Are Freelancers Ever Really “Free”? - The inevitable tradeoff for a flexible schedule

When, eleven years ago now, I decided to quit my office job to pursue a freelance career, I worried about being too distracted to succeed. “What if I feel like a nap in the middle of the day?” I remember asking a friend who’d been on her own for a few years. “Then you take a nap,” she said.

Everyone thinks freelancing is a great life, and it is. I work from home (or the coffee shop, or the library) in my yoga clothes (or whatever, really) and make my own hours (mostly). I can throw in laundry between calls. If I feel like a nap, I take one (sometimes). To me, freelancing requires no more discipline than any other job—though it allows for far more flexibility.  

I also work on vacation. A few weeks ago my husband and I were lying on the beach in Mexico; the warm sun beating down on us, the soft lullabye of the waves crashing in the distance, when an “urgent” (read: not at all urgent) email came in. I got up, two margaritas deep, and went inside to deal with it.

But wait, you say, even entrepreneurs deserve time off! Of course we do, and I take plenty. I’m just not always the one deciding exactly when it happens. Because while I might not have a boss, I have many clients, and I can’t expect their schedules to always align with mine. If they need something, it’s my job to give it to them. My business thrives on dependability and consistency. I’m a writer, but I’m also in the service industry. I strive for happy clients, above all else.

Not everyone shares my philosophy, of course. A good friend owns a clothing store for which she keeps odd hours. Her thinking: I deserve to have a life, and if they want it enough, they’ll come back. My thinking: Are you sure? I’m not sure. I’ve been the customer who unsuccessfully tries to shop a store whose hours are inconsistent. At a certain point, I stop trying. I’ve also been the editor who’s stopped trying to assign a story to a writer who’s always too busy to say yes. Which is why I’d far rather deal with doing a bit of work while on holiday than lose a potential or, even more crucially, future job.

I don’t think I’m sacrificing anything in the way of work/ life balance or personal sanity by doing so. In fact, I travel far more than I ever did when I was on staff. Luckily, I can write from anywhere. And I have: from the back of a Jeep during a drive through Rwanda; at a slope side café in Chile. I was sitting at the bar on a beach in Tel Aviv when a client emailed with some silly need that surely could have waited. But responding took me five minutes. And was my quick response appreciated—and rewarded? You bet.

Certainly, there are times that, as a freelancer, I’m overwhelmed. I probably say yes too much. I don’t have a boss on whom I can count for taking something off my too-crowded plate. When I’m overworked, I have no one to blame but myself. But also no one but myself to thank. Is it the perfect job? Of course not. But it works for me, even if, just like any other employee, I often work for it. Sometimes, even with a margarita in my hand.



Alyssa Giacobbe has spent more than 20 years writing and editing for magazines, landing her first job gratefully fetching lattes and editing the Table of Contents as an assistant editor at ELLE. She's held staff editing positions at Harper’s Bazaar, InTouch Weekly, Teen Vogue, and Boston, and contributing editor positions at Architectural Digest, DuJour, and Lucky. Her work has also appeared in a wide range of publications that include InStyle, New York, Details, Self, Elle Decor, T: The New York Times Style magazine, Women's Health, and the Boston Globe magazine. In addition to travel assignments that have taken her from Rwanda to Tel Aviv, Santa Fe to the Moroccan Sahara, she has co-authored two books in the field of fashion, writes often about both food and feminism, and, thanks to a longtime health and fitness beat, knows more about manboobs than any woman should. She lives with her family in a beach town north of Boston.