Author and stand-up comedian Paul Ollinger shares how seeking a reasonably happy retirement makes for a greater sense of satisfaction.

From growing up in a Depression-era mindset to retiring early to becoming an author and full-time comedian, Paul Ollinger’s story is quite a journey. On this week’s episode of “Retirement Revealed,” Paul joins the show with a different perspective than you might expect from someone with such a unique journey. Paul’s perspective on money, happiness, and retirement is refreshing, and his insights can help all of us think differently about what it means to retire well.

Paul believes that happiness isn’t about achieving a perfect 10 out of 10 on the satisfaction scale. Instead, he argues that being “reasonably happy”—consistently at a seven or eight—is a more realistic and sustainable goal. Many people chase an elusive idea of ultimate happiness, only to find themselves disappointed when they don’t reach it. The key, according to Paul, is to accept the ups and downs of life and focus on what truly brings fulfillment.

Paul’s background in the corporate world—where he experienced significant financial success—gives him a unique perspective on money’s role in happiness. He shares that the richest he ever felt wasn’t when he had millions in his bank account, but when he paid off his student loans. That moment of financial autonomy gave him a sense of security and control that even large sums of money couldn’t replicate.

His takeaway? Money can relieve stress and provide stability, but beyond a certain point, it doesn’t necessarily bring more happiness. What matters most is using money wisely to support a lifestyle that aligns with your values and priorities.

One of the most powerful concepts Paul discusses is the idea of “enough.” In a society that constantly encourages us to want more, it can be difficult to determine when we truly have enough. Paul suggests taking a close look at your financial situation and lifestyle to decide what is necessary for your happiness and security.

For many retirees, the biggest financial question is, “How do I know I have enough?” The answer isn’t just about numbers; it’s about defining your ideal lifestyle and ensuring your financial resources align with it. Whether it’s travel, hobbies, or spending time with loved ones, having a clear vision of what you want in retirement can help you feel secure in your financial choices.

Many people, especially those who grew up with financial insecurity, struggle to spend money even when they can afford to. Paul shared the example of his father, who saved diligently but could have used some of that money to create more meaningful experiences with his family. This highlights an important lesson: once you’ve determined you have enough, it’s okay to enjoy it.

Whether it’s traveling, taking up new hobbies, or simply spending more time with loved ones, retirees should feel empowered to use their money in ways that bring joy and fulfillment. After all, what’s the point of saving if you never allow yourself to benefit from it?

Paul doesn’t consider himself retired in the traditional sense. Instead, he sees retirement as an opportunity to work on his own terms—pursuing passions like stand-up comedy, writing, and podcasting. He emphasizes that retirement isn’t about stopping work altogether; it’s about shifting focus to what truly excites and engages you.

Many retirees struggle with identity loss after leaving their careers. Paul’s advice? Think of retirement as a blank slate where you can reinvent yourself. Whether it’s learning a new skill, volunteering, or pursuing a long-held passion, having a sense of purpose can make retirement more fulfilling.

Financial planning is essential for a secure retirement, but emotional and psychological planning are just as important. Paul suggests asking yourself:

Answering these questions can help retirees create a meaningful and engaging lifestyle that extends far beyond financial concerns.

Paul Ollinger’s insights remind us that retirement isn’t just about financial security—it’s about finding purpose, staying engaged, and being “reasonably happy.” By focusing on what truly matters, defining what “enough” means to you, and giving yourself permission to enjoy your wealth, you can create a retirement that is both fulfilling and financially stable.

Don’t forget to leave a rating for the “Retirement Revealed” podcast if you’ve been enjoying these episodes!

Subscribe to Retirement Revealed to get new episodes every Wednesday.

Apple Podcasts: https://podcasts.apple.com/us/podcast/retirement-revealed/id1488769337

Spotify Podcasts: https://bit.ly/RetirementRevealedSpotify 

Additional Links:

Connect With Jeremy Keil:

===

Disclosures

Videos/Podcasts/Blogs (media) published prior to June 30, 2025, were recorded and approved while the advisor was affiliated with Thrivent Advisor Network. These media reflect the advisor’s views and interpretations at that time. The information and disclosures contained in those media were believed to be accurate and complete as of the date of recording, but may not reflect current market conditions or Alongside, LLC, policies.

All content is provided for educational purposes only and does not constitute personalized investment advice. Read below for current disclosures and potential conflicts of interest.

This media is provided for informational and educational purposes only and does not consider the investment objectives, financial situation, or particular needs of any consumer. Nothing in this program should be construed as investment, legal, or tax advice, nor as a recommendation to buy, sell, or hold any security or to adopt any investment strategy.

The views and opinions expressed are those of the host and any guest, current as of the date of recording, and may change without notice as market, political or economic conditions evolve. All investments involve risk, including the possible loss of principal. Past Performance is no guarantee of future results.

Legal & Tax Disclosure

Consumers should consult their own qualified attorney, CPA, or other professional advisor regarding their specific legal and tax situations.

Advisor Disclosures

Alongside, LLC, doing business as Keil Financial Partners, is an SEC-registered investment adviser. Registration does not imply a certain level of skill or expertise. Advisory services are delivered through the Alongside, LLC platform. Keil Financial Partners is independent, not owned or operated by Alongside, LLC.

Additional information about Alongside, LLC – including its services, fees and any material conflicts of interest – can be found at https://adviserinfo.sec.gov/firm/summary/333587 or by requesting Form ADV Part 2A.

The content of this media should not be reproduced or redistributed without the firm’s written consent. Any trademarks or service marks mentioned belong to their respective owners and are used for identification purposes only.

For important disclosures visit: https://keilfp.com/disclosures/

===