I am the underdog.

The only business I ever owned cost me about $15 to start; it made no money, and shut down within a week. Its brevity was all part of the plan, but the business still was not the success that I’d hoped it would be.

The year I turned 16, I was to spend the whole summer at camp—starting with a leadership program, and finishing with regular teen camp. I was very excited because I loved camp and because I assumed I was going to get a girlfriend. To guarantee the latter, I took the precautionary measures of hitting the gym and taking an extremely strong acne medication over the winter and spring. By the time summer arrived, my body was definitely ready to reel in the babes.

Unfortunately, because I focused all of my energy on preparing my exterior, I completely neglected my interior—most notably, my low self-confidence. I guess I assumed that when I did the work to get my body to a certain level, my confidence and personality would follow suit, leaving girls no option but to throw themselves at me.

Unsurprisingly, the babes did not come. Without so much as a nibble, I was forced to realize that ‘camp girls’ were no different than ‘high school girls’, which meant they needed me to show a remote interest in them before they could regard me as a potential suitor. Showing interest was far too risky of a proposition, and I was devastated when I figured out that I had missed my chance with every girl in the leadership program.

After mourning this loss, I began to see the light. Teen’s camp, which was at the end of the summer, would bring new girls that hadn’t had the chance to reject me yet. From that moment on, I put all of my energy towards figuring out how I was going to get a girl interested.

The best idea I could come up with was to promote my inadequacies.

Since my first approach of trying to attract women to me by highlighting my strengths didn’t work, I figured highlighting all of my shortcomings made the most sense. Instead of motivation through raw sex appeal, I thought pity might throw a make-out sesh my way. Whatever I was to do, I was aware enough to know my message of self-hatred had to be laced in irony, because it was the closest thing to sincerity that would allow me to get my point across. You can’t go around plainly admitting you’re pathetic; people can’t handle that kind of directness. So irony helped me say, “I’m serious, but I’m not really serious, but I’m totally, painfully, pathetically serious… heh heh heh. Please love me in spite of myself.”

I felt my best course of action to bring attention my shortcomings would be some kind of explicit advertisement (lest my message get lost). The day before teen’s camp I went into town and bought four undershirts and a permanent marker and that’s when my clothing line, known as ‘self pity’, was created.

The first t-shirt I made was the ‘self pity’ logo, which was smiley face that was frowning instead, with hair covering his eyes. Then below “self pity” was written in lowercase letters (obviously). This shirt laid the groundwork for the rest of my brand messaging: I’m an insecure guy who only recently realized he had even less going for him than he initially realized. The second shirt said, “He’s hot. I’m not.” The third was “I didn’t know I was the ugly brother.”[i] These two shirts expressed a liberating realization I had partway through my summer, which was that I might be uglier than other people. Since I had never been sexually attracted to a man and never really considered male beauty up until that point, I’d always been confused why certain guys were getting girls over me. One day it clicked, “Ohhh! I’m not as good looking as the other guys.” It had honestly never occurred to me.

The final shirt was a diagram of a stick figure labeled “him” with his arms around stick figures labelled “babes”, and then a stick figure labelled “me” and a stick dog, labelled “dog relieving himself”, peeing on me. No dog had actually peed on me; it was more of a philosophical representation of how I saw things at that point.

I debuted the shirts on the first day of teen’s camp and they were an immediate hit. People thought they were funny and girls even talked to me about them. I thought I was a genius until I realized girls weren’t talking to me in the way I’d hoped. I got a lot of comments like, “Those are funny”, “You’re not that ugly”, and “Can I meet your brother?” No girls threw themselves at me. There were no pity make-out sessions. The closest I actually got to anything was sneaking out on the final night and falling asleep in the same room my friend was simultaneously using to make-out with someone.

The problem with the shirts was that I couldn’t gauge what part of them the girls were responding to. Did they think the shirts were funny or true? I couldn’t ask because it would have either ruined the effect of the humour or it would have hurt my feelings.

In hindsight, I think I may have had opportunities with some girls but that would have meant making the first move, which was never going to happen.[ii] Ironically my brother, who’d been working at home all summer, met a girl at teen’s camp that he has now been with for over 15 years. What a dick.[iii]

This story has been a long case study to demonstrate my self-worth issues, which still plague me today. Whether it’s related to work ethic, appearance, charm, whatever, it takes a lot for me to convince myself I’m not human garbage, and even more to acknowledge my strengths.

In situations where I’m up against someone or something, my go-to assumption is my opposition has the upper hand. In my head, all of the scenarios where I attain greatness contain a near-miraculous element where God smiles upon me and everything works out in my favour. If it were left to do with skill, ability, or quality alone, my mind decides I stand no chance.

I write all of this to give some understanding as to why I have such an affinity for the underdog. I not only love the underdog, but I feel like it’s a part of my identity. It needs to be, because it’s what gives me hope that not all outcomes are fated—otherwise there would be no point in trying. History, mythology, religion and Disney sports movies tell me the weak sometimes win. Sometimes.

And every time the underdog does win, it only gives me more hope that it could be me one day.

In that spirit, I’ve decided to blog about an underdog every week. Underdogs will vary from person to place to object.

I want to explore different types of underdogs, the degree to which someone is an underdog, how it is possible to lose underdog status, and whether there are underdogs not worth cheering for. Sometimes, I’ll flesh out why the subject is an underdog, other times I’ll just write about them. I might write about a theme some weeks instead, but I doubt it because that would take more work.

[i] The second and third t-shirts were in reference to my older brother. I used to wonder why he always had a girlfriend and I didn’t. It never crossed my mind that he was any better looking than me, much less way better looking. Partway through the summer my brother visited me at camp and upon his arrival a bunch of girls told me, unprovoked, that he was really attractive. And, unless I’d missed it, those same girls never directly commented on my beauty (they did however tell me over and over again how different he and I looked). Eventually, I was forced to conclude that my brother was better looking. Ten years later, I was forced to conclude he is also more likeable.

[ii] Devastatingly, I would find out a year later that the girl at teens camp I had been most interested in had also been interested in me only I never saw it at the time. The catch-22 of the self pity lifestyle is that I hadn’t built in the ability to extricate myself from the “performance” long enough to see if it was yielding any promising results. I was so immersed that I genuinely lost the ability to see myself as a person someone may in fact be attracted to. The fly in the ointment – one of the many flaws of the self-pity approach.

[iii] It took me 13 years after the fact to realize therapy would be extremely helpful.