Be Fearless

In the bustling corridors of America Online during the 1990s internet revolution, a young executive named Jean Case was helping to connect millions of Americans to the digital world for the first time. Her journey from a small Midwestern town called Normal, Illinois, to becoming one of the most influential philanthropists and social innovators of our time represents a remarkable transformation driven by an unwavering commitment to empowerment and change.

Case's story is one of deliberate fearlessness in the face of uncertainty. From her early days navigating the male-dominated tech industry to her current role as Chairman of the National Geographic Society and CEO of the Case Foundation, she has consistently chosen the path of greatest impact over the path of least resistance. Through her experiences building one of the first major online communities and later dedicating her wealth and expertise to social causes, readers will discover how authentic leadership emerges from embracing discomfort, learning from setbacks, and building bridges across unlikely partnerships. Her approach to creating transformational change offers both inspiration and practical wisdom for anyone seeking to make their mark on the world.

Jean Case's transformation from a small-town girl to a global changemaker began in the most unlikely of places. Growing up in Normal, Illinois, during the 1960s, she lived in a world of contradictions. Her backyard was a cornfield, yet her mind wandered far beyond the narrow rows of corn stalks. Her family struggled financially after her parents' divorce, with her mother working night shifts as a waitress to make ends meet. Yet it was precisely these early challenges that would forge the resilience and empathy that would define her later work.

The pivotal influence in her early life came from her German immigrant grandparents, who had arrived in America during the Great Depression with nothing but determination. Her grandfather hauled pianos up flights of stairs while her grandmother made beer in their bathtub during Prohibition. Their hotel business in nearby Bloomington became young Jean's first classroom in entrepreneurship, where she learned to greet guests and discovered her natural ability to connect with people from all walks of life.

Her mother's fearless decision to uproot the family and move a thousand miles away to Fort Lauderdale when Jean was eleven demonstrated the kind of bold risk-taking that would later characterize Jean's own approach to life. This leap into the unknown, made with few resources and no connections, was driven purely by a mother's belief that her children deserved better opportunities than their current circumstances provided.

The scholarship to a new Presbyterian school that Jean received after testing above grade level became her gateway to possibilities she had never imagined. Here, she encountered teachers like Miss Neal, who went out of her way to nurture a latchkey kid new to town. These early experiences of receiving philanthropy while witnessing the struggles of working-class families instilled in Jean both gratitude for opportunity and a deep understanding of how transformative support can be when it reaches those who need it most.

Perhaps most significantly, her time living with her grandfather during her teenage years taught her the discipline of seizing each day. His daily ritual of pounding on her bedroom door at 7 AM with the cry "It's seven a.m.! Are you going to sleep all day?" became a metaphor for approaching life with urgency and purpose. This early lesson in not wasting precious time would later drive her sense of mission in both business and philanthropy.

Jean Case's entry into the technology world came at a moment when the digital revolution was still a distant dream for most Americans. In the early 1980s, when she joined her first online service company, only three percent of Americans were online, and they spent an average of just one hour per week connected. The idea of democratizing access to information and communication seemed almost fantastical, yet it became the driving force behind her most transformative work.

Her role at America Online represented the ultimate big bet, both for the company and for her personally. When she left a secure position at General Electric to join the scrappy startup that would become AOL, friends and colleagues questioned her sanity. Why would she abandon the safety of a Fortune 500 company for an uncertain venture in an unproven industry? The answer lay in her recognition that AOL's mission aligned perfectly with her core values of empowerment and access.

The early days at AOL were marked by constant uncertainty and the need for creative problem-solving. When Apple abruptly canceled their partnership deal, leaving the young company scrambling for survival, Case and her colleagues had to quickly pivot and create their own brand. This crisis became an opportunity to build something entirely new, freed from the constraints of working under another company's umbrella. The $3 million termination settlement from Apple became the seed funding for what would become one of the most successful internet companies of all time.

Case's approach to building AOL's user base demonstrated her intuitive understanding of human psychology and community building. Rather than focusing solely on technology features, she emphasized the social aspects of the online experience, creating virtual communities where people could connect around shared interests. This vision of the internet as a place for human connection rather than just information consumption was revolutionary for its time.

The success of AOL, which grew to serve 30 million subscribers at its peak, validated Case's belief that technology could be a democratizing force. Her work helped bring the internet to mainstream America, transforming how people communicated, learned, and conducted business. This experience taught her that the biggest opportunities often lie in ideas that seem impossible to others, and that success requires not just vision but the courage to act on that vision even when the path forward is uncertain.

The path to transformational leadership is rarely smooth, and Jean Case's journey included several high-profile failures that would have derailed less resilient individuals. Perhaps none was more public or painful than the PlayPumps initiative, an ambitious effort to bring clean drinking water to sub-Saharan Africa through an innovative technology that used children's merry-go-rounds to pump water. Launched with great fanfare at the Clinton Global Initiative, the project seemed to embody everything Case believed about innovative solutions to global problems.

The PlayPumps failure taught Case one of her most valuable lessons about leadership: the difference between admitting defeat and learning from setbacks. When it became clear that the program wasn't meeting its objectives, Case faced a choice that would define her approach to failure for years to come. She could quietly withdraw from the project and hope the failure would go unnoticed, or she could publicly acknowledge what went wrong and share those lessons with others.

Her decision to write "The Painful Acknowledgment of Coming Up Short" represented a watershed moment in both her personal development and her approach to philanthropy. By openly discussing the failure, she discovered that transparency about setbacks could be just as valuable as celebrating successes. The response from fellow philanthropists and social innovators was overwhelmingly positive, with many thanking her for having the courage to discuss failure openly in a sector where such honesty was rare.

This experience led to the creation of "fail fests" and safe spaces for nonprofit leaders to discuss their setbacks and learn from each other's mistakes. Case recognized that the social sector's aversion to discussing failure was actually hindering innovation and preventing organizations from taking the kinds of risks necessary to achieve breakthrough results. By normalizing conversations about failure, she helped create a culture where experimentation and learning were valued over perfect track records.

The PlayPumps experience also reinforced Case's belief in the importance of staying true to core values even when specific tactics fail. Her commitment to providing clean water access didn't waver; instead, she redirected her efforts toward supporting Water For People, which took a more comprehensive approach to the same problem. This demonstrated that strategic failure in one area doesn't negate the underlying mission, and that persistence often requires the flexibility to change methods while maintaining focus on ultimate goals.

One of Jean Case's most distinctive qualities as a leader has been her ability to forge partnerships between organizations and individuals who might never have found common ground without her intervention. Her approach to collaboration goes far beyond traditional networking; she actively seeks out partnerships that might seem counterintuitive but offer the potential for exponential impact.

Her work on the President's Emergency Plan for AIDS Relief (PEPFAR) exemplified this philosophy in action. Bringing together conservative Christian leaders, Catholic bishops, pharmaceutical executives, and liberal AIDS activists required navigating deeply held beliefs and political differences. The tension in the Roosevelt Room was palpable as these unlikely allies grappled with fundamental disagreements about abstinence education, condom distribution, and abortion policies.

Yet Case understood that the urgency of the AIDS crisis in Africa demanded that these groups find a way to work together. Her role wasn't to eliminate the differences between these stakeholders but to help them focus on their shared commitment to saving lives. The resulting $15 billion commitment represented one of the most successful global health initiatives in history, demonstrating that even the most unlikely partnerships can achieve extraordinary results when united by a common purpose.

The National Geographic Society partnership with 21st Century Fox represents another example of Case's willingness to embrace unconventional collaborations. As Chairman of the Board, she helped navigate the complex process of partnering a 130-year-old nonprofit scientific organization with a major media and entertainment company. The partnership seemed counterintuitive to many, but it has allowed National Geographic to reach nearly a billion people globally while maintaining its commitment to science, exploration, and education.

Case's approach to partnership building is rooted in her recognition that diversity of perspective leads to better outcomes. Whether she's working with corporate leaders, government officials, or grassroots activists, she consistently seeks out voices that might challenge conventional thinking. This approach has led to innovations in everything from disaster relief to entrepreneurship support.

Her Rise of the Rest initiative with her husband Steve Case exemplifies this partnership philosophy on a national scale. By bringing together investors, entrepreneurs, and political leaders from across the American heartland, they've helped shift attention and resources away from the coastal elite centers toward the innovative potential that exists in every community. This work demonstrates Case's belief that breakthrough solutions often come from unexpected places when the right partnerships are formed.

The defining characteristic of Jean Case's leadership philosophy is her belief that urgency must be allowed to conquer fear when important work is at stake. Throughout her career, she has consistently chosen action over analysis paralysis, recognizing that perfect information is rarely available when the most important decisions need to be made.

This principle was tested dramatically during the early days of the internet revolution. When America Online was still a struggling startup, Case and her colleagues faced a critical decision point when Apple canceled their partnership. They had limited time, resources, and information about whether their alternative plan would succeed. Rather than conducting endless market research or seeking guarantees of success, they chose to act quickly and decisively, using the three-month termination settlement to launch their own branded service.

Case's approach to urgency is not about recklessness but about recognizing that inaction in the face of important challenges carries its own risks. Her work in global health, education, and disaster relief has consistently demonstrated that waiting for perfect conditions or complete consensus often means missing the opportunity to help those who need it most. Whether responding to the Haiti earthquake, the Ebola crisis, or educational inequity, she has shown that effective leaders must be willing to act on incomplete information when the stakes are high.

The concept of "being the one" is central to Case's philosophy of leadership. Rather than waiting for someone else to address problems she encounters, she consistently asks herself whether she can be the person who steps forward to make a difference. This mindset led to her decision to leave the private sector and dedicate her wealth to philanthropy, but it also shows up in smaller daily decisions about where to focus her time and energy.

Case's call to action extends beyond individual decision-making to organizational culture. At the Case Foundation, she has created systems that reward calculated risk-taking and experimentation. The organization's color-coded assessment system includes red flags for initiatives that may fail, and Case has expressed concern when no red projects appear on their annual review, recognizing that this might indicate insufficient boldness in their approach.

Her message to current and future leaders is both simple and challenging: the world needs people who are willing to step forward when they see problems that need solving. The combination of her personal story, practical wisdom, and passionate advocacy creates a compelling case for choosing courage over comfort and action over analysis when faced with opportunities to make a meaningful difference.

Jean Case's life demonstrates that extraordinary leadership often begins with ordinary circumstances transformed by an extraordinary commitment to service and growth. Her journey from a small Midwestern town to global influence shows that the most important qualification for creating change is not privilege or perfect preparation, but rather the willingness to act when opportunity and need intersect. Her failures have been as instructive as her successes, proving that resilience and transparency can turn setbacks into valuable learning experiences for entire sectors.

The principles Case has developed through decades of experience offer a practical framework for anyone seeking to make a meaningful impact. Her emphasis on making big bets, taking calculated risks, learning from failure, building diverse partnerships, and allowing urgency to overcome fear provides a roadmap that can be applied across industries and contexts. These lessons are particularly valuable for leaders who want to create systemic change rather than incremental improvements. Case's story will resonate most strongly with entrepreneurs, nonprofit leaders, corporate executives, and anyone who has ever felt called to tackle problems that seem too big or complex for individual action but too important to ignore.