Many people spend decades planning financially for retirement—but very few plan for what life actually looks like after they stop working.

In this episode of The Stroke It Podcast, Jenny Townsend sits down with former CFO turned retirement coach Lisa Haynes to explore the emotional and identity shifts that happen when a career ends and the next chapter begins.

After more than 30 years in corporate America, Lisa Haynes realized retirement isn’t simply about leaving work—it’s about reinventing yourself, rediscovering purpose, and designing a life that still feels meaningful.

They discuss why traditional retirement is changing, why more people are choosing entrepreneurship later in life, and why planning your purpose is just as important as planning your finances.

You’ll learn how to prepare for the transition before retirement arrives, avoid the isolation many retirees experience, and start asking the bigger questions about legacy, fulfillment, and what you truly want your life to look like.

If you’re approaching retirement, considering a career pivot, or simply wondering what your next chapter might hold, this conversation will challenge you to think bigger about what comes after your career.

In This Episode

• Why retirement today looks different than it did for previous generations
• The emotional side of retirement most people never plan for
• How identity shifts when you leave your career behind
• Why many retirees end up “unretiring”
• The importance of rediscovering purpose and passion
• How to reinvent yourself at any stage of life
• Practical strategies like pause before you pivot and stack small wins
• The legacy question everyone should ask themselves

Connect with Lisa Haynes

Website: https://retiredandkillingit.com
LinkedIn: Lisa J. Haynes
Instagram: @retiredandkillingit

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Ep 215 Why So Many Retirees Feel Lost (And How to Reinvent Your Life After Work)