Why James Chartrand Wears Women’s Underpants

You know me as James Chartrand of Men with Pens, a regular Copyblogger contributor for just shy of two years.

And yet, I’m a woman.

This is not a joke or an angle or an analogy — I’m literally a woman.

This is my story.

Once upon a time, I found myself having to make some hard decisions.

The welfare application was on my kitchen table. It was filled out and signed, waiting for me to bring it to the people who would decide whether I’d be able to make rent next month or put food on the table.

I hated looking at it. I didn’t want to be in this situation. I’d thought that when you start over, make a clean break, life was supposed to get better, right?

But here I was, out of money and out of choices.

I had two young daughters to take care of. I was single and alone, having left an unhealthy relationship, and I was living in a crappy, tiny apartment.

I’d used up my savings trying to make ends meet, supplementing as best I could with the money I earned from a dangerous part-time job that gave me all of 4 hours pay a week at minimum wage. I had been looking for a better job, but there were none to be had in the low-income/high-unemployment area where I lived.

And I couldn’t get a full-time job anyway — I was still on the waiting list for a spot in daycare.

How did I get here?

It was ironic. I’d once had a respectable, safe job in a corporate office. I’d had the nice salary, the paid vacations, the opportunity for advancement. I had formal education, diplomas, brains, and skills, and life had been good.

Now it wasn’t.

My older daughter told me she could look for work to help pay the bills.

She was 12.

As a last-ditch resort, I turned to the internet. There must be something I could do. There must be jobs out there . . . maybe in writing. I was a good writer.

And sure enough, there was writing work for me on the ‘net, work I could do from home that paid quickly. I signed up with the company, thinking I was so lucky to have this chance to pull myself out of the mess.

I...