Considerations before leaving. So you want to sail into the sunset. To Sea or Not to See

The top 6 questions you should ask yourself before becoming location- independent

Considerations before leaving

Is living and working overseas in your future? There’s always so much to do and so little time. How do you tell the difference between the must-dos and the would-like-to-dos so you can stop procrastinating and get on the road? What are the important considerations before leaving?

1. What can you automate?

If there’s a will, there’s a way. That includes finding things to stop you from making a jump that will change your life forever. As they say, the only things that are certain are death and taxes. So the decision you have to make is: what will you do with the time you have left?

If you have your heart set on traveling the world, one of the decisions you will have to make is what can you automate.

Is the job you are currently doing something you could do from anywhere? For example, consulting, conducting webinars, writing, online teaching, and many tech careers could just as easily be done from Hawaii, Tahiti, or the top of a mountain provided you have access to a laptop, a phone, and internet service. So what’s holding you back?

If you can, or already do work online, half the battle is already won. 

Rent out your house to pay your mortgage. If you are not sure how long you will be gone, you could offer your residence as a vacation rental for a few months or half a year. Even if it doesn’t cover the entire mortgage, your cost to try out location independence is greatly reduced. If you use a management service, expect to pay about ten percent of the rental income for peace of mind while you’re away. 

You can use bill pay to automate payments and set up a trusted person with power of attorney to sign for things while you are away. Additionally, there are services for long-term travelers that include a permanent address you can use to renew your driver’s license, passport, as well as your voters, boat, and car registrations. The service most often recommended by full-time cruisers is St. Brendan’s Isle in Florida. For about the cost of breakfast, they will collect and sort your mail. Your mail can be forwarded or scanned for you to receive a virtual copy. You don’t have to worry about missing important correspondences or the dead-giveaway pile of mail at your front door while you are traveling.

2. Do you really need a safety net?

If traveling consumes your soul, if there is nothing in the world you want more, if wanderlust is in your blood, and you are chomping at the bit to get started, maybe the safety net is not as important to you. So, sell the house, the car, and all your worldly goods. Use whatever leftover money you have to help fund your travels. You can always re-acquire these things when, and if, you return. Remember, St. Brendan’s Isle can save you from having to modify your itinerary to renew your information.

3. Is everyone all in?

Does your family share your desire to relocate? Are you and your spouse on the same page? How old are you kids? What are their goals? 

Our kids viewpoints weighed more heavily in our decision to travel because they are older. Our daughter will be a junior during our gap year. We would have liked to have left sooner, but our youngest was just starting high school last year, so we also wanted to give her the experience of having a formal high school experience. 

Our plan will allow us to be back for my daughter’s senior year of high school, which she wants to complete with her friends. We will probably stay on land an additional year for her sister to graduate as well, before taking off again permanently.

Can you make a compromise within your family that everyone can live with? Asking your kids for input shows that you value their opinion and might help get them on board if you show them that this is their trip as well. Encourage them to research locations on the itinerary to discover their own places of interest that you could incorporate into the trip.

4. Will the experience outweigh the possible negative outcomes? Can these be mitigated?

One of my considerations before making the jump was giving up the security of my career. However, I always knew waiting to travel until I retired was not an option. Still, fear was an issue. What if I couldn’t get another job in my field after I return? What if we lost our house? What if we regretted it?

I had one major experience to draw confidence from, as well as lots of advice from people who had lived to regret not going.

A few years ago, I had the opportunity to teach English in China. I got on a plane for my first English teaching position with faith and a language dictionary. I returned home with wanderlust. It was scary and uncertain, but I wouldn’t trade the experience. And the negative outcomes never materialized. In fact, all of those fears and what-ifs were in my head. They were just excuses. Now, my biggest fear is what if we don’t go, or even what if we wait to go.

As we prepare to sail away, I have met both people who live with regret because they waited too long and their partner died unexpectedly, as well as people who waited so long they have given up on their dreams. We recently met a man who built his sailboat over the course of ten years so that he could sail the world. Now that the boat is done, he is preparing to sell it because he says he is too old for his dream.

Anything we lose, we can get back, except for time. The only for me to avoid negative outcomes is to live without regrets. Spending time with my family traveling is my way of living without regrets.

5. Can you manage fear and uncertainty?

That is a question you are going to have to think long and hard about. Nothing in life is guaranteed. Your job may be secure now, and in a few years, you could be let go from work. In fact, we had a friend who had this exact thing happen to him. A year away from retirement, and he was fired so the company could save some money. So, what are you afraid of? Make a list. Brainstorm solutions. For example, if you are afraid of running out of money, develop skills that will make you money as you travel. 

If you can’t find a solution that works for you, reach out to others. There is a wealth of knowledge available to you, if you ask. Once you set off, you will face times of fear and uncertainty, but in the meantime, you will have developed the skills and the confidence to keep going. 

6. Would you regret not doing it?

I have met many people who will spend their entire lives in one place. They enjoy being a member of the community and relish the tradition of doing the same things year after year. 

I work with teachers who have had three generations of students from the same family or now work with colleagues they once taught in elementary school. Losing that sense of community would be a regret for them, not traveling the world, and definitely not living in a foreign country. So, the answer to the question of regret is a very personal one. The answer cannot be black and white. For many people, somewhere in between the always and the never is best; traveling during the summer or during the holidays feeds their souls enough to have no regrets.

How about you? How would you answer the question?

Decision Time!

Once you have worked your way through these six questions, you will be better prepared to decide if location-independence is for you. Moreover, when you should leave should be clearer as well. After looking at the considerations before making the jump, will you jump? 

I can’t wait to hear from you. As always, don’t forget to subscribe and follow us on social media!

Fair winds and following seas!


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