Freelancing on the Side to Full-Time

Freelance Folder lists things to consider when you’re freelancing on the side and trying to decide whether to go full-time. I started freelancing in 2000 at the height of the dot com boom. Initially, I aimed to work in Web design, but it didn’t take long to discover I had no eye or talent for design.

I entered a contest where you submit a Web design-related article and if they published it, you win Photoshop. I did. Of course, I didn’t decide right then I wanted to be a writer as I knew many people hoped to be writers. I didn’t want to be unrealistic about that. The work started coming in slowly — however, I didn’t consider that I could make a full-time living as a writer with many talented writers out there.

Financials and Health Benefits for Freelancers

Writing also made it possible for me to remain in my day job part-time when my husband got laid off shortly after our youngest was born. I knew if I switched back to full-time, the company would never let me return part-time. So the freelancing made up the difference.

After four years of “on the side,” I felt ready for “all the time.” Since we have three children — health benefits were a big thing especially with several taking pricey medicine. Paul finally landed a job with decent health benefits and I resigned about three months after he started (to ensure he wasn’t going anywhere).

My situation doesn’t apply to everyone. Some people may not need the kind of health benefits my family needs. A private insurance plan might work great for a single person.

Freelancing does make it hard to enjoy yourself when you’re not working. As not working = not getting paid. Whereas, working for a company = get paid every two weeks regardless of how slow things get or taking a vacation.

Social Isolation

As for seclusion, I never feel that way. I love the quiet of working in my office without neighboring speaker phones disturbing me. Hanging out with others isn’t an issue considering my family, involvement with non-profits like PTA, two tennis teams, and a weekly mah jongg game. An e-mail from a friend is more satisfying than a phone call for me.

Working in your own business “on the side” is the best way to get started in your dream business or working for yourself. Some people unrealistically risk everything and quit their “day jobs” for their dream job. While starting your own business means taking a risk — going cold turkey may not be the best way to start.

1 thought on “Freelancing on the Side to Full-Time”

  1. Finally, someone who thinks like me. I am told repeatedly by business associates, some techy friends, and on blog after blog after blog about how freelancing and web based applications are going to succed in the future of onlne world, well said, basically everything.


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