The Year I Woke Up and Became a Jewish Entrepreneur

For years, it was drilled in to me to follow my strengths. With a spatial sense that was and remains virtually non-existent, I was told to focus on what I could do. So I went to drama camp, and Jewish camp, and became a camp counselor and then – before I knew it – I was a community developer,  a non-social work social worker, paid to be proficient in what I was really good at.

Unfortunately, I was running away from myself. By the time I hit my mid-twenties, I could teach the class on how to transform, by which I mean dress-up failure. Faced with a series of doomed relationships, a litany of academic rejections and, at one point, the possibility of being homeless, I spent most of my time trying to seem okay with the next wave of devastation around me. Life wasn’t pretty, but I sure made it look that way – touting the learning experiences at my job and, yes, the next deceptive selfie, as the sort of positive turn-arounds that redeemed a world of unconfronted pain. Sure, I was showing parts of myself, but the rest of me was hiding.

And there was something else to this faux okay-ness. See, I wasn’t just failing, I wasn’t purposefully failing. While I was bragging about all the useful skills I accrued while being at various points abused, confused and removed from how I really wanted to be living, I wasn’t staking a claim on what I wanted. I wasn’t raising the stakes to the highest level, crying out from the bottom: “I may die or, worse, fail going after the truth of who I am…but that is worth everything compared to another moment living the lie of who I am not.”

I had to stop being okay in order to step forward. I had to stop confusing being useful with being purposeful because the conflation was not only antithetical to facing my sheer distance from living the life I wanted, but also pursuing the kind of spiritual proximity that only comes from honest failures, the spoils and toils en route to what one really wants to be doing. Failing in a direction of my choosing did not make the hard parts more bearable. Or even less rare.

But it did make me re-learn what it means to be alive.

It also brought me to learn Hebrew (I mean really commit, failing badly, outrageously, often) after years of being told I would never master a single language. And, as I continue to muck up on the winding path to mastery, I now understand why taking on this learning curve was the precursor to my decision to become a rabbinical student and then a poet and blogger. As my spatial sense grows stronger, so does my sight into my own soul. I have to continue failing at what I really want in order to end up in the places I desire most. And I have to forsake the failsafe of what is comfortable and okay to get there.

In a month where, according to the medieval work, The Zohar, Jews make the existential move from back-to-back to face-to-face, seeing ourselves for who we are and setting out on the tasks we crave to do could not be more pressing. For there is nothing more forward-facing and, as it happens, entrepreneurial, than failure when it meets the sincerity of a veritable purpose.