Against All Odds

Why We Fall in Love with Underdogs, And How to Become One

11 min readMar 30, 2024

Seems a bit backwards, no? In a world where the riches often seem reserved for the rich, it is the underdogs who we often latch onto as a beacon of hope.

These underdogs exist everywhere around us, from the silver screen to the sports arena. In movies like Rocky, The Pursuit of Happyness, and age old tales of David vs Goliath, we can’t help but root for the struggling protagonist who found the determination deep within them to overcome roadblock after roadblock that stood in their way.

In TV shows like The Office, The Queen’s Gambit, and Stranger Things, it is this journey of how characters like Michael Scott, Beth Harmon, and the kids from Stranger Things evolved over the seasons that captivate us. Their journey of growth through repeated failures is what makes us connect with these characters so much, despite the fictionality of it.

In sports, movies like Moneyball or Rocky, and real-life events March Madness upsets and crazy comebacks from players and teams attaches us to these stories of resilience and triumph against the unlikeliest of odds.

Even in day-to-day life, hearing the inspiring stories of how some of the most successful people on Earth went from childhoods of poverty to lives of prosperity makes us feel happy for their success.

But what is it specifically about these underdog stories that resonates with us so deeply? And how can we learn to embrace this mindset to transform our own lives?

The Schadenfreude Within Us

Schadenfreude — pleasure derived from another person’s misfortune.

Our affinity for underdogs traces back to our innate human desire for justice to prevail. We connect with these stories because of how much others struggled along the journey to get to where they are. Witnessing events like these can ignite a spark within us, reaffirming the incredible power of the human spirit.

In a weird way, we have greater admiration for underdogs the more they have suffered. The greater the delta is between where they used to be and where they reached, the greater the hill was to climb, the more incredible it makes their achievements.

Even if they don’t reach their end goal, the hope they offer in the face of adversity is what we often remember. For example, in the NBA, big 4th quarter comeback stories can be remembered for quite a while. But what sort of comeback might one remember for longer; one where the better team was losing all game and then finally came back in the last 5 mins , or one where the weaker team was getting destroyed and then came back?

The more unlikely the odds to success, the more we want attach ourselves to that journey of others.

Another example is in a college men’s basketball game between Alabama and Minnesota. All of Alabama’s bench players got kicked out for running on the court during a scuffle, and then 2 of their 5 players on the court got either fouled out or injured. So basically, it was 3 Alabama players against 5 Minnesota players on the court, plus Minnesota had a fully fresh bench unit to sub in whenever they wanted.

Alabama was already the underdog before the game started and was down 15 points with just over 6 minutes left in the game. But in an almost impossible way, Alabama cut that deficit down to only 3 points within 5 minutes. Though they weren’t able to make the full comeback and ended up losing by 5 points in the end, this story is known for the never-say-die attitude that was shown by these 3 Alabama legends.

In no sensible way should that game have even gotten close with it being 3-on-5. Everyone was talking about the failed comeback instead of the win by Minnesota after the game. It goes to show how sometimes even the final result is not what people care as much as the journey that was taken.

If you climb 80% of the way up a hill that no one has dared to climb before, it will be a story that people remember for a long time. There have been many times where teams came back from done 15+ points in the last few minutes, but this story is still so much more well known because of the odds stacked against them.

For the last 10+ minutes of the game, Alabama was in a 3-on-5 deficit and still outscored Minnesota

In a separate way, we also tend to root for underdogs by the default of not wanting the same result as usual. Whether it’s a sports team that continues to dominate the league, a TV show or movie that keeps winning every single award, or a person who just can’t seem to make a wrong choice, it is the added pleasured of unexpected success which we end up cheering for.

When we knew from the start that the Golden State Warriors dynasty was going to win another championship, it didn’t make the journey of the season very remarkable. When we know that Goliath is supposed to beat David, him meeting those expectations doesn’t surprise us. But it’s when a major upset occurs, when the people at the top are knocked down from their throne, when David beats Goliath, that the lack of predictability makes us stand strong behind these loveable champions.

My Under-dawg Philosophy

It’s easy for us to jump on the bandwagon of the next great underdog we see in the world. After all, we’re not the ones facing the mental pains, the sleepless nights, and the self-doubt that creeps into their minds all the time. But when it comes to being the underdog in our own lives, we can often be quick to jump right off the wagon.

In my life, I’ve often used the underdog within me to propel myself forward. Sure, I was more gifted in areas like math and hand-eye coordination, but in my mind, I always looked ahead at the people who were further ahead of me that I could chase. In sports, math competitions, school, or outside clubs, I used my perspective as an underdog compared to those with more skill than me as a way to accelerate my growth.

Having an underdog mindset allows you to worry less about who’s on your tail and focus on the road ahead of you. If we live too much in fear about falling behind, instead of in optimism of getting ahead, it can paralyze us. And since underdogs are never expected to achieve greatness, they’re better able to focus on the process of evolving and improving as opposed to the materialistic goal of winning a competition or winning the battle for a position. Since expectations and priorities aren’t put on us, we create our own versions of them that align us to our own goals.

Whenever I’m in the heat of battle in sports and facing an opponent who I know is stronger, I crave the doubt that people put on me. The more they dismiss my abilities, the more shocked they are when I make the upset. I have the unwavering confidence in my own abilities to dig deep and be successful in whatever I focus my mind on.

A determined underdog will always go above and beyond expectations of others, constantly questioning how they can improve. First place winners often assume that everything went right, but as an underdog, always assuming that you’re underrated keeps you questioning what went wrong so that you can fix it next time.

As a life-long athlete, I’m most present in life when I’m playing a sport against someone slightly better than me. Competition lights a spark up my ass that very few other things can recreate.

Whether it’s playing against sports against national level opponents, competing in science/business competitions against other schools, or just some friendly competition with friends, being an underdog is a lifestyle that energizes me.

In a weird way, it’s this balance between being the hunter and the hunted. An underdog’s greatest fear is to become the top dog, because for them, it seems like there’s nowhere higher to go. This happened to me before when my team won the provincial baseball championships (there were no nationals at the time) and when I made the A-team for the University of Waterloo in table tennis.

I felt like I had reached the ambitious goals I set for myself so much faster than I imagined, and since my mind was often focused on these finite achievements, once I reached them, I lost the motivation to keep going.

Embracing your Inner Underdog

In no sense of the word was Michael Jordan viewed as anything less than an all-time great player during the peak of his career. He had it all; scoring, defence, awards, championships, everything.

But as The Last Dance documentary revealed, in what has now become a meme across the internet, he was notorious for taking any narrative against him personally. Any article he saw, question he got, or remark he heard where people doubted his abilities was another part of the fuel to his fire that made him so great.

If used in the right way, having the mindset of an underdog, even when you might be at the top of your field, can unlock a part of you that you didn’t know you had. To build this underdog’s mindset, here are 3 key pillars:

1. Fail Early, Fail Often

To be a successful underdog, you have to take what you can control to the absolute max to be best prepared for any situation. Mistakes are what make you better, so the earlier and more often you make them, the greater the service you’re providing to future you.

Society wants you to be flawless. While true flawlessness is like an asymptote that can never be reached, we can get closer and closer to that line by exposing our flaws and then working to correct them.

I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed. — Michael Jordan

2. Play infinite games

If your success is determined by reaching a certain achievement, like a certain ranking in a sport, a job title in your career, a monetary value in your business, or a follower/subscriber count on social media, you’re playing a finite game. It’s a reason why so many athletes who win gold medals at the Olympics or social media stars quit while they’re on top.

The climb to where they got was so focused on the destination instead of the journey. All they had in mind was the end number, so all the practice and training to get there was not something they enjoyed for the sake of practicing and training.

If we strive for goals just for the sake of those goals or to prove others wrong, soon after achieving them we will no longer want to keep striving. 99% of the time is spent training, while 1% of the time is spent celebrating our achievements, so why not optimize for where the majority of our time is being spent? The results will inevitable come if we enjoy the process.

Playing infinite games means focusing on sustainable goals that are never fully “achieved” in the traditional sense. It means focusing on how to enjoy and accelerate the journey of growth instead of the destination to which that growth will lead you.

The world currently optimizes for finite games. Yes or no. Win or lose. This mindset makes us focus on short-term transactions that often aren’t in the best interest of our long-term success.

Also, most people optimize for the rewards on their current path. Many students I’ve met at university are studying STEM because of the money they’ll earn later or the cushy perks of being in a big tech company, not because they actually like the work they spent 8 hours per day doing.

This infinite game mindset reframes how we choose to spend our time. Instead of optimizing for rewards, it helps us optimizes for pain. What work can we bear the pain of to be great? In what areas do we not mind spending the majority of our time to reach our long-term goals, despite the many ups and downs that come with it?

These are questions to ask yourself if you want to play the infinite game; where the only goal is to just keep playing.

3. Know Your Surroundings

To be prepared against surprise is to be trained. To be prepared for surprise is to be educated. — James Carse

In finite games, you train for the rules so that you can bend them in your favour. In infinite games, you focus on developing the education to adapt to new situations.

Focusing too much on yourself makes you lose perspective of the greater landscape. If you lose awareness of what’s going on around you, adjusting and repositioning yourself based on changes in the world will be so much more difficult.

Always understanding the bigger picture and remaining humble along the journey will help you be grounded in your decisions. You’ll never have all the answers, so being a life-long learner is the best way to prepare yourself to dive into the unknown. Underdogs are better at this than anyone!

A Fair Warning

Living like an underdog is not for the faint of heart. It requires unwavering dedication and perseverance amidst doubt, uncertainty, and failures.

Nobody likes to lose, but as an underdog, you don’t fear losing. You know that people are rallying behind your hopes and dreams, and that is one of the biggest advantages you can ask for.

But just as quickly as someone might start cheering for you, they can suddenly turn their back on you too. When the underdog becomes the top dog in the minds of others, their incredible story loses its magic.

People love to see others sacrifice and try, but not for them to succeed more than them. For most, life is a game of competition and status in society of who can toot their own horn the loudest. But the underdogs of the world are the trailblazers who throw their horns to the curb and let their actions do the talking.

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