Before we ask whether a rural community is “ready” for investment, we may need to ask a different question: What level of readiness are we willing to invest in? Dreama Gentry explores how generations of investment—and underinvestment—shape the capacity we see in communities today, and why readiness may tell us as much about an investor’s strategy as it does about a place.

Today's piece is a portion of a speech that my friend Tim Deaton-Conway, Executive Director of the Appalachian Arts Alliance in Hazard, Kentucky delivered earlier this year.

I was in the room when Tim shared these remarks as leaders from across the country gathered in Hazard to learn from the community and the work happening there.

Tim’s affection for his place felt instantly familiar and his words have stayed with me. He reminds us to focus less on what rural communities lack and to look instead at what rural communities already possess: creativity, resilience, ingenuity, relationships, and an extraordinary capacity for building with what they have.

As her youngest son prepared to graduate from college, conversations with rural students across the country had Dreama Gentry thinking about the question so many young people from rural places are asked: Will you stay, or will you leave? Her advice to rural graduates is to ask a bigger question—one centered on opportunity, purpose, belonging, and the freedom to build a life of their own choosing.

Dreama Gentry has spent her life in Appalachian Kentucky and her career working alongside rural communities across the country. In this first edition of Roots and Wings, she shares why she is opening a new window into rural America—one that moves beyond single stories and makes room for the complexity, possibility, and rural brilliance she has witnessed throughout her life and work.

Some of Dreama Gentry’s earliest lessons about listening, trust, and finding her voice happened around her grandmother Ma’s kitchen table. Drawing on that memory and a remarkable transformation in Leslie County, Kentucky, she explores what can happen when we stop treating communities as problems to be solved and start listening to the people who know them best.