I quit ‘the dream’ of freelancing to return to a 9–5.

Tiffiny Costello
The Startup
Published in
9 min readAug 28, 2019

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Wait, isn’t it the other way around?

A nautical image for a nautical metaphor.

It was six years ago, when I jumped the 9–5 ship for the bright and shiny freelance life. Like the Titanic, nobody could have warned me of the icebergs I was steering towards, until I was already crashing towards an icy mental breakdown.

In 2014, freelancing was really taking off. I decided to quit my full-time job and go for it.

My first client was the company I had just quit. I agreed to work for them as a contractor until they replaced me. They paid $40/hour, 30 hours a week and I managed their Facebook Ads (400+ ads — it was the account that taught me a lot of what I know about Facebook Ads). What a warm welcome into the freelance world!

At that time, only the brave entered the world of no dress code, open hours, and no coworkers. We were a self-validated crew of ‘entrepreneurs’ simply because we found quotes on Pinterest that talked about ‘hustling’ while we scoffed at peasants working their stable, 9–5 jobs with benefits and a 401k.

I had also quietly departed from the sobriety train about three months prior to leaping into the freelance world. To be fair to myself, I would also get sober again, two years before quitting freelancing, but I am sure the confidence I had at the start of…

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Tiffiny Costello
The Startup

https://www.tiffinycostello.com/ professional hobbyist. creative, emo cat-mom queen. making #ambient sounds on pianos. studying space physics.