Misconceptions about the freelance lifestyle, based on 5 years of freelancing

Rosemary Richings
The Startup
Published in
5 min readSep 30, 2019

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Recently, I shared my take on the misconceptions about flexibility and freelancing.

But, now that I’ve had an open discussion about how I work, I wanted to share the harsh truths about freelancing that aren’t common enough knowledge. Because I’d be richer than Bill Gates, if someone gave me a dollar every time someone has said to me:

Lucky you, I wish I had your lifestyle!

In fact, I’ve had just as many conversations with people who want to start their own businesses, as the types who wonder when I’m going to get “a real job”. The truth is, it takes a very specific type of person to go through the challenges of freelancing, and not give up too quickly.

In fact, every freelancer I’ve met has character traits such as resilience, an ability to thrive under pressure, a stubborn belief in the value of what they do, and a strong stomach for constructive criticism and rejection.

Because freelancing, when it gets tough, forces you to make challenging decisions.

Yet freelancing has plenty of privileges, which make the not-so-great parts worth confronting.

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Rosemary Richings
The Startup

Writer, editor, author, neurodiversity advocate with a lived experience, dyspraxic POV