Riffing on Jane Jacobs’ habit of carrying on imaginary conversations with Thomas Jefferson and Benjamin Franklin as she went about her day in the city, my hope is that this post-pandemic pre-Mother’s Day 2022 Jane’s Walk might validate for us all to listen more deeply to a whole village of fore-mothers who carried us to this moment. What are some of the ways a world-famous neighborhood like historic Benefit St does and does not honor the diverse lived realities of women navigating family? Can we come together to share stories about our own mothers and those we mother and mentor? What kind of courage and self-leadership does it take to persevere, and where is the spring of renewal? This is also my way to open up a space to share some thoughts about two unsung fore-mothers, tied to Benefit Street, that I keep thinking about. With compassion and generosity, let’s make a space for our own stories to jump into new imaginary conversations on this street drenched with women’s histories, especially those out-of-register and yet unheard.