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This post was written by TCCS member, Libby Hakim


Or, how I finally found the nerve to quit a secure job for the fabulous world of freelancing

In this post, TCCS member Libby Hakim shares her story of transitioning from the security of her work as a government lawyer to the freedom of freelance copywriting.

Career change stories are often accompanied by a photo of an exuberant woman leaping through the air. Yes, she’s following her career dreams in a single leap.

My career change from lawyer to freelance copywriter was three years in the making – hardly a leap. And when I did eventually reach tipping point, I wasn’t exuberant. I’d been juggling two careers and a family, I was exhausted.

The cliché about not looking back, though, held true. I really haven’t. Until now.

Here, I look back at the 5 stages of my three-year career “leap.”


Stage 1: Finding the P word

My writing business started, and keeps growing, because of one thing. That much-talked-about P word: Passion.

On maternity leave in the middle of January, the heat and hormones were sending me a little crazy. So, I enrolled in a 5 week online course to feed my brain up until the due date. The topic was writing feature articles for magazines and newspapers. I’d always loved reading them.

Why not write them?

My aim was to get just one article published.

I got that one article published… and I was hooked. Writing features on parenting, health and careers became a hobby which gradually turned into a nice little side income. I eventually returned to work as a lawyer on a part-time basis and continued freelancing as a writer.

Through the challenges of juggling a job and freelancing (and a family) and the doubts (why would I give up a career as a lawyer to write), it’s the thing that kept driving me. I loved writing and I enjoyed having my own little business.


Stage 2: Lots of late nights on WordPress instead of Netflix

As my writing “hobby” turned into “freelancing,” I realised I needed an online portfolio.

I set up a small portfolio on but was soon wishing I had a place of my own online.

But I couldn’t justify going all out on a fancy website for my little writing lark.

So, I decided to build a website myself.

A self-hosted WordPress website, no less. It couldn’t be that hard, right?

It wasn’t easy. And by the time I realised how tricky it was, I’d invested too much time to give up. The only thing to do was to keep plugging on and navigating the steps via Google and YouTube.

It was worth the trouble. I taught myself a new skill and can now manage and update my own site (plus sprinkle a little SEO goodness over it thanks to the  Recipe for SEO Success e-course).

But if I could go back and give the WordPress-virgin version of myself some advice, it would be this:

  • Themes: Buy a great user-friendly theme, don’t bother with the free themes
  • Freebies: take advantage of the online course craze and enrol in a few DIY WordPress taster courses before you start
  • Plugins: once you discover the power of these, you’ll enter a whole new world


Stage 3: Getting social (and developing a few career crushes)

A big part of my career transition involved watching the social spaces of those who were already doing what I was starting to think of as my dream career.

I knew how to pitch. I knew how to write.

However, via Facebook and Twitter, I learned the subtleties and kept up to date with the information many writers generously share via blogs and podcasts. I was an observational learning junkie.

As my confidence grew, I joined FaceBook groups, met other writers online and in person and went along to writing workshops.

I started to think about diversification and niches, about platforms and personal brands. I was slowly working out how I might operate in the fantasy land that was writing for a living.

And, yes, I did develop a few career crushes along the way (wink wink, Kate Toon, Valerie Khoo and Darren Rowse).


Stage 4: Letting go of career baggage

As my writing career strengthened, my law career was starting to get me down. I’d fallen in love with writing but still felt married to the law. I couldn’t possibly leave law for a flaky thing like writing. That’s what I told myself and the conflict was making me miserable.

I hired a careers coach to help me deal with my career conundrum.

At our first meeting, I was ready for her to tell me the mechanics of how I should advance my career – perhaps using my combined legal and writing experience to enter a policy or precedents legal role. Instead, she asked me about my upbringing and values.

It was painful to admit, but I was still emotionally bound to my childhood views of success.

I grew up in a working class area and held simplistic views of success, involving doctors, lawyers and their shiny cars.

My parents, who had both been forced by circumstance to leave school early, didn’t have the opportunities I’d had. I was finding it hard to let go of the idea that I was throwing away my shiny honours degree in law.

As I cried into my teacup during those first career coaching sessions, I realised just how strong a hold these long held emotions and values had on me. My career coach kindly pointed out that they were holding me back. I had to reframe my thoughts, work out what I really wanted and move forward.


Stage 5: Making my dream career a viable one

I let go of enough baggage to give myself the freedom to dream about making writing a reality. And dream I did.

I spent lunch breaks in Kikki-k, buying pretty notebooks to jot down my business ideas and inspiring quote cards to keep me focused on moving forward.

I spent my commute listening to podcasters who sold me on ideas like passive income, personal branding and the power of creativity.

I investigated what accounting software I’d use when I was pumping out all those invoices (I settled on Wave).

I knew I’d be happy.

I knew I’d be successful. But to get past the dreaming stage, my role as joint breadwinner meant I had to develop a clear financial case for freelancing before I felt comfortable making it a reality.

Here are the things that helped me build my case:

  • Toggl: to calculate which parts of my writing work were most lucrative
  • Adding SEO and website copywriting: to my existing feature, content and business writing services
  • Developing a legal copywriting niche: although I was trying to move on from the law, I realised I needed it to escape
  • Testing the waters: I spent a crazy few weeks taking on as much work as I could find to gauge how quickly I could ramp things up

I built my case but continued to teeter on the edge, afraid to jump into the unknown.

In the end, it was a random comment from a former colleague who’d made the switch to journalism and a rather crappy week in my law job that pushed me over the edge. After all that working and careful planning, I finally listened to my gut. It was now screaming at me: “You have to do it NOW.”


The result: a very happy freelancer

While I may have felt more like someone finishing a marathon than a woman gleefully leaping when I made the switch, I still feel like a big winner. I absolutely love my work. I’m learning every day and am excited about the possibilities ahead. My earnings are so far on par with my law job.

After 3 months of freelancing, I’m starting to feel like that happy, leaping woman.


Have you made the leap?

Or are you still dreaming? We’d love to hear your story or tips below:


About Libby

Libby Hakim

Libby Hakim is a Sydney-based copywriter, specialising in website and SEO copywriting for small business and legal copywriting for law firms, legal publishers and other law-related businesses.

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