Welcome to a special episode of Closet Philosophy where Jennine and Kristen open up about the challenges and rewards of reinventing yourself—especially after taking a work break to care for family or shifting gears in midlife. They share their personal journeys of returning to the workforce, navigating ageism, career gaps, and finding new purpose.

In this episode, we discuss:

• Personal experiences of leaving and re-entering the workforce after motherhood or caretaking

• The surprising roadblocks and opportunities that come with a career gap

• Ageism and the difficulties faced by midlife women in today’s job market

• The importance of meaningful work, creativity, and autonomy—and why these are non-negotiable for some

• Why so many women turn to entrepreneurship in their 40s, 50s, and beyond (with fresh statistics!)

• How personal style is a secret networking weapon and catalyst for engaging with the world

• The unique struggle (and privilege) of figuring out what you really want from work at this stage of life

• The power of community: you are not alone in your quest for reinvention!

Resources & Mentions:

• EvolveMe: an organization supporting midlife women re-entering the workforce

• Recent LinkedIn and demographic statistics on career breaks and entrepreneurship

Whether you're feeling invisible, itching for a new chapter, or struggling to make your experience relevant, you'll find humor, hope, and good company in this conversation. Be seen—by your community, and by yourself!

Share your story! Have you tried to return to traditional work and ended up an entrepreneur? Are you struggling with finding purpose or translating your experience? Email us or leave a review—your story could inspire a future episode!