In her latest book, Be Fearless, philanthropist Jean Case offers five principles for living a life full of breakthroughs and purpose. We must make big bets, be bold, take risks, make failure matter, reach beyond our bubble, and let urgency conquer fear. It’s no surprise that these principles also apply to the intersection of technology and philanthropy. After all, Case is a former senior executive at AOL and early tech adopter.

As the Women’s Philanthropy Institute (WPI) gears up for its 2020 symposium – Philanthropy Plugged In: Creating Community in the Digital Age – we’re thinking about how these principles inform the experiences and stories of the more than 20 speakers who will join us in Chicago between March 31 and April 1. Register now.

Philanthropy Plugged In will look at how the digital transformation is reshaping philanthropy.  How does the use of technology influence women’s ability to connect through philanthropy, encourage more strategic giving, build a more diverse community of engaged donors, and increase giving? In this context, the symposium speakers embody the essence of Case’s five principles. Here are a few examples.

Make a Big Bet: Shannon Farley, founder and executive director of Fast Forward, recognized that declining computing costs meant entrepreneurs could start a social enterprise for as little as $5,000. She took a chance by creating an organization that focuses on accelerating impact through technology. Within five years, Shannon and her team have touched 51 million lives and raised more than $102 million for the projects they support, such as CommonLit, a completely free, common-core reading curricula platform created by a former Teach for America educator in rural Mississippi. Initially, the teacher worked at her kitchen table and served about 10,000 students. Fast Forward helped her reach 1 million users quickly and now she serves more than 5 million users.

Ellen Remmer is another woman who is making a big bet that a web-based marketing campaign will inspire more women to Invest for Better. Like many of the entrepreneurs at Fast Forward, Ellen’s own experiences motivated her goal to demystify impact investing and help women leverage all of their assets for good.

Be Bold, Take Risks: After several years in fundraising and a nagging thought about how to improve the giving process, Tiffany Williams took the leap into technology and created Givly, an app to help organizations communicate more effectively with their donors. To get it off the ground, she turned to Chicago-based WISTEM, a program designed for women entrepreneurs to develop, launch, and grow tech businesses faster.

Reach Beyond Your Bubble: Sheryl Olitsky stepped outside of her network to drive change. How else could a marketing executive for a Fortune 100 company start a nonprofit dedicated to building strong relationships between Muslim and Jewish women living in the same communities? The Sisterhood of Salaam Shalom is the first national grassroots organization of its kind with more than 3,000 women in about 170 communities across the United States and Canada working together to end religious bigotry.

Let Urgency Conquer Fear: WPI first met Alia Whitney-Johnson after she created Emerge Global, a nonprofit she founded in Sri Lanka after the 2004 tsunami. Whitney-Johnson volunteered to help those affected by the disaster and discovered that girls as young as 11 had survived rape or incest and had the courage to stand up for themselves in court after being cast out of their own families. Emerge Global provides Sri Lankan girls who have been sexually abused with the skills needed to thrive as adults.

But, Whitney-Johnson did not stop with one nonprofit. Trained at MIT as a civil and environmental engineer, she is a serial social entrepreneur. Now living in the Bay area, Whitney-Johnson learned that young people are exploited there every day. From her research, she found that youth of color and LGBTQ youth are disproportionately affected and more than half have been in foster care. They often have no place to turn. She founded Freedom Forward to create an ecosystem of service providers, technology experts, and youth to provide holistic solutions to this vexing challenge.

Make Failure Matter: At conferences we often hear only about the successes. Many of the scheduled speakers at Philanthropy Plugged In have experimented, tested, and tried different approaches before settling on the way forward. All who are using technology understand the risks and rewards and they’ll share their experiences in candid conversations.