Fasting, Unmasking, and the Joy of Yom Kippur

Welcome to Venturing Into the Parsha, a weekly(ish) e-mail intended to provide insights from the Jewish holidays and weekly Torah portions that impact and uplift our roles as investors, founders, and operators. These are intended to be ~5 paragraphs and intentionally brief. Questions or comments are always welcome in response.

Ask practically any Jew what the most important day of the Jewish calendar is and you’ll get the expected response: Yom Kippur. But surprisingly, that answer is arguably incorrect. The 16th century mystic, Rabbi Isaac Luria – also known as the Arizal – proved this point from the following inference: though we call it by its colloquial Yom Kippur, the full biblical Hebrew is Yom HaKippurim. In the Hebrew vernacular when we say something is “ki’” something else, we mean it is like something else. In this case that translates to the day (yom) that is like (ki’) the holiday of Purim. And when we say something is “like X,” for example, that your startup is “like Uber but for laundry,” it implies that Uber is the primary subject and your laundry startup is the derivative. So too, commented the Arizal, Purim must be the primary day of the year and Yom Kippur its close derivative.

Perhaps in a few months we can discuss the depth of Purim’s primacy in Judaism, but in the meantime, we’ll try to unpack the unlikely connection with Yom Kippur. Ostensibly, they could not be more dissimilar. Purim is a day when Jewish people – from adults to young children – wear costumes and disguises, bring gifts to friends, eat hearty meals, and the adults will generally drink alcohol to the point of either falling asleep or inebriation (fwiw, this is not common; Purim is the only day of the year we are meant to drink in this manner). Yom Kippur appears to be the direct inverse. We are commanded not to eat or drink. Not to wash hands or take showers. To uncomfortably stand for hours on end in prayer services with our legs tiring and knees buckling. Jews young and old try to wear only white to synagogue in an aim to reflect angelic purity. One day appears to focus exclusively on physicality; the other on spirituality. So where is the relationship between the two?

My teacher and mentor, Rabbi Immmanuel Bernstein taught me the following idea: the commonality between the two holidays is that they are the two times of the year where we pretend to be someone we’re not – but in doing so, reveal our truest, underlying selves. By wearing costumes and getting inebriated on Purim, we become untethered to our social identity and lose our sense of correctness and propriety. Therefore, if we have an inherently vulgar and unhappy demeanor, that side of us will come out. If we are inherently fulfilled and kind, then that, too, should emerge. Conversely, Yom Kippur forces our hand in the opposite direction. Throughout the year we tweet, e-mail and speak in ways that represent a given identity – often one that intends to promote a positive or embellished portrait of ourselves. In contradistinction, the prohibitions of Yom Kippur that cause hunger, exhaustion and discomfort will wear down whatever embellished image we usually project – as we lose the wherewithal to maintain it – and reduce us to our pure essence. The hope, of course, is that we like what we find, and leverage Yom Kippur’s prompt as an opportunity to re-connect with that essential authentic core of ourselves that exists beneath our ego and projections. Thus, both holidays in fact promote and encourage the ultimate expression of our true selves.

My friends are always surprised when I share that in classical Jewish philosophy, Yom Kippur is actually the most joyful day of the year, not the most somber. And the reason is because of this reconnection with our actual selves – in a similar to vein to how deep work in therapy, even if exhausting, leaves us feeling more confident, more fulfilled, and more hopeful for the future. We feel our best when we are fundamentally honest with and aware of ourselves.

I think about this concept a lot in regards to the startup world. There is a certain bias towards positivity and exaggeration that exists in our world – and to a certain degree, it’s a necessary delusion for survival. But if Jewish philosophy suggests that certain periods of getting completely, unabashedly, real is necessary for our long-term health, it follows that the same should hold true in our professional lives. One area where this plays out is at the company board level. Founders can tell their employees, the press, and prospective investors whatever they want to frame a narrative; but board directors have a transparent view into the underlying data of the business, and the data – like our true essence – doesn’t lie. These board conversations – once all the embellishments have been stripped away – can be exhausting, vulnerable and uncomfortable. But similar to Yom Kippur’s outcome, nearly every entrepreneur I’ve worked with has walked away stronger and ultimately more fulfilled when they can be honest about what they’ve built, areas for improvement, and the challenges still to overcome. Similarly, organizational teams also need these moments of stripped down honesty – and that can be difficult to cultivate when individuals’ livelihoods are on the line.

One of my curiosities for the coming year that I’d like to explore are best practices leaders use to enable these authentic moments and conversations in their orgs. Yom Kippur is a necessary day for my own spiritual sanity and I’m confident similar moments are long-term optimal for our professional sanity as well.