Retirement isn’t just an exit—it’s a reinvention. But with endless choices, how do you find purpose beyond work? Former Facebook exec-turned-comedian Paul Ollinger shares insights, struggles, and laughs on navigating life’s next big chapter.

In this episode, Len Hayduchok and our guest, Paul Ollinger discuss:

• Retirement presents an identity crisis
• Choosing how to spend retirement time can be overwhelming
• Pursuing passions and finding purpose is important in retirement
• Accepting imperfections and being "reasonably happy" is valuable
• Intentionality and planning are key to making the most of retirement

Key Takeaways:

• Leaving the working world means walking away from an established community and sense of self.
• The abundance of options in retirement can be both liberating and overwhelming.
• Pursuing long-held dreams is an opportunity in retirement, but it requires honest self-reflection on what truly matters.
• The elusive state of "happiness" is better framed as contentment and gratitude for what one has, rather than chasing exuberance, and embracing the ups and downs of life with self-compassion leads to a "reasonably happy" retirement.

“Give yourself the opportunity to make some mistakes, give yourself the opportunity to be uncomfortable for a little while, because it's a new thing and it's and there's; there's no worn path for you to follow."

— Paul Ollinger

About the guest, Paul Ollinger:

Paul Ollinger is a writer, stand-up comedian and host of the 'Reasonably Happy' podcast (fka, 'Crazy Money'). He also has an MBA from Dartmouth's Tuck School and was one of the first 250 employees of Facebook, where he served as VP of Sales for the Western United States. His super-hilarious POV on business and work has been featured on Huffington Post, Entrepreneur and Funny or Die. A finalist at the Boston and San Diego Comedy Festivals, he has opened for top comics like Dave Attell, Daniel Tosh, Chelsea Handler, and for musical acts, Styx, Collective Soul, Shawn Mullins, and Edwin McCain.

Connect with Paul Ollinger:

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

Podcast: https://podcasts.apple.com/us/podcast/crazy-money-with-paul-ollinger/id1452395408

About the host, Len Hayduchok:

Len Hayduchok is a Certified Financial Planner with over 25 years of experience in the financial services profession. He is the founder and President of Dedicated Financial Services and Dedicated Senior Advisors, providing comprehensive wealth management programs to individuals in their retirement and retirement-planning years. Len is committed to advising clients based on their best interests and has extensive training in securities and life insurance. He is a graduate of the Wharton School of Business and Biblical Theological Seminary. Len is dedicated to client and community education, offering various resources and instruction on retirement-related topics.

Learn more about Len’s book:

MaxAMAZING Your Retirement: Practical Guidance for an Enjoyable and Fulfilling Capstone to Your Life

Book website: https://maxamazing.com/

The book "MaxAMAZING Your Retirement" challenges the conventional view of retirement as merely accumulating assets and emphasizes the importance of aligning financial resources with one's true values and desires. Len introduces his Life/Money System, guiding readers through a journey of self-discovery and financial planning to achieve a meaningful and fulfilling retirement.

Dedicated Financial Services (Company website): https://www.dedicatedfinancialservices.com/

CONNECT WITH LEN:

https://maxamazing.com/len-hayduchok/

Show notes by Podcastologist: Hanz Jimuel Alvarez

Audio production by Turnkey Podcast Productions. You're the expert. Your podcast will prove it.