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In the first episode of Then Again... Maybe I Won't, Daniel Bryant sits down with Sophia Shaw, former President & CEO of the Chicago Botanic Garden, nonprofit leader, and co-founder of PlanPerfect.

In this conversation, she shares insights from her distinguished career in the nonprofit sector. As a guiding light in nonprofit leadership, she discusses her time as president and CEO of the Chicago Botanic Gardens. Her experience extends to nonprofit management, where she educated MBA students on nonprofit organization governance through the Kellogg Fellows program.

This episode is about more than leadership. It’s about redefining success, embracing uncertainty, and realizing you don’t have to follow the path others expect.

Key Takeaways:

We lead differently at every stage of life

Purpose doesn’t fade—it evolves

Life is hard, but we can do hard things

Don’t wait. Live and give like the future is wide open

🎙️ Then Again is a podcast about reflection, reinvention, and the moments that change our direction.

00:00 – Nonprofit Leadership Journey | Sophia Shah Intro

01:05 – Career Transition After Success | “Then Again, Maybe I Won’t”

02:23 – Financial Freedom & Career Decisions | What’s Next After CEO?

05:11 – Nonprofit vs Corporate Leadership | Key Differences Explained

08:31 – Fundraising Strategies for Nonprofits | Authentic Leadership Wins

11:32 – Nonprofit Board Governance & MBA Leadership Training

14:54 – Nonprofit Software & Strategy | Building PlanPerfect

21:00 – Finding Purpose in Life & Career | Reinvention at Any Age