Upswell Chicago 2019

We have work to do. Let’s – Do it together. Share more knowledge. Coordinate more activities. Inspire one another. Energize one another. Heal. Make each other more comfortable. Make each other more uncomfortable. Push. Be brave. Get the job done. These were the messages from Upswell Chicago. Here is how the event was described:

Upswell Chicago isn’t a conference. It’s a high-energy, three-day experience in community building, where changemakers of every stripe are invited to learn, share, connect, and re-charge. It’s where local know-how meets national ambition in to bridge divides and build relationships that just might change the world.

Rousing Main Stage speakers, in-depth workshops, immersive neighborhood exploration, hundreds of creative events, thousands of diverse voices and big thinkers from across the country – Upswell is going change the way you think about changework.


Please read my earlier post on the Equity in the Center (EiC) pre-convening focused on building a race equity culture. It was excellent, and I was very pleased to see Independent Sector create this opportunity to team with EiC to deliver this very strong learning and feeling experience.

Day One

My official Upswell experience started with the workshop presented by the Stanford Center on Philanthropy and Civil Society: A Digital Policy Roadmap for Civil Society. As the presenters pointed out, civil society increasingly depends on digital data and infrastructure, which creates risks and laws around data privacy and ownership and concentrations of power. Yet many nonprofits are not prepared to mitigate the risks or help shape the laws to protect themselves, their missions, and those they serve.

We were powerfully engaged to think about the digital issues through breakout groups playing a game in which we matched social issues with data security and governance issues CardsAgainstHumanity-style. I plan to use this game for our business of nonprofits class at Columbia University. Many thanks to Nicole Ozer, the Technology and Civil Liberties Director for the ACLU of California, who helped our table play the game, which was made even better because I had the chance to sit next to and play with Sherry Salway Black (more on her below).

The next workshop I attended was titled: Enough Talk — How Foundations Can Live Their Racial Equity Strategy. The panelists started by each stating something they were excited about and the list included spaces created for young leaders, foundations rebuilding (not modifying) inequitable structures, and grantmakers holding grantees accountable for equity initiatives. Among the many great takeaways were the following:

  • Foundations should make their processes transparent for their grantees to ensure equitable practices are not dependent on just one person of color contact person/partner at the foundation.
  • Foundation staff can call out directors/trustees/executives that are propagating inequitable practices (e.g., asking 3 years of financials from POC-led organizations but not from the opera or ballet). At the base of white supremacy is white mediocrity. Challenge it.
  • The phrase “I have the check, I don’t have the answers” needs to shift to “Because I have the check, I don’t have the answers.”
  • Foundations should give grantees the space and safety to be open, honest, and aspirational about what they need. Have conversations. Be ready to cede power to intermediate funders that have deeper relationships with the grantees.
  • National funders that fund in the space of poverty alleviation must fund in the South.
  • If your foundation wants to fund education, positive outcomes for young people, and equity, make sure it funds arts and music. It’s not just about the product; it’s about communication, storytelling, creating relationships and trust, and mental health.
  • Foundations can require grantees to diversify their boards tactfully (e.g., withholding part of a grant until receiving a diversity, equity, and inclusion (DEI) plan or achieving a DEI benchmark.

From the Main Stage, Heather Miller, Executive Director of American Indian Center of Chicago, delivered a land acknowledgment that recognized and respected Indigenous Peoples as the original stewards of the land, and reminded us of the unwavering relationship between Indigenous Peoples and their traditional territories.

Dan Cardinali, President and CEO of Independent Sector (IS), then delivered his opening remarks about Upswell. He described how organizers learned from last year’s inaugural Upswell and where the attempt to reimagine the IS annual conference went well and where it ran into some bumps. He emphasized receiving feedback from those with and without positional authority in various communities with the help of regional accelerators. Dan then discussed the changes made from last year’s convening, including the creation and communication of more guided pathways from out of the 300,000 possible options that a participant could select. Personally, I found the Upswell app very helpful in creating my path. Throughout his monologue, Dan accentuated the importance of continually shaping Upswell with our collective wisdom. And while we should each own our views and expertise, we need to be humble and recognize our limitations.

Swami Jaya Devi Bhagavati followed Dan on the Main Stage, humorously noting that Dan left his phone at the podium and that she could do a lot of damage with it. Not a comment I expected from a Swami [lol]. But then she powerfully stated: “Authentic leadership is rooted in self-awareness.” Swami Jaya Devi illustrated how meditation weaves together our dualities into a harmonious wholeness and self-awareness. To close, she led us to take three breaths. As my wife has also been teaching me, the physical poses are just a minor part of true yoga. And true yoga can improve the quality of our lives and our changemaking work.

My first day concluded with attending the Independent Sector Members Town Hall. At this interactive forum, we heard from several IS leaders about IS plans and initiatives and were invited to share our thoughts, questions, and perspectives. The forum made me think hard about IS’s choices about its policy priorities and focus on creating space for its members, that admittedly have much greater and deeper expertise on most specific policy matters, to advocate on hot button issues like immigration, racial equity, and climate change.

Independent Sector advocates for policies that encourage Americans to contribute to the charitable causes of their choice by providing tax deductions for their gifts and tax incentives for volunteer service, removing tax obstacles to charitable gifts, and maximizing gifts from private foundations.

The IS Vision, Purpose, and Beliefs follow:

Vision and Purpose

Independent Sector advocates for policies that encourage Americans to contribute to the charitable causes of their choice by providing tax deductions for their gifts and tax incentives for volunteer service, removing tax obstacles to charitable gifts, and maximizing gifts from private foundations.


Collective Solutions – We find better solutions to complex problems when diverse groups, committed to the common good, come together in networks of responsibility.

Opportunity, Respect, and Inclusiveness – Societies thrive when all people have equal opportunity to succeed, are treated with respect, and can fully participate in the life of the community.

The Power of the Charitable Community – By taking bold risks, encouraging creativity, fostering collaboration, and inspiring optimism, the sector is a vital, leading force in improving lives and the natural world, and strengthening democratic societies.

Responsible, Transparent Institutions – Democratic societies rely on transparent, ethical, and accountable institutions and people.

I certainly understand the decisions made by IS regarding its path. But my sentiments, which I rapped to the 1,500 attendees of the Independent Sector Annual Conference in 2015, still remain:

… And I.S. that’s what we expect of you
Courageous positions on each issue
‘cause when the problems are so big and getting biblical
We can’t just say that we ain’t political.

Independent Sector Threads: Oakland Style (full lyrics)

Regretfully, work prevented me from attending one of the Community Dinners, but they looked awesome and further exemplified how Upswell evolved from a single national organization conference to a national and regional convening with deeper connections between IS and the host region and some of its anchor organizations.

Day Two

I was greatly looking forward to the morning’s first session, Presidential Campaign Forum on the Nonprofit Sector, at which senior representatives of some of the presidential campaigns were to share their candidates’ positions on a wide range of issues that impact nonprofits and civil society. Unfortunately, because of weather or last minute scheduling issues (perhaps partly related to the impeachment hearings?), the session had to be restructured on the fly with only one campaign’s representative present.

Fortunately, the session was restructured into two thought-provoking sessions at which I noted the following takeaways:

  • If you don’t care about politics, it’s because you have the luxury [privilege] of not having to care about politics.
  • Nonprofits need to be persistent and concise in getting their messages to the campaigns, and they should have an ask at the end. Story telling is extremely effective in conveying a need and/or a solution. You should tug at their hearts and connect candidates with their communities.
  • Nonprofits should ask candidates what they think about the charitable deduction and making it more equitable. It may not even be on their radar and they may be swayed by the voices they hear.
  • Tax policy is critical for all of us to understand better so we can be involved in the debates and not just leave it up to others. It’s a core issue for developing a society that works for all of us.
  • Philanthropy is more timid than it should be. Foundations should fail fast and learn (“fail forward”). Experimentation can be advanced through more general operating support that allows those who know to take informed risks. And the grantee must have a voice on the desired results.

I next attended a focus group discussion on Understanding the Effects of Tax Policy on Charitable Giving. The universal charitable deduction (UCD), variants of the UCD, and a 25 percent tax credit were contrasted. Key takeaways, which are also described in this report by the Indiana University Lilly Family School of Philanthropy in much greater detail, included:

  • Providing a non-refundable 25% charitable giving tax credit to non-itemizers has the largest positive impact on both the amount of charitable giving dollars ($37 billion) and the number of donor households (10.6 million) of the five policy options analyzed. However, it is also the most “expensive” proposal for United States (U.S.) Treasury revenue (-$33.0 billion).
  • Non-itemizer charitable deduction (i.e., UCD): Extending the charitable deduction to non- itemizers could generate up to $26 billion in additional donations and induce up to 7.3 million additional households to donate in 2021. It would reduce Treasury revenue by up to $22 billion.
  • Non-itemizer deduction with a modified 1 percent floor: The non-itemizer deduction with a modified 1 percent floor is also estimated to have the largest net impact on charitable giving dollars compared to the cost to the Treasury; it could bring in up to $7 billion more in charitable giving than is lost in Treasury revenue. However, it brings in the fewest donor households.
  • Non-itemizer deduction with a $4,000/$8,000 cap:The non-itemizer deduction with a $4,000/$8,000 cap has the largest impact on donors per dollar cost to the Treasury. This policy would bring in up to 352 new donor households per million lost in Treasury revenue.

Michele Norris, former host of NPR’s All Things Considered, founder of the Race Card Project, and Executive Director of The Bridge (Aspen Institute), spoke on the Main Stage at noon and delivered perhaps the more memorable insight of the convening (liberally paraphrased below):

Finding common ground may not always be the answer to conflict. You know what holds a bridge up? Oppositional force. It’s called tensile strength.

Next up, a focus group on Oversight and Our Sector: Building a Better Regulatory Framework. Cindy Lott, Academic Director and Senior Lecturer in Discipline for the Master of Science in Nonprofit Management program at Columbia University’s School of Professional Studies, led the open discussion. A small but accomplished group of participants discussed various policy concerns regarding the regulatory and enforcement framework for nonprofit oversight, including those related to online solicitations, multistate registrations, opportunity zones and the participation of small investors, and whistleblowers.

At the Leadership Awards Reception, the John W. Gardner Leadership Award was awarded to Sherry Salway Black. As a member of the Awards Committee, I can attest to how deserving Ms. Black is, and it was an honor to see her receive the Award. The second award winner of the night was Megan Jacobs, recipient of the 2019 American Express NGen Leadership Award. The American Indian Center, the primary cultural and community resource for nearly 65,000 American Indians in Chicagoland’s six county region, performed at the Reception.

Day Three

Work (and exhaustion) got in the way of my participation in some of the morning workshops, which included several on policy and advocacy; diversity, inclusion, and racial equity; and religion and spirituality.

The Closing Main Stage featured Chicago Mayor Lori Lightfoot, who discussed equitable change in Chicago based on “comprehensive investment, comprehensive coordinated economic planning, and true access to community building blocks, making sure we are empowering and strengthening individuals and families and communities by investing in them and frankly just acknowledging and seeing them through our government policy and in partnership with business and philanthropy.” Eddie Bocanegra and Policy Link CEO Michael McAfee engaged in a challenging discussion of gun violence and healing. And Tonika Johnson and Roy Kinsey performed. Kinsey rapped:

You live from your flesh
You should live for your mind
You should die for death (only)
And live for your life

You should just stick around
Find out what you like
Seek what gets you down
Find your purpose for life

As a bonus, for my own self-care, after checking out of the hotel, I took a brisk walk to the one of the world’s best museums, the Art Institute of Chicago, and re-energized myself before my flight home and the opportunity of reflecting and synthesizing all I learned. I’ll see you all in Pittsburgh for Upswell 2020.

Additional Resources

Upswell Chicago: Day 1

Upswell Chicago: Day 2

Upswell Chicago: Day 3