Freelance writing is either a daring adventure or nothing

I’ve been freelance writing in a part time capacity for fourteen years. Still, the idea of turning my business into a fulltime venture has been daunting to say the least. Add to that – uncomfortable, nail-biting and then there was that eerie dream about a blood red moon (interpretation: I’m either going to die a violent death soon or resolve a current issue).


Then yesterday I remembered this quote by Helen Keller:


“Security is mostly a superstition … Avoiding danger is no safer in the long run than outright exposure.”


I like it because it’s almost anti-inspirational. No warm fuzzy feelings here, just the uncomfortable truth that life is indeed unpredictable. I find it strangely comforting that, no matter what we do, there’s always risk involved. And in my experience, good risks generally pay off.


Having said that, there is something in business called “risk management” and, while that sounds a bit jargon-y, I wish I had taken heed of this the first time I launched into fulltime freelancing. It makes sense to eliminate the kinds of risks that don’t pay off, right? I started by fronting up to my weaknesses.


My biggest weakness is marketing my freelance business
I had a sneaking suspicion many blood red moons ago that I should acknowledge my weaknesses. But as a newbie writer, I was a bit cocky, perhaps immature. The first ever article I sent on spec was commissioned and I got paid for it. The next article I sent on spec to the AFL record, I was invited to meet with the MD to discuss writing more paid comedy articles. I wouldn’t say I thought I was the next big thing – my confidence about being a “real writer” was still crushingly low – but I thought this freelance gig was, you know, meant to be.


It took me too long to realise that pitching articles and being commissioned wasn’t going to provide a decent living (especially with the halcyon days of print media over). It also took me too long to realise that having a website and answering job posts for freelance copywriting roles (the pay of which is often dismal) wasn’t sufficient enough to market and sustain a business.


It was time to get my marketing mojo on:
So this time, I knew I had to seriously rethink my marketing strategy. These are some of the tactics I’m using to improve my potential for success:



• I’m reading and following other freelance writers to find out how they’re doing it – successfully.

• I’m listening to podcasts about marketing a freelance writing business.


Listening and sharing

• I’ve joined more freelance writing networks to see what challenges other writers are having, and I’ve also started to post more regularly.



• I wrote a marketing and content marketing plan. I even wrote a bloody five-year plan!


Making myself more visible

• I’m sending out Letters of Introduction (otherwise known as LOI’s) to businesses. Sure, cold emailing still gives me cold shivers, but now I know it as an absolute necessity for building a strong client base.

• I’m asking clients for referrals to new clients and testimonials for my website.


Support and coaching

• The best, best, best thing I’ve done so far is to book a coaching session with Lindy Alexander where we focussed on marketing. After the session, I received a potential job offer within two days for which I’ve now written my first proposal. Fingers crossed. Lindy also gave me the confidence to increase my fees to match my level of skills and experience. I can’t recommend coaching or mentoring sessions enough. I’m already thinking about a follow up session down the track.


The other major weakness I’ve identified is confidence, not an uncommon trait among writers. As a raving perfectionist, I have no problem delivering on my work – if only that damn voice in my head that says ‘You’re not good enough’ would shut up! Aside from all of the above, and just accepting for now that things feel uncomfortable, I’ve also found it useful to reflect on my freelance writing super powers.


Harnessing your freelance writing super powers
A few months ago, I chanced upon the podcast ‘Confessions of a Misfit Entrepreneur’ by Kate Toon. If you’re a copywriter and you don’t know the Toon-Meister then seriously check her out – she’s got so many goodies: tips, templates and courses for freelance writers. Like she’s ALL OVER IT. The podcast episode I listened to featured Melanie Springs, a woman who’s passionate about marketing without having swilled a jumbo size cup of influencer hype. I really liked the idea of thinking about your professional strengths in terms of super powers.

My list of super powers to remember when I doubt myself:

1. Wordsmithery

2. Efficiency

3. Humour

4. EQ

5. Reliability


And with this, I’ll leave you with the end of Helen Keller’s quote which always gives me chills it’s so simple and beautiful:


“Life is either a daring adventure or nothing.”


So, do you think considering your strengths and weaknesses increases your chances of success?

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