In 2013, I met a girl – we’ll call her Elizabeth. We initially connected on an online dating site, and after messaging back and forth, we decided to meet in the real world. Our first date consisted of us walking around the old port, chatting, and eating at a restaurant in Chinatown. She was a frequent traveller, one that would fly from city to city, and stay a few months in each location, exploring the world, all on her own. She spoke of crazy adventures overseas – tales of freedom, exploration, adrenaline. Meanwhile, my stories revolved largely around carefully typing things on a keyboard, quietly tweaking computer programs, websites, written works. As the night progressed, this contrast between worlds made it difficult for us to relate. Her stories were great – for example, one involved her racing down the side of a mountain on a bicycle, with lamas roaming around in the nearby slopes (if I remember correctly). In a way, she reminded me of what I had wanted to achieve when I was younger, but hadn’t – travel, exploration.
Overall, we didn’t really hit it off. To this day, I feel our different lifestyles had a lot to do with it. There were a few awkward moments throughout the night, but one was particularly amusing, and yet, completely accidental. We were walking downtown, and at a certain point, I asked her if she wanted to grab a bite to eat. She looked at me and said, with a laugh, “Where, McDonald’s?”, and pointed ahead of us. Sure enough, there stood a McDonald’s – a common “joke” restaurant for bad first dates. I didn’t realize there was one nearby, but the comedic timing of the moment was impeccable.
Anyway, as the end of the night neared, it was clear that we weren’t a good match – or at least, we weren’t at that point in time. We parted ways, and I left with a kind of weight on my shoulders. As I walked home, I found myself comparing my own achievements to hers, and after doing so, my spirits dropped. I was regretting that I hadn’t followed my aspirations, while I was younger. It was the type of moment where I questioned my own worth – I had a hard time accepting that my conquests, while hugely different, were conquests nonetheless. I was clearly in a self-conscious state of mind, which made me more doubtful than I should have been.
In the days that followed, I thought of Elizabeth and her conquests, every now and then. I remembered her mentioning, among many things, that she loved to walk, and would roam for hours whenever she arrived at a new city. I was inspired by this habit of hers, and eventually decided to try it out for myself in my very own home town – what if I was visiting Montreal for the first time? I took the metro downtown, and wandered the city streets, with no particular goal in mind, other than to explore. I discovered stores, enjoyed the green areas, and, eventually, I found myself at Mount Royal‘s lookout.
After a few days of doing this, I had an idea. I wanted to commit to the process of exploring the city, but in way that wasn’t at all casual. I wanted to push myself. Looking back, on a certain level, I can admit that I was looking to prove, to myself, that I had value, worth, and that even without accomplishing those youthful dreams, I was someone I could be proud of. This is how my first 30-day challenge was born.
Now, when I mention the idea of a 30-day challenge, you may immediately make the connection to Matt Cutts, one of the main guys at Google. Matt had previously done a TED talk specifically on 30-day challenges.
At the time, I wasn’t aware of Matt’s adventures, but it’s entirely possible that I saw the video before, and forgot, simply. But, whatever happened, I found myself craving the same thing Matt had recommended – trying something new for 30 days. I just… took it a little bit to an extreme. I ended up doing two somewhat complex 30-day challenges, back-to-back, with no break in between.
My first challenge was as follows: I had to reach the Mount Royal lookout every single day, and take a photo of the city from there. 30 consecutive days, with absolutely no tolerance for missing days. If I missed one, the challenge would be considered a failure and I’d have to restart. And, I also decided that I would need to accumulate 5km (3.1 miles) of walking while going to and from the metro and the lookout. This would allow me to explore Montreal, discovering new stores, art, the like. Furthermore, to challenge myself a little bit more, I decided I would also exit at semi-random metro stations, and would then navigate to the lookout without consulting any maps, or my phone… no directions. I had to rely on my memory of the streets, and, of course, Montreal’s not-so-challenging geography (when in doubt, head up the mountain).
I also had this really strong belief that it was a bad idea to tell people what I was working on before I was done, especially given that I was really enthusiastic about my initiative. I had multiple memories of moments where I shared my enthusiasm in the past, and was faced with pessimism in return, which sometimes took a lot away from my motivation. So, I didn’t tell anyone what I was up to until I was 25% through the challenge. I could have said nothing until the end, but I figured 25% was a good compromise. (Plus, I work as a social media guy, after all, I kinda like sharing what I’m up to.) And so on day 8 (26.67%) of my first challenge, I let my Facebook friends in on my little bit of madness.
Annnnnnd, 30 days later, I successfully finished. I completed the objectives every single day, regardless of the weather, regardless of how I felt – I just did it. The resulting photos were awesome – in my opinion, they showcased the natural beauty of Montreal, and offered an interesting perspective. I think this had a lot to do with me reproducing the same angle every day, and the fact that I wouldn’t always head out at the same time. The full set of 30 photos can be seen below.
My second 30-day challenge started immediately after the first. (In fact, on the last few days of the first, I finished testing out what I’d do for my second 30 day challenge – meaning I pretty much did two challenges per day for the last ~2 days.) As per my procedure, on day 8, I announced what I was doing on Facebook:
“30-day challenge #2 is one where I have to bike at least 20km a day for 30 consecutive days. As part of my rules, I have to complete one lap of the Gilles Villeneuve circuit every day (Parc Jean Drapeau) – but after that’s done, I’m free to do my usual exploration. Oh, and like last time, I have to take at least one photo per day, and make it available online. However, these photos can be of anything, not just the Montreal skyline.”
It was a different adventure, but, like the first, I also completed it successfully. Here are the photos I took:
Unlike my first challenge, I also wrote a title and description along with each photo. To see these, and to see higher resolution copies of the pictures, I recommend viewing the album on Flickr. When I completed this second challenge, I took to Facebook with this message:
“I’m happy to announce that I’ve successfully completed my second 30-day challenge. As part of it, I biked 20km (12.4 miles) a day for 30 consecutive days (that’s 600km, or 372.8 miles!). (In fact, due to spare kilometres every now and then, the total distance travelled is beyond 700km/434 miles.) The result? I’m pretty damn happy, but also really looking forward to resting.”
As the post suggests, by that time, I had realized that I was a bit nuts for doing 60 consecutive days of exercise, without allowing my body to take a day off (particularly in the second 30 day challenge). That’s why my third 30 day challenge started a few days after, and get this… it had no mandatory fitness component. Its main focus was on me purging my apartment of useless belongings, donating as much as possible, and trashing where there was no other solution. It was a psychologically sound idea, but, due to a lack of a fitness component, I quickly found myself getting bored of it. It wasn’t long until I abandoned the idea altogether. I did take three photos during that time, however, and only one was particularly noteworthy:
So, after 60 consecutive days of fitness challenges, I finally allowed myself to rest. There were days where I hadn’t felt particularly well, but I still pushed forward and continued my obsessive pursuit, in an almost machine-like fashion. Looking back, the challenges were amazing experiences – they kept me physically fit, and allowed me to accumulate a beautiful collection of photos to share afterwards. And, they reminded me that I did, indeed, have value – something I had lost sight of after that night, with Elizabeth. Of course, had I thought more clearly that night, I would have known my value, without embarking on a crazy 60 day journey… but then again, where’s the fun in that?