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Playing to win, not to not lose

My sons,

A good friend recently recommended I read The Pathless Path by Paul Millerd, a book that describes the author’s journey in finding meaning and fulfilling purpose in his life. In the book, Millerd lays out a concept that he calls the Default Path, a blueprint for life that outlines purpose, value, and success. It is a one size fits all path that we are all expected to adhere to. He asserts that for most people, the notion that a second path exists is almost entirely unbelievable.

The Default Path, Millerd argues, is the one that our upbringing, background, social, and economic systems work together to daily reinforce. It is the model for our lives that has been imprinted and reinforced in every interaction and every experience. It is so deeply engrained, so fundamentally expected that we never stop to ask if life must in fact be led this way. And when we eventually (and, arguably, inevitably) question the path at an inflection that many have taken to calling the midlife crisis, there is such an overwhelming amount of peer pressure and societal structure to overcome that we often end up concluding that rather than being an issue with the path there is instead something wrong with us.

For North Americans, that default path often resembles what’s globally known as “The American Dream” - the belief that anyone can achieve financial and social success through hard work and dedication to that work. Images of single family homes with white picket fences, a pair of cars, a pair of kids running around with a happy spouse, and financial independence - all attained through hard (and recently updated to include meaningful) work.

Everything in our upbringing reinforces that message so strongly that most of us never stop to consider if there is another path. Legendary economist John Maynard Keynes (aka “Our Hero, Lord Keynes” to anyone who has ever had the great privilege to have taken Larry Smith’s Econ classes at Waterloo) famously said that “worldly wisdom teaches us that it is better for reputation to fail conventionally than to succeed unconventionally”.

And so we play to not lose.

We play the game of life in a way that doesn’t seek to win, doesn’t seek to conquer new horizons and be filled with awe-inspiring experiences and journeys. No, we play in a manner filled with fear of losing, fear of failing. We fear missing out on what everyone else is doing, fear being left behind by the masses moving in the direction of the inevitable path.

We feel so strongly that not only is this the right path, but it is the only path. And so, on we go, putting all our energies and resources into working harder, making more money, having more social influence, and raising children who do the same.

We play this fear-driven and defensive game with the hope of not losing for so long that we inevitably wake up one day sometime in our 30s and 40s and wonder what it was all for. We have spent the entirety of our youth and the majority of our most productive years on a path that we didn’t even set for ourselves! No wonder we come to a moment of crisis. Coined in 1965 (coincidentally a short decade or two after the beginning and wide-adoption of the 9 to 5), the midlife crisis is a recognition that we have been passive players in the direction of our lives, and this terrifies us.

A rude awakening

We wake up one day realizing that we don’t have any earthly clue what our life’s purpose should be, and that our goals to this point were not in fact our own. Worse, we are thoroughly unequipped to set meaningful goals for ourselves and define what a rich and fruitful life looks like, so we revolt. We buy sports cars. We get plastic surgery and update our wardrobes. We do any number of nonsensical things in an attempt to silence that inner voice telling us that we’re playing this game wrong. What many of us never realize until much too late in life is that there is another way to play this game, another path that we can be on.

We can play to win.

We can learn to play the game differently. We can endeavor to gain much more clarity on the rules of the game, the terms of engagement, and, most importantly, the conditions for victory.

Most people spend the majority of their lives sitting in the passenger seat, having fully assumed the role of spectator in the unfolding narrative of their life and having fully accepted that the majority of decisions are made for them. We were never told that there is another way to play, another path to victory, and another role that we can assume.

Think back to the first big decision you made in your life; the one where you felt the true gravitas of the situation. For a fair amount of us, this was the act of deciding which college to apply for, and hopefully to attend upon acceptance. Think of how that decision was made, of the inputs, the factors taken into consideration. How small a role did one’s passions play in that significant decision? How much more did we consider things like future earning potential, prestige of the school, respectability of the profession, desires of our parents, or just plain ol’ common wisdom?

Discover yourself

From that early age we were taught to make decisions by someone else’s standards. Playing to win means that we need to throw out those standards and to come up with our own. We need to first discover ourselves, to do the hard work of uncovering the things that bring us joy, that excite us and ignite the passion within us.

We need to let go of the need for external validation, the compulsion to measure against what our peers are doing. We need to remove the mental pollutants in our lives - the likes, the retweets, the perpetual feed of an abundantly glamorized default path - and instead look within for validation, for meaning. We need to learn to trust our internal compass.

Own it

And then we need to own it. Once we’ve discovered what makes us tick, what things bring us joy, what types of people we desire to become, we need to unapologetically own it.

One of my great mentors told me once long ago that as a society we have become so focused on the next big thing - the next promotion, the next million users of our product, the next milestone in our children’s lives - that we forget to think about the people that we are becoming. We get so wrapped up in impressing someone else that we forget about what it does to our character, our morals, and our decision making framework. If left unchecked, we become like the environment we place ourselves in.

So we need to own it. We need to own how we show up at work, what we’re willing to do based on our boss’ orders or company expectations, and how we determine what a successful time in our place of employment looks like. We need to own what we work out with our children to actually be the best for them, and not what all their peers happen to be enrolled in. We need to own what traits in a partner make us happy, whole, healthy, and growing human beings, regardless of their social standing or their pedigree.

Playing to win means playing by your own standards, and not conforming to the expectations of the world. It means being okay with walking off the beaten path. It means spending the time and effort to discover your unique personal path that will bring you much lasting joy. And that is an incredible thing.