Don’t Quit Your Day Job: You Can Freelance and Still Work Full Time

Published on the Work at Home Woman site.

I was raised by parents who lived through the Great Depression. My father was born in 1923, before it began, and my mother was born in 1933, as it was well underway. In both instances only their mothers were able to hold on to their jobs. My paternal grandmother was a schoolteacher and my maternal grandmother worked as a domestic (today we’d call this a combination chef and housekeeper) to a wealthy family.

Both had job security.

Having lived through such extreme economic uncertainty, my parents, along with many others from that era, believed the only way to all but guarantee financial security was to get an advanced education, followed by a job in a financially stable company—ideally a Fortune 500 one.

And of course they were right … to a degree.

In their eyes it made more practical sense to pursue one’s dreams and talents as a hobby and work toward a profession that would ensure achieving the American Dream.

Despite the fact that both my parents had made successes of themselves as writers (my mother was an editor for The New Yorker Magazine and my father was the head writer for ABC News), they were dead set against me becoming a writer and instead they wanted me to be a lawyer.

I had as much interest in being a lawyer as I did in becoming a mathematician or an accountant. They absolutely had my personality pegged, though. I’m a talker, an arguer and a champion of everything from children’s and animal’s rights to the environment and civil rights (PoC, women and the LGBTQ).

I just didn’t see the necessity in being lumped in with a group many love to loathe in order to advocate for causes I believed in.

We battled, and I won. Well, sort of …

I went to journalism school and got a job in radio in 1986. I hated working in broadcast journalism. Although I got to write about cool stuff—the New York Mets’ 1988 winning year, including interviewing some of the players in the locker room, and the so-called Preppie Murderer Robert Chambers’ sentencing—writing news briefs that could fit into two-minute on-air stories wasn’t my idea of writing. Unfortunately, working alongside New York Times’ sportswriters Ira Berkow and Dave Anderson seemed pretty elusive to me.

You Can Freelance and Still Work Full Time

And so after three years in radio, I left and went into marketing.

I did well for myself in the twenty years I spent in corporate America. I suspect my parents were proud of me even if I robbed them of the opportunity to introduce me as “my daughter the litigator.”

About the time I was planning my 40th birthday in 2006—an 80s themed costume party—my husband of six years began expressing dissatisfaction with his career.

By this time were both at Amgen, the world’s largest biotech. We made googobs of money; we had a house in the suburbs, a white picket fence, his and hers cars and motorcycles and two cats we rarely saw.

I drove a hybrid and my husband drove a natural gas car. Parties, like the one I was planning for myself, were always well attended. We took European vacations and we had lots of money saved for a rainy day.

We had certainly arrived, by all accounts. We were also bored to tears and bordering on dissatisfaction, and we exhibited myriad stress-related symptoms.

Raised by similarly minded parents, Paul studied computer science and broke into information technology (IT) long before it was en vogue. What he’d actually wanted to do was be a park ranger.

“Not practical,” his parents told him. “You’ll never make enough to support a family.”

Of course both our parents were right. There’s no way we could have made the money we made, driven the cars we did, taken the vacations we did and lived in the large house we bought in Southern California had we not followed their sage advice, succumbed to practicality and drank the corporate Kool-Aid.

We fed our unrealized desires by pursuing them the best way we could. We spent most weekends outdoors hiking and biking. Sometimes we’d wake up on a Saturday morning and get a bug up our butts to jump in the car and drive somewhere … anywhere. Sometimes we’d end up in another state or at a national park.

And I wrote most days. Sometimes I wrote in my journal; I also wrote lengthy holiday and year-end letters, and when I read articles in newspapers or online that set me off, I sent letters to the editor expressing my distaste.

Clearly these aren’t ways to live out one’s dreams.

Shortly after my blowout of a birthday celebration, Amgen sent Paul to their Puerto Rico manufacturing facility to upgrade their storage backups. He called from there to tell me he’d fallen in love and that he’d like to return on vacation.

We did. When we got back home, we hatched a plan to quit our jobs, sell our house and use the proceeds, along with our savings, to buy a farm on the island we were now both in love with.

Paul would be an organic farmer and I would write books.

Our family and friends thought we’d lost our minds. “How can you give up all of this?”

“Easily,” we both said.

In 2008 we made good on our promises. We sold or gave away 75 percent of our possessions and uprooted our two cats and ourselves and moved to Puerto Rico.

Now living in our small farmhouse on 18 acres of plush land, Paul was working it. We got a few goats and chickens. Eventually we planted a bunch of fruit trees from around the tropical world, and I was ghostwriting. Things had obviously changed a lot in the years since I dreamt of being the female version of Ira Berkow. 

In between helping Paul on the farm, I could do content writing on a freelance basis for a variety of clients—although none of it turned out to have anything to do with sports. I ghostwrote books, articles and blogs.

We never imagined that my ghostwriting would take off, and I’d get so busy that I’d spend more time behind the desk than I would on the farm. Today I do a combination of ghostwriting and bylined writing (which I'm still new at). I also own a content writing agency, which means I essentially work round the clock at a day job and write for publications at night or on the weekends. I get to write about the things I'm passionate about, and despite working so much, I don't feel stressed out or unfulfilled. I love what I do.

You Can Have Your Cake and Eat it Too

Having a personality of two extremes (I blame it on being born on the cusp between Sagittarius and Capricorn), I don’t know much about moderation or compromise. Because my husband and I were so unhappy in the all-consuming, consuming all lifestyle we’d achieved, it wasn’t an option for us to remain in our corporate jobs and be true to ourselves at the same time.

Maybe you are very happy in your profession. Perhaps you weren’t cajoled into a career of your parents’ choosing that you have no desire to leave. It’s quite possible you want to write on the side.

Whether you want to earn extra money, try out a new career without having to leave your old one behind or complement the one you’re in with new skills, there’s never been a better time to break into freelancing.

Estimates suggest that by the year 2020 more than a quarter of the world’s and half of the U.S.’s population will be freelancing. For a variety of reasons, this works well both for those who want to work for themselves and those who want to hire people on a freelancing/contractor basis.

Corporations are no longer just outsourcing their manufacturing to “far off places” like China, India, Pakistan, Bangladesh and the Philippines. Today many of them are eschewing the traditional route of looking for full-time employees and are instead looking to bidding sites like Upwork and 99 Designs and many others to fill their part- and full-time hiring needs. Saving on everything from healthcare and worker’s comp to electricity and rent, it behooves business owners to consider hiring virtually for many of the jobs they used to keep in-house.

Our four clients all work from home. Two work for companies that have a brick & mortar presence, but like most freelancers, they work remotely in their home-offices. My thoughts on this are that if they can do it, why can’t we as freelancers?

We can and we are, and so can you. Part- or full-time, you can give your clients as much or as little help as your schedule allows you to. That’s the beauty of freelancing. You are your own boss and you can set your schedule, run your business the way you want and charge what you want and feel you’re worth.

We are all at different stages of our lives. Some have googobs of professional experience while others have spent the last ten years at home raising kids—which is, let’s face it, the most important job of them all. Regardless of where you are, the thing you’ll love about freelancing is that you needn’t have had twenty years of corporate experience in order to break into it.

You may hear advice to the contrary, but it’s simply not true. When I started writing on a freelancing basis, I had absolutely no relevant experience. Some may point to my days in radio as relevant, but I can assure you that there are no similarities with writing about a game between the New York Mets and the Chicago Cubs. How many different ways can you say “pop fly,” “home run” and “runs batted in?”

When I was brand new at bidding on Elance jobs (the predecessor to Upwork), I never listed my gig in news radio. In the beginning, I was honest and said I had no experience and that in exchange for the experience, I’d work for peanuts. And I meant it. And better than that, it paid off. I got great feedback; in two years I replaced my Amgen salary and in four years I replaced my husband’s and my combined Amgen salaries.

There are those who find this tactic appalling, but many clients who hire virtually don’t believe in the old motto, “you need experience to get experience.” Some are happy to hire a newbie, despite how green you are. Just be careful not to fall victim to the ones hoping to take advantage of you.

While you may be green in the field you’ve chosen to pursue work in, you weren’t born yesterday. It’s OK to express your naiveté while at the same time letting potential clients know you have life experience and confidence.

So whether you are looking at freelancing as a means to supplement your income, because you want to get back into the workforce, because you have youngins’ at home and your availability isn’t conducive to full time employment or because you’re going through a change in marital status and need to make more money than you used to, freelancing is definitely for you.

I started freelance ghostwriting in September 2009. A little late by some standards, given my age at the time (42) but I was reinventing myself after serving a 20 to life sentence in corporate America. I didn’t have any professional writing experience when I started and I had to do a lot of on-the-job training. Every time I learned something, I made note of it and tried not to make the same mistake twice.

While I was registered with Elance (an online bidding platform that matched clients with freelancers that no longer exists) I was very active and visible. I was a member of their 10-person panel they tested new features on before they rolled them out site wide. I wrote a regular column for their blog designed to help freelancing newbies.

I established my content writing agency a year after I started freelancing and went from a freelance force of one to an agency owner.

None of this means I'm an expert. It just means I have many years' experience as a freelancer and I'm hoping some of my advice can be helpful to you.

If you have a question ask here.