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Tim Draimin, Cassie Robinson, Vani Jain, and Aatif Baskanderi

This discussion brings together people working at the intersection of philanthropy, innovation, and foresight to explore current and promising philanthropic approaches to addressing its paradoxical moment, understanding wicked problems, and enabling humanity-centred transformation. It is also a reference point for designers working with the tensions between futuring and defuturing, innovation and contra-innovation, the imperative for impact, and the urgency of markets and our times.

The paradox

After decades of philanthropy playing a low-profile and mostly assistential role, many foundations have become more visible as social change actors working with complexity. They have moved into the space between the shifting boundaries of infrastructures and influences and the layered, iterative relationships between people and organisations. Some philanthropic leaders are seizing the opportunity to re-design philanthropy to respond to the systemic crises we face and align with global commitments, such as the Paris Accord (2016), the UN Declaration on the Rights of Indigenous Peoples (UNDRIP), and the UN’s 2015 Sustainable Development Goals (SDGs) for 2030. In addition, some foundations, for example, the UK’s Lankelly Chase Foundation, acknowledge that “philanthropic institutions are structured in ways that inevitably repeat the harms and patterns of colonial capitalism that we urgently need to interrupt and stop”. (See their FAQs on their decision to dismantle their foundation and redistribute their assets over five years.) Other catalysts for change include a new generation of philanthropists, the rise of venture philanthropy, shifting societal values, and the influence of social movements—for instance, Black Lives Matter, Me Too, Idle No More, Fridays for the Future, and Occupy.

Arguably, systems thinking and design methodologies have influenced philanthropy and the role of foundations in society, leading to modernisation and the emergence of effective, efficient, and impactful charitable organisations addressing social and environmental challenges. Some philanthropists and charity managers have embraced a more systems-oriented mindset leading to critical insights. For example, a growing number of foundations now prioritise discretionary philanthropic capital for vital R&D investments and enable diverse experimental approaches to advance critical goals, like the transition to net zero, racial justice and social inclusion. There’s plenty of empirical evidence that modern philanthropy is becoming more humanity-centred, collaborative, innovative, and impact-focused—and, therefore, better equipped to address complex social challenges and create positive, sustainable change that crosses political, societal, and cultural boundaries.

How the philanthropy paradox shifts will depend on how well foundations co-create and engage with emerging learning systems and communities and whether they can manage, as this symposium suggests, “complexity as normality.” To this end, we explore philanthropy and the expanding global debate about its re-design—and identify some promising pathways and learnings from the experiences of newly re-designed charitable grantmaking platforms that approach system change by seeking power-sharing alliances with emerging issue-ecosystems composed of increasingly allied changemakers.


Tim Draimin

PANEL CHAIR | Tim is Senior Fellow, Community Foundations of Canada (CFC) and a Board member of Trico Charitable Foundation, Social Innovation Canada, and Green Economy Canada. He consults with nonprofits, business and government. He is a member of the hosting team of Wasan Network, which undertakes research and learning around the question: “How do we successfully apply collaborative approaches (communities, networks, ecosystems, alliances, field building) in our work for systemic social change?” He recently authored “Getting started on designing a philanthropy innovation ecosystem agenda,” published April 2023 by Philea, Philanthropy Europe Association.

Cassie Robinson

Cassie is the Associate Director of Emerging Futures at the Joseph Rowntree Foundation, on the team of Arising Quo, an emergent initiative of transformative wealth redistribution in Europe and is the field-building Co-lead at Partners for a New Economy globally. She’s the founder of Stewarding Loss—supporting civil society organizations to die, and the Co-founder of the Centre for Collective Imagination in London. She runs a Philanthropy in Transitions Lab for Philea and has Fellowships at the Institute of Innovation and Public Purpose and the Leverhulme Centre for the Future of Intelligence at Cambridge University. As a creative entrepreneur and strategic designer, she’s won awards from Nesta as a Creative Pioneer, an Ideas + Pioneers award from Paul Hamlyn Foundation and a Leader in Philanthropy award from the European Foundation Centre.

Vani Jain

Vani is a dedicated and experienced leader with a passion for systems change. Throughout her roles in medical education, mental health, corporate social responsibility and philanthropy, the key thread in Vani’s career is a true passion for meaningful, long-lasting social impact. She loves to explore and understand vital social issues with the goal of uncovering new solutions and leverage points for change. A matchmaker at heart, Vani enjoys bringing diverse stakeholders together to achieve common goals. Vani is the founding Executive Director of the Daymark Foundation, a new foundation established by the Michael McCain family to have a transformative impact on mental health. Prior to this, Vani was a Program Director at the McConnell Foundation, where she led the Foundation’s well-being and K-12 education portfolios. She has previously held roles in communications, public policy, government relations, and program development. Vani’s greatest growth and learning comes from raising her two young boys.

Aatif Baskanderi

Aatif is the CEO of The Northpine Foundation, one of the largest private philanthropy foundations in Canada, funding to unlock opportunities for Canada’s most underinvested and underserved communities. He is the Co-Founder of Salaam B’y, an anti-racism education initiative built with his wife and health equity physician advocate, Dr. Nazia Sharfuddin, based on a documentary film about his life growing up as a Muslim Newfoundlander. The film has toured internationally, including with the United Nations, screened at over 20 film festivals, won multiple awards, and Aatif’s interfaith efforts were recognized by Queen Elizabeth II by being the third Canadian to be awarded Her Majesty The Queen’s Commonwealth Points of Light Award. He was recently a Fellow with the Energy Futures Lab and a Member of the Next 30 Possibility Panel in Alberta. Other notable awards include the Memorial University Alumni Tribute Horizon Award and the inaugural GlobalNL Community Champion Award. Prior to his current role, Aatif was the Executive Director of Startup Edmonton, the city’s early-stage tech entrepreneur incubator. His previous work has spanned from designing smartphones at Blackberry, researching olive farmers in Palestine, malaria prevention education in Sierra Leone, leading Engineers Without Borders chapters around Canada, developing international science policy and diplomacy with the British High Commission, and leading innovation at a multinational electric utility company. Aatif’s education includes a Bachelor of Electrical Engineering and Master of Technology Management degrees at Memorial University, and a Master of Social Policy & Development at the London School of Economics and Political Science.


Special thanks to Tim Draimin, Senior Fellow, and Michelle Baldwin, Senior Advisor, Transformation, Community Foundations of Canada for co-organising The Philanthropy Paradox. 

RSD12-Toronto and RSD12-ONLINE




Citation Data

Author(s): Tim Draimin, Cassie Robinson, Vani Jain, and Aatif Baskanderi
Year: 2023
Title: The Philanthropy Paradox
Published in: Proceedings of Relating Systems Thinking and Design
Volume: RSD12
Article No.: pre-release
Host: Georgetown University
Location: Toronto, CAN | ONLINE
Symposium Dates: October 6–20, 2023
First published: 13 July 2023
Last update: no update
Publisher Identification: ISSN 2371-8404
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