Things To Know About Freelancing Before Quitting Your Job Time Doctor
19 Jun

Things To Know About Freelancing Before Quitting Your Job

I didn’t know freelancing was trendy when I decided to do it. After I completed my masters in journalism from NYU I was looking for a way to write the stories I wanted to write and have independence over my schedule, workload, and life. So I started selling a few articles I wrote in class. And then I came up with new stories and sold them. It took me about six months to finally call myself a freelancer and even longer to stop looking for full-time jobs and accept this as my life.

Two years ago, when I started this career, I was the only one I knew freelancing. Now it seems like everybody is becoming their own boss. According to It’s My Business, a coalition formed last year by a former Arkansas Senator to protect independent contractors, there are 10.3 million people in the United States working for themselves, a number expected to grow.


Yes, freelancing can be empowering, challenging, even freeing – but it’s far from perfect. I can’t help but wonder if all these people making the switch know it’s not just boozy lunches on Tuesdays and working from the beach (although there is that!), but also cash flow issues, loneliness, and perpetual fear? And that it certainly isn’t for everybody: you have to love to motivate yourself and hustle to make this work.

The list below isn’t your average “struggles in starting a new business” rehash. In addition to my own experience, I’ve included sage advice from Michelle Ward, a life coach in Cobble Hill and author of the book, “The Declaration of You: How to find it, own it, and shout it from the rooftops” who specializes in helping clients become independent contractors.

Here is what you need to know:

  1. There are some days when you will have nothing to do. As a freelancer, nothing gets put on your calendar automatically. Everything – every meeting, and assignment – has to be scheduled by you. And it isn’t like a full time job where you still have to report somewhere regardless of how packed your day is. So there are days, or even months, where there is literally nothing scheduled. Some find this exciting; you can do anything you want with your day from get new business to go check out that new exhibit. But others find it difficult. “It gets overwhelming, and they don’t know where to start,” says Ward. “They don’t know what happens when they wake up in the morning.”
  2. The only person you are accountable to is you. When I started freelancing I knew I wouldn’t have a boss; that was something I was most excited about! No one to make me do an assignment with which I didn’t agree or look over my shoulder. But something I didn’t take into account was that not having a boss also means not having anyone to push you or stimulate you or measure your progress over time. And it also means there is no one there to say, “You said you would do this; what happened?” I’ve found other people to fill these roles – editors with whom I’ve become close, parents, former journalism school professors – but it’s hard work. With a full time job, this support network is built in automatically.
  3. You have to talk about yourself. A lot. As a freelancer, especially one who is just starting off, you are your own marketer and promoter. And you never know where business is going to come from so you end up tell everyone from family friends at holiday parties to the stranger you meet on the subway, what you are offering. Some people love this but not everybody, says Ward. “If you are the type of person that really is very very private and doesn’t want to tell anyone what they are doing and you don’t have a little bit of that hustler in you then it probably isn’t going to be a very good fit.”
  4. There will be times when business is slow. And you will probably freak out. Regardless of the industry, every freelancer is going to hit a slow time of year when no business is coming through the door. “Then that panic button goes off,” says Ward, “Because you go, ‘Oh my god, no one is ever going to pick up the phone and call me again. The work is just going to dry out!’ Immediately, that’s where your mind goes.” The good news is that the longer you freelance the more you see trends, and you can start to expect the drought and prepare. But it takes a while to get there.
  5. Freelancers are Renaissance Men and Women. Most people start freelancing because they have a passion for something and want to offer it to the world. But something they don’t realize is that to get your company off the ground you also have to do a bunch of other things: taxes, bookkeeping, marketing, new business promotion, etc. And often times you end up spending even more time on these tasks than you do on your main job.  Do you like to learn new skills? Does it excite you to run every aspect of your business? That is something to think about.
  6. You will be alone. Physical loneliness is easy to solve as a freelancer: go to a coffee shop to work and gchat with your friends while they are at work. It’s the emotional loneliness that’s difficult. No one, not your best friend or your mother or your former boss who you still talk to, is invested in your business like you are. And while people might find your business fascinating and want to hear about it all the time (I’m lucky to have wonderful friends and family members who do a lot of listening) they aren’t living, breathing it like you are.
  7. You have to throw your own parties. Freelancers don’t get the normal types of recognition: promotions, pay raises, bosses saying you did a good job. But marking progress and milestones is super important. As Ward says, “you have to throw your own parties.” Get a new client? Treat yourself to a nice dinner. Worked out a very challenging situation? Take your friends to a bar and buy a round. Because, if you really think about what it means to be a freelancer and you decide to go for it anyway, you will have a lot to celebrate.

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Read 2597 times Last modified on Thursday, 19 June 2014 15:07
Kenneth Pabon

is a web developer/designer from Laguna, Philippines. He specializes in web development using open source content management systems such as Joomla, Drupal, Magento and Wordpress.