Four years ago on a sunny April morning, I slinked into my new office building, suit slightly too big, 24-years-old and clueless. It was my first day working at a large, prestigious bank in downtown Boston. The first day of the career that would ostensibly define the rest of my life.

I felt strangely powerful as I collected my new security badge and gained access to the sleek silver elevator. This was it. I was finally a real, live, functioning adult.

But that sense of power vanished once I was led to my new cubicle. Grey, sterile, joyless. I looked around and noted the smattering of other ambitious 20-somethings about me, awkwardly stuffed into cheap suits and business attire. Some worked furiously at their consoles, invigorated. Others slinked in their chairs, lifeless and a paper jam away from putting a shotgun in their mouth.

I would soon be one of the latter.

I sat, nervously sipping my energy drink as I waited for my new supervisor to come train me for the morning. She arrived around 8:30AM and by 9AM had shown me enough pointless procedures to make even the most drab college textbook shout with a vibrant life in my memory. I woke up at 6:30AM for this?

By 10AM I silently asked myself when the soonest I’d be able to quit would be. I was two hours into my lifelong career choice of finance and I was already contemplating an escape route. “This is not a good sign,” I thought next.

I quit six weeks later.

I would love to tell you leaving the bank was one of those triumphant movie moments, where I walked out of the office with a sly smile and Kevin Spacey fist pump. The reality is that I felt like an idiot. I trembled as I put my two weeks in to my manager. When he asked what I planned on doing instead, my shaky reply of some sort of website blog thing sounded just as ridiculous to me as it probably did to him. By lunch, the news has spread around my team. Most of them were so confused, they awkwardly avoided talking to me and didn’t say goodbye. I imagine they believed I had just flushed my future down the toilet. Part of me believed the same.

I get a lot of emails from readers asking me how I manage to travel the world without holding down a so-called “steady job.”

The short answer is the internet. Before this blog, I ran a number of websites and projects that earned some money. Then I did some freelance work. Then I wrote a book. Then people started telling me to write more stuff and jump ahead five years and about 500,000 words and here I am.

Many people dream about dropping out of the rat race. They want to let go of the career ladder and find a way to spend more time doing what they love. I wholeheartedly endorse this life decision. Although I felt stupid when I left the bank and would spend most of the next two years scared out of my mind, broke, and working all hours of the day and night, it was one of the best decisions I ever made in my life.

There’s already a lot written out there in this area: quitting your job, making money online, starting a business, vagabonding around the world, etc. A lot of it’s great. But a lot of it doesn’t talk about the emotional realities — dealing with doubt, finding the motivation, addressing the strains on your friends and relationships. I want to paint a realistic portrait of this life change. There are a lot of challenges, both mental and emotional, but I encourage you to take the leap.

WHY YOU SHOULD TERRIFY YOURSELF

Honest question. Do you love what you do?

If the answer isn’t a resounding, knee-jerk, “Yes! I live for this shit,” then I encourage you to seriously consider doing something about it. That may sound extreme, but seriously, in 100 years you and everyone you know are going to be dead and your great-grandkids aren’t going to get misty-eyed remembering how you got that quarterly bonus or a corner office. This is your life and every breath you take is killing you. Stop screwing around.

Chances are the thought of leaving your day job terrifies you. This is normal and expected… good even.

When I left the bank that day, I had only a vague idea of what I would do. I made a little bit of money here and there online. It wasn’t anything close to a full-time living, but I knew it was a new market that was growing quickly. And with some hard work combined with my savings, I (naïvely) believed I could have a full-time business up and running within a few months.

It turned out to take almost 18 months for me to earn a full-time steady income. I went broke a number of times, was supported by my ex-girlfriend for a time and then moved back home with my mother. For most of 2008-2009 I worked 10-16 hour days and the majority of my projects failed and made little or no money.

It was stressful to say the least.

People ask me what motivated me through this period. The answer is terror. Complete and unequivocal daily terror. I was absolutely terrified to fail. Granted there was some love in there as well (I loved my job and still do). But that’s also where the terror came from: the idea that I would never make money doing what I love; the terror that I’d have to go back to living off a job I hated; the terror that I would have wasted two years with nothing to show for it; the terror that all of my friends and family who thought I was crazy would be proven right.

This fear kept me up at nights, and more importantly kept me up at nights working.

I’ve met a number of people over the years who want to quit their jobs, to start their own businesses, to develop new streams of income. And they’re scared. Obviously. They should be. But instead of leveraging their terror into action, they spend all of their time planning and planning and planning and not doing anything.

90% of your plans are going to fail no matter what you do. Get used to it.

It’s not because we’re poor planners, it’s because there are simply too many unknowns. And the only way to uncover the unknowns and adjust for them is by getting out there and failing. So yes, you should be terrified of failing. And that is why you should do it anyway.

When I wanted to leave the bank, a number of friends and family members suggested that I continue to build my business on the side until I had a steady income. In hindsight, I think if I would have done that, I would not have made it. Giving up would have been too easy. I wouldn’t have had the time or energy necessary to do it. That ever-present fear motivating me would have been gone.

The terror that jumping in headfirst gave me was my most powerful asset. I was committed. I’d win or die trying. I sold my possessions (video games, computer, furniture, guitars — everything). I stopped most of my hobbies. I lost contact with a number of my friends. I knew all of these things would return once I became successful. But failure was not an option.

Intellect is great. Work ethic is great. Ability to adapt is definitely necessary. But you also need the emotional drive to push you to achieve your dreams. Everyone’s had the feeling where you know what you should do in your gut, feeling it and wanting it, but not having the emotional drive or wherewithal to actually get up and do it. So you continue sitting in the desk you hate day after day, year after year, waiting for something that’s never coming, trapped by your comfort and safe in your mediocrity.

Terrify yourself. Use it as your ally. Give yourself no option but your dream.

“There’s no reason to do shit you hate. None.”

PLANNING YOUR ESCAPE

OK, that’s all well and good, but let’s talk about reality. Especially if you have kids, house payments, car payments, student loans or health problems. What do you do?

1. Sell all your useless crap and get your financial house in order. Excess possessions are counterproductive for pursuing a remote lifestyle. And they’re often counterproductive for achieving happiness in general. If you own something that is eating away at you financially (furniture, car, etc.), consider cutting your losses and getting rid of it while you can. Debt is the devil. I wrote an entire post on getting rid of excess crap you don’t need here.

Doing this may make you squirm at first. Or you may be sitting there (once again) thinking I’m a total nutcase and unrealistic and you could never get rid of your super-double-upholstered Italian sofa that just ties the room together, but fuck you, sell it anyway. There are a million sofas in the world, your life experiences happen once. Get on it.

In extreme cases, this may involve selling your house. That may sound insane and may be completely unreasonable for you, especially if you have a family. If so, then rent it out. Obviously mileage may vary depending on who you are and what your life circumstances are. Why be miserable and financially stuck in a house when you can be happy and free in an apartment? Boom.

2. Figure out your source of income. People seem to believe they’re trapped within the typical 9-to-5 career track, but in fact there are a lot of options. In the US, we’re rarely exposed to the options we have outside of our nation’s borders (minus the military). You just have to be willing to take some risks and work a bit harder.

An incomplete list of options to get your ass abroad and exploring the world:

Join a volunteer organization. If you don’t mind getting your hands dirty and putting yourself in some extreme environments, then volunteer organizations, both NGO’s and otherwise (i.e., Peace Corps) are always looking for help. You’ll most often be sent to developing countries, but some developing countries are surprisingly pleasant to live in (Thailand, Colombia, Philippines, Peru, etc.). Once you’re on the other continent, bouncing around from country to country is rarely more than a $50 bus/train/plane ticket away.

Teach English. The pay is low and the work is hard, but this will get you a paid trip to another continent and often with really good vacation time. Asia and Latin America are the go-to continents for this with no experience or foreign language required. If you teach in Europe, you’re going to have to know the destination language at the least. A friend of mine taught English in South Korea for six months, took the money she made and went to India for three months, then taught in the Philippines for another six months and then bounced around Southeast Asia for a while after that. Not a bad experience.

Find a source of mobile income. Poker. Stock/options trading. Freelancing. Consulting. Internet marketing. Blogging. Graphic/Web design. Writer/journalist. These are all professions I’ve run into on the road. These are all forms of income which can be earned regardless of location (and I’m sure I’m forgetting a few). Some of them have a steep and long learning-curve, but there’s never a better time to start than now.

Start an online business. This is a massive topic which other people can cover much better than I ever could, but internet startups can often be created and managed from anywhere. In fact, there are a number of startup “incubators” around the world where internet entrepreneurs congregate in places with high qualities of life and very low expenses (Chiang Mai in Thailand, Bali in Indonesia, Medellin in Colombia, etc.).

Convince your company to let you work remotely. Not an option for everybody, but if you’re a programmer, developer or designer, then this could be an option for you.

Get transferred overseas. Another option if you work for a large international corporation such as Procter and Gamble or Yahoo! is to get transferred to various locations around the world. You can often gain a lot of vacation time by working in other countries as well which will allow you to explore.

Find odd jobs as you travel. This is easy in some countries and impossibly hard in others. But finding jobs in hostels, bars and restaurants in cities you travel to can be done to support yourself wherever you go. A number of people do this. It takes time and effort and obviously is quite stressful, but it can be done.

Work on a cruise or for an airline. Seriously. These people have amazing flexibility with their time at sea and where they get to go. I met a woman who worked on a cruise in Costa Rica and she had been to over 75 countries, living in a dozen for more than six months. She was in her early 30’s. Same concept applies to working for an airline but to a lesser extent (and far more jet lag)

Start your entire career abroad. In a number of developing parts of the world, particularly Asia, there’s an extremely high demand for university-educated Westerners for high-paying management positions. Countries like China, Brazil, Malaysia, and Singapore, are importing a lot of western talent. Not only can a recent college graduate skip multiple rungs on the corporate ladder by moving to one of these countries, but they can see a major quality of life increase at a lower cost-of-living. Let’s just say that making $60,000 a year in Shanghai goes a LOT further than making $80,000 per year in New York City.

You can combine a number of these strategies. Sometimes you can just take off with your savings and begin to figure it out as you go. Someone can leave with their life savings, start a blog on the way, do some freelance consultant work online, work some odd jobs here and there, and by the time their savings run out, they have a modest location-independent income. But as always, Google is your friend. There’s no shortage of websites and resources on NGO’s, internet startups, marketing, expatriation, backpacking, vagabonding, etc.

3. Calculate your “Escape Velocity”. Do some research and choose your first destination(s). Do you want to try an internet startup in Asia? Work for an NGO in Central America? Backpack through Europe and pick up odd jobs on the way? A lot of people come to me and say, “I want to live abroad, how can I do it?” Well it depends where you go. You can live like a king off $1,000 in Thailand or the Philippines, or spend that much in a week in Brazil. It depends where you’re going and what you’re doing.

The other factor is your financial obligations. If you have debt back home you need to factor that in. If you have health problems, then you need to do a lot of research on that as well. The good news is if you’re an American, you’re going to save a LOT of money on health care by leaving the country.

Calculate the amount you need to earn passively per month to survive wherever you want to go. This may involve getting a job once you’re there. It may involve saving up a bunch of money now and selling stuff. It may involve creating passive streams online. Either way, budget it out so you know when you’re ready.

4. Pull the trigger. Once you know your target level of savings and/or location-independent income, work towards it with everything you have. This may involve killing your day job off immediately in order to free up more time to work for it. This may mean setting a financial goal for the day you can put your two weeks in.

Get creative and don’t have an ego about it. A friend of mine decided to throw himself into this lifestyle 100% and moved back in with his parents for almost a year before he got on his feet and running. I lived on a friend’s couch for a while. Later I moved back in with my mother until I had enough money to buy a plane ticket to Argentina. Once I was there I could live well off about half the income I needed to live in the US. From there I built my business up further.

But, like I said, planning will only take you so far. Plan the best you can, but then throw yourself into the fire. Leave yourself no option but to come out on top. It will be hard and nerve-wracking, but that’s how you grow. That’s how you squeeze all of juice out of life. Terrify yourself. Then laugh about it.

Further Reading:

[Image credits: Sam Judson and Michael Lokner and Unsplash]

Mark also published this on markmanson.net and it appears here with his permission