The Daily Freelancer: April 14, 2020 — Origin Story

Hi folks! I’m starting up a blog series here called “The Daily Freelancer” (Ok, it might not be daily, but let’s see) to give you an intimate glimpse into my venture into freelance writing: how I got here, what my day is like, how the heck I’m figuring this thing out (and paying rent), and more. Hopefully it’ll help those who want to journey along with me, and I’ll take any advice from those who have gone before!

Goodbye, 9-5

I’m into my seventh month doing this part time, and about to be kicked into doing it full time when my day job term appointment ends in two weeks. Oooo, here we go! September 20 was my last day as a full 9-5 employee before I took the leap. I fortunately was able to switch quickly into a part time position that’s still fully benefited, which is such a boon. But that part time job ends for the summer (fortunately the benefits keep going), but that means my initial leap off the cliff and learning how to fly is going to really turn into learning how to fly! But how did I get here in the first place?

Three Words: Grand Jury Duty

I’ve always courted the idea of freelancing. As a writer, that seemed the ultimate goal, right? To do this independently, full time. I had been doing some writing, mostly website content management, in my day jobs, and in my personal life I’ve been writing fiction and essays and all that for twenty years. I’ve also been running the Boston Book Blog since 2012. But with the tasks I really loved getting gutted from my full time job, and with a two hour commute each day in addition to working 40 hours a week, I had little time for writing, and was squeezing my creative endeavors into the margins. And I wasn’t happy. But financially, I had no way out. I had to keep my full time job to survive.

Then I got an envelope: Grand Jury Duty. Not a trial, not a few days or a week. Four months, three days a week. For those four months, three days a week I was required to go to the courthouse and sit, whether there was testimony or not (for real).

I was essentially forced into a sabbatical from work.

And while overall it was a shitty experience that I would wish on no one, it allowed for a few things:

  • I didn’t have to go to work three days a week (they hired someone to backfill for me, so I was free).

  • I didn’t have to commute the hour to and the hour from work, since the courthouse is a 15 minute walk from my apartment.

  • I didn’t have to get dressed for work (business casual/formal), and could wear jeans and a t-shirt everyday.

  • Since there was SO MUCH downtime, I could read during jury duty, or play or research on my phone.

  • They let us out by 2pm every day. A few days we stayed later, most days we got out earlier. More free time.

  • Because I was so close to the courthouse, I could enjoy my time during the day in my neighborhood, instead of getting back to my neighborhood at 6pm each night. (I mean, I moved here to enjoy being here!)

I suddenly had all this free time to myself - I didn’t have to work my day job from home, so I was resting and doing more writing. And I started researching what being a true freelance writer would look like.

What I Discovered

I don’t want to be all sales letter-y and go, “What I discovered shocked me!” But that’s what happened. I discovered that there were freelance writers out there doing what I’ve done for years, making a lot more money than I ever made as a salaried employee - including in the manager job I was in at the time, which I thought was such hot stuff. I found freelance writers doing tutorials on how to write blog posts and craft brand voice and I could’ve done those tutorials. What I discovered was that writers can be paid for value. I apparently possessed a bunch of skills and talents that freelancers were getting well-paid for.

Suddenly I thought, well maybe I can do this. But I wasn’t going to embark on it. I just knew my next step was to transition into a marketing and communications role at my current company.

And I found the perfect job for me! A content writing job, one tier up, utilizing all the skills I have, and I would come to it with a deep knowledge of the company’s culture and a network already. Perfect.

Three More Words: Reorg and Restructure

It was good that job opened up to apply to, because when I returned to full time, I was met with a team reorganization — i.e., new bosses — and a job restructuring — i.e., I thought my role was gutted before! Long story short to cut down on time and because I probably can’t talk about what happened, I had three options: I could either stay and be miserable, or it was “advised that I leave,” or hope the marketing job came through.

Well, the marketing job did not come through, so I jumped ship to the part time position and left the full time world, with no clue how it was going to work out.

Suddenly, I needed to make the freelance thing happen. I actually didn’t have the income to jump ship; the part time job was my salary cut in two, with a $10/hr pay cut. I was leaping off a cliff, and needed to learn how to fly on the way down….

….and here we are. More tomorrow!