The Highs & Lows of My Freelance Writing Career

The tarot card reader eyed me over the card I drew. She asked: “Have you met others who’ve gone through what you have? Such as a failed business?”

The Wisdom card, she explained, pointed in my case towards the wisdom of others. To learn from them, I had to first open up about my experiences.

Huh. We had only just met. How did she know I was a failed freelance writer?

Romantic expectations

When I left full-time writing to freelance in 2021, I didn’t think it could possibly go wrong. After all, I was good at my job and enjoyed it. If I freelance, it would only get better, right?

Well, to begin with, I had a very romantic notion of the freelance life. I imagined writing in cool cafes all the time, freed from the shackles of other duties like All Hands meetings and editing others' work. Writing remotely from some Bali beach shack. Haunting the yoga studio every weekday afternoon.

So I was already set up for failure. Obviously, reality didn’t meet my expectations. I still had to talk to clients and send invoices. That was fine. But I never felt financially secure enough to indulge in the fun side of freelancing.

Highlights from the early days

When I started freelancing in 2021, my initial forays went pretty well. I enjoyed dashing off quick and fun articles for my former workplace, like How to Achieve FIRE by 50 and Can You Start A Business With Just $1,000 or Less? 

A lot depends on the editor I worked with. My editor at MoneySmart knew my style and she was great at matching me with clients who liked that style.

Another editor I enjoyed working with was at 99.co. He must’ve pegged me as one of the tofu-eating Guardian-reading wokerati, because he assigned left-leaning articles like Wealth tax in Singapore, Should we raise the BTO income ceiling again? and 3 harmful social consequences of parents buying property in trust.

Back then I actually quite enjoyed meeting clients and checking out where and how they worked. I even met the editor of The Simple Sum and pitched a deal: discounted writing fees in exchange for a spot in their co-working space. In the end it didn’t work out, but I did write 4 Ways To Spend Smarter On A Date for them.

Then I started chasing the money

But it all started to go south in 2022, when the content market suddenly got flooded with money from crypto companies, wealth management and private banking firms. And I started chasing it.

I did a few fun light pieces like Take This Quiz to Find Out How Ready You Are For Crypto, but ended up doing a lot of super serious crypto guides and wealth management content.

I started wondering what on earth I was doing. Yes, I was technically still a “finance writer”. But now I was writing stuff that was worlds apart from the minimalism and frugal living ideas that drew me to the field in the first place.

Because the clients had money to throw around I started raising my rates. Pretty soon I was charging clients $1K a day for facetime.

The money was so good, I just couldn’t say no. Which created a weird paradox. Whenever I got a brief I wasn’t keen on, I would quote ever-higher rates ("fuck off fees”) to deter clients. But it seldom worked. Instead, the fees drew clients even higher up the food chain.

So to sum up, after a year-plus of freelancing I was making scads of money, and also at my unhappiest as a writer.

ChatGPT: the nail in the coffin

Fortunately for my sanity, my work dried up in 2023. Whether it’s due to the death of crypto, a changed business climate, or being replaced by AI, I couldn’t say. But you know what? I’m kinda glad ChatGPT put me out of work.

All 2023, I rested. I travelled. I worked in a bookstore. I read books. I drew. I blogged. The only paid work I did after the spring of 2023 was this travelogue of the UK train trip in Her World, which I am at least quite proud of.

That said, the lack of freelance writing jobs had its downside. The loss of money, I could deal with. But it slowly killed my confidence. At any rate, how could I call myself a freelance writer when I hadn’t made a cent from it in a year? I started thinking of myself as a “failed freelance writer”.

Learnings from failure

So my freelance career, or at least what I had set out to do, failed. But I learnt a lot:

1. Financially, it’s not the end of the world. There’s more than one way to skin a cat.

2. Don’t chase the money.

3. If you want to chase high-paying gigs, learn to compartmentalise. They don’t call it “compensation” for nothing.

4. “This is the last job I’m ever gonna get” = the least useful mindset ever! Just say no if you don’t want it. The next job will come.

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.