By Jaime Rapaport Barry

Just a week after Yom Kippur, many of us still have more questions than answers in our hearts. The process of cheshbon hanefesh – an accounting of one’s soul – rarely yields simple, executable solutions. Rather, this annual process of immersing with ourselves frames the questions we need to answer in the coming year: “How can I be a better ________?” In many ways, this process aligns with design thinking, a problem-solving framework UpStart teaches to Jewish leaders across the country. First, you immerse with people to unearth their needs, then you frame the opportunities for change in a question: “How might we________?” Asking the right questions sparks the creative process needed to generate the right solutions.

Every year, the UpStart network engages in our own immersion process. Just a few weeks ago, the twenty organizations in our Accelerator came together to learn, collaborate, and experiment at the UpStart Lab. And this year, we experimented by co-hosting a live, crowdsourced podcast recording with Judaism Unbound, featuring the innovators themselves. Similar to on Yom Kippur, we asked them to look back to look forward. We asked, what have you learned about Jewish innovation, and what questions are on your mind as we move ahead? You can listen to the full podcast here, but below are a few of the questions Jewish innovators are thinking about in 5777:

How might we create safe spaces to collectively learn from our failures?

As part of the podcasting event, former Ideo.org editor Aaron Britt joked that “here in Silicon Valley … the only thing better than succeeding is failing,” poking fun at the widespread adoption of terms like “fail forward.” But his point was less to demean the value of this critical innovation mindset and instead to elevate its importance beyond the realm of mindless jargon. Failure, he noted, is one of your best opportunities to learn more about the people you’re trying to serve.

At UpStart, we encourage innovators to act from a place of ometz lev / courage of the heart. We believe in taking risks, rapidly testing your ideas, and learning from failures and successes alike. Yet while “failing forward” has become a more widespread notion, many innovators wonder whether this mindset is actually compatible with the expectations of their partners and funders. They wonder if disclosure of their failures would be punished, rather than rewarded. So we ask, how might we design community spaces where we can learn from each other’s successes and failures?

How might we expand our community’s definition of scale?

The mission of the UpStart Accelerator is to empower innovators to transform their vision and passion into sustainable, scalable business ventures. And we teach that scale – the ability to grow the impact of your offering – depends entirely on whom you serve and the unique value you offer them. But in response to the hard, cold reality of declining Jewish affiliation, the definition of “scale” has increasingly narrowed towards one meaning – a steady increase in volume of customers served. Many innovators question whether the pressure to scale participants quickly might actually be shortsighted. Many early-stage organizations are still prototyping new forms of engagement, often with previously under-affiliated participants. The push to scale quickly could actually cut short important learning processes and force organizations to scale a not-yet-perfected model. In addition, some innovators wondered whether different organizations are meant to scale in numbers, while others exist simply to provide unique value to a niche audience who wouldn’t otherwise be served. So we ask, how might we articulate and invest in a spectrum of scaling models that work cumulatively to increase Jewish engagement?

How might we remove barriers to Jewish social entrepreneurship?

If you ask someone to describe the qualities of an entrepreneur, you’ll likely hear similar words – passion, vision, go-getter, risk-taker. And while these qualities are often accurate, there are undoubtedly other factors that facilitate the ease with which someone can just “go for it.” When one innovator was asked during the recording what made her follow her vision, she cited as a factor that she was “young, single, and had nothing to lose.” During a different part of the Lab, another innovator noted the role that his own economic privilege played in getting his venture off the ground; he received financial support from his family to endure not earning a salary for a year. Others noted the minimal racial diversity among the innovators. And while UpStart entrepreneurs certainly come from all walks of life – and overcome many barriers to success – many wondered who wasn’t in the room. Perhaps there are others who would make incredible contributions to Jewish life, but who don’t have the financial resources, access, or life circumstances to facilitate their taking the leap. How do we empower their leadership, too?

These are some of the questions we’ll be thinking about in 5777. And in the spirit of both Yom Kippur and design thinking, we know that it will be the actions – and the risks – we take as a community that will ultimately lead to the answers.

Listen to the full podcast episode.

Jaime Rapaport Barry is the Director of Marketing and Communications at UpStart, an organization that partners with innovators to redesign the experience and expression of Jewish life.