Sisyphus, skateboarders, and the value in endless failure | Psyche

A skateboarder on the South Bank, London. Photo by Andrew Testa/Panos Pictures


Sisyphus, skateboarders, and the value in endless failure

A skateboarder on the South Bank, London. Photo by Andrew Testa/Panos Pictures

by Andrei A Buckareff + BIO

In the US talk show Comedians in Cars Getting Coffee (2012-19), the host Jerry Seinfeld remarks in a conversation with Chris Rock that ‘Those skateboard kids … are going to be all right.’ Rock expresses his agreement with Seinfeld, and they quickly move on to other topics. Their discussion about the value of skateboarding is quite brief (lasting about 20 seconds). But they agree that skateboarding provides skaters with a means of learning a life lesson. The lesson follows from the success of the skater in executing a manoeuvre after repeatedly failing (and falling). While some may nod their heads in agreement, it is worth considering whether Rock and Seinfeld are right. Does skateboarding teach a life lesson? If it does, is it a valuable lesson? Going further, why should we think that skateboarding is not, in fact, a meaningless activity that lacks any value?

The following will be a familiar scene for many readers. A group of people are riding skateboards. They might be doing it in a location that was not created for the purpose of skateboarding, or they could be skating in a dedicated portion of a local park that was designed just for skateboarding and similar activities. To the casual observer who does not skate, the people in question appear to be somehow throwing themselves on their skateboards and up on to ledges, making loud grinding noises with the turning apparatuses (that is, the trucks) on the bottom of their skateboards. The same skaters are also probably jumping off these ledges, somehow flipping their skateboards around in the process. Some of the skaters under observation might be flowing around fast in what may appear at first glance to be an emptied swimming pool, once again making loud noises as they grind, slide and occasionally fly out of (and back into) said pool-like hole in the ground.

What our observer who is not a skateboarder may find puzzling is that many of the skaters they are watching will often fail in their attempts at executing the manoeuvres they are trying to do. The result may be that the skaters fall multiple times and may even appear to have injured themselves. But the observer will no doubt notice that, so long as a given skater is not rendered immobile owing to crashing on a failed attempt, that skater will get back up after being unsuccessful and try again.

Importantly, the nonskateboarder may notice that a particular skater they are watching never enjoys success on that occasion and appears to be quite frustrated (perhaps even to the point of throwing their skateboard and cursing loudly). If our hypothetical nonskateboarding observer were to return to the same location on another day, they may witness the same skater trying to do the same thing, enjoying limited or no success. It would be natural for our observer to ask why the skater keeps trying the same thing only to fail in their attempt. This may lead to questions about whether such attempts are reasonable, which inevitably leads to questions about whether the skater is engaged in an activity that is meaningless. Is the skater’s time better spent pursuing some other ends? Suppose our skater is quite a bit older than the other skateboarders around them. They may (like your author) be in their 50s. Why would they waste their time engaging in such an activity? Isn’t skateboarding for children? Why doesn’t the skater just grow up and engage in a more age-appropriate activity, such as golf or lawn bowling?

An activity or goal is objectively pursuit-worthy if engaging in that activity is conducive to the cultivation of virtues

While our observer may feel confident that the skater is wasting their time on childish pursuits, is the spectator justified in feeling that way? Not obviously. In fact, there are good reasons that favour both the skater’s continuing to skateboard and their continued attempts at pulling off a manoeuvre. I maintain that what they are doing is, contrary to appearances, meaningful. Why this is so is perhaps best understood by exploring where philosophical work on the explanation and justification of action intersects with the theory of value.

It may be helpful to compare the scenario involving the skater with the story of Sisyphus from Greek mythology. In brief, as punishment for various misdeeds against the gods, Sisyphus was condemned to roll a boulder endlessly up a hill, with the boulder having been enchanted to roll back down when Sisyphus nears the top. Philosophers going back at least to the 1st century CE have commented and drawn lessons from this myth. The general takeaway has been that it represents the futility of various seemingly meaningful endeavours. In his 1942 essay, the French philosopher Albert Camus went further, arguing that the myth represents the absurdity of human existence. In 1970, the US philosopher Richard Taylor concluded that any meaning that our activities have is purely subjective, given that, from the perspective of the Universe, what we do is not of any lasting significance.

In her book Meaning in Life and Why it Matters (2010), the US philosopher Susan Wolf has argued, against Taylor, that even if Sisyphus is feeling fulfilled, owing to the nature of the activity in which he is engaged, his feeling fulfilled is not reasonable. She argues that the object of an agent’s feeling of fulfilment is represented in the mind of the agent as being something that is objectively good. In the case of Sisyphus, even if he is fulfilled, he misrepresents the source of his fulfilment as good. So Wolf argues that the meaningfulness of an activity or goal is a function not only of one’s being fulfilled in engaging in it/pursuing it, but the feeling of fulfilment also needs to be a fitting response to the activity or goal. And it is only a fitting response if the activity or goal is objectively pursuit-worthy.

What would render an activity or goal objectively pursuit-worthy? Objective pursuit-worthiness is in part owing to the value of the end or activity coming from outside of oneself. Wolf admits that determining objective pursuit-worthiness is not easy, and involves a process of discovery. A possibility not explicitly endorsed by Wolf (but not rejected by her, either) is that an activity or goal is objectively pursuit-worthy if engaging in that activity is conducive to the cultivation of virtues. My suggestion is that, so long as an activity is generally conducive to developing character traits and intellectual traits that will enhance and not impede the flourishing of both an agent and those with whom they interact, it is objectively pursuit-worthy.

It is natural to ask at this juncture what is characteristic of an individual or a group that is flourishing. I take it that an individual or a social group is flourishing to the extent that the wellbeing (understood holistically) of the interested parties is, on balance, positive. They are functioning well. Flourishing is multifaceted, including, but not limited to, an individual’s and a group’s psychological and bodily wellbeing. Importantly, to the extent that an individual and a group are flourishing, they are more happy. If this is right, then it seems reasonable to assert that at least one way of determining the objective pursuit-worthiness of an activity or a goal will be by considering whether or not it is conducive to the flourishing of an individual and, by extension, the social groups of which they are a member.

Any activity that involves the cultivation of a skill that is not easily achieved will have similar results

If it is true that an activity or goal is objectively pursuit-worthy, the facts that make it true provide a reason for engaging in that activity. That is, they provide a normative reason that favours the activity. Normative reasons can be contrasted with motivating reasons. Motivating reasons explain why someone is doing something. They are subjective considerations that move an agent, and in the light of which an agent’s actions can be rendered intelligible. I assume that an agent’s acquisition of some motivating reasons is rational when being so motivated is a fitting response to some normative reasons that favour what the agent is motivated to do. When our explanations of the actions of ourselves and others involve motivational states that are fitting responses to the objective pursuit-worthiness of an activity or goal, we have meaningful activity. Importantly, I would maintain that the agent need not realise that their desire to do something is a fitting response to the activity or goal they desire in order for the activity to be meaningful. This may be something they only discover at a later time.

Meaningless activities are often labelled as Sisyphean. Is skateboarding a Sisyphean activity? It may appear to be so at first glance. Consider again the skater who keeps trying a manoeuvre, enjoying only limited success (at best). Now imagine that same person who first tries that trick at the age of 15 still trying to successfully execute it at the age of 50. Surely this seems meaningless to our hypothetical nonskateboarding spectator. But the observer’s impression is mistaken.

We should deny that the skateboarder is engaged in a Sisyphean pursuit because their motivation to skate is a fitting response to an activity that is objectively worthy of pursuit. The skater has reasons for skating, given that it is an activity that will contribute to their wellbeing and, furthermore, may enable the skater to contribute to the flourishing not only of themselves, but also their larger community. Success in learning to ride a skateboard well and then learning how to execute various manoeuvres is not easily achieved. In the process of learning to skate or learning a trick, the skater cultivates virtues. In particular, they develop perseverance and fortitude. And every skater, in virtue of imagining possible lines (that is, sequences of tricks) and making up manoeuvres, develops creativity. These virtues, among others, then translate into other dimensions of the skater’s life outside of skateboarding. I take it that this is why the ‘life lesson’ of which Seinfeld speaks in his conversation with Rock is valuable.

None of this is unique to skateboarding. Any other activity that involves the cultivation of a skill that is not easily achieved will have similar results. But that this is true of skateboarding is not often recognised by those who do not skate.

Consider again the nonskater watching a skater trying a manoeuvre and failing, only to try again, and possibly never succeeding. The nonskater may not like skateboarding and even think it is pointless. But they owe the skater a reason for why they should just ‘grow up’ and stop skating. The skater, for their part, has good reasons for rejecting this advice and their desire to skate is a fitting response to this fact.





1 December 2021