2024 Week 36: My Failed Freelance Writing Career

The tarot card reader had me draw a card from her deck. It said "Wisdom". I tried to laugh it off with a joke, but she looked at me seriously and enquired if I was struggling with a certain experience, such as a failed business. She suggested that I could move forward by seeking the wisdom of others who had been through the same thing. I was shocked at how well she read me, considering it was the first time we met and we barely spoke. Maybe I'm not great at hiding my pain, or maybe (cynically) everyone is going through something.

My "failed business" is, of course, my freelance writing career, which began in 2021 after I left MoneySmart and mostly petered out by 2023. I have never tried to make sense of it. Because really, it's beyond confusing. I loved my writing job, yet I hated freelance writing? It doesn't add up. There must be something wrong with me.

To begin with, I had a very romantic notion of freelance writing, so maybe I was already set up for failure. I imagined that I'd get to write all the time, and not do any of the other boring shit like attending All Hands meetings and editing others' work. The reality was that I still had to do dreadful things like deal with clients and send invoices. I had these cliched ideas of working from a Bali beach shack and doing yoga at 3pm on a weekday. Well, guess what? I didn't do any of those because I didn't feel financially secure enough for remote living or a yoga membership.

At the beginning, in late 2021, my freelance forays went okay. I made some easy money writing fun pieces for my former workplace. I wrote for a couple of other fun places, including one where the editor seemed to peg me as  one of the tofu-eating Guardian-reading wokerati and assigned me articles on wealth tax and other topics that concern the informed lefty. I even pitched a deal with another company where I'd contribute 4 articles a month at a pretty low rate, in exchange for a spot in their co-working space office. (didn't work out)

In 2022 I started getting and chasing Big Money assignments. The high-paying clients were invariably in the wealth management/private equity/investment banking/crypto/business consulting space, and I was a squicked out yet attracted by the money in equal measure. My rate went from $500 per article to $600 to $700. Then I started charging $1,000 per day. I charged this day rate for editing, coaching, event coverage etc.

Not knowing how to say no to work I didn't want created a weird paradox. I kept quoting ever-higher rates ("fuck off fees") hoping clients would go away, but all that did was create an aura of competency and get me even more work. Pricing yourself high is a technique espoused in freelance self-help books like Book Yourself Solid, and I guess it works. It's just not my thing. Although I made a lot of money at that point, it was pretty much a new low for me, creatively and mentally. 

I never got a chance to learn to say no, because fortunately the Big Money died out in 2023. Due to chatGPT/inflation/death of crypto/whatever there wasn't a lot of work going around that year, which gave me a much-needed rest. I travelled. I worked in retail. I read books. I drew. I blogged. That was my recovery. The only writing I've done for pay since 2023 is this UK train travel article for Her World. I feel embarrassed to admit that. No work = no self-confidence.

OK. Fine. So it wasn't the total and complete failure it is in my head. It's not like I gambled on this freelance thing and lost my entire life savings along with my mind. I guess I am just overreacting as usual to things not turning out as per expectations. To be sure, chasing Big Money was a mistake, but an understandable one. 

As for what's next... Right now I'm interested in writing about humans, labour, culture, travel and lifestyle. These are a departure from my former niches of SEO and finance writing. Topics that I feel very much a beginner at. The idea that anyone would pay me one day for such work is, at the moment, high fantasy.

In any case I still feel very unsure about writing for money. On the one hand it has a certain glamour; there's nothing like seeing your byline in a reputable media brand to stroke one's feeble ego. On the other, I'm not really interested in contributing to either the media machine or some company's bottom line. And I already know that freelance writing seldom offers the joyful experience I had as a full-time writer. I have to move on from that.

MON: writing, check-in Coco, mass grooming session (5 bunnies), yoga, dinner at Fulton

TUE: writing, e-book, meet Nadia to talk about my future, yoga, grocery shopping, beef noodles for dinner, Only Connect

WED: writing then book meetup at Crane, came home to make wanton mee, watched Slow Horses

THU: lunch with parents, cleaned air con & felt gloomy, yoga, Kinds of Kindness part 1

FRI: yoga, cold chicken repast for lunch, e-book, check out wedding venue, NOW Pizza for dinner (because Little Caesars is ded), Kinds of Kindness part II

SAT: lunch with dad at Sims Vista & test ride e-bikes, yoga, AMK library, dinner at Fulton