Why Freelancers Need To Be Gutsier Than Regular Workers [Partner Content]

Why Freelancers Need To Be Gutsier Than Regular Workers [Partner Content]

In order to make an impression that drowns out the competition, confidence is key.

Kyana Gordon
  • 3 february 2013

The modern work landscape is one that is constantly changing. Today’s office is no longer one filled with cubicles and fluorescent lights, and more and more people are striking out on their own and joining the freelancing world in order to have more control over their careers. PSFK shares stories from various freelancers, who comment on what they know now that they wish they’d known when they started out.

What’s most attractive to me about freelancing is that within the term is the word “free.” The type of freedom associated with waking up in the morning and being completely in charge of your day –  no one telling you what to do or how to do it, and no one micro-managing your workload. Everything flows from you.

One summer afternoon in July 2008, I decided that becoming a freelancer was most aligned with how I wanted to live. Previous to the leap, my past working life included everything from a gig at an art museum to one at the U.S. Consolate in South Africa, a stint at a music PR firm for five years, architecture firm, strategy at a record label, DJ’ing, and slinging pizza.


Starting out, my approach was a bit more fly-by-the-seat-of-my-pants, and I hadn’t the slightest clue about how to jumpstart my career. Which is why I was intrigued when recently I stumbled across The Freelancer’s Bible — a need-to-know guide that helps independent workers do everything from plan their career goals to pay their taxes. Back then, a guide like the The Freelancer’s Bible would have been invaluable. The first chapter outlines “Seven Start-up Steps” that serve as a platform to help anyone get going. These beneficial steps are simple:

Know why you’re freelancing • Figure out your key strengths • Figure out your customer’s needs • Know what you’ll charge • Do your budget • Gather your brain trust • Make a game plan for going public.

Sounds like sage advice from a friend who’s been there. However, with no Freelancer’s Bible in sight, guidance came from my boyfriend at the time who had been a freelance designer for over fifteen years. He handed me a sheet of graph paper and told me to look at my attributes, skills, passions and map out what my best work options were, and who I could contact to get where I wanted to be. I wrote the words: writing, people, anthropology, cultural strategy, research, music and dance. These were at the core of everything I did, and I was then able to connect the dots to make it clear who the people were who could help get me started.

I contacted every small, medium and large agency in New York City, from traditional to creative to innovation shop, and set up a meeting, spouting my talk about how there was a desperate need for field work, cultural authenticity, and how I was well equipped to carry this kind of work out.

At the same time, writing was where my real passion lay. I wrote little pieces here and there but I really wanted it to become a part of my daily life. So in August 2009, I reached out to Piers Fawkes and set up a meeting, the following Monday I was writing and researching for PSFK. It was a huge step for me.

One thing no one tells you when you begin freelancing is how to balance it all — from a to-do list, client expectations, to knowing what you’re worth. When you are representing yourself, confidence is key.


Fast forward five years and I am working as a cultural strategist and writer. I’ve been able to fly to South Africa on very short notice for a job, something I would never have been able to do as a full-time employee. This past December, I moved from Brooklyn to Bequia, a tiny island in the Caribbean for four months to focus solely on writing and creative projects of my own. I could have never have imagined that this is where I would end up five years ago, but I’m so grateful I took the leap.

Header image by Karen Evans.

PSFK has partnered with the Freelancer’s Union to bring you a content series written by freelancers for freelancers, about how to succeed in the business – whether you’re just starting out, or are a seasoned member of the community. Click here to buy the book.

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