Growth, Sin and Forgiveness: Why Yom Kippur is Necessary in Today’s World

“You know what’s interesting about Yom Kippur?” my father told me on a Connecticut road, “It’s the only holiday that hasn’t been successfully commercialized.”

Ever since I began to fully grasp the concept of Yom Kippur at age ten, the holiday remains one apart from all others, Jewish and otherwise. For one day a year, I was deemed perfect with all past imperfections having vanished (with a handful of caveats laid out in the Talmud).

On that day, I felt the past year play back to me in my photographic memory with each sin laid forth in the liturgy, all the while wondering which great victories would come to me in the coming year. The relative lack of symbolism present in other holidays like Rosh HaShanah and Pesach meant that I and other worshipers could truly focus on the state of the world, our communities, and our lives and realize what could be done to prevent an evil decree for the coming year. Yom Kippur has a relative lack of material props – without matzah, bonfires, apples and honey, nor sacred species (or food of any sort, for that matter).

When I walked away from Jewish Orthodoxy in the early 2010’s, one great pain I felt in my coming to doubt religion was the idea that the world is a judgmental and unforgiving place. This idea was re-enforced by norms of educational systems and ruthless testing and, very much unlike my childhood self, my young adult self was less forgiving of myself than any Divine Being full of mercy could be.

After getting Lyme Disease and recovering under circumstances contrary to expectation, I took on the life of an entrepreneur and freelancer and, before long, I realized that – contrary to what I had heard in Hebrew Days Schools and taken in from secular schools – mistakes were not only necessary for growth, but essential.

There is a catch, however…. With each set of errors, there has to come a time – sooner rather than later – in which the negative sides of oneself are laid out with vulnerability and, thereby, cast into the river, much like the bread crumbs in tashlich.  True growth doesn’t happen with avoiding kheyt, avon and pesha altogether, but, rather, recognizing their existence and realizing that they should be taken in and, thereby, disposed of. (There is also recognition throughout Talmudic writings that the yeytzer hara can present spiritual and growth opportunities if harnessed correctly).

When I was a kid in Jewish day school, I thought that sins of any sort made me a terrible person, that they would somehow forever lock me out of the World to Come if I did the wrong thing. As an adult, I realize that missteps are a necessary requisite for gaining opportunities for growth, healing and peace. As a student, I was afraid of making mistakes of any sort, but once I left the school system and became someone with my own visions as my first priority, I came to know that no great story anywhere happened without slip-ups or mistakes.

However, in the backdrop of all of this, there was this holy idea that forgiveness, improvement, and reflection is always an option, and that, once a year, the errors of one’s past selves will be left to the past, never to return. Upon closer inspection of the many stories in the Bible, it seems that God, Himself, isn’t above a journey of self-improvement.

May this Yom Kippur be a reflection and a turning point that you remember well!

Beyond Deadlines and Compromise: Learning to Tend to Your Work Soul

It begins innocently and self-indulgently: It’s close to midnight and you would rather just go to sleep.

That report you have been compiling gets a lot shorter than it should be. Rationality enters: You have no caffeine, three looming deadlines, and an early morning meeting.  Is this not the perfect time to re-watch Seasons 3-5 of Grey’s Anatomy? (By the way, nothing says “deadline” like eight hospital break-ups and a motivational speech you choose to ignore from the Chief of Surgery).

More than enough has been written on being busy, whether the psychological, political or the existential ramifications, let alone what it does to your marriage, body, and brain. I won’t add to the corpus. But I will say this: we are becoming quite selective with our teams, with our information, and with just about everything that involves working with others. And our selectivity is not only eating up our time, but it’s starving us of what we can collectively accomplish.

Entrepreneurs are notoriously rich in over-scheduling and the trap of what one might call over-aspiring. We want to move mountains and we want to move at light speed. But the problem is that, in our quest to cross the finish line, we are are compromising our work and leadership quality. 

We’re all guilty of it. We’ll take on a new project, but we won’t call the team to gather feedback. We’ll carve out time to create a vision, but make no time for ongoing research or discussion. We’ll collect the data and, because we are tired – or, worse, uncomfortable – we’ll prune it to the bare minimum, so, by the time we are finished with it, it looks like exactly what we want it to be. And it ends up being tidy and without the complexity of thinking or including anybody.

This is precisely the kind of conundrum that links Jewish entrepreneurs and their sages. When the rabbis were faced with even the appearance of impropriety, they were so concerned that they tended to ban all associated acts completely (just take a look at what they had to say about picking up coins in front of idols). Why the fuss? Because every impression mattered and, in every action, existed the possibility for teaching.

The work of entrepreneurs benefits not only from self-reflection, but even more: from communal accountability.

Entrepreneurs are enriched by assessing where they stand in the arc of their tradition and, whenever possible, consulting it. Any movement forward should not come at the expense of difficult conversations, consultation or community. When the approach to our work becomes self-serving, we owe it to the people we work with to re-consider how we work.

Now I am not suggesting we ban prioritization, multi-tasking, or even Grey’s Anatomy, but I am suggesting we seek an alignment between our actions, our intentions and, also, our tradition.

How we select our priorities relates directly to how we choose others and how we choose to engage in living. And, as we create our works and our lives, all of our doings must be accompanied by Jewish teachings.

That’s why I implore you to ask a new question this week. Talk to the people who work closest to you and ask them about your work soul: Who are you at work and how does your soul reflect in what you do?

Feel free to post what you find.