Ep 426 Can You Be Reasonably Happy with Paul Ollinger
Richer Soul, Living A Life on Purpose!
Release Date: 01/22/2025
Richer Soul, Living A Life on Purpose!
Happy Soul, Hungry Mind: Why Success Still Feels Empty "I made the money. And where is the happiness? Where is happiness? Can somebody answer that? Society, parents, friends, everybody said, make money, make money. Don't think about anything else. Work like a dog, make money. I made the money. And where is the happiness?" You've hit the number. The bank balance looks good. You've done everything "right." So why does something still feel... empty? In this profound Richer Soul episode, author and executive coach Ravi Kathuria reveals why even a million dollars a month can't buy peace and...
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Super Performance From Firefighting to Super Performance: How Systems Free You From… Most owners secretly know the truth: their business only runs well when they’re watching. The minute they step away, problems surface, customers get frustrated, and the “superhero” has to swoop back in. In this Richer Soul episode, operations coach and author George Pesansky shares how to escape that trap by building systems that work without you — so your business performs at a high level and your life gets a lot richer in the process. Key Insights: Vision, Strategy, and...
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The Real AI: Authenticity + Intention in Life and Business In a world where AI can write emails, produce video, and even mimic your voice, the greatest competitive advantage left is being human. Brian McRae reminds us that emotional loyalty, being known, valued, remembered, is what creates opportunity, referrals, purpose, and a life of meaningful success. Social media may get you attention, but it will never create devotion. Relationships do. If you’ve been feeling alone, stuck, or unsure how to expand your circle of opportunity, this conversation is your roadmap back to...
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Spiritual Leadership: How to Inspire by Being Inspired Most leaders try to think their way to clarity — only to get stuck in anxiety, over analysis, and pressure. In this episode, Dr. Yosi Amram reveals a different approach: using the wisdom in your body, not the noise in your mind. His story moves from trauma, military service, and a meteoric rise as a tech CEO… to a spiritual awakening that shattered his identity and led him into a lifetime of inner work. Key Points with reflection prompts: Your Body Doesn’t Lie. Your Ego Does. Your body gives you truth signals long...
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Ep 470 Building Wealth Keeping Your Money is Rare Skill! How to Actually Keep Your Money: Why Financial Literacy Matters More Than Income Most people think their money problems would disappear if they just made more. But as financial coach Alanna Abramsky shared in this episode of Richer Soul, that belief keeps countless high earners feeling stressed, behind, and ashamed. Alanna has worked with realtors, lawyers, doctors, professional athletes—and even with impressive income, many still live paycheck to paycheck. The issue isn’t intelligence or effort. It’s...
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The Money Habit on How to Finally Take Control of Your Finances What if your biggest money problem isn’t how much you earn—but how you manage what you already have? In this week’s episode of Richer Soul, bestselling author Mike Michalowicz (Profit First, Clockwork, All In) returns to share insights from his new book, The Money Habit. It’s a simple, behavior-based approach to mastering personal finances—no spreadsheets, guilt, or complicated budgets required. Key Insights from the Conversation: Making Money Is One Skill—Keeping It Is Another. Most people...
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From Trauma to Triumph: Dr. John A. King on Living from the Inside Out Most of us carry invisible stories — old pain, expectations, and patterns that shape how we live, lead, and love. Dr. John A. King knows that journey firsthand. After surviving years of childhood abuse and losing everything when his repressed memories resurfaced at 45, he had to rebuild his identity from the ground up. Today, he helps men recover from trauma, rediscover authenticity, and live from the inside out through The Phoenix Collective and Mindfire Challenge. This conversation isn’t just about...
info_outlineCan You Be Reasonably Happy
In this episode of Richer Soul, I had the privilege of speaking with Paul Ollinger, a stand-up comedian, podcast host, and author who left a lucrative career at Facebook to chase his dream of comedy. Through his podcast, Reasonably Happy, Paul explores the interplay between money, happiness, work, and purpose. His life journey, marked by bold choices and valuable lessons, offers incredible insights into navigating life’s financial and emotional complexities.
Key Takeaways:
- Childhood Money Scripts Matter: Paul grew up in a large Catholic family where money was stable but never abundant. This upbringing shaped his initial belief that wealth equates to freedom from stress—a script he reevaluated later in life.
- Chasing Dreams Is Risky but Rewarding: Paul’s decision to leave Facebook to pursue stand-up comedy was financially unprofitable, but it brought him immense personal growth and fulfillment.
- Money and Happiness Are Interlinked but Complex: Paul’s podcast and essays examine how financial success can coexist with personal happiness, emphasizing balance over blind ambition.
- The Power of Giving Back: From supporting his family as a child to providing thoughtful insights through his podcast, Paul embodies the spirit of contribution, proving that fulfillment often lies in lifting others.
Money Learning:
Paul’s journey reveals that our financial habits often stem from childhood experiences. His early lessons about saving and frugality played a pivotal role in his career choices. However, he emphasizes the importance of not letting outdated beliefs limit your growth. For Paul, real financial wisdom lies in balancing practical discipline with pursuing meaningful experiences.
About Paul Ollinger:
Paul Ollinger is a stand-up comedian and the host of Reasonably Happy, a podcast where he discusses money, happiness, and work with renowned guests like Judd Apatow and LL COOL J. His latest book, Reasonably Happy, compiles over 200 interviews into humorous and insightful essays. Based in New York City, Paul lives with his wife, two teenagers, and their French bulldogs, Theo and Colonel Tom Parker.
Key Discussion Points:
- Early Money Lessons: Paul shared how his upbringing in a frugal, Catholic family shaped his financial mindset. His parents’ values emphasized stability over luxury, which initially instilled in him the belief that wealth equated to stress-free living.
- The Psychological Impact of Wealth: Paul discussed the emotional challenges of growing up with financial stress. He later learned to untangle these experiences to adopt a healthier relationship with money.
- Balancing Career Risks and Fulfillment: Leaving a well-paying job at Facebook for comedy was a gamble. Paul explained how this decision was fueled by the desire for purpose and authenticity over monetary gain.
- Cultural Narratives Around Money: Paul touched on societal attitudes towards wealth, noting how Catholicism often associates financial success with moral compromise—a narrative he actively worked to rewrite.
- Teaching Financial Lessons to the Next Generation: As a parent, Paul is mindful of the lessons his children absorb from him, ensuring they learn the value of money without developing unhealthy attachments or anxieties.
Conclusion:
Paul Ollinger’s story is a testament to the fact that money, while essential, is just one piece of the happiness puzzle. His journey from corporate success to personal fulfillment through comedy and podcasting showcases the courage it takes to align your financial habits with your values and passions. Tune in to this episode to gain deeper insights into how money, happiness, and meaning intersect.
Links:
Book on Amazon: Reasonably Happy: Essays on Money, Work and Other Things that Piss Me Off- https://www.amazon.com/Reasonably-Happy-Essays-Money-Things/dp/0997270659/ref=sr_1_1?crid=326TDOT9XWWGI&dib=eyJ2IjoiMSJ9.dLZOV_Igvsr40nXuxzsMbULjnDLojjeLCAnUkSK67wDL2ByRXdMpN6QwaDis5Ewq.RqJ-nLbHhL2CsP6768q3Ko-D9W2Wo1HMtxKDr_cs7Es&dib_tag=se&keywords=paul+ollinger&qid=1733763670&sprefix=paul+ollinger,aps,208&sr=8-1
Substack: https://words.paulollinger.com/
Watch the full episode on YouTube: https://www.youtube.com/@richersoul
Richer Soul Life Beyond Money. You got rich, now what? Let’s talk about your journey to more a purposeful, intentional, amazing life. Where are you going to go and how are you going to get there? Let’s figure that out together. At the core is the financial well-being to be able to do what you want, when you want, how you want. It’s about personal freedom!