Taking Risks and Learning From Mistakes

About this collection: This NCFP Content Collection provides context for how generous families can assess philanthropic risk, tame and mitigate risk, and even expand their comfort zone to embrace uncertainty and learn from their mistakes.

Philanthropy is often described as society’s “risk capital.” This NCFP Content Collection provides context for how generous families can assess philanthropic risk, tame and mitigate risk, and even expand their comfort zone to embrace uncertainty and learn from their mistakes. Know of other good resources on this topic? Please suggest a resource.

NCFP Passages Issue Brief and blog posts

Expanding Your Comfort Zone: A Window Into Risk in Family Philanthropy

Passages Issue Briefs
Philanthropy is often described as society’s “risk capital.” Our generosity can support causes and ideas that business and government agencies cannot or will not. We can use our resources to inspire new ideas, challenge existing thinking, or continue supporting an organization when others won’t.

To Make a Difference, Family Philanthropy Must Take More Risks

Article
Many of us in family philanthropy are driven by a grand vision of a better world. We are motivated by bold ideas, and finding ways to use our philanthropy to make a difference and leave a lasting impact. And, at the same time, we are too often hamstrung by a…

Learning from mistakes

Failure Reports: A how to guide

Tool
This document, developed by Fail Forward, is intended to support organizations who are interested in documenting and learning from their failures, and using the process as a launch point for organizational change. It is largely based on the process developed by Engineers Without Borders Canada (EWB), an organization which has…

Samples, checklists, and templates

Case Foundation: Be Fearless framework and foundation profiles

Be Fearless: The 5 Core Principles

Tool
Those charged with finding or funding solutions to social challenges — philanthropists, government, nonprofits — seem to be moving too slowly and often operating with the same set of tools, concepts and caution of the generations before us. To tackle today's big and ever-changing social challenges, we have to Be Fearless.

Be Fearless: A framework for action

Tool
A step-by-step guide from the Case Foundation for leaders and organizations that want to be fearless and create transformative change. Inside, you'll find assessment tools, ideas and discussion prompts specially designed for social sector changemakers like you who want to make a greater impact.

Jacobs Family Foundation: Be Fearless Case Study

Impact Story
An abandoned lot, an experimental initial public offering (IPO) and a culture that believes that failure leads to learning inspired the Jacobs Family Foundation to transform its business model from traditional grantmaker to place-based funder to maximize impact without sacrificing its core values and mission. A Be Fearless case study,…

Additional resources from NCFP colleagues

Risk in Philanthropy: A Framework for Evaluation

Tool
To help both grantmakers and NGOs better identify, assess, mitigate, and plan for risk in their portfolios, Open Road Alliance offers this framework for evaluating risk. This brief framework is designed to provide grantmakers and NGOs with tools to conceptualize and describe risk and its implications within the scope of…