How We Made the Decision to Pursue a Freelance Writing Career

No more half measures

Mike Ehrmantraut, Breaking Bad  Bob Recotta

Like most good ideas, the notion that I should try freelance writing came from my wife.

From day one of my unemployment, I took my job search very seriously. I was up by six, showered by seven, writing cover letters by eight, pants on by 11:30.

Pants - the enemy of all freelance writers.
So we meet again, my old adversary. Photo by MNZ.

Ann watched, quietly supportive, letting me do my own thing.

With every cover letter I wrote and every email I sent, in the back of my mind was the idea that each one was stained with the Scarlet F. I wasn’t sure if I’d find an employer that would take a chance on a fifty-something who had recently been fired. I was sure that I was competing against people younger, more qualified and with a better employment record and references.

And better general hygiene. And pants.

I felt myself starting to slide into the Slough of Despond. Before spiraling all the way into self-indulgent hopelessness, I shared my concern with Ann. During that conversation I said, more out of self-derision than any attempt to advance a viable idea, that my best course of action was to work for myself.

With not a scrap of irony, skepticism or doubt, with nothing but love and support in her voice, she said “I agree.” In that moment, everything changed. I just got permission from the most important person in the world to take a huge chance with our future.

I want to make one thing clear. Ann would say I didn’t need her permission, but we are equal partners. In my mind, of course I needed her blessing. I needed to know it was okay to roll the dice on my talent and passion. Even more than that, I needed to know that, at 57, recently fired and utterly rudderless, she still believed in me.

You know, like that Kenny Rogers song. The one where he’s a lounge singer or something and he comes home after playing the Hyatt Regency down by the airport and he sits down and picks out a clumsy song on his old guitar and thinks about his wife.

Islands in the Stream. Exactly. 

Kenny Rogers was not a freelance writer, nor was he Canadian. He might have been neuro divergent. I'll check on that.
This is the first image that came up when I searched for “Kenny Rogers” on the free stock photo site I used. I can see why. Photo by Paige Thompson

***

I don’t know if it’s part of my ADHD, part of my personality, or just human nature, but when there’s uncertainty involved in a decision, my instinct is to hedge. This is no different.

Actually, that’s not entirely true. I would love to completely abandon my job search and charge full steam ahead into creating a freelance writing business, but two things prevent me.

The first is the Pennsylvania Department of Labor. According to the regulations governing unemployment benefits in Pennsylvania, someone receiving unemployment can’t take any actions to start a small business. Understandable.

That can be worked around.  The second reason, however, can’t be. We can’t afford it. I’d have to be ramped up to full time in three months. That sounds a little unrealistic.

So I find myself splitting my time between looking for a job and laying the groundwork for a freelancing career – feeling guilty when I do one and resentful when I do the other.

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