Hustle and Flow: on knowing when to grind and when to hang it up

Our culture is full of advice on how we can live better, happier, more meaningful lives. This advice often falls on one of two ends of a supposed spectrum. One side tells us to hustle harder, to never give up; to keep pressing on towards our dreams at any cost. The other side tells us to be present in the current moment, to be thankful for what we have, and to not get sucked into thinking that we are entitled to satisfy all of our desires. Entrepreneurs and celebrities tell us to dream big, persevere through failure, and to get back up every time we're knocked down. Yogis and mindfulness practitioners tell us that we would be better off giving up on the idea that we always need to be satisfying more and more of our desires. They tell us that winning isn’t everything, and that our culture of desire-satisfaction makes us less, not more, happy. There’s a barrage of such advice from both ends of this spectrum, all of which I find incomplete and misleading. While hustle and acquiesence are often seen as opposing personal philosophies, I find it more helpful to see them as two sides of a single (life-) coin. 


In the tradition of philosophy, the two ends of this spectrum can be represented by two seemingly distinct schools of thought: pragmatism and stoicism. Pragmatism is a relatively recent (19th cent) American tradition bred out of the rightfully ambitious attitudes fostered by the industrial revolution and the successes of the physical sciences. It focuses on how human intelligence can help us assert control over the world in order to satisfy our desires and the desires of others. It’s a philosophy of hustle. Stoicism dates far further back to around the 3rd century BC and its focus appears, at first, to be quite the opposite. Where pragmatists tell us to go out there and work to get what we desire, Stoics tell us we should teach ourselves to desire what we get. They tell us that the world is full of things that are outside of our control, and instead of trying to tame it, we should let its' winds take us where they will. In order to do so, we need to cultivate the inner disciplines of lowering our expectations, minimizing our desires, and learning to be happy with what we already have. 


Though philosophers often depict pragmatism and stoicism as opposing worldviews, they’re more compatible than they may at first appear. Their difference is but a difference of focus, and both tend to oversimplify our lived experiences. Pragmatists tend to hi-light that in life which we can change, while stoics hi-light that which remains out of our control. Pragmatists often gloss over how much of life we cannot control while Stoics tend to underestimate how much of life is receptive to our influences. Pragmatism reminds us that technological advancement allows us to control things that were once wholly outside of our influence. We can now grow vegetables in the dessert, walk the depths of the ocean, eradicate diseases, and alter our anatomies. Stoics remind us that our upbringings, what others think of us, our age, and the weather, remain as indifferent to our desires to control them as ever. Life is full of both that which we cannot change and that which is susceptible to our influence, and if we’re looking for a philosophy capable of helping us guide our lives, neither pragmatism nor stoicism seem to do the trick on their own. A philosophy capable of providing some guidance for our lives must incorporate both of these attitudes at appropriate times. Particularly when we face adversity, how do we decide whether to keep on keeping on (trying to change things) or to gracefully bow out of the race (accept things as they are)? Enter: stoic pragmatism.


American culture loves to tell the stories of those who kept pushing and pushing and finally made it. Legend has it that Colonial Sanders of Kentucky Fried Chicken fame tried to sell his secret recipe over one thousand times before anyone bought it. While at some point he succeeded in making his first sale, his continued efforts were no guarantee of that success. There are many more lesser-told stories of people like the Colonial who were never able to sell his or her recipe to anyone. I played hockey growing up and have a few friends who at thirty years old are still chasing the dream of becoming professional hockey players. More than one of my former teammates has ended up with a career-ending injury in their mid to late twenties with no higher education or job experience to speak of. Were they right to keep pressing on like Colonial Sanders or would they have been wiser to quit while they were ahead? I don’t claim to know the answers to these questions, but I do know that limitless resolve (hustle) is tiresome on the soul and doesn’t guarantee positive results. So what do we do? Quit striving to satisfy our desires and take up the stoics’, Buddhists’ and yogis’ advice to lower our expectations in order to be content with what we have and not be (too) disappointed by our failures? Or do we keep pressing on, even as it kills us, with the hopes that one day our efforts will pay off? 


Luckily this question presents a false choice because life’s problems are far more complicated than to be solved by being just a pragmatism or just a stoic. But popular culture doesn’t typically have time for such nuance. People want easy answers, sound bites, and pre-prescribed solutions to life's problems. What I would like to call for is a far less popular position: that of lowering our expectations while simultaneously working very hard to satisfy our desires. We can work our asses off to get what we want, but we would be wise to do so with the understanding that we very well may fail. And at some point, it’s okay to say that we’ve in fact failed enough, and quit without (too much) remorse. Sure, quitting may exclude the possibility of eventual success, but it might also protect us from devastating disappointment that, in the end, may lessen our resolve even further.


This stoic pragmatism aknowledges that we can work very hard to change the world without holding onto the dillusional optimism that if we just try hard enough, things will eventually work out. Luckily pragmatic effort and stoic expectation-lowering are more compatible than most philosophers and self-helpers usually admit. This is counterintuitive because our culture teaches that optimism is what leads to success. But often times in life things are uncertain enough that optimism is unwarranted. American culture seems to endorse this unwarranted optimism, where we are encouraged to believe in our eventual success even when we aren’t justified in doing so. To me that just seems silly, but I used to fall for it too.


Many will reply that without a strong sense of optimism and high expectations of ourselves we will never achieve the growth we could otherwise. But upon further reflection, this simply isn’t true. When we have very high expectations we often become disappointed with ourselves for missing the mark, and this disspointment does not embolden our motivation, but in fact lessens it. And do lowered (read: more realistic) expectations kill our drive to succeed? Paradoxically, no, they do not. Desire is not a fire easily put out. By becoming a little bit more of a stoic you will not lose your competitive edge. You’ll just be less of an asshole when you lose. And you might be a little wiser when choosing when to quit chasing the dream and hang up your skates.