Failing

I never learned to drive.

As I’ve gotten older I’ve thought off and on about this, about how I managed to skip such a typically formative step in life. Looking back I can’t claim I made a specific decision not to get my license. It really was a combination of avoidance, lack of need or desire, and circumstance that led me to never learn.

The lack of need was born of the fact that, living in a city, through a combination of cycling and public transit, it was easy enough to get around, and I had little desire to go further afield. My passions were in school, in front of the computer, or on the basketball court, and all those were close enough that driving wasn’t really necessary. And as I got older, I had a girlfriend and eventually wife who not only could drive, but loved it and was happy to do it.

As for circumstance, I grew up a latchkey kid. My mom, who I now realize was a bit insane, typically worked two or three jobs to ensure we had a roof over our head, food on the table, and to my astonishment in hindsight, a computer to keep her nerdy kids occupied. Simply getting time behind the wheel back then was not easy, and we certainly couldn’t afford to pay for lessons.

As for avoidance, looking back it’s now obvious that as early as my late teens I had some issues with anxiety. I think I was genuinely afraid to get behind the wheel, recognizing the risks and responsibilities that driving entails.

But let’s not forget the greatest anxiety of all: the fear of failure.

I didn’t realize it at the time, but that fear of failure often ruled my life well into my mid-twenties. I chose my education not only because it was something I was already interested in, but also because it was something I was already very good at. I chose my career for the same reason, and stayed there, doing the same basic things, for quite a while before I found the will to shift my career into something new. I even delayed proposing to my now wife because I was afraid I’d get it wrong.

But over time I gradually became more comfortable with the prospect of failure and, oddly enough, in part I think I have knitting to thank for it.

Knitting has a pretty darn steep initial learning curve. When you first pick up a pair of needles and grab that yarn, the whole thing just feels weird and awkward. How do I hold the needles? How do I hold the yarn that keeps slipping out of my fingers? Why can’t I pull that damn yarn through that damn loop?? It’s a lot!

My decision to learn to knit was entirely spur of the moment. One day Lenore and I were walking through a Michael’s and without thinking I blurted out something along the lines of “You know, I’ve always wondered how knitting works.” My wife, ever encouraging, replied “Why don’t you learn?” and the next thing you know I was walking out of the store with an instruction book (which I still have), a pair of needles, and a couple balls of yarn.

I’ve joked many times about that first weekend teaching myself from that book, the hours spent swearing and sweating as I wrestled with this beast I’d decided to slay. But it wasn’t long before I had completed my first long-tail cast-on, and then eventually my first row of knitted stitches, and from there emerged, after many more hours, that initial prototype project that everyone is familiar with: a dishcloth.

Now, the reality is, that dishcloth? It wasn’t a good dishcloth! The stitches were uneven. The edges were ragged. It was, as all first projects are, a bit of a mess. But I’d done it!

In that moment, that joy of accomplishment completely outweighed any frustration I’d been feeling, or any embarrassment about what I’d created. In fact, rather than embarrassed I felt the polar opposite: I couldn’t have been more proud of what I’d achieved, even if it was far from the best work I would end up doing.

And that’s when I re-learned something that, as a kid, we all know instinctively but somehow, in our teens and early adulthood, often forget: doing something for the first time, badly, isn’t just okay, it’s something to be celebrated. Succeeding, after all, is easy. But risking failure or embarrassment? Now that is hard.

In subsequent years I would take on all sorts of new and scary challenges. Whether it was backcountry hiking for the first time on the Skyline trail, or learning the basics of rock climbing¹, I rediscovered a joy in learning and challenging myself, and having done so, opened myself to experiences that I would have otherwise missed.

I particularly remember the experience of learning to ski for the first time in my early thirties.

One of the things I’ve come to realize as I’ve gotten older is the value of professional instruction, and so when I decided to learn to ski, I booked private lessons out at Rabbit Hill south of Edmonton.

When you first learn to ski they take you up a few different grades of hill, starting with a gentle starter slope that you often ascend on what amounts to a moving walkway with a continuous rubber surface. I remember first boarding that “lift”, surrounded by excited little four and five year olds, and I think about what people would’ve seen as my instructor and I trundled up the hill, those little kids lined up ahead and behind us.

Then, after managing to get off at the top of the hill without falling over, I pizza’d my way down as those same kids zipped around me.

It would be easy to feel embarrassed in that moment, but the enthusiasm and fearlessness of those kids was utterly infectious. I mean, I was doing it! Yeah, slowly and carefully, but wow, I was learning to ski!

Eventually we graduated to my first green run, and man, learning stem turns for the first time… just, so many falls. But every fall brought a smile to my face because I was simply having fun, out there in the sun and snow, doing something new and exciting. And every fall I learned something new, not the least of which was learning to laugh with myself, to recognize the joy and silliness that paradoxically exists in failure.

By the end of that first season I was skiing blue runs, and to a great degree that rapid advancement came because of my willingness to take controlled risks² and accepting, if not expecting, failure.

Looking back now, my only regret is not learning sooner. On the other hand, maybe I wasn’t ready then. Maybe I needed that experience sweating and swearing with needles and yarn before I could graduate to bigger challenges.

I started off my career as a software developer, working right in the center of my wheelhouse. The company I joined was a little pre-investment startup that would eventually be known as Invidi, but at the time was just a little operation funded and working out of the offices of a company called Interdynamix.

When I first joined Invidi, I had no idea what I was getting into. I mean, Interdynamix had, like, offices, and a conference room, and an office administrator. It seemed like a perfectly normal business.

It wasn’t until a little while later that I realized I’d hitched my wagon to a high-risk startup venture that, as with all startups, had a pretty low chance of success.

This was the first professional risk I took. Looking back I wish I’d better understood what I was doing, as I could’ve taken that risk with greater intention. But it was a risk nevertheless.

The next ten-ish years I worked more or less in my comfort zone, contributing to, and eventually leading, a number of projects over the years.

And then the big decision came: to move into Product Management.

Like learning to ski, the pivot into PLM was a potentially frightening and intimidating one. But, like skiing, I had a good instructor in Howard Fiderer, as well as colleagues who were patient and supportive through my many missteps in my new role.

But I was also finally in a place where I could accept that I would fail. Some of those failures would be small. Others much bigger. But, in diving into a very different kind of role, I knew that failure was inevitable, and that was okay.

That decision opened new professional doors for me, exposing me to new ways of thinking and new experiences that I would learn from and build on, eventually giving me the tools to take on bigger and more satisfying professional challenges.

And I don’t know that I would’ve taken that path had I not started to build a habit of taking risks and finding the joy in failure.

I’ve been thinking about learning to drive for a while now, and for a few reasons:

As we grow older and our family members do the same around us, being able to drive has become an increasingly important skill for me as husband, son, and caregiver. Being able to drive someone to an appointment or take someone to the hospital is a lot more relevant to me, now, than it used to be.
As I’ve gotten deeper into road cycling, I now look forward to being able to take myself out to rides without needing to ask Lenore to drop me off and pick me up.
My wife likes a drink now and then, and I’ll finally be able to act as the DD!
We’ve talked a lot about doing more road trips and visiting more of Canada and the US rather than going abroad, and I’d love to pitch in with that.

But in the past there’s always been a couple of barriers in the way.

First off is simply the issue of time. Learning to drive takes focus and effort. With a day job it’s tough to find hours to learn, and particularly hours that don’t put you in rush hour or weekend traffic. Plus, frankly, work is, like, work! Finding the mental fortitude to learn to drive–which is pretty darn stressful–is difficult when you have all the other tasks of daily living to contend with. So if I’m going to learn to drive, there is no better time than during this break.

And then, of course, there’s that anxiety.

Now, to be clear, I’m only mostly okay with not being a great driver. I do get a bit embarrassed when I rev the engine accidentally–I’m learning manual, which is a journey–or fail to shoulder check properly. But I consciously try give myself the grace to fail and try, instead, to turn that embarrassment into good humour. And as I’ve spent more time behind the wheel, that’s gotten easier and easier.

I mean, I’m learning. I’m supposed to suck!

But the bigger challenge is simply the risks inherent in driving. After all, driving is dangerous, and holy cow, as I’ve learned more about what to do, I’ve become even more aware of just how bad your average driver is³.

But I am learning, and every time I get behind the wheel I usually get a little bit better, and a little bit more comfortable.

Of course, just as with skiing, I’ve enlisted the help of a professional teacher who has been just wonderful. In fact, if you’re reading this and considering learning to drive, I don’t care what age you are: pay for lessons. Being a professional teacher is a skill itself, and mine has been exceptional. Not only is my instructor skilled at breaking down the act of driving into teachable steps, observant about what I’m doing well and what I need to improve, and knowledgable about what matters when I test for my license, above all else, he is calm and patient and kind. He understands that part of learning is failing (safely!)

And in experiencing his patience with me, I’m able to give myself a little more grace as I again remember that the hard part is trying, that the bravery is in failing and continuing, that grit and determination are what is most worth celebrating.

I’m not going to claim I’m now always and forever happy to face any challenge while gracefully accepting failure. If only that were the case! Heck, during our first few days in Mexico to see the 2024 total eclipse, I was utterly miserable (and a terrible travel companion) as I struggled with (among other things) my embarrassment about being unable to communicate.

In fact, as I start to consider steps for beginning my new job search, the greatest challenge I find myself facing is imposter syndrome and fear of failure⁴. Yup, a pretty successful twenty-five year career spanning a range of roles and I’m still afraid folks will discover I don’t actually know what the heck I’m doing.

But as I continue working toward my license while, in parallel, beginning the hunt for a new job, I will continually remind myself that odds are good it’s not going to come easy; that I will experience a great deal of failure before I eventually succeed; and that I should delight in those failures because they’re the proof that, no matter what phase of life you’re in, you can always challenge yourself to stretch and change and grow.

Though I never really got into climbing in earnest. For some reason, outside of a bit of bouldering, it never really sparked anything in me, and I do have a bit of height anxiety that’s tough to shake. ↩
“Controlled” is doing a lot of heavy lifting, here. I’m a very cautious skier, but I also know my body and, now, the sport well enough to judge when I’m in the comfort zone, riding at the edge of my ability, or exceeding it. ↩
I honestly think all drivers should have to take a re-licensing exam every ten years or so… ↩
Yeah, okay, and also a tendency toward a bit of procrastination, and a loud voice inside me that really wants this break to continue because, you know, as much as we need an income stream, not working is pretty darn nice. ↩