How to Jailbreak Your Life So You Can Live the Way You WANT

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This is a part of a continuing series of posts on the topic of how to be taken seriously. And if you wonder why a post about how to live your life while having fun is part of a group of posts on being taken seriously, think about it – If you can be a professional, while having fun and enjoying your life, there’s nothing more respected than that.

Before you read this post, read this one first. Chances are, if you’re gonna leave a snarky comment, it’s already been left there. Now then:

I’m writing this blog post on a flight back from Frankfurt, a connection to end a trip that started four days ago at Newark Airport, led me to Cape Town, South Africa, to be someone’s date to a birthday party of someone I’d never met, and included hundreds of moments I’ll remember forever. I did it without ever being out of contact with my clients, and as I fly home, I’ll arrive at 2pm on Monday afternoon, get a good night’s sleep in my own bed, and be fresh for an 8am Keynote tomorrow morning.

Yes, it was an AWESOME trip. No doubt at all. It was amazing, I saw things I’d only dreamed about, I ate fish and chips on a beach, drank wine more expensive than my apartment, and even met another random friend at the airline lounge in Frankfurt on the way back. So no, there’s no question that the past four days have been freaking AWESOME.

BUT – Here’s the thing – While I was on the trip, I got a bunch of tweet responses to my photos and posts with the hashtag #jealous. No one meant it in a snarky way, it was all good, and that hashtag inspired this post.

I talked to a few people who tweeted, and asked what in fact were they jealous of. They were jealous that I took the trip. As if they couldn’t. Of course they could! They just didn’t know it. And that part slays me.

See, I don’t care what you do, I don’t care how much money you make. If you’re reading this blog, you have access to the Internet, and you have enough money to own a computer or mobile device. That said, YOU CAN DO THE SAME THING I DO.You can pack it all up and start somewhere else, you can work from amazing places, you can do whatever you want to do, without worrying about being different. Here’s how. In the blog below, I’m going to debunk the top six reasons that people use when they don’t do something they really want to do. My hope is that you’ll read this and do something totally outside your comfort zone, get addicted, do it again, and make it part of your life.

Top six reasons you think you can’t jailbreak your life, and the rebuttals to prove you can:

1) I can’t do what you do. I don’t have the money.

Bull to the shit. You think people who have money know how to live? Please. They’re even more clueless than we are. And let’s understand: “Money is only something you need in case you don’t die tomorrow.” –Martin Sheen in Wall Street. (Martin – not Charlie – the one who hasn’t imploded.)

The system is so screwed up right now, we can go anywhere for virtually nothing and live for even less. You can head to countless countries where the Internet is fast, and live in a gorgeous apartment for less than four hundred American per month. Want more? A thousand US a month will get you a three-bedroom in over 50 different countries where the governments are stable and a beach is close. Want to stay in America? For what you’re paying for your shitbox studio in NYC, Chicago, or LA, you could have a mortgage on a four-bedroom house in Iowa, Georgia, or Washington State, and still have money left over for a nice digital media room. If you’re really all about breaking free, the location shouldn’t matter. The end of the story is thus: ARE YOU HAPPY? Can you come to your home, sigh, and go “I belong here” If so, then screw what anyone else says, and live your freaking life. What do you care what other people think? Who cares where you are? One of the most successful clothing CEOs I know lives in freaking IDAHO. IDAHO! He lives there with his wife and multiple poodles, and while I’m bitching about the 1 train being delayed because of track work, he’s skiing down a mountain to his freaking office.

You don’t need money! Do you have any idea how many economy class “back of the bus” flights I’ve taken in my life? Enough to circle the globe and back. It’s not all about BusinessFirst and Champagne! I hate Champagne, anyway. It’s about getting from point A to point B to continue living your life. How you get here is bullshit, and doesn’t matter. The richest people I know have no problem whatsoever with flying in coach to get where they’re going. This is the one time where it’s not about the journey, it actually IS about the destination. Get there however you get there. Economy class. Hitchhiking – A damn floating car door from Cuba. It doesn’t matter. Just get there, and live your life once you arrive.

To take it a step further, think about it – Want to take a week and work from somewhere else, just to prove it can be done? What’s a flight to the other side of the country? A few hundred bucks? Give up Starbucks and dinners out for two weeks – Boom. There’s your few hundred bucks. Do it for two months, and you’ve got enough to head to Phuket, Thailand for a month. Check out Daily Worth for tons more tips like that, and soon, you’re on your way. Couchsurf or hang with friends once you get there, and spend the week working from the beach, or the woods, or the mountains. There. Simple enough for you? It’s really not harder than that! I have a few good friends who have made careers out of doing it.

2) I can’t do what you do because I have a 9-5 job where people pay me to be at an office.

This is hands down, the number one reason those who’ve tweeted “#jealous” give me when I ask them why they aren’t doing this. And I get it. You have a job. I understand. I have a job too. I’m not sitting here being a douche and saying “Well, just quit.” The majority of us can’t just quit their jobs. We have bills, we have families, we have lives that we can’t just uproot for the hell of it. Or at least, that’s how it seems. We might not just able to flat out “quit” – But we can make changes. Significant changes. Let’s break that down:

What’s the purpose of your job to you?

Is it to make money? Unless your job requires physical daily movement of things from point A to point B, you can make money from anywhere. Think about it – What do you do? PR? Marketing? Advertising? Banking? Consulting? Do you work for someone else? An agency? Chances are, where you work is at a company started by someone else. And chances are, you could do the same thing your boss does, perhaps on a smaller level at first. But you can. So what are you waiting for? Want to do it? Then do it. Stop complaining about it, and just do it! Hell, talk to your boss and see if you can open the new Phuket, Thailand office. When I started my first agency out of my apartment with one computer and one cat, I did so with the following tagline: If this fails, I’ll just go and get another job. And it’s still true. If this doesn’t work, I’ll simply go and do something else.

I mention “daily” above because part of my job (speaking) requires me being physically present for speeches and keynotes several times a month, if not a week. OK, great – That’s what airplanes are for. As I fly back to New York today, I know I have a keynote speech tomorrow morning. I’ll make it without a problem. Flight schedules are such nowadays that geography is a secondary concern. Could I live in South Africa and keep my schedule of speaking, which is 80% in the US? Probably, but it’d be a true pain in the ass. But it’s a big world. Who says you only have to do what you do in the US? Who says that over the course of two years, I couldn’t shift my focus to the EU, or South America, or even Asia, like my friend Jesse has done? He’s been in Asia for years, and thanks to the Internet, is one of the most PR/Marketing savvy people I’ve ever met. He’s at the forefront of PR and Internet Marketing and PR in Asia, and he hasn’t been to the US in years. Just because you live in the US now, doesn’t mean the US is the end all and be all of civilization.

I know people who live one place, usually a warm, tropical place, and come to NYC once a month for three days chock-full of face-to-face meetings. Then they go back to their paradise. What are they really giving up by doing that? No random Wednesday night networking events? Bummer. Life goes on. Nothing usually gets done with a martini in your hand at those events anyway. Networking is something you do 24/7 in your life. It’s not tied to one city or another.

I’ve said this tons of times: IT’S NOT ABOUT GEOGRAPHY ANYMORE.

Is your job to help people and make the world a better place? Great. Get a MacBook Air and an unlimited wireless plan. Then go continue to do that from anywhere. EMBRACE THE TECHNOLOGY! Go volunteer somewhere while servicing your clients for a few hours before you go to bed at night, which is their AM anyway. BTW – mobile communication works so much better overseas than it does in the states.

Everyone wins.

Is your job to be somewhere in a physical place, five out of seven days a week? If you love your job, I mean truly love your job, love the people with whom you work, love your office, love your commute, then hey, you know what? RESPECT. You’ve got it. Enjoy it, baby. You’re done with this blog post, and I give you mad, mad props. For real.

3) My friends would never understand.

Are you kidding me? That’s a reason? I’ll say what an old skydiver told me when I told him my friends didn’t understand why I skydived. He said simply “If you can’t change the people around you, it’s time to change the people around you.” End of story. If you’re being hindered from living the life you want because you’re afraid of what other people are going to say if you do, then you’ve got much bigger problems than achieving your goals.

4) I have a wife and kids.

So do lots of people who travel all around the world and change their lives. My good friend Leigh spent the past five years traveling around the world with her husband and newborn. Now that the kid is six or something, they’ve settled down in Salta, Argentina, where they’re buying a house. The kid goes to public school, and guess what – is already bilingual! How many of our kids are bilingual by six years old? In Europe, almost everyone you meet is bi or trilingual! The problem here is that English is spoken in all of America, and America is a damn big country. Overseas, you move thirty miles and it’s a different base language. And that’s cool.

5) I’m scared. I have direct deposit, and even though I hate my job, at least that’s something.

This is actually a valid reason. I will never, ever begrudge someone their fear. If what you’re doing works for you, that’s fine, but if you’re jealous, then you got a problem. See, being happy and being jealous don’t mesh. So it usually comes down to you being angry about your fear. But here’s the thing: Fear keeps us healthy. Fear keeps us alive. It’s what got us through the age of mountain lions and other big-ass animals that could have us for tea. But here’s the thing – Fear is built-in because we used to have no other options. Wanted to eat? You had to face your fear and kill something. Back in the age of the stone, Dean and Deluca didn’t exist. Fear now exists primarily to hold us back. There are still a few moments when fear is useful – “don’t walk down that dark alley, something doesn’t seem right.” Those are instincts we have for a reason. But nowadays, we confuse those life-saving instincts with the lack of fire under our ass all the time.

Fear is good. But never let it hold you back. Thrive on it. Worried that you won’t make as much money? Work harder. The fact that you’re doing it from a beach next to your home that costs 1/4th of what you were paying in the city should be helpful in getting over that initial fear.

6) I don’t have the time.

Yes you do. No matter from where you work, you have the time. Lots of presentations to give? Write them on the plane. Lots of emails to answer? Answer them on the plane. Gotta be on a call? Skype from your hotel room. Meetings to attend? Attend them virtually, from the beach.

Countless studies have shown that people are actually more productive when they’re allowed to work from where they want, as opposed to having to work in a confined space.

If you really want to make more time to do the things you “have” to do, thus allowing you to do more of the things you “want” to do, you need to do a few things differently. One of them has to be getting up earlier, but that’s a different post entirely, because in the end, if you want to change your life, you’re going to find the time.

End result: We all need to work. We all need to make money. With the exception of trust fund babies, we all gotta find a way to make some cash and live our lives. Some people just choose to do it a different way than others. Some of us choose to work for a living, and some people choose to incorporate work into living. For the past 16 years, I’ve worked harder than almost every person I know, yet I’ve never felt like I’ve worked a day in my life.

Thoughts? Comments? Agree? Disagree? I want to hear it below. And if you like what you read, or think I’m completely full of shit, click the FB and Twitter buttons below and let the world know.