My Best and Worst Freelance Writing Side Hustles

Don’t believe the hype

Do not get sucked into the idea that side hustles are an easy way to pay down debt, build your financial freedom, stick it to “The Man” etc etc etc.

Sure, they CAN do that.

But ignore the rainbow and unicorns illusion created by certain articles on Medium. It’s not easy.

I often wonder whether the authors have actually tried the side hustle. They simply regurgitate a narrative…which they found…on the internet. The irony.

The thing is, for real traction it’s tough. It’s trial and error. And some side hustles can be a waste of time. I should know — I’ve tried more than a few.

Should you give up on side hustles? Absolutely not. Just go into them with your eyes open.

Time to keep it real

I’ve dabbled with several, particularly when I was between jobs and a bit lost. Circumstances dictated…

I was also inspired by Nick Loper’s Side Hustle Nation podcast and the accompanying Buy Buttons book.

Sometimes I had a nice payday. But, honestly, sometimes I really struggled to cover my bills.

So here’s my unvarnished view of my best and worst freelance writing side hustles, and what I’ve learned. I’ve scored them based on my own experiences.

I will touch on my other side hustle experiences in future articles (and there were some wrong ‘uns).

Freelance writing

Long before I dabbled with Medium, I anchored a lot of my side hustles to freelance writing.

Here they are:

Resume/CV writing

As I indicated in my About Me, I trained in career coaching, which led me to CV writing.

I posted my services on Fiverr and PeoplePerHour with limited results. But things really took off when I replied to an ad from a premium UK resume writing company looking for writers with sector expertise.

In the first month, they trained me up, ripping to pieces my earlier efforts. I wrote consistently for them for more than two years, consulting with MDs, heads of business, and all the way down, all looking to sharpen their CV, LinkedIn profiles, and bios. This was no content mill.

I pivoted what I learned into writing contracts with a couple of universities for their MBA students. I was also invited on LinkedIn to consult at an annual finance professionals conference.

Difficulty: 5/10. Not that hard once you know what you’re doing, particularly if you are able to niche down as a sector specialist. When I had Skype calls with industry pros I had credibility.

Money: 8/10. My university gigs paid very well, as did the conference for 3.5 days ($3,700 for the conference alone — but was a one-off). Working as a contractor for the resume writing firm was ok, even after their sizeable cut (I got $100-$250 for each client, depending on whether they wanted add-ons) — and it produced a solid portfolio of work.

Investment writing

I found various gigs through Upwork and PeoplePerHour, including two long-term ones for a website and a newsletter. The fact that I was writing about investment markets was good for my resume.

Difficulty: 5/10. It wasn’t too challenging, given that it was a field I understood and knew where to research. I may have struggled if I had to provide specialist insights in an unknown area.

Money: 5/10. They weren’t the best-paying gigs ($50-$80 a time for the website and newsletter). That’s the nature of platforms like Upwork. Clients often start with price, even if high-quality writing candidates exist. But the gigs lasted for almost a year and became part of that side of my portfolio.

Career writing

Surfing around Facebook I found a gig writing on career topics for a start-up website. I leveraged my resume writing experiences to write every two weeks.

Difficulty: 4/10. Not too hard at all. I had the ideas already and merely repackaged them.

Money: 4/10. Again, not the best paying ($50 a piece I think). But it was simple and there wasn’t a platform like Upwork to take their cut.

Award writing

Now, this was lucrative.

A UK contact approached me via LinkedIn to see whether I would write submissions for two companies bidding for awards at the annual FT Innovative Lawyers Awards Asia.

One-hour calls with company bigwigs and then an 800-word write-up. It was all done and dusted within a few days. And I still don’t know whether or not they won.

Difficulty: 8/10. Yep, I didn’t understand half of it. But where there are challenges, there’s always Google.

Money: 8.5/10. This was a winner: $1000 per submission. It was great while it lasted.

Miscellaneous

I dipped my toe into various writing fields. The ones I remember are:

• Travel writing. I wrote a few pieces for International Living Australia. It paid ok.
• Scripted. I wrote a handful of times for them but the editors kept getting on my nerves.
• CrowdSource. Random product reviews, though I don’t recall much more than that.
• Daily Two Cents. It’s a revenue-sharing site for freelancers but it really didn’t pay much.

Difficulty: 5/10. Not too taxing.

Money: 4/10. These tended not to be high-end so didn’t pay well.

There you have it

Overall, my freelance writing worked out pretty well, even if some required a lot of effort for minimal return.

My advice would be to find ways to move up the value chain if you can. Fall back on any specialist knowledge you may have.

Find your niche. Become a go-to expert. Seek out non-mainstream opportunities (e.g. the FT Innovative Lawyers Awards Asia I had).

If I ever do go full-time, that would be my focus.

Part 2 of my personal side hustle round-up will be a whole lot messier.

I’m a finance guy with a career and life coaching background and a past. Find out more on my About Me page.

Essentially, I created Spiritworth to help others “raise their spirit and raise their (net and self) worth.”

Join as a member to get access to thousands of Medium writers. Tap this link.

Connect with me on Twitter.

You may find affiliate links within this article.