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 happiness
• The identity and lifestyle challenges of early retirement
• Importance of purpose and planning beyond financial security
• Using humor as a lens for self-reflection and fulfillment

Key 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.

"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

Connect with Paul Ollinger:

Website: https://www.paulollinger.com/

Show: Reasonably Happy with Paul Ollinger: https://podcasts.apple.com/us/podcast/reasonably-happy-with-paul-ollinger/id1452395408

LinkedIn: https://www.linkedin.com/in/paulollinger/

Twitter: https://x.com/Paul_ollinger

Get a free copy of Shawn’s book “The Priority of Retirement” here- https://www.retirewisepro.com/the-priority-of-retirement

Contact Shawn:

Website- https://www.retirewisepro.com/

YouTube- https://www.youtube.com/channel/UCiIMGdosN-snkV5gFt7FRSg

LinkedIn- https://www.linkedin.com/in/shawn-maloney-retire-wise

Instagram- https://www.instagram.com/retirewise_llc/

Facebook- https://www.facebook.com/ShawnMaloney.RetirementPlanning/

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