Freelance writing is not all cool, calm, and collecting checks. Like other "for hire" industries there is plenty of freedom (work from anywhere) and lots of uncertainty (when's the next job coming..??). And yet, despite the unknown of the paycheck, many millennials opt to freelance over full time work. Freelancing has steadily been on the rise. 

BUT is it worth it? 

Caroline Tell is a New York-based writer who recently chatted with Hey Mama about the ups and downs of the trade. As an editorial consultant and regular contributor to The New York Times, Condé Nast Traveler, Travel + Leisure, The Cut, and The Observer, she has successfully turned a love of words into a career she loves. 

"Freelancing is not about two hour lunches and shoe shopping," Tell writes on Hey Mama. "Certain aspects of freelancing are challenging – namely that I lack a financial safety net and I don’t have a magazine or newspaper to rely on as my 'brand,' so to speak. My name and my work is entirely my own. I’m also constantly at the mercy of my editors, and however much I earn is directly correlated to how much I work. But these very challenges are what make the job rewarding. I pick and choose my work. I’m not boxed in by one specific 'beat,' but I write stories that inspire me across a range of topics. As I grow older, my interests have grown more diverse, and writing about new experiences has been very exciting."

On whether you should take the l leap or not, Tell writes: 

"Here are a few questions to ask yourself. Do you have a way of getting health insurance? Do you have any clients you can work with while you get set up? Are you prepared to make more money at certain times, or do you need the same level of income each month? Can you be disciplined enough to self-start and manage your schedule? If you answered 'No' to any of these questions, it’s not a deal breaker, but it’s worth doing the exercise."

Knowing what to charge is another struggle. Says the writer, 

"Some publications have set rates. At times you can negotiate your rate if you have a nice relationship with an editor. A successful friend once told me that payment will always balance out. So you may take a job where you’re vastly underpaid, and then turn around and take a well-paying gig for zero effort. Also some opportunities may not pay well but are great for your career. You can’t put a price tag on a widely-read platform that will get your name out, or on the chance to write your dream story."

And of course, every freelancers' struggle: Tell explains how to effectively pitch, 

"You just do. And it’s the rule of numbers – the more you pitch, the more you work. So pitch pitch pitch! I still pitch like crazy. 99 percent of my stories come from my head, which is actually very gratifying. So take a walk, scroll through your Instagram feed, go on vacation. Keep those antennas up and stay inspired. And use your own life as inspiration! I certainly do. Tweet at editors, Google their email addresses, hit them up on Linkedin. And don’t get disappointed when you hear No. I pitched The  New York Times 10 story ideas before my first one was approved. And follow up. And do your research. Google whether or not the story has been covered elsewhere. Check out the kinds of stories your dream publication covers, and tailor your pitch accordingly."

Are you a freelance writer? What are you tricks of the trade?

You can read the original, full version of this piece here on Hey Mama. 

MORE FROM OUR BLOG