This February marks my two-year anniversary of being a Freelance Writer. This is a huge accomplishment for me. For the last 24 months I’ve had the privilege of living out the job’s root word. I’ve been FREE.

My laptop and I have gotten cozy in New York cafes. We’ve set up shop at mama’s house in Baltimore, with my brothers and nieces in Kansas City, and on my boyfriend’s couch in Newark. This life of liberation has afforded me a flight to Los Angeles to bring in the 2010 New Year, a trip to Detroit for the Allied Media Conference, an RV camping excursion to Tennessee for the (amazing) Bonnaroo, and countless bus and train rides up and down the east coast. If I were working in an office, under the iron fist of two-week vacations and permission slips, I would have been fired a long time ago.

I’m technically my own boss right now, but don’t get it twisted; this life is far from a bed of roses. There were months when I was chained to my desk for hours, enduring pointless meetings and back-to-back deadlines. I’ve taken on lame assignments just to keep my cell phone from being disconnected. I’ve incurred several overdraft fees waiting for payments that never came. My mom and boyfriend stepped up to give me financial boosts when my bank account balances showed up in the red, and when the creditors started checking off their monthly “Naughty” lists. I even put on 20 extra pounds in the first year thanks to my daily runs to catch the subway being replaced with hourly runs to raid the fridge.

Yes, it’s been a tough two years. I discovered that I was much lazier and shyer than I thought. That life is pretty fucking depressing when you’re down to your last $20, have no clue when more money will be coming in, and cashing out your piggy bank is your only salvation. I learned that I have a difficult time asking for help. It sucks, but I’m ok with alternating between the same two pairs of shoes. I’m much more familiar with the subjects that are easier for me to write about, and which put me straight to sleep. Oh yeah, and I just learned that, as a writer trying to get her name out, I really need to step up my Twitter game.

Freelance writing requires an unusually high level of confidence. You have to be able to put yourself out there. Promote yourself and your work. Update your Facebook status regularly with links and comments that reflect your “brand.” Network at events and gatherings for potential clients. You become a business, and have to sell your talents and personality accordingly. For someone who’s borderline Queen of the Wallflowers, that can be a hard pill to swallow.

Despite the rigors of this life, I’m pushing forward. Armed with an even stronger sense of self and of my vision, I’m continuing along this path to become way more of a freelancer than a freeloader. I couldn’t have done this last year of freedom without the support of my family. Everyday I dream of six-digit bank statements, book deals, publishing profits, interviews with awesome people and my beautiful words commissioned to describe them. Every day offers another chance to try again and put myself out there to maintain this life of freedom.