Tomorrow Talk: Beyond Imposter Syndrome - Leading with Confidence
Wed. Jan 20, 6:30pm
Tom Tom Foundation, 100 W. South St
As we prepare for the 15th Annual Tom Tom Festival (April 21–25, 2026), whose theme is NEXTGEN, the Tomorrow Talk series invites us to explore what innovation looks like—in our personal lives, our neighborhoods, our communities, and our society.
Leadership doesn’t always feel like confidence. Sometimes it looks like wondering whether you belong in the room, second-guessing your instincts, or feeling like everyone else somehow got the handbook you missed. Even accomplished leaders can wrestle with imposter syndrome—and the pressure to prove themselves can quietly keep them from stepping fully into their power. So how do we move beyond self-doubt and lead with greater confidence, authenticity, and purpose?
In this candid Tomorrow Talk, Kimberly Sheffield and Teira E. Fairley draw from their own leadership journeys to explore what it really takes to grow into your voice and claim your place. They’ll talk about the role of mentorship, community, representation, and even failure in building confidence—and how letting go of perfectionism can open the door to greater impact.
Whether you’re stepping into leadership for the first time or still figuring out what kind of leader you want to be, this conversation will challenge you to stop waiting until you feel ready and start recognizing the leadership that’s already in you.
Registration is required.
General Admission: $25
Tomorrow Society Members: $20
Students: $15
FACILITATORS
Kimberly Sheffield
At the heart of Kimberly Sheffield's story is a genuine love for people, a passion for service, and a belief that we are all called to make a difference beyond ourselves. For Kimberly, leadership has never been about titles or recognition. It is about showing up, creating opportunities, and leaving people and places better than she found them.
As Executive Director of the Jefferson School Foundation, Kimberly is committed to honoring history, strengthening community connections, and creating opportunities for future generations. Her leadership bridges legacy and progress through meaningful partnerships, community engagement, and sustainable growth.
Beyond Jefferson School, Kimberly serves as Vice Chair of the Board of Directors for the American Red Cross Central Virginia Chapter and Commissioner of Madison County Youth Cheer, extending her passion for service through community leadership, humanitarian efforts, and youth development.
Guided by purpose, driven by impact, and grounded in service, Kimberly believes the greatest measure of success is not what we accomplish for ourselves, but what we make possible for others.
The Jefferson School Foundation
The Jefferson School Foundation is dedicated to preserving and sustaining the history of The Jefferson School. They strive to enhance the quality of life by supporting and advancing the Jefferson School City Center as a vibrant community resource and hub for diverse services and programs. Through strategic stewardship and community engagement, the Jefferson School City Center serves as a vital asset in our community. Their vision for the Jefferson School City Center is to flourish as a cornerstone of community vitality, fostering a dynamic environment where individuals and organizations come together to learn, grow, and thrive.
Teira E. Fairley began with the Community Investment Collaborative (CIC) as the Director of Communications + Engagement and currently leads the team as its Chief Operating Officer, overseeing programs and operations across all regions.
Teira serves as the chair of the board of People and Congregations Engaged in Ministry (PACEM), is a member of the Monticello Area Community Action Agency (MACAA) board and the Minority Business Commission for the City of Charlottesville. A dual graduate of Florida A&M University, she holds a Bachelor of Science in Business Management and a Master of Business Administration, with management and marketing concentrations, respectively, underscored by over twenty years in branding, logistics, and non-profit management. She is the owner of the coloring box, a SWaM certified brand + business development company, and a published author.
Her collaborative approach and genuine leadership create healthy, empowering, and educational spaces for clients, team members, and community partners to thrive in purpose and impact.
Community Investment Collaborative - Charlottesville
CIC’s mission is to strengthen the community and contribute to economic development by fueling the success of under-resourced entrepreneurs through education, mentoring, financing, and networking. Based in Charlottesville and serving Central and Southern Virginia, its signature program, a 16-week Entrepreneur Workshop provides vital education to help individuals evaluate the viability of their business ideas and build actionable plans. The program has over 725 graduates, and more than 250 entrepreneurs have acquired over $6.5 million through CIC’s microloan program.
ABOUT THE SERIES
The Tomorrow Talks are a year-long series that picks up critical themes from our April Festival and continues the conversations to create impact in Charlottesville. Each session is facilitated with an emphasis on participation, connection, and new collaborations. Tomorrow Talks begin with a connection exercise or meditation, and proceed into a presentation and breakout activities. They aim to impart knowledge that is practical and relevant to people's lived experience; combining academic or theoretical insights, alongside pragmatic tools, and experiential and somatic learnings.
