They are the “golden” demographic, the mid-20s to 30-something generation eagerly sought after – but not always reached – by the organized Jewish world.

So how do we engage these emerging Jewish leaders?

We do it by taking risks.

In the 1950s, a good Jewish boy by the name of Harry Markowitz began using mathematics to analyze the stock market. Markowitz realized that contemporary stock pricing models did not account for the impact of the risk factor. What emerged is known in the financial world as Modern Portfolio Theory, and it earned Markowitz a Nobel Prize.

Modern Portfolio Theory was innovative in that it was the first successful attempt at quantifying and mathematically analyzing risk. This led to a new era in which investors could begin to correlate their expected returns with their appetite for risk taking. Many people talk about calculated risks. Markowitz actually did it.

From a social science perspective, more powerful than Markowitz’s mathematical model is how human behavior is affected when risk taking can be calculated. The expression “no pain, no gain” is no longer arbitrary. According to the theory, one should be able to determine just how much pain will be required in order to achieve a certain gain, and vice-versa – how much can be gained for a certain amount of pain.

Jewish peoplehood enthusiasts who understand that the emergence of a vibrant global Jewish community is in the hands of today’s young people ought to take a note from Markowitz and embrace risk with a sense of purpose.

Risk Our Comfort Zones. According to Steven Johnson, the author of Where Good Ideas Come From, the key to fostering innovation is openness and connectivity. “We can think more creatively if we open our minds to the many connected environments that make creativity possible,” he writes.

In other words, innovation is nurtured by bringing together what on the surface doesn’t go together – like the poet and the engineer. Creating safe spaces for these kinds of encounters and gatherings requires a readiness to accept unintended consequences.

It’s almost impossible to predict the outcome of putting a bunch of passionate Jews from diverse geographies, career paths, and levels of observance in a room together. But rest assured, the more variety, the more creativity. By exposing these different people to new perspectives we will reap the rewards of the synergy and ideas generated. It sounds simple, but most organizations invite only a narrow network of people to be part of something with a narrow scope.

Risk Listening. Albert Einstein once said “I never teach my pupils; I only attempt to provide the conditions in which they can learn.” Today’s young Jewish leaders are operating in unprecedented times of freedom and opportunity made possible by the break-neck speed at which technology is advancing. While there is much merit in our oral tradition of passing down knowledge from one generation to the next, there is also reason to trust that today’s young leaders know best what skills and competencies they need to acquire in order to improve their impact and success.

Whether it’s deeper Jewish education, better management skills, or raw technical know-how, trust that today’s young leaders have the ability to identify what’s missing from their tool-kit. By creating frameworks for these agents of change to learn, to teach and to support one another, we will make it possible for them to make it happen.

Risk Widening the Circle. Mark Twain once advised to “keep away from people who belittle your ambitions. Small people always do that, but the really great make you feel that you, too, can become great.” The notion that a small group of power brokers will develop solutions that will engage young Jews en masse in a sustainable way has failed.  For every programmatic one-hit wonder, along comes the challenge of “follow-up.”

Instead of continuing to rack our collective brain about how to best excite the highest number of young Jews about Judaism, we ought to make more room for a growing number of committed young leaders who are creating community in their own image. Let’s do more to make it possible for young leaders to engage their peers in new ways that only they could ever imagine.

Risk Failure. Jim McMahon remarked that “risk taking is inherently failure-prone. Otherwise, it would be called sure-thing-taking.” In the Jewish world we have been quick to label any initiative that ceases to exist as a failure. In many ways, the risk takers behind such initiatives are our frontline action researchers, helping the community learn in real time.

Consider the volume of lessons that can be discerned from so called failures in which entrepreneurs faced challenges in unchartered territory.  Certain kinds of failure are the best building blocks for ensuring success down the road if lessons are learned and acted upon. By quickly dismissing those who try and don’t succeed right away, our community is tossing aside its investment in their professional development and education. We would be well-served to think like long term investors when it comes to the promising young leaders among us.

If we want to harness the creativity and passion of young people who want to build our community in their own image, we must take risks. We need to develop a balanced communal appetite for risk, and we need better tools to understand and analyze it.  Most attempts probably won’t succeed exactly as we hope. To this end, I am inspired by the explosion in Jewish social entrepreneurial hubs, like PresenTense, JHub, Bikkurim and Upstart, now operating in many cities around the world. All nurture risk taking for the Jewish future.

Markowitz taught us about diversifying our investment portfolio in order to manage these risks. The principle applies to our Jewish Peoplehood portfolio as well.

Embracing unintended consequences, investing in individuals as lifelong community builders, and reframing our perceptions of failure are the kinds of measured risks that will yield a long-term positive return on investment for the Jewish people.

Hockey legend Wayne Gretzky said it best, “you’ll always miss 100% of the shots you don’t take.”

Adapted from an article which originally appeared in The Peoplehood Papers, June 2012.