Every ending carries within it the seed of a beginning. To leave something behind—whether it’s a beloved job, a familiar city, or the comfort of a community—requires not only courage but also an embrace of uncertainty. In this first episode of Season 11, we step directly into that tension: the sacred space between goodbye and a new hello.
Carrie Fox sits down with nonprofit leader Mike Pope and theater founder Elisa Pupko at the very edge of a new chapter. Together with their two young children, they’re leaving behind steady careers, a home in Brooklyn, and the familiarity of everyday life to embark on a yearlong journey around the world. It’s a leap that began with a fleeting thought on a run and grew into an intentional act of re-imagining what family, leadership, and community might look like.
As Mike reflects on stepping aside from his nonprofit after 15 years, he asks what it means to honor an organization by knowing when to let go. Elisa, meanwhile, navigates the delicate balance of letting her company grow stronger in her absence while choosing presence with her family. And together, they invite us to consider what it means to say yes—not when the plan is complete, but when the possibility feels alive.
Their story is not only about travel; it’s about perspective. About the way children learn to smile at strangers on playgrounds in foreign cities. About how leaders discover strength in stepping back. About how the question “what if?” can open doors we didn’t realize were waiting.
With this conversation we invite you to wonder what might happen if we—all of us—leaned into the space between goodbye and hello, and allowed it to teach us something new.
Follow along with Elisa and Mike and their whole family at https://twokidsoneworld.com/.
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This episode is supported by The Johnson Foundation at Wingspread. At their Frank Lloyd Wright–designed campus, Wingspread brings leaders and communities together to turn dialogue into action. Learn more at johnsonfdn.org or wingspread.com.
This episode is also brought to you by Positively Partners. When HR starts to slow down your mission, it’s time for a better solution. Positively HR is the fully outsourced HR partner that understands nonprofits—and acts like part of your team. Learn more at PositivelyPartners.org.