My Path to Freelance Writing

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. Unfortunately, I had already planned a trip to Las Vegas before knowing my income stream was disappearing. I honestly wasn’t feeling too lucky at that point, but nothing was refundable, so I went and tried to have fun.

Starting over, but with a slight hiccup

The slots ate a little of my severance money, but when I came home, things started looking up—I was expecting a baby. I was elated, but potential employers eyeing my growing baby bump didn’t share my enthusiasm. Just as I was ready to give up hope, I secured an interview with a large corporation that shall remain nameless. After meeting with three groups of people, the HR representative told me to expect an offer letter in the mail by Christmas. After nothing arrived, I tracked down the HR person who had promised me the letter. Only then was I informed they had made a last-minute decision to go with an internal employee. By then, I was pretty noticeably pregnant. My husband and I had already made the sacrifices needed to live on one salary while I’d been looking for work, so I hung up my briefcase and called it a day.

After taking a step back from the workforce for several years, I realized I didn’t want to go back to the 40-60 hours per week being a PM demanded. Amelia was used to me driving her to school in the morning and picking her up in the afternoon. Once in a while, we’d stop off for a snack, pick up groceries, or go somewhere fun. Even when we just went between home and school, we’d talk and laugh the whole way. I’d also help in the school library and with Girl Scouts. Throw in a chronic illness that sapped my energy, and some days, I had no more to give. In short, I already had a life, and I couldn’t afford to go back to a career that took so much of my attention and energy. I needed a job that would fit into my life.

Within a month, I had found a flexible, remote, part-time job doing some writing for an AI-assisted recruiting firm. It didn’t pay anywhere near what I’d been earning as a PM. However, what it lacked in monetary compensation was made up for with the ability to weave it into my life. I enjoyed the work and the chance to interact with adults again. Adults! After a series of promotions, I was once again a manager—this time for the writing group. Although it was a full-time position, the flexibility was still there, and I worked with some outstanding people. I thought I’d found my ideal situation. A month after I became a manager, the company shut its doors. Officially, it “pivoted” to a different purpose that required no employees or contractors, but I was out of a job regardless of the reason. I saw an opportunity to either forge a new path or return to a former life.

Starting over…again

I thought about returning to PM work, finding more contract writing work, or becoming a freelance writer. Although freelancing had the most appeal from a flexibility and creativity standpoint, I was unwilling to commit to an unproven path with an unpredictable income stream. I put feelers out in all three areas and ended up as a technical writer on a short contract. Unfortunately, a lack of planning and the unwillingness to delegate decision-making led to my work drying up. The company spent over a month promising there would be more tasks right around the corner. Eventually, I gave up and went away.

I was back looking for work, but this time the world economy was reeling from pandemic-related issues, and progress was slow going. I started inching my way toward freelancing while also keeping an eye out for contract work. After about a year, I was writing more and finding my footing, but financially I wasn’t getting anywhere. A friend of mine from the pivoted company suggested I work with her. It was part-time work I could do whenever I liked. The task wasn’t terribly taxing on my brain, but that left me free to create, with a safety net that wouldn’t take over my whole life. It felt like I’d come home. The first day I dropped into Slack to introduce myself, three people I knew said hi and welcomed me back into the fold. Once again, I thought I had the ideal situation. A month in, the company suddenly shut down. After almost a year of searching and applying, I’d finally found something, and it was over before I’d even been paid.

Maybe it’s me?

It has taken long enough, but I’ve learned what I believe is a valuable lesson. There is no such thing as a sure thing, so why take points off for lack of job security when choosing a path. After talking with my very understanding husband about the relatively long ramp-up time to having real success as a freelance writer, we agreed I should push forward in earnest. I will still check out other opportunities and pursue truly awesome-looking ones, but I plan to work toward a solid existence as a writer. Once in a while, you need to go down a path, even if you have no idea where it will lead.

2 thoughts on “My Path to Freelance Writing

  1. I’ve always ping-ponged between freelance writing and getting a secure job too, and during these times, Jim Carrey’s words always come to mind: ‘You can fail at what you don’t want, so you might as well take a chance on doing what you love.’

    Hopefully you find your path. I too have a long ways to go to find mine. All the best, Lisa!

    Liked by 1 person

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