In this Virtual Gathering, Chip Conley, Founder and CEO of Modern Elder Academy (MEA), joined Cheryl Rosner, Board Chair of Conscious Capitalism, to discuss how to discover purpose during life’s second phase. Chip shared insights on the questions we should ask ourselves to uncover our purpose, the importance of intergenerational, community-focused connections, and why he believes life improves with age.
Drawing from his journey, Chip shared three key takeaways to help individuals transitioning into “second adulthood” channel their wisdom and purpose for the next stage of life:
The Right Questions Can Unlock New Paths
During a challenging period, Chip adopted a practice of journaling in what he calls his “wisdom book.” Each weekend, he spent 20 minutes reflecting on key lessons from the week, asking questions like:
- “What was a painful lesson, personally or professionally?”
- “How will this serve me moving forward?”
- “How can I turn this into something meaningful?”
- “How can I transform this experience into wisdom?”
This reflection led to a breakthrough moment—what Chip calls his “Baha aha.” While running on the beach, he wondered why midlife wisdom schools didn’t exist to help people make sense of their personal and professional lessons while charting a path forward. This realization inspired the creation of MEA, designed for those in their 40s to 60s who seek relevance and growth while balancing teaching and learning. Chip calls this approach “being a mentor and an intern at the same time.”
Support Systems Are Critical in Midlife
Midlife often brings significant transitions—career changes, divorce, empty nests, or the loss of parents—similar to the hormonal, emotional, and identity shifts of adolescence. However, while adolescence is supported by social systems, “middlescence” often lacks the same structures.
Chip observed that without adequate support, these life transitions—what he calls “life quakes”—can feel overwhelming and isolating. Reflecting on his own experiences of loss and hardship in his late 40s and 50s, he saw the need for safe spaces where people can navigate midlife transitions. MEA became that space, offering resources, care, and connection to help individuals reimagine and repurpose their lives.
Central to MEA’s approach is cultivating awe and wonder. Chip emphasized the role of “moral beauty”—acts of kindness and compassion—and “collective effervescence,” a sense of communal joy where ego dissolves and connection takes center stage. These elements create an environment where individuals feel supported and open to transformation.
The Best Years Are Yet to Come
In a culture focused on anti-aging, MEA takes a pro-aging stance, reminding individuals that life satisfaction often increases with age. Research, including the “U-shaped curve of happiness,” shows that while satisfaction dips around 45-50, it tends to rise steadily after 50. Shifting from a negative to a positive mindset about aging can even extend life expectancy by seven and a half years, according to studies from Yale.
Chip encourages midlife individuals to explore new interests, embrace being a beginner again, and rediscover curiosity. MEA alumni have seen profound impacts through the program, including an example Chip shared of two participants—a retired investment banker with money but no purpose and a social worker with purpose but little money. Their shared experiences highlighted Chip’s belief that “wisdom is not taught; it’s shared.”
Through MEA and its alumni, Chip reassures individuals that midlife is not the beginning of decline but the start of some of life’s best years.
If you’d like to dive deeper into Chip’s insights, watch the full video here!