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