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My Path to Freelance Writing

Not a straight shot, but I think I’ll make it

Lisa Dexter
5 min readAug 1, 2021
Maze of stairs
Photo by Mitchell Lou, on Pexels

Before my daughter, Amelia, was born, I had been a successful IT project manager for over a decade. Project management is one of those things that sounds boring on its face, but depending on the environment and how much the PM needs to accomplish, it can be exhilarating-and exhausting. One of my favorite projects was the last major company-wide upgrade I managed. There were dozens of people involved between the business team and IT folks, and they all worked well together. The final push was a weekend-long stint involving one bleary-eyed project team and a lot of junk food. That Sunday night, business users were supposed to confirm everything was fine, but we kept pushing the verification time out as we found more issues. Granted, that doesn’t sound pleasant, but those verifiers believed in us and stuck with the IT team until we got it right. Finishing something like that is Christmas morning with a fireworks show.

Unfortunately, project work is predicated on having the budget to make changes. The last company I worked at as a PM ran out of money, and they laid off all of the project managers. This layoff was the worst kept secret ever, so everyone had prearranged to go down the street to get drunk and commiserate. My only solace was that I had vacation plans the following week. Somewhat…

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Lisa Dexter
Lisa Dexter

Written by Lisa Dexter

I am a freelance writer from the Chicago area. I have one awesome child, one sweet husband, one clingy cat, and one website: www.thinkingwhiletyping.com.

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