About Paul Ollinger Paul Ollinger is a nationally touring comedian and author of Reasonably Happy The Skeptic s Guide to Achievable Contentment He has performed over 1 000 shows including at top festivals and opened for legends like Norm MacDonald Dave Attell and Roseanne Barr A former Facebook VP of Sales and one of its first 250 employees Paul managed a team responsible for 35 of the company s revenue After retiring at 42 he launched the Crazy Money podcast to explore the connections between money happiness and meaning featuring guests like Judd Apatow LL Cool J Dr Drew Pinsky and Guy Raz In this episode Shawn and Paul Ollinger discuss The nuanced relationship between wealth and happinessThe identity and lifestyle challenges of early retirementImportance of purpose and planning beyond financial securityUsing humor as a lens for self-reflection and fulfillmentKey Takeaways Leaving a high-powered corporate career may not deliver the anticipated happiness as many retirees underestimate the extent to which work provides a sense of identity structure and a social community that can be challenging to replace Early retirees are often surprised by the emotional and psychological adjustment required highlighting the need to envision a meaningful post-career life that goes beyond financial readiness to focus on purpose and fulfillment Financial freedom can reduce daily stressors and enhance quality of life but without a clear alignment with personal values and goals additional wealth doesn t necessarily translate into greater happiness or satisfaction Success in a creative career like comedy requires a strong tolerance for uncertainty and setbacks underscoring the importance of intrinsic motivation personal resilience and a commitment to one s unique creative voice nbsp Work provides you with a place in the world peers that sometimes can be frustrating but are really your community whether you believe it or not Paul Ollinger nbsp Connect with Paul Ollinger nbsp Website https www paulollinger com Show Reasonably Happy with Paul Ollinger https podcasts apple com us podcast reasonably-happy-with-paul-ollinger id1452395408LinkedIn https www linkedin com in paulollinger Twitter https x com Paul ollingerGet a free copy of Shawn s book The Priority of Retirement here- https www retirewisepro com the-priority-of-retirementContact Shawn Website- https www retirewisepro com YouTube- https www youtube com channel UCiIMGdosN-snkV5gFt7FRSgLinkedIn- https www linkedin com in shawn-maloney-retire-wiseInstagram- https www instagram com retirewise llc Facebook- https www facebook com ShawnMaloney RetirementPlanning Audio production by Turnkey Podcast Productions You re the expert Your podcast will prove it
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