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This post was written by TCCS member, Nigel Bowen


Notes from the gig economy underground


My transition from communist journo wage slave to capitalist content provider has been long and bumpy.

So to save you wasting a similar amount of time, money, and energy, here are the 10 most important lessons I’ve learned over the past 10 years as a freelance copywriter.

1. Decide whether you’re following your bliss or chasing cash

I enjoy talking about politics and popular culture. I also enjoy free holidays. So when I embarked on my freelancing career, I tried to support my family by writing about politics and pop culture for the Fairfax papers and getting travel mags to send me on trips.

It wasn’t a complete failure. But it soon became apparent I was fighting a losing battle against the laws of supply and demand. Lots of people want to provide hot takes about the latest political development or hit TV show and get sent to five-star resorts in Mauritius. In economic jargon, it inevitably results in a flooded market.

If you were sensible enough to choose the right parents or spouse, and don’t need to worry much about making your monthly mortgage payments, then by all means follow your bliss. If some long-lost childless boomer relative bequeaths me their portfolio of 10 investment properties, that’s what I’ll certainly be doing.

But if you need a reliable income to cover housing, food, and education costs, memorise the following formula: dull = dollars.

I haven’t been on a famil or written a think piece on the latest political crisis for years. But I do enjoy the comforts that flow from a six-figure income – an income almost exclusively generated by churning our content related to such glamourous subjects as accounting software, zero-trust cybersecurity systems, and aged-care funding mechanisms.

2. Understand that your clients aren’t your friends

Early in my freelancing journey, I became – in my mind at least – friends with a client I’ll call Virginia. For five years, Virginia gave me lots of work. We spoke on the phone frequently, and while those discussions focused mainly on the job at hand we also talked about our private lives. I even had a ‘real world’ meeting with Virginia once at a Christmas lunch.

Then, out of the blue, Virginia ghosted me.

I’ve spent a lot of time wondering what happened with my particular Virginia. But the reality is the Virginias of the world always end up ghosting you.

That’s because you ultimately have a business relationship with them, not a personal one.

You can (and ideally should) have amicable relationships with your long-term clients. But never flatter yourself that you’ve established a lasting emotional bond with someone paying you to provide a service.



3. Accept that your competitors are your colleagues

Even if you’re in a specialist niche, you’ll be able to take on only a fraction of the work available at any one time.

So it’s personal and often professionally enriching to dispense with the scarcity mentality and establish relationships with those who, at first glance, might appear to be your competitors.


4. Don’t get complacent during the feast

Even the most successful freelancers are prey to the feast-and-famine cycle. It took me a long time to learn that while the famine stage of the cycle can be confusing, it’s the feast stage where you really need to keep your wits about you.

When you’re snowed under with work, it seems obvious to stop marketing yourself. And knocking back established and new clients who offer you jobs doesn’t seem like a big deal either. But in the same way, Virginias always ghost you, busy periods always end abruptly. If you’ve spent weeks or months passively or actively repelling work, you’ll struggle to refill your pipeline from a standing start.

There are no easy solutions here. You can’t take on an urgent job from Client X if you’re already working 80 hours a week trying to complete an urgent job for Client Y. But you should at least make it clear to Client X that you value their business, and will make yourself available to them at the earliest possible opportunity


5. Don’t kid yourself that bad relationships will magically improve

Few things are as soul-suckingly demoralising as working for a client who doesn’t respect you or value your work. No matter how much money they’re offering (or promising to offer once their start-up starts turning a profit), don’t do it. If your relationship with a client has degenerated, end it as soon as possible.

6. Be reassuringly expensive

Imagine you need brain surgery. One brain surgeon you visit says he’s just starting out, so he’ll operate on you for free for “the exposure”. One says he hasn’t got much work on at moment, so he’ll do it for $500. The third surgeon unapologetically declares that the price of the operation is a non-negotiable $10,000.

Which surgeon would you choose to saw open your skull?


7. Quantify everything

Being a successful micropreneur rather than a starving artist largely comes down to knowing the numbers. How much money do you want to make every day? How many words do you typically write in a day? How much do you need to charge for each word to make a reasonable day rate? And so on.


8. Realise you’re not being rejected, you’re being redirected

I used to believe you eventually reached a stage of your career where you no longer get rejected (much). Sadly, that doesn’t seem to be the case.

Rejection always stings. But it stings a little less if you accept the idea that business opportunities are like buses. If you miss one, another will inevitably be arriving shortly.


9. Implement systems rather than setting goals

“I’m going to bill $100,000 this financial year” is a goal. “I’m going to keep my portfolio up to date, ask satisfied customers for testimonials, and approach at least one new potential client a week” is a system.

You’re more likely to become successful by following systems than by setting goals.

10. Buy the ticket, take the ride

Nobody put a gun to my head and forced me to become a freelancer. Even at my age, I could probably find an employee role if I put my mind to it. Given I’ve made my own choices in life, I’ve never seen the point of spending countless hours in online forums lamenting the downsides of the freelancer life.

If you’re in a situation where the pros of being a freelancer are no longer outweighing the cons, stop venting in cyberspace and start planning a new career path.


About Nigel



A former print journalist, Nigel Bowen now produces business, finance, and technology content for clients in Australia, Singapore, and the US. You can find out more about him at Content Sherpa