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How to Be On Vacation Every Day for the Rest of Your Life (Really)

Yes, it’s true that Americans take really half-assed vacations. Here’s the unexpected upside.

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BY Bill Murphy Jr. - 03 Sep 2015

Bear with me--I think Ive figured this out. I wish Id done so years ago, but better late than never. (Hint: it involves entrepreneurship.)

Recently, I asked hundreds of entrepreneurs, CEOs, and other leaders for their best tips on taking great vacations. The result, 17 Habits of Highly Effective People Who Take Really Amazing Vacations, seems to have struck a nerve, since its been shared more than 14,000 times.

A lot of the advice was about staying productive while youre away--things like finding a vacation office, or coming home on a Saturday to get ready for the workweek. I wont rehash it all; you can go back and check it out if you like. But honestly, writing the whole thing made me a little bit depressed. Are we really this horrible at relaxing?

Then, I heard from a reader named Karena de Souza--and something she told me changed my thinking entirely.

About a decade ago, de Souza and her husband and their kids set off on journey around the world--a trip that lasted a full year. They werent independently wealthy; they pulled this off despite facing all of the same kinds of challenges that most normal people would face. Ill save all of the particulars for another column. (Let me know if youd like me to write about it.)

More important for now was an insight. Since Americans are almost never totally unplugged and not working, even on vacation--that means, ironically, that its a lot easier than you might think to be on an American-style vacation almost every day of your life. Heres how:

1. Establish your happiness.

That this isn't just an academic exercise for me. A few years ago, I almost chucked it all and moved to the beach in Spain. I was divorced, no kids, and running a ghostwriting business that provided a nice income, and that was 100 percent mobile. My plan involved buying a condo in St. Pete Beach, Florida (no state income tax), and renting a former coworkers apartment in a Mediterranean town called Altea, about midway between Barcelona and Gibraltar.

Then, I went to my college reunion, got back together with a woman I'd dated in my early 20s--and was engaged within four months. (Best decision I ever made.) It might have been great to live on the beach in Spain for a while, but I realized that wasn't truly what was going to make me happy.

So, before you set out, take the lot of time to evaluate your goals, and figure out what truly makes you happy. Do you want to travel? To go hiking and rock climbing every day? To be able to participate in high culture and treat yourself to world-class art? Be sure you can answer: where do you really want to go on this journey? Your answers will affect everything else.

2. Embrace your passions.

I don't just mean follow your passions no matter what. That's horrible, horrible advice. Instead, figure out what it is that you truly love, and make this vacation lifestyle part of your quest to find a way to make it possible.

I know this sounds a little philosophical at the outset, but its important. If what you're truly passionate about is building software for example, or playing violin, or U.S. politics, that clearly will affect where you decide to go and what you decide to do.

For that matter, if you are a parent--or if you really hope to have kids--of course you need to keep their well-being in mind as well. Its not impossible to pull this off however; remember de Souza and her husband had three children while they spent a year traveling.

3. Structure your income.

Now we get to the real grit of this exercise. I'm assuming that you will need to earn money to survive. However, even if you can land a job wherever you decide to travel to, it sort of defeats the purpose if you have to spend all of your time working. So, you have to find a way to become your own boss, and to do so with a largely virtual business that requires at the absolute most, a 40-hour workweek.

There's probably nobody who has done more to explain how to do this than Tim Ferriss, in his book (and blog) The Four Hour Work Week. As of January of this year, he says hes collected more than a thousand case studies of people pulling it off. (He calls these businesses muses by the way.)

I hope this doesn't sound like a compromise--keep in mind, its the realization that most Americans are working during their measly two weeks (if they're lucky) of vacation a year, anyway, that makes this possible. In my case, I couldn't have even considered doing this were it not for my business, ProGhostwriters.

4. Evaluate your expectations.

If your idea of a vacation requires lounging for weeks at the Four Seasons Bora Bora, I'm not sure we can really help you here. But if you can manage your expectations--and your expenses--its very possible to pull off.

This can mean traveling places during off-peak times, staying in rooms and apartments you find on AirBnB--or even couch surfing or renting locally as opposed to hotels. Of course, it also means learning to shop and eat like a local, no matter whether you're spending time in Phuket or Panama City Beach, Florida.

Bottom line, the whole thing is much more possible if you can live like a vacationer but not spend like a tourist.

5. Establish routines.

I really wanted to write this column without including phrases like be reasonable, but the truth is--in order to live a vacation-style lifestyle over the long term, you really do need to be reasonable. Part of that involves setting up routines, and sticking to them.

Maybe you should even figure out the vacation office thing that the company president in my other article was talking about.

A perpetual vacation doesn't mean perpetual debauchery and lack of structure. (Don't worry--it will still be a heck of a lot more fun than working like a drone.) Knowing that you have to work for two or three hours every morning on your muse, for example, is part of what will make the whole thing possible.

6. Maintain connectivity.

I mean this in three ways: First, its about making sure you maintain connections with friends and family back home. Trust me, this is important.

Next, its about making sure you maintain and increase connectivity with people who will help you grow, both professionally and personally. We all know older people who retire, spend a few years maybe chasing a little white ball all over a golf course, and then seem to deteriorate quickly. You don't want to follow their example.

Finally, its about making sure you have sufficient digital infrastructure. I once had a guy who was living this sort of life working for me. He was a great guy, but it was a nightmare trying to do phone calls with him when he was always on a crappy cell phone in some noisy cafe.

(If you've pulled off this perpetual vacation lifestyle yourself, Id like to know. Send me a note, and perhaps well feature your advice in a follow-up article.)

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