5 Side Hustles I Quit and 4 I Successfully Sidestepped

$6 as a freelancer, $2 as a t-shirt designer and $0 trying to be Seth Godin

Kieran MacRae
The Startup
Published in
7 min readMay 24


Photo by Pedro Araújo on Unsplash

I’m a quitter.

Every side hustle I quit had the promise of a pot of gold at the end of the rainbow. Most side hustles left me standing up to my arse in a bog with the rain beating on my head.

Even worse, I was often out of pocket. Instead of starting some of them I may as well have walked into a casino and put $100 on Black 13. At least gambling would only have wasted money, not my time.

The Side Hustles That Broke My Heart

1. $6 for My One and Only Freelance Writing Gig

“Write a 300-word review of a toothbrush”. That was the brief. I excitedly hurried to pen out the most majestic review ever written about a Phillips Sonicare. I redrafted it four times to be safe and sent it over. The feedback I received? My writing was ‘very very not good’…


But the kicker was that Upwork’s 20% fee bumped me under the minimum $5 payment threshold, so I couldn’t even withdraw it! Talk about insult to injury.

The rage bubbled inside me as I read the feedback. I quit on the spot. I vowed never to work as a freelance writer again, I’d write for my own niche sites instead. I’d show them.

Arrogance won the day. The site I went on to build became my full-time income for the next 5 years.

2. Selling the World’s Least Attractive T-shirt

I was there for the opening of the Merch By Amazon program after coming across it on Reddit. “Hells yes” I thought. Ol’ Tim Ferris says you gotta be first, best, or cheapest, to win at business and I was ready to be first.

Only… I forgot one crucial detail.

I have the same eye for design that an elephant has for ballet. I can’t tell a great design from a shitty one to save my life so guess what happened when I started designing T-shirts to sell on Amazon? Absolutely nothing. No sales and a whole load of time wasted.



Kieran MacRae
The Startup

Over 1,000,000 words published online and two 6-figure blogs sold. I run a Scottish history podcast and write about online business, podcasting, and marketing