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When we grow up, we want to be just like Caroline Tell. This New York-based mama of two is an inspiration to anyone who’s ever lingered a little too long in the local café, dreaming of a career as a writer. An editorial consultant and regular contributor to The New York Times, Condé Nast Traveler, Travel + Leisure, The Cut, The Observer and other esteemed publications, Caroline is the definition of the successful self-made writer, who first took the plunge into the freelance writing world six years ago and never looked back. Here, she shares her tips on starting a freelance career so you can figure out whether it just might be the right path for you, too. Read on…

I took the leap into freelance writing almost six years ago. It was, without a doubt, one of the best decisions I ever made, but it was scary! At the risk of sounding cliché, I discovered the idea of freelancing through Sex and the City. As Carrie Bradshaw gallivanted around New York, covering events and writing stories in her skimpy pajama sets, I couldn’t help but wonder: Could I freelance too? At the age of 22, I saw her life as one of freedom and excitement, and a part of me wanted that for myself.

But freelancing is not about two hour lunches and shoe shopping. 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.

 

Caroline Tell

 

Often when I tell people I freelance, I’m met with slightly puzzled looks followed by a series of questions. I’m going to do a little Q&A with myself, so that if you’re thinking about taking the plunge into freelance, you can gage if it’s right for you:

Caroline, should I freelance?

I mean we just met, how should I know? In all seriousness, 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.

OK, so how do I start?

First, get out from behind your computer. Go to that party you don’t want to go to. Get drinks with your old coworker. Head to that lame store opening because you never know who you’ll meet that can help you. Once you meet that one friend who has that one contact, use it, and build from there. I remember going to a fashion party where I was introduced to Bee Shapiro, a fellow freelancer with a regular gig at The New York Times. She was amazing to me. She met me for a coffee, laid down her knowledge and inspired me to go freelance once and for all. We’ve been friends ever since. Find your Bee.

How do I 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.

Should I work from home?

That’s a personal preference. I live in New York, where we have an abundance of co-working spaces, but they are expensive. I also have two kids, so I can’t work from home if they’re around. When I got pregnant, I joined Soho House, where I can work, meet publicists and catch up with people in my field. It makes the “writer’s life” less singular. But if you can buckle down, by all means work from home! Where do you think I am when it’s pouring rain or snowing? I am lit-er-ally working from under my covers. Also, if there’s a coffee shop with good wifi and a great chai latte, try that too.

 

Caroline Tell

 

Do you ever get lonely?

I actually don’t get lonely. And sometimes I worry that I don’t! But I’m constantly interviewing people for stories, meeting with publicists, texting my sisters/husband/mother/mom friends/nanny. I feel like I interact with seven people before I even leave my building, so I’m constantly stimulated. But if you’re the kind of person who likes chatting with others all day, having meetings and pre-meets and post-meets, communing with coworkers in the office kitchen, freelancing may not be for you (and probably neither is writing).

What should I charge?

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.

 

Caroline Tell

 

Is it hard being your own boss?

I always say that I have no boss yet I have a million bosses. I treat every assigning editor like my boss, because ultimately they’ll decide whether to hire or assign me again. Just know that at times it will be frustrating when you don’t hear back on a pitch you worked really hard on, or when you haven’t heard from your editor in months and suddenly she wants to run your story tomorrow and needs a full re-write. I remember editing a story for The New York Times while breastfeeding my TWO-DAY-OLD. But just remember – you get to visit your bestie in Miami without asking permission. You get to take that 1pm pilates class. You get to accompany your son on a playdate or volunteer at his school to go on a nature walk. You get to sit on your couch watching the snow fall instead of trudging through it. And while I haven’t figured out how to spend an entire month in the South of France, I know that I can. To do what I love, on my own terms, is living a life I always pictured.

 

Caroline Tell

To learn more about Caroline and her work, check out her website here.

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