THE PENNY PUB

I Failed at Freelancing Until I Learned to Bet on Myself

You can’t clutch the ground if you want to fly

Ellen Eastwood
The Penny Pub
Published in
5 min readMay 31, 2024

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Woman at laptop with coffee smiling at camera
Image by ansiia on Freepik

I took a break from work following years of caring for my ailing father. When it was time to re-enter the workforce, I realized I had a golden opportunity — instead of finding a new job right away, I could try my hand at freelancing.

As an employee, I’d fantasized about being my own boss, but the prospect of foregoing a regular paycheck was too daunting. Now, I had no income coming in, anyway, so why not try? Surely, things could only go up from zero.

I’d worked in market research for thirteen years, so I knew my stuff. I’d also built up a long list of contacts — former clients and co-workers, to tap for potential projects.

My first call was to my former employer of seven years. Within an hour, they assigned me three projects, all starting Monday. But — they quoted me an hourly rate that was eye-wateringly low, non-negotiable. Reluctantly, I agreed, thinking it would at least give me experience.

Thus began two years of juggling way too much work while being paid too little. I worked exclusively for my former company, mostly taking on jobs they didn’t want to do. One day, I realized I’d traded in a plush job for lower wages…

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Ellen Eastwood
The Penny Pub

Culture and lifestyle writer | Generalist | Curious | Witty on a good day | Contact: elleneastwood@outlook.com