The dichotomy of being conventional or unconventional is a strange one, especially in a North American culture. A capitalist society seems to encourage us to be ambitious and to be individuals, to strive for success and to be better than everyone around us. We stress individuality, perhaps more so in Canada (cultural mosaic) than in the United States (bubble on o’ melting pot), because that’s what separates multi-billionaires like Bill Gates from the average person who slaves away for ten bucks an hour. Bill Gates, Steve Jobs, Ted Turner, Rupert Murdoch… these guys, for better or for worse, are visionaries and set out to do things that other simply do not do.

On the other hand, there is also a prevailing wind in Canada and the United States that urges you to conform. To think, to act, to be like everyone else around you. This is probably best illustrated in the high school environment, where “in groups” and cliques are established very early on, and — for the most part — everyone wants to popular and no one wants to be shunned as an outcast. Even when you look at emo kids, goth kids, and other individuals with anti-establishment tendencies, it’s clear that some young people affiliate themselves with these groups in order to fit in, if only with other emo kids.

I wouldn’t say that I’ve been conventional all my life, but I wouldn’t say that I set out on a wholly novel path either. Like everything else in life, it’s not black or white, but rather varying shades of grey. Growing up, I was very good at math, understanding concepts early. This skill transfered reasonably well to the sciences as well, and while other people with this innate ability would naturally feel inclined to pursue a career in that kind of field, I didn’t. I remember talking to a classmate in high school, and when I told him that I was not going to apply for the Faculty of Science at the University of British Columbia, instead going for a Bachelor of Arts, he immediately asked, “Why?”

He seemed to have the notion that the Faculty of Arts was for people who couldn’t make it into the sciences. Moreover, he associated the Faculty of Arts with fine arts (music, painting, sculpture, acting, etc.). Clearly this is not the case. I eventually decided on a major in Psychology and a minor in English Literature, because that material actually interested me. I tried taking first year economics and I was bored out of my mind (although I still got very good marks in both economics and mathematics). Being practical didn’t really appeal to me.

The same can be said about what I’ve decided to do with my career post-graduation. I did reasonably well in Psychology, so again, a classmate asked me if I was going to pursue a Master’s Degree and eventually a PhD in the field. I eventually decided not to, because I couldn’t see myself doing that as a career. The expectation after graduation is to go find yourself a conventional 9-to-5 kind of job. I did, initially, but again, I found that it wasn’t really for me. I had experienced the 9-to-5 before during my co-op work terms, but the most enjoyable work terms were the ones where I was assigned a project and pretty much worked alone, when and where I wanted to. I did not like the structure imposed upon me at Enterprise Rent-A-Car as a management trainee. I wanted my own structure. I wanted my own freedoms.

I suppose it was that line of thought that led to my career in freelance writing. To my knowledge, among my high school graduating class, I am the only one that is a full-time entrepreneur, running his own business. A friend of mine, Jenn Best, runs her own photography business, specializing in weddings mostly, but it is a side project for her. She has a 9-to-5 job as her primary source of income. Everyone else is either still in school or has found themselves in a pretty conventional and conformist kind of job: accountants, HR recruiters, software developers, retail store managers, and the like.

There are many risks and rewards to doing things your own way. When I first started freelance writing full-time, my parents had their doubts. They did not see it as a long-term possibility for me, but rather as something for me to do until I found a “real job.” My dad, as far as I can tell, still expects me to go back to a “normal” line of work, because he says things like:

“It’s good that you have your car insured as pleasure only, because you save a couple hundred dollars a year. When you go back to a real job, you can always switch it back to regular work plus pleasure insurance.”

Notice that he said “when you go back”, not “if you go back”. He may not know this, but I have absolutely zero intention of ever going back to the 9-to-5 grind. That’s not one of my goals. There are sacrifices and risks that are made by being a freelance writer — unstable income, lack of immediate social contact with co-workers, the increased difficulty in “growing” your resume — but the advantages and rewards, for me, far outweigh the negatives.

If I were to pursue my writing career in a more conventional kind of way, particularly if I wanted to do something in journalism (I had a pretty heavy interest in doing that for quite some time), my life would be very different than how it is today. In all likelihood, if I were to do what most other aspiring journalists do, I would either be fetching coffee for a mid-range columnist or slaving away at a small town newspaper that no one cares about. Instead, I work from the comfort of my home, waking up more or less when I want to, working anywhere that has a broadband internet connection.

I’m glad that I didn’t do the normal thing. I’m glad that when I wake up in the morning, I don’t have to put on a suit and tie before I can go on my half-hour commute to the office. I’m glad that I don’t have to deal with corporate politics. All in all, I’m glad that I took the path least traveled by and that has made all the difference. (one million brownie points to the first person to get that reference.)

There’s nothing wrong with being conventional — I still put on my slacks one leg at a time like everyone else — but there is definitely something that can be said about doing things a slightly different way. It’s all about calculated risks.