Freelance 101: Chronicles for the self-employed

by Leanne Rollins, Membership Manager

January 4, 2005 was a momentous day in my life. I was 'restructured' out of my full-time job, set loose upon the world with nothing but time to reflect upon what I should do next.

For years, I had considered freelancing, casting away the constraints of captive employment and flying free to seek out individual assignments wherever the wind took me. I talked about this idea to my friends and family, but in reality, I was all talk. Then, a decision was made for me, and I was handed a gift—the chance to put all my talk into action and see if I could truly make a go of freelancing. And so, I did it.

I'm writing these chronicles for those of you who wonder if this freelancing gig is really all it's cracked up to be. Each month, I'll share the successes, the mistakes, and the lessons learned as I get my business up and running. I hope you enjoy the ride!

Questions to ask yourself before you take the plunge

Can I handle the financial risk?

If you have a family to support, giving up a full-time gig not only means giving up a steady salary, it also means giving up benefits and any nice little bonus cheques the company doles out. You need to have at least two months operating experiences set aside to sustain your lifestyle. In the event of a dry spell, you'll then have those two months to find more freelance work or find a full-time job. Getting that first contract is a huge win, but don't forget that it takes hard work and commitment to source out clients and keep them.

Best case scenario—get restructured out of your job, collect a tidy severance, and then you'll have a nest egg to provide that little bit of security!

Can I handle the emotional risk?

Branching out on your own is a lonely business at first. Since it's your brainchild, the onus is entirely on your shoulders to put together a plan, execute it, and consistently deliver on it.

Not only that, but I've found it tough to work pretty much in isolation most days. If you're used to an office environment, you might miss the ability to head to the coffee maker for some human interaction. My dog and I have a lot of conversations, and while she is smart, she's not quite the conversationalist my co-workers were.

If you're a very social creature (which I admittedly am not), you can arrange on-site work arrangements with your clients, schedule lunches with friends each week, or hit the mall at lunch simply to be near people. Since I have two small children, I tend to enjoy the quiet that my home office affords, but it's definitely not for everyone.

Do I have enough experience?

Throughout my full-time career, I've also taken on freelance work. As my career steered into management roles, I became a little concerned about losing my tech writing know-how. So, I'd prepare online help or training material by the light of the moon just to keep my writing skills current. By doing this, I learned a few things. First, I had the discipline to work odd hours to get the job done. Second, I loved to learn about new technologies and subject matter. Third, the money could be terrific.

But clients hire contractors for very specific jobs. They won't train you or invest in any time you need to get up to speed on their product. You need to walk in and be the 'expert' not only about professional writing, but also about tools, techniques, and timing. These are things you learn from experience, and you need enough work experience under your belt to lend an air of authenticity to your skills.

Do I have the chutzpah to network and cold call?

Unfortunately, jobs don't just fall from the sky. It really does take work to put yourself out there. As soon as I made the decision to freelance, I made a list of friends, acquaintances, former employers and co-workers. I then let everyone on that list know I was freelancing, either by phone, e-mail, or over lunch. I had so many lunches with old acquaintances in those first few weeks that I gained about seven pounds! These lunches netted me two jobs, so they paid off despite the extra weight.

Cold calling is so hard. I am not a shy person at all, but something about picking up that phone and putting yourself at the mercy of some stranger is heart-rending. The funny part is that people are fundamentally nice, and they won't generally be mean or nasty if you get quickly to the point. I made just two cold calls in those first few weeks, and I netted interviews for both of them. One turned into a job offer, but alas, it was a full-time job offer. (Look for more about over-selling your services in a later installment of the chronicles.)

"Do or do not. There is no try."

Yup, Yoda said it best. Once I took the plunge, I determined to give it my all. That said, in the weeks after losing my job, I applied to a select few full-time job postings just to cover my bases. In the back of my mind, I knew freelancing was really what I wanted, but I also needed the reassurance that someone, somewhere, valued my skills on a full-time level. It seems silly now, but restructuring is also rejection, and my pride took a hit. Having a few full-time job offers renewed my confidence, and now there's no looking back.

Next month, I'll chronicle the fine art of cold-calling—how to pick the targets, how to position your pitch, and how to follow through and seal the deal.

About Leanne Rollins

Leanne recently became a self-employed contractor, escaping management roles for the first time in years. This newfound freedom has allowed Leanne to take on extra-curricular activities such as a more active role in the STC. When not writing or playing with her kids, Leanne enjoys running and soccer.