Pivots: Positive and Candid Stories from the Field

By Becky Adelberg, Rachel Cort, Judy Levey, and
Dara Weinerman Steinberg

You know that “pivot” may be an overused term when your friend, an elementary school teacher, starts asking when this became a “thing.” And 6+ months into this pandemic we’re all feeling some degree of fatigue around trying to shift our programs and operations to emerging ways of delivering programs and services. Nonetheless, the ubiquity of the term pivot also indicates its continued importance. In early August, several organizations came together for a Charting A Course: Pivoting for Organizations at Sketchpad (a community for mission-driven Jewish organizations and entrepreneurs) to discuss past and current pivots – and the conversation was a positive and invigorating look at what’s possible, while frankly acknowledging the realities of making a pivot.

There are three types of pivots: personal, programmatic, and operational. While personal pivots are also an important topic, our session focused on programmatic and operational, and acknowledged that programmatic shifts often necessitate operational shifts (and vice versa). We wanted to share interesting examples of pivoting from both before and during the pandemic to illustrate the fundamental ideas that underlie this work and see that this skill will serve us well in both ordinary and extraordinary times. An earlier article in eJP shares some of the ideas that were reiterated during the panel of defining what you want to achieve and what you want to measure. During the panel, three other themes emerged through the examples of how to successfully pivot. First, that a pivot is really an ongoing experiment. Second, that it often brings new possibilities to light. And third, that being attentive to audience needs is a key factor in successfully creating and adapting your work.

The Youth (Programs) are Alright But We Can Make Things More Relevant!

The Jewish Council on Urban Affairs mobilizes the Jewish community of Chicago to advance meaningful social change in coalition with diverse community groups. One of JCUA’s programs focuses on youth engagement, in which teens and college-aged students learn community organizing through a Jewish lens.

In recent years, their two-week summer immersion program for teens, Or Tzedek, had been struggling with enrollment due to the many competing summer opportunities in the region. It became evident that JCUA needed to revitalize Or Tzedek by developing a new structure for the program. They proceeded to co-design a new Or Tzedek with deep engagement and input from key stakeholders, including youth, program alumni, parents, and youth educators. Stakeholders reached a consensus that JCUA should offer Or Tzedek as a full-year program to coincide with the academic school year. The program envisioned would have several monthly touchpoints for training, actions, and community building, guided by dynamic staff with experience in community organizing and youth leadership development.

Initially, JCUA wasn’t certain that the newly envisioned Or Tzedek would capture the attention of teens otherwise busy with demanding academic endeavors. However, their pivot took place at exactly the right moment, as youth were coming together in high schools as leaders and change agents. (Youth have always been agents for social change, but our current political environment made the shift especially timely.) JCUA’s deep experience in social justice work and their ongoing grassroots campaigns around police accountability, immigration and progressive taxation provided a fertile environment for youth engagement. 

Rebranded as the Or Tzedek Teen Internship program, and complementing JCUA’s similarly-structured College Fellowship program, the program is now in its second full year, drawing 15 teens from across the city and suburbs to learn about critical issues, policy implications, and disinvested communities. Recent Or Tzedek participants have reported that they are animated and activated by their immersion in the social justice landscape of Chicago. They appreciate the opportunity to learn with JCUA about systemic inequality and racial injustice. JCUA has been working in partnership with diverse communities in Chicago for over 50 years, and the teens recognize the unique opportunity they have to get exposure to how JCUA’s work in Chicago has had a profound impact.

Following the program, the teens are able to continue to pursue this work as valued JCUA members or apply their skills to organize for change in their own communities. Organizationally, the redesigned Or Tzedek program is now fully enrolled and thriving as a key programmatic piece of JCUA’s multigenerational Jewish community organizing.

Life After Death over Dinner

For Becky Adelberg, Chicago Manager of Reboot, the major pivot was adapting the program Death Over Dinner: Jewish Edition as the first pandemic stay at home orders were rolled out. Death Over Dinner: Jewish Edition (DOD-JE) is a conversational program that guides participants in speaking about death to help them uncover what is important to them. These intimate conversations were predicated on being in person. Reboot moved to training facilitators online, hosting DOD-JE virtual gatherings and creating a virtual toolkit. Reboot was already accustomed to working virtually and rapidly testing programs. They quickly uncovered that the conversation was even more rewarding during a pandemic and created additional prompts that spoke to the specific moment.

This pivot spurred three other new programs. The first was Death over Expression. Recognizing both Zoom fatigue and that people felt like they were doing a lot of talking in their lives, but not much creating, Reboot developed a parallel program that focused on other ways of expressing feelings about death, life and this moment we are living in through writing exercises, music and art. This pivot had the added benefit of paying artists to facilitate these virtual gatherings at a time when many of their job and income opportunities had been eliminated by the pandemic. It also responded to the need for a creative outlet. The second new program is Death Over Dinner: Ask An Expert which begins by accessing one of the prompts from the many DOD-JE decks (Jewish Edition, Interfaith, Vegan, LGBTQ+), followed by an expert presenter delving into the many topics touched upon in the DOD conversation from Jewish views on the afterlife, to ethical wills, to finances and more. The third new program in the works is Death over Racial Injustice (rolling out soon). This extends Reboot’s commitment to providing programming that responds to the current moment that was successful in the other pivots. In addition, Reboot had been building relationships and having conversations with social justice organizations over the past several years. Reboot recognized that it was now time to collaborate with those potential partners and leverage their other Death Over Dinner pivots, to co-create a timely and intimate conversation about race.

Reboot utilized some organizational strengths in making these pivots: the existing virtual mindset in the organization and prior relationships with artists and social justice advocates. What could have been one pivot (online training) turned into a series of experiments. Reboot shifted, adapted and made changes when necessary from creating breakout rooms when participants were above the 6-8 suggested number for these talks to adapting on the spot when the number of registered participants changed (increased/decreased). The new programs led to other unexpected programs as well as an unexpected benefit to staff – as programming went virtual, regional staff had the opportunity to collaborate across communities and take on different responsibilities (since program execution wasn’t tied to geography) and to work together on ideation, program development and facilitation. Becky also pointed out that the audiences knew these were experiments and didn’t expect perfection; a great reminder to all of us, as consumers and producers of Jewish programming that some kindness about rough edges can lead organizations to take more interesting risks and create great things.

Some of Reboot’s other contributions during this year have included co-producing the “Saturday Night Passover Seder,” DAWN – an all night virtual Shavuot cultural arts festival with the Jewish Emergent Network, the “Joy of Quarantine” YouTube series, “In the Quarantine with Steve Bodow” podcast series, offering a series of virtual programs originally designed to be at the Reboot Ideas Festival in March, the addition of 10 pandemic prompts to the popular 10Q annual reflection project offered during the 10 days of repentance and working with Hillel international to offer a Higher Holidays livestream experience for both Rosh Hashanah and Yom Kippur.

Shabbat Experimentation Sets the Virtual Stage for High Holy Days

Mishkan is an independent post-denominational spiritual community based in Chicago. One of the core questions they ask themselves is what Jewish space can look like. Focused on innovative worship and community, as the pandemic hit they had to give up, one by one, things they formerly thought were essential – building community over shared Shabbat meals, meeting in person at all, and even voices harmonizing together in prayer and song. However, constraints breed creativity. Since Mishkan didn’t have a space of their own, previously the cost of space was a constraint and they held two Friday night and two Saturday morning services a month. However, with the low barrier to entry created by being able to stream services on Facebook they could begin streaming Shabbat every Friday and Saturday. This allowed them to rapidly prototype while responding to the need their community had to connect with others and find spiritual solace right after the first stay at home orders. This prototyping yielded several innovations over several weeks; including trying out digital greeters, creating slides of prayer book to lower barriers to entry, inviting different creative contributors to participate in services (not just local spiritual and song leaders), and improving access with the addition of an ASL interpreter, and later utilizing captions. Mishkan also learned where they didn’t have expertise – specifically that as an organization that had previously focused on event production, they now needed to develop a new expertise in broadcasting and media skills.

Mishkan also intuited that more was needed to help people maintain a sense of connectedness and community in these times. They invested in curating small groups around anti-racist learning and began offering a daily online minyan, along with other small-group opportunities. These groups have been hugely important to maintaining community members’ sense of connectedness to one another and to Mishkan, which ultimately enabled them to grow their membership/Buildership even in these challenging times.

These experiments set them up for the bigger challenge – the High Holy Days. Knowing they would have to pivot to socially-distanced and online opportunities, these earlier pivots gave them valuable information to assess what they had learned and what they still didn’t know, both about their audience and on the technical side. The planned series of High Holy Day events draw on the new ways they can build community and meaningful spiritual engagement, as well as utilizing new skills about creating digital content. Additionally, they partnered with a digital production firm for the High Holy Days to help with the technical learning curve.

Rachel also noted that it was important for her and the team to grieve what had to let go. They had to acknowledge that their biggest professional project of the year would be radically different from the past, and moreover this was also a shift that would have profound impacts on how they personally celebrated the holidays as well.


Judy, Becky, and Rachel, together with their colleagues, were willing to keep experimenting, find the best in their work and build on it, and keep theri audience in mind. Creativity, relevance, and accessibility are all hallmarks of JCUA, Reboot, and Mishkan’s pivots. These pivots provide examples not only of what some quick, but thoughtful experiments can lead to in terms of organizations fulfilling their missions, they also provide an inspirational look at what our collective Jewish future could hold – relevant, fulfilling, exciting, moving opportunities – tackling social justice, the way we live our lives, nurturing our souls and communities to become our best selves.

Becky Adelberg is Reboot’s Chicago Manager. Her experience involves conceptualizing and executing large community events, overseeing educational and social programming, volunteer management, leadership development, travel abroad and entrepreneurship programs. She is also the Founder of Community Connect Consulting, a mentor at 1871 Chicago and a voice over artist.

Rachel Cort has been the Executive Director of Mishkan for the past five years, overseeing its growth from a dynamic start-up to a thriving spiritual community serving over 4,000 unique people in 2019.

Judy Levey has been the Executive Director of JCUA since 2012, leading JCUA’s embrace of a community organizing model to advance its core work. Her extensive experience in community and program development have helped JCUA to spearhead new programs for racial justice and leadership training.

Dara Weinerman Steinberg is Principal of Steinberg Consulting which counsels nonprofits and philanthropists to advance their strategy and organizational development.

Sketchpad, which hosted this event, is a shared workspace in Chicago and a community for innovative, ?mission-driven Jewish organizations and entrepreneurs.