ON BECOMING A BETTER HUMAN AND INVESTOR IN 5779

A rabbi, a hedge fund manager and a sailor walk into a bar.

A few disclosures: the rabbi was Yitz Greenberg, manifest via his book The Jewish Way; Ray Dalio played the part of hedge fund manager, also appearing via Kindle in Principles; the venue was more accurately a pizza joint; and the sailor was me, an American-born impact investor from Tel Aviv working my way through a dozen or so books I believed could offer wisdom on becoming a more successful human and investor as 5779 approached.

I knew definitions of success might diverge radically between hedge fund managers and Orthodox rabbis. But synthesizing these disparate views is part of the fun. Impact investors are typically adept at bridging universes – most commonly those of finance and social change.

Dalio’s ‘success’ is straightforward. Be an exceptional investor, delivering consistent above-market returns.

Yitz’s objective, in a summary that will do him little justice, is to guide Jews toward what he views as our shared central purpose – slowly and tirelessly molding the world into its most perfect form. He describes this as a state where every living being embodies their birthright of being “made in the image of God,” meaning they are recognized as unique, of infinite value, and indisputably equal. Yitz teaches that the fundamental Jewish task is to eradicate those factors – poverty, sickness, oppression, slavery, environmental degradation, etc. – that prevent many of our planet’s seven billion inhabitants from living these dignities. This is a mission that resonates clearly with impact investors.

So what advice could professional investor and rabbi possibly have in common? It turns out, quite a lot. Page after page, Yitz and Dalio provide shockingly parallel guidance on how to become a better human and investor, respectively. Here are four of their shared principles that I’ll be using for personal and professional course correction in the year (more likely, years) ahead.

Radical Transparency

Yitz explains that Elul, the thirty days before the Jewish new year, is a time when we are encouraged to take deep and critical stock of what is working and what is not as individuals, as couples, as families, and in all of our personal and professional relationships. We can only take action toward positive change by first forcing ourselves to become truly conscious of the reality we’ve created or, often times, fallen into.

Dalio actualizes this same guidance in a number of management practices designed to encourage radical honesty and transparency: an “issue log” where employees must write down any mistake they make so that others may learn from them; openly scoring employees on strengths and weaknesses so as to assign projects to those most likely to excel; and deliberate encouragement of “thoughtful disagreement” to allow as many ideas as possible to be thrown in the ring.

Practicing radical honesty and transparency is hard. It is uncomfortable and time-consuming to engage, partners, peers or those seeking our grants or capital in difficult conversations. It is cognitively and emotionally challenging to recognize our own limitations – that we are often misguided and inevitably abounding with weakness. And yet, radical transparency is likely the most necessary precursor to becoming better.

Evolve Constantly

Both Yitz and Dalio employ a heavy dose of metaphor from evolutionary biology, emphasizing that we only grow through continuous iterative learning. Ideally, we pause for reflection, make subtle tweaks, and move forward as a slightly improved version of ourselves.

Yitz presents Yom Kippur as an annual catalyst for a new growth cycle, one that begins with acknowledging difficult realities. “Those who confront their own guilt and failure in human and divine relationships – in the context of community oneness and divine forgiveness – can correct errors, develop new patterns, and renew life (187).” However, yours truly could stand to use Shabbat as a more regular opportunity to step out of the routine and recommit to active improvement of myself and the world around me. As any sailor knows, long journeys require frequent course correction.

Yitz sees this self-improvement as key to changemaking, writing that “routine and stagnation are forms of death in life. People often stop growing long before they are recognized as dead. Such a “dead” person cannot be an agent of redemption. The tradition holds that the key to vital living is perpetual renewal of life; it seeks to attain that renewal by generating a continual process of examining life and constant rebirth. The awareness of being judged for life and death is a stimulus to stop living routinely (185).”

Dalio believes this evolution is our only constant. “Evolution is the single greatest force in the universe; it is the only thing that is permanent and it drives everything,” he writes. “Evolving is life’s greatest accomplishment and its greatest reward.”

Listen Deeply

In the series of essays included in A Torah Giant: The Intellectual Legacy of Rabbi Dr. Irving (Yitz) Greenberg, one essayist notes Yitz’s incredible ability to be wholly present and deeply listening to every individual he encounters. I smiled in agreement reading that description, as I’m sure others who have known Yitz, even only briefly as I have, would too. How much of this quality is innately him and how much of it can be learned, I do not know. But the ability to deeply listen to each person in each moment with full consciousness of that person as a unique individual with a distinct and valuable perspective is uncommonly gracious and a surprisingly difficult practice. It requires pushing away our assumptions, stereotypes and preconceptions, tuning out the noise, and operating from a position of believing that the person before us holds a spark of the divine and something meaningful to teach us.

Yitz writes, “the goal of the human in God’s image is the fullness of life: to become more and more like God, who responds out of the infinity of life, not in a pre-programmed fashion without necessity or determinism but uniquely and appropriately to each person and situation. The normal processes of routinization and numbing are the enemies of this growth (200).”

Dalio, a lifelong practitioner of meditation and a student of psychology and neuroscience’s approaches to expanding the consciousness, similarly emphasizes the importance of deep listening skills in his investing. An astounding number of his principles entail practices designed to broaden our consciousness: letting go of our desire to be “right;” actively seeking out as many opinions as possible, particularly from those who disagree with us; sincerely believing that we do not know the best path or right answer; suspending judgement of others in order to fundamentally empathize and understand their point of view; and maintaining an awareness of and humility for the fact that we will never have perfect information.

As investors (or philanthropists selecting among grantees), much of our job is to rapidly determine how to assign limited attention and resources to the best ideas. Yet how frequently does this programmed approach result in my judging before I’ve fully listened? How often do I allow preconceived notions and the pressure of a schedule to limit my full attention and openness to new ideas, people, and investment opportunities? How often do I neglect to internalize and honor the fact that every single individual before me has experience form which I can learn?

Live with Death

Meditations on death feature prominently for both Yitz and Dalio. While the versions differ, both see reckoning with the possibility of death – a mental exercise not totally unfamiliar to a sailor – as a necessary component to living more successfully. For Dalio, embracing this polarity means continual references back to his “abyss.” In 1982, seven years after founding Bridgewater, he was loudly and publicly wrong about his bets on what he saw as a certain and imminent depression. As the economy instead recovered, his bets turned against him and he lost his money, his team, and his company.

“In retrospect,” he writes, “my crash was one of the best things that ever happened to me because it gave me the humility I needed to balance my aggressiveness. I learned a great fear of being wrong that shifted my mind-set (35).” Bridgewater’s early ‘death’ left Dalio with an extreme and constant awareness of all that could be lost, training him to seek every strategy possible to mitigate the risk profile of his investments. This diligence – and the humility that fuels it – enabled him to grow Bridgewater v2.0 into one of the world’s leading investment management firms.

In The Jewish Way, Yitz explains much of Yom Kippur ritual as a way to shock us with the possibility of death, and thereby stimulate us to embrace life with full dedication. Only by having our eyes wide open to all that is at stake, recognizing the threat and ubiquity of death, can we properly engage life as the awesome and ephemeral experience that it is.

“Human beings cannot be mature until they encompass a sense of their own mortality. To recognize the brevity of human existence gives urgency and significance to the totality of life. To confront death without being overwhelmed, driven to evasions or dulling the senses is to be given life again as a daily gift. People generally experience this gift through a trauma: an accident or a critical illness or the death of someone close. Too often the encounter fades as the presence of death recedes and the round of normal life becomes routine reality. In the Jewish calendar, the Yamim Noraim (Days of Awe) structure the imaginative encounter with death in an annual experience in the hope that the experience will recur to liberate life continually (Yitz, 184).”