Image by Guille.

Today’s interview is with S. Brian Smith – a 25 year-old Generation Y-er, who left a lucrative investment banking career to pursue the freedom of a location independent lifestyle by starting up his own web business. He’s currently on his first big trip overseas.

In this interview Brian shares his experience of quitting his high-flying career to pursue the location independent lifestyle that so many of his peers are aiming for…

Brian, can you give us some background to your professional life & career to date?

I busted my butt to get a good job. In school I studied maniacally, first for a Bachelors, then for a Masters. I graduated with my Master of Science in Finance and walked into my shiny new investment banking job two weeks later.

My first position out of University was as an analyst. I worked long hours constructing endless financial models in Excel and writing pitchbook after pitchbook. On two occasions, I actually slept in my cubicle, which is unheard of in Denver (it’s not New York!). Hard work paid off and I was promoted to Associate.

Not only was I one of the youngest associates in the company’s history, I was ten years younger than the next youngest associate in our office. I was the happiest guy alive.

If things were going so well, what made you decide to quit?

After a few months, the happiness wore off. I began to think about what it meant to be “alive.” Working in a cubicle surrounded by guys who are “in it for the money” was certainly not my idea of being alive. I spent several months considering why I took this job and how reality differed from my expectations.

A few weeks ago, I walked into my boss’s office and informed him of my decision: I quit.

While I made much more money than the average 25 year old, I also spent more. I knew I was in no better position to take a stand against cubicle servitude than the next guy; but I did it anyways.

Quitting certainly wasn’t easy. I knew deep down that I wanted the freedom of an independent lifestyle. So I planned for it and implemented safeguards to make sure I actually pulled the trigger.

Can you walk us through the process you went through to actually quit? What steps did you take?

#1 Set a Date: Having decided that it was not merely a passing fancy and that I really did want to quit my job, I set a deadline to do so. When I first set my quit date, I gave myself about five months to plan. The date was Monday, September 21st. Don’t ask me why I picked this date, it just felt right!

#2 Establish Milestones: In order to quit my job, I needed to get my life in order. This involved many steps, the most important of which was starting a location independent business that would provide me income to survive.

Some of the other milestones for my independence were building a website, getting the website online, giving away 1/2 of my clothing, selling anything of value that I didn’t use on a monthly basis, and reducing the number of physical documents I keep to one file drawer.

#3: Tell People about Your Plan: I don’t know about you, but I can make up some awesome excuses for why I didn’t do something I said I would do. The problem is, these excuses sound really good in my head, but they sound ridiculous when I tell someone else.

To make sure I executed on my plan to quit my job, I told friends who I knew would be supportive. They all knew that by September 1st I would have an online business up and running and on September 21st I would quit my job. If I didn’t do those things, I would be a liar and lose the trust of my friends.

#4: Ask for Help: Starting a business is hard work! I knew I couldn’t do everything myself, so I asked for help. I approached people I knew who had skills that would help my business, told them about my plan to quit my job, and asked them for their assistance. This accomplished two things: it got me free labor and ensured that these people were invested in what I was doing.

I also know that traveling can be expensive, so I contacted my friends overseas and told them of my plans to travel and stay with them. Now I really had something to look forward to!

After getting my friends on board, I would get constant calls, IMs and emails from these people asking me how I was progressing and if I was still on track to execute on my schedule. It served as great motivation!

#5: Visualize Quitting: I spent weeks figuring out how I would approach my boss. What would I say? What time of day was best? What should I wear? What did I need to do in the office before I quit? Ultimately, I decided that I would walk into the office on Monday morning, copy all of my essential personal files onto a USB thumbdrive, then walk into my boss’s office and tell him it was time for me to quit my job and move on with my life.

#6: Do It: My deadline was fast approaching and Monday was going to be a huge day for me, but I slept like a baby on Sunday night. I knew exactly what I wanted to do on Monday morning. I had made up my mind; there was no turning back.

I woke up extra early on Monday – not because of nerves, but because I wanted to work on my new business and my blog. I got to work earlier than usual so I would be sure beat my boss to the office. When I arrived, I sat down at my desk, inserted my thumbdrive and copied my personal files. I walked to the bathroom and then to the break room to get a drink of water. Next stop: boss’s office.

I walked by my cubicle and nearly stopped, but I forced myself to keep going. When I got to my boss’s office, he was facing his computer and didn’t see me. I turned to walk away, took a deep breath and stepped back into his office.

The actual act of telling my boss that I quit was pretty easy. After clumsily getting all of my thoughts out, he told me that he thought that I was making the right decision. He was 100% supportive.

Not only that, after he sent out an email letting the local and corporate offices know that I quit, I had every person in the office over 40 years old approach me and tell me that they wish they had done the same thing when they were my age. These are guys that make several hundred thousand to several million dollars per year and they wish they quit long ago!

Quitting your job is much harder than it sounds if you only rely upon yourself. Enlist the help of people you know, trust, and love. You don’t have to do it alone – and it is your good friends who will remind you that you are never alone, no matter what you do.