Dona-SI  promised Laurie, my editor, I wouldn’t joke about working in pyjamas when she suggested I write about being self-employed for this particular edition of Rearview. Yet, here I sit at a very odd hour of the night eating Italian wedding soup and contemplating whether I should don the plaid flannel onesies (right tartan) or the cream silk and lace lounging outfit to write this.

Well, in truth, I went to bed after the soup. I woke up still in the T-shirt and leggings I slept in last night because I wanted to get up early and finish editing the last leg of a client’s autobiography. I sent it off, and was able to corral a quickie appointment with my accommodating dentist to take care of a sore tooth without having to formally book a time based on a “real job” schedule.

Yes, I’ve been one of those self-employed folks for most of my adult working life, with perhaps 10 years total working at a full-time position in a conventional office. They were “good” jobs, with decent position titles, salaries and coworkers. I left them all, despite the medical and dental benefits and paid vacation, for various reasons: (a) working five days a week, same hours, for 50 weeks a year (two weeks vacation); (b) working in the same physical location daily (cubicles, “bull pens,” once even a converted broom closet); and (c) a mutually agreed opinion by both parties that I was just too “colourful” to fit in.

Fortunately, I have many of the characteristics recommended for self-employed people. I’m dedicated to my profession of writing, editing and teaching. I’m self-disciplined and hardworking. With the help of an intelligent accountant, I’m pretty good with the financial side of things. And not too shabby when it comes to looking for new work.

Percs? I’ve travelled — much of it on assignment. I’ve written articles and books on topics I probably never would have if I’d been in one job. And the fascinating people I’ve had the good fortune to meet — writing subjects, students who have turned into friends, and peers — many bon vivants, buccaneers and just darn interesting people who create their livings independently, just like I do. I’ve even made some pretty good money in my time.

Downsides? As the cliché goes, it truly is feast or famine. Sometimes there’s been so much work, I felt like I was going to explode, working memorable overnight, weekend and holiday shifts to meet deadlines. And during the down times, I felt occasionally it was time to go and get a regular job.

One strong piece of advice for prospective self-employed types: make sure you have a solid self-paid insurance plan for extra medical and dental requirements, as well as some type of disability program in case you are not able to work for a period of time because of injury or illness.

Perhaps what I’ve come to appreciate most about being self-employed is being able to move my “office” (the laptop) to work in any part of the house that takes my fancy. I’ve worked amongst the plants in my little glassed-in balcony, at the dining room table, standing at the kitchen counter, on the cozy couch, often in bed (between Netflix, of course), and any coffee shop or waiting room.

Do I recommend being self-employed over working at a real job for someone else? I would say definitely, if you’re committed and organized, like variety in a work environment, and certainly if you are, ahem, too colourful to fit in with a conventional company.

So now that I’ve finished this piece in the middle of a Friday afternoon, I can book off, change into those silk pyjamas, grab a glass of rosé and pay some serious attention to that spinach/ham frittata I’ve been meaning to cook all week. Tomorrow is Saturday, the start of a weekend when I have to edit 30,000 words for a client by Sunday night. Eek!