Just Some BS

Why Retirement Feels So Hard – Identity, Purpose & What Comes Next

Brandon Episode 43

After 32 years at the same company, John Landis is stepping into retirement—but not without a mental and emotional battle. In this honest and deeply personal episode, John shares the real reasons why retiring is harder than most people think—especially for a generation whose identity is tied to their work.

We explore:

  • The emotional rollercoaster of preparing to leave a job you love
  • Why retirement hits harder when your work is your identity
  • How John built trust with coworkers and clients over 3 decades
  • What younger BD pros can learn from old-school face-to-face sales
  • The unexpected fears about fixed income, self-worth, and purpose
  • Advice for anyone nearing retirement or struggling with “what’s next”

Plus: legendary stories about Al Stewart, busted minivans, business travel in a shoebox-sized car, and the unforgettable truth behind why churches have high ceilings (you’ll see).

If you're building a legacy, considering retirement, or just love a good story from someone who’s lived it—this episode will hit home.

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Chapters

00:00 Introduction and Career Overview
04:00 Transitioning to Sales and Key Projects
10:57 The Importance of Team Relationships
17:52 Lessons from Leadership and Mentorship
25:04 Adapting to Change in Business Development
29:58 Company Evolution and Future Outlook
32:02 Navigating Workplace Policies and Conflict Resolution
34:05 Preparing for Retirement: A Personal Journey
36:54 Identity and Work: Generational Perspectives
40:10 Finding Purpose Beyond Work
44:21 Family Dynamics and Retirement
46:08 Retirement Bucket List: Simple Joys
49:03 The Importance of Connection in Sales
52:31 Staying Connected After Retirement
54:02 Advice for Future Retirees: Embracing Change