At the age of 35, I successfully retired from reality. For 15 years I was a slave the early morning alarm clock shattering dream state sleep, cold showers to get out the cobwebs, mindless commutes to an office. Monday to Friday, 9 to 5. Taking work home evenings and weekends. Falling asleep while reading memos and reports.

The middle manager, white-collar life.

I needed a break. At least a temporary reprieve from insanity. It wasn’t as if work was a nightmare. It was just so bloody, mind-numbingly… dull&ordinary. A long dark tunnel with no light at the end. More of the same — alarm clock, shower, commute — every day every day every day until I retired. Or died.

Retired. Or died. That thought woke me up.

If I wanted a break free from my job as a continuing education program manager at a community college, I’d have to make my own break… Rather than dream, I started to scheme. If teachers at community colleges could take sabbaticals, what about middle managers? I checked the employment policies. No sabbaticals for chumps like me. But what was this? A pre-paid leave? If I wanted to fulfill my dream, even though I didn’t quite know what my dream was, I’d have to pay for it myself.

For two years, I pumped money into a savings account so that I could afford my one-year reprieve, or pre-paid leave of absence as it was technically called.

I wasn’t sure what I was going to do with my time off, but the possibilities seemed endless. I could write. Travel. Learn how to play the guitar, finally. Sleep in. But not too late. Didn’t want to dream away my entire year. I only knew that I was not going to work. At least not the way I had been working for the last 15 years.

I could not have predicted, would never have predicted, that I’d never return, no I’d never return, to my job. But I could not go back, not after a one-year leave during which time I traveled the eastern seaboard of the United States and western Canada, wrote short stories and poetry, took art courses and creative writing and freelance writing workshops. But never did learn how to play the guitar. (Darn!)

Instead of returning to reality after a full year off, I launched a freelance writing career. That was 15 years ago. I have since written hundreds (thousands?) of articles about small businesses, technology, electronic commerce, the arts, beer marketing, new home buying, dog walking and many other topics. I have written case studies, web copy, media releases and brochure copy for countless businesses. I have conducted business writing workshops for corporate and non-profit clients. And I have conducted how to write and business of writing workshops for my peers. And I have even taught online webinars. And. And. And.

And I now consider myself successfully retired from reality. However, success, as I define it, did not come over night. Initially, pay cheques were few and far between — at least for the first couple of years. My first paid freelance writing gig was with a community newspaper. I pitched an article idea by mail. (Yes, snail mail; it was that long ago.) The editor called and accepted the idea. We negotiated the angle, word count and due date. Then I asked about… Payment.

“We’re a community newspaper, we don’t pay!” In need of bylines so I could tackle larger markets, I agreed to write the article. However, I had to travel by public transit to cover an event and asked for streetcar fare. The editor reluctantly agreed to pay my transit expenses. I filed the article and invoiced the paper for four dollars. The editor, no doubt feeling somewhat sheepish, sent me a cheque for … $10.

It was my first freelance cheque. I would have taped it to my computer so I could stare at it in awe each day, but I needed the money. So I cashed it.

After two years of freelancing, I found myself earning a decent living. No more writing for transit fare. I spent far less time marketing my article ideas and writing services and far more time writing. However, my Protestant work ethic told me I was having way too much fun going for walks in the middle of the day, working late when I felt like it and sleeping in on weekdays when I didn’t have early morning interviews scheduled or pressing deadlines to meet.

So I abandoned the freelance life and took a full time job as editor of a computer magazine.

Best thing I ever did.

You see, after going into the office from 9 to 5 (more like 8:00 am to 8:00 pm) for a month, I was convinced that I had made one freaking huge muther of a mistake. Fortunately, it was not fatal. I handed in my two-weeks notice and soon returned to freelancing.

I think I needed a final taste of prison, um, full-time employment, to realize that I really wanted to run my own business. I have not once regretted my decision to return to the freelance fold. In fact, I have sworn an oath that I will never, ever take a straight job again — not even a contract position that involves working away from home for someone else.

As I said, maybe I needed a final taste of life as a drone to convince me that I’d much rather run my own business, on my terms — even if it means giving up the security of a steady pay cheque. And the fact is, I am now doing well enough financially, thank you. In addition, I have interviewed scores of fascinating people and have work that I enjoy immensely. And I still have time on my hands. It’s as if I’m on a permanent leave from reality.

Who knows? Maybe one day I will actually learn how to play the guitar.