In this episode of Surfing the Quicksand, Kathy sits down with Jen Greene, an educator and newly minted first-grade teacher who made a bold midlife shift after nearly three decades in marketing and advertising and life in the technology start up world. Jen shares the intimate story behind her transition, struggling with “what’s next,” to going back to school with students half her age, confronting unexpected academic challenges, and staying the course through fear, self-doubt, and age bias in the job market. 

Jen discusses the realities of grief, the power of community, and how her father’s words, “You can always come home,” gave her courage to take meaningful risks throughout her life. She reveals the mindsets and habits that kept her moving forward, what she learned about ambition and compromise in midlife, and how she ultimately found joy and purpose in the classroom. 

Grounded, funny, and deeply honest, this conversation is a testament to resilience and reinvention. Jen reminds us that it’s never too late to change direction, and that balance - in motion, in care, and in life - is something we build one brave step at a time. 

Key Takeaways 

• Reinvention at midlife requires courage, but not perfection. Jen’s path wasn’t linear, but each step, even the setbacks, moved her toward clarity. 

• Fear often disguises itself as practicality. When you challenge it, options expand. 

• Community and support matter. Family and friends provide the support we need to take risks without shame. 

• Age bias is real, but resilience is powerful. Staying committed to your goal helps you navigate an imperfect job market. 

• Balance is active, not static. Using creativity, rest, and self-compassion, Jen found new grounding in a demanding season of reinvention.