Motivation | Success

How a Penny Board Taught Me Failure and Success

July 27, 2017

The summer after my first year in university, I decided to buy a penny board – small, portable, and fast, I thought it was a great way I could get around the city. So I trekked to the store and ended up choosing an all-black board, brought it to the cashier, and got the trucks tightened and secure. At that point I was pretty sure I would be able to ride it down the hallway to the elevator, if not all the way to the metro. To my dismay, despite my previous “experience” skating on a classic skateboard a few years back, I wasn’t able to have any control or balance on the penny board – it was a more difficult feat than I had thought it would be. However, I was determined to become an expert, so I practiced every week by skating in my living room from one wall to the other, skating in the park, and eventually on an outdoor running trail amongst a crowd of runners. I fell often, and at one point even shed some skin off my knee and bled like there was no tomorrow, but I was able to get up (embarrassed because a whole family just watched me fail), run into the public bathroom, tie some toilet paper around my wound, and continue skating.

Mirror this story to an experience where you were determined to succeed but failed. Chances are, like me, you were probably extremely disappointed in yourself, and began having doubts about whether you would ever succeed again. Finding success in failure is only possible if you are radically honest with yourself, and extremely aware of your weaknesses and your strengths. Fail early, fail fast, and fail often, because what you learn during challenging times will most likely improve your chances of succeeding in the future, especially if you choose to learn even from something so minor and unimportant such as riding a penny board.

It is through several experiences, some major, and some vastly insignificant, that I was able to realize the power and importance of resiliency. Telling yourself you’re going to commit to something at the start, and then seeing a glimpse of failure (or what you believe could be failure) and not following through with the rest of your deal, is in fact the actual failure. I’ve had moments where I’ve felt like I’ve wedged myself in the in-between phase; where I feel as though I’m too far in, but also not far in enough to not simply give up on what I had started.

A year later, I sold my penny board. Though it wasn’t because I gave up – I was able to confidently ride the board around now. It was because I felt like I was expert enough, and succeeded enough at what I had set my mind on doing. At that point I knew skating wasn’t for me anymore. What was key was that I had accumulated a bunch of silly failures and united them into what I felt was success. That was the true success – failing to stick to my initial purpose of buying the board, which was to get around the city (practical), but then succeeding in leisurely riding the board around running trails and sidewalks and at the lake, and realizing the penny board as an emblem for tenacity.