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 a.d.u.l.t.

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 8:30 AM and by 9 AM had shown me enough pointless procedures to make even the drabbest college textbook shout with a vibrant life in my memory. I woke up at 6:30 AM for this?

By 10 AM 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 relationsh.i.p.s. 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.