WHEN I LOOK over my life, I see failures. You’ve heard the sayings: “success consists of going from failure to failure without loss of enthusiasm” (Winston Churchill), “I have not failed. I’ve just found 10,000 ways that won’t work” (Thomas Edison), “we are all failures – at least the best of us are” (J.M. Barrie). The only alternative to failure is to not try, and once you’ve made that decision you’ve placed your chances of success in the realm of absolute certainty, at zero percent.

My teenage son skateboards. When the weather is decent he skates the city, and in Winter I take him to an indoor skate park. This Spring he’ll be going to Camp Woodward, a sprawling, multi-purpose facility in Woodward, PA that is skateboarder heaven.

I love that he skateboards for one reason above all the others: it’s the perfect life training in the discipline of failure. Everyone at the skate park is trying to figure out a trick, and most of them are failing at every attempt. I’ve spent days at the park watching people fall down, get up, fall down, get up, fall down, get up, hour after hour after hour. And they do it without shame, and without drama. It’s expected in skateboarding that you’ll fall over and over again, many dozens and hundreds of times, before you get it right it. And after you’ve got it right? You’ll fall down some more, of course.

Everything in life is exactly like that, but in most of life’s pursuits the guts of the thing are all hidden away from the casual observer. The concert pianist walks into the spotlight and performs. The audience will never see the thousands of hours he’s spent learning his scales and how to invert chords and transpose a Dorian passage into the Mixolydian modality. Even the baseball player who “fails” at 75% of his at-bats – a decent professional average – is showing you only the polished surface of his efforts. He’s had to struggle for his seventy-five percent failure rate. There was a time it was one hundred percent.

Sometimes failure leads you in a new direction. In my teens and twenties I sent my writing to newspapers and magazines. No one was interested in publishing my work, so I started my own print publication. To do this I had to learn every aspect of publishing, from editing and layout and design and marketing to how to get your publication into stores and libraries. I registered a publishing business and put together an editorial team and sent out a call for submissions. It was a great experience, and it only happened because I had failed at something I really wanted.

Who knows what would have happened had my work been accepted? I had dreams of moving to New York to write for the Times and the David Letterman show, but these didn’t happen. What did happen was that I learned a dozen useful and lucrative skills I wouldn’t have today had a newspaper shown interest in my work, skills I’ve been using ever since. In the ‘90s my work was being turned down by folks on the Internet, so I started my own website. I learned HTML and applied my design skills to the world wide web. (The Internet was primitive back then, and it didn’t require much by way of design.) Everything I was doing throughout these years supported my writing. Whether I was publishing in print or online, I was also working hard at being a better reader, writer and editor. Failure was fuelling my personal evolution, sending me off in new directions.

By the time I was thirty, I had run several publications and had worked on a number of interesting DIY projects. I’d met and collaborated with a lot of interesting people. Everything I had done had a failure of some kind at its root. I started out in life thinking I’d be a writer with a single publisher-employer, and my job would be to send things regularly to my publisher and get a pay cheque in return. That model simply does not exist for most writers, and in recent years even the prestigious papers like the New York Times have been shedding jobs and looking for new ways to remain viable as a business. The publishers are now facing their own failures, and they’re trying to adapt. I believe that one day a new and exciting model of journalism will be born, and for this we’ll be able to thank failure.

This website is the latest in a series of platforms I’ve adopted to further my writing. I do a lot of professional paid work that never appears on this site. And I still practice my scales, as it were. I change the title of my website from time to time, and right now it is “A Life Sentence,” because for me that’s what writing is: a life sentence, but also about life rather than making a living. There are several meanings to the word sentence, all of them relevant. I write sentences that express my perception and my judgements, all of which derive from the material of my life.

A few years ago I decided to give the newspapers another try. I sent samples of my writing to the national dailies. The answer was, again, “No thank-you.” A National Post editor told me some of my work might be publishable if it were re-written. By this time I was well into my 40s, not exactly a good time in life to be telling yourself “keep at it, and maybe one day ….” I’d been writing for thirty years, and even getting paid decent money to ghost write. But I still felt like a failure, because I couldn’t get anyone interested in something that had my name on it.

So, again, failure. But I kept writing, because that’s what I do. And I put my writing on this website, thinking that if only one in a million people cared for what I did, so be it. Within a few weeks of being turned down (again) by the papers, I got a lovely email from the writer and columnist Terry Glavin. He’d found my work and enjoyed it. I thanked him and bitched a little about how I was having no luck with the papers. After he’d read my email, he sent my work to another editor at the National Post, Kelly McParland. Kelly was (and is) my favourite Post columnist, and he must have liked my work, too, because a few days later I was writing for the National Post. See how easy it is? It only took thirty years of getting on that particular skateboard and falling off, and getting on again, before I pulled off the trick.

I’m not sure anymore what success is. For me, I think it’s a moving target. I get restless and I want something more, something bigger – a new challenge, a new vista. Now that I’m writing for the papers I have other goals in mind. (You know, for when I’m 80.) Things haven’t turned out the way I imagined and hoped they would, and I’m mostly better off for it. I’m not saying this to impose a rosy interpretation on my failures. I hate failing. There isn’t a single failure I’ve welcomed, wanted or enjoyed. If you have a weekly column gig that pays big dollars, I’ll take it. I’m happy to let someone else take the failure this time around.

Only it doesn’t work that way. You get the failures, like them or not. And the truth is I’d be less of a person, and less of a writer, had I not had them. My focus these days is on leveraging the experiences of many failures. As Churchill says, I go from failure to failure always expecting eventual success. I build up an audience for my work, one day at a time. I keep working on my skills. I keep my passion for writing alive. Success in this case means only one thing: to keep going, to keep working, to keep getting up when you tumble. And above all, to keep being willing to fail.