Who Gets To Fail? Reflections from Kataly’s Board

The Kataly Foundation
5 min readOct 12, 2022

Within an institution, fear of failure can originate from leadership. If people at the top of an organization are averse to failure, or projects turning out differently than expected, a culture of fear trickles down to the rest of the team. Alternatively, embracing experimentation and letting go of an attachment to a particular brand of success can set a tone where staff feel empowered and confident in their abilities.

At Kataly, our board members have worked actively to de-center themselves and trust the staff to make strategic decisions for the Foundation without fear. In this Q&A, two of our board members, Regan Pritzker and Chris Olin, share reflections on how they have ceded decision-making power without disengaging, what failure brings up for them, and what it means to lean into the messiness of relationships.

Photo credit: Bethanie Hines

As board members and founders of Kataly, you both have made a strong commitment to de-centering yourselves and ceding control and power to the team. What has come up along the way?

Regan Pritzker: The biggest issue has been how to engage appropriately. De-centering doesn’t mean passing the buck on our commitment to the goals of the Foundation or the goals of this work. It has been challenging to balance being supportive and finding a way to participate, while still ceding decision-making control to other people on the team. It’s not about stepping back completely, it’s being really clear about governance and decision-making processes so that my voice isn’t overbearing because I was the donor at the beginning. I don’t feel a sense of attachment to the resources or the decision making, and I’m excited those areas sit with the team. But I think as a donor and a funder you have to be mindful of the risk that your voice gets overly valued because of a fear you’re going to change something if the team isn’t agreeing with you. There could be a sense of obligation to meet the desires of the donor — I trust our team to not fall prey to that because it’s been an open topic of conversation.

Chris Olin: The process of believing that I could be in the room and listen to the conversation and share thoughts from time to time without influencing the outcome required a lot of explicit conversations with folks: can I be here and not disrupt your process? I kept being explicit with the team that they have discretion to tell me when I shouldn’t be in the room. The only thing that has been challenging is when I’m in conversations with other funders trying to network. When folks come to me with projects they want Kataly to fund, I’ve had to educate people to say I don’t have any influence over the program staff.

How do you manage situations where people/organizations you have previous relationships with come to you with requests for funding or access?

Regan: If someone reaches out to me with a request for funding, it is genuinely complicated and confusing because we are still doing philanthropy individually — there is a messiness to those relationships and partnerships. We are giving resources to some of the groups being funded by Kataly. With one organization, I was helping them raise money and Kataly also gave a grant. The organization would ask me to participate in calls and be part of their fundraising work because I had already established a relationship, but I also had to say specifically that they needed to be in touch with the team at Kataly. People generally want to get upstream to the donor. I had to make clear that I was there in my own capacity, but I really had to spell out the relationships and decision making capacities.

What came up for you as you were thinking about failure?

Regan: One theme was the idea of who gets to fail and what is failure. There’s an anti-failure culture in philanthropy, whereas there’s a pro-failure culture in tech — fail faster. But we think about our grantee community as organizations, people, and projects where the impact of failure is much more damaging potentially. The goal for Kataly is to be partners with these projects so that they do not experience failure in a damaging way. We want to be the first phone call versus the last when there is a challenge, and we’re not going to be judgmental if a group hits a stumbling block. We know that the groups we’re funding are facing headwinds. The risk of failure is quite high, and on the other hand, what we want for them is an opportunity to experiment to launch and model a project. We want to avoid a judgment of success or failure as a binary. We are not trying to protect ourselves from some kind of failure.

Chris: We want the staff to feel liberated from a dynamic that seems to be very common in philanthropy about how the board is going to respond either to a docket or to reporting and evaluation. The last thing we want is for the staff to be worried about how we would perceive challenges grantees are facing. We want to take any concern about telling us about failures off the table.

What are the ways that the two of you feel have failed in relation to Kataly?

Chris: Once the Mindfulness and Healing Justice team staff was on board, I switched my focus to do donor outreach. I have been disappointed at the extent to which funders already have their own areas of focus and how different Kataly’s areas of focus are. My goal still is to motivate other funders to fund in the areas we do. I’ve had many initial conversations with folks, and there’s lots of interest, but when it comes down to moving money, it all seems to peter out. Speaking to mainstream funders and trying to get them to create a new focus on social justice has been much harder than I thought it would be.

Regan: I would echo that at the foundation level as well. Kataly is a big project, but it’s not big enough to contend with systems we’re trying to take on. It continues to be a goal for me to get other funders to think about decision making and who is at the table to decide where resources go.

This blog post is a part of a series from the Kataly Foundation on failure and philanthropy. Read the first post here.



The Kataly Foundation

The Kataly Foundation moves resources to support the economic, political, and cultural power of Black and Indigenous people, and all communities of color.