Sisyphus kept on pushing. Be like Sisyphus.

Silhouette of young businessman pushing large stone uphill with copy space

The myth of Sisyphus tells us that the most dreadful punishment is interminable, futile labor. Like doing laundry and dirty dishes.

To me, though, this story also speaks to the friction between the reality that our toils are often performed with no clear outcome and our longing for clarity. We want to see a direct link between our actions and our achievements, and we prefer clear beginnings and endings. We have strong cognitive leanings toward simplicity, efficiency, and clarity. But this desire is simply at odds with the world we live in. It’s messy, convoluted, and complicated. We give our all to endeavors we have no guarantee of achieving. We have seemingly mutually exclusive goals. We are required to make difficult decisions, compromises, and trade-offs. And the goal posts keep moving; there is no end in sight.

This is beautifully articulated in a recent HBR piece we shared this week, Both/And Leadership about the strategic paradoxes we face every day. One such paradox described in this article is also illustrated in the TEDTalk by Knut Haanaes about how organizations need to learn to balance the need to explore (innovate) and exploit (capitalize on current capabilities) to survive and thrive. While in the long term, these endeavors serve the same distal goal – the prosperity and longevity of the company – in the short-term, they are so different in nature that they can lead to internal conflict in the form of competing priorities, culture clashes, and challenges over resources allocation.

Conflict is uncomfortable, uncertain, and can lead to disaster. Without conflict, there is stagnation, and where there is no growth there is collapse. Therefore, conflict is necessary and even desirable. Attempting to cope with paradoxes yields another paradox! Half of the challenge in addressing these paradoxes lies in coping with the conflict that inevitably arises. And I say coping because, like our paradoxes, we cannot simply resolve conflict and move on – we deal with the part of the dilemma is in front us at the moment, but we must not convince ourselves it has been solved for good. As the HBR article makes clear, this process is ongoing – we have to deal with the long-term in the short-term, day after day, never sure the choices we made were the “right ones.” It makes me tired just thinking about it. It feels…Sisyphean.

This is life, though. To thrive, in business as in the rest of our lives, we have to be willing to do the Sisyphean thing, and do the hard work every day running interference between competing goals, between stakeholders, between the short term and the long term, even as the horizon recedes indefinitely before us. We have to be willing to accept that it’s complicated, live with the messiness, and cope with the ambiguity and conflict that are part and parcel of this work. We can try to reduce our misery by not exacerbating things. First, by not pretending complex problems are simple, by raising the level of our thinking and problem-solving. Second, by making the inevitable conflicts that arise work for, not against you.

Research on the effect of conflict on performance consistently shows that relationship conflict damages performance, while task performance can potentially be of benefit – but only in the absence of interpersonal conflict. The problem, of course, is that we are not just thinking beings but also feeling beings, and we quickly become personally attached to our goals and subcultures, turning task conflict into relational conflict in short order. Organizations need to ensure that their process for resolving strategic paradoxes reduces interpersonal conflict so that task conflict can be resolved effectively. The foundation for a healthy conflict resolution process include personal calm, interpersonal trust, and a common vision. Cognition and emotions are not truly distinct things – there is a feedback loop between them. A calm mental state will lead to clearer thinking, which helps resolve the conflict more quickly and effectively. When people trust the people with whom they’re engaged in conflict, they are far better able to depersonalize the matter and remain calm. Trust is often rooted in knowing that they are trying to achieve the same higher-order goal, even if the immediate goal seems discrepant.

The nature of work for many of us today demands things of us that simultaneously highlight the amazing faculties of the human mind and its foibles. To rise to the challenge presented by complexity, ambiguity, uncertainty, and conflict, we must abandon our longing for clear answers and short time horizons. We have to commit to thinking more deeply about the paradoxes we face and be more thoughtful about the conflicts they present. And we have to be willing to push that rock up the mountain again and again.


“How wonderful that we have met with a paradox. Now we have some hope of making progress.” –Neils Bohr