On this episode of The Retirement Readiness Podcast, Tim Regan welcomes back his daughter, Maddy Reagan as they further the conversation of Tim’s book, "Shatter Your Fishbowl: Live Your Two Comma Life®." Together, they share the story behind the book’s creation, what inspired Tim to turn years of family lessons into a manuscript, and how the writing process unfolded.

Tim and Maddy talk about the metaphor of the “fishbowl” - the personal boundaries we grow up with - and how anyone can break free to find new possibilities in life and finances. Maddy shares her perspective as both a marketer and family member, while Tim explains his motivation, the various writing approaches he explored, and why faith became central to the final product.

“If you have a calling on your heart to write a book, God's putting that calling there. It's probably meant to be written,” Tim notes, reflecting on the role of faith and legacy in the writing journey.

Listeners will also hear stories about family, the idea of living a “Two Comma Life®,” and practical advice for anyone thinking about capturing their own life lessons and aspirations in writing.

3 Key Takeaways

• Writing a book, or taking on any big new challenge, often means exploring different paths and accepting that the final outcome may look very different from the original plan.
  
  

• The “fishbowl” concept offers a way to reflect on your own life’s boundaries and consider where growth and change might be possible, both personally and financially.
  
  

• Legacy, faith, and willingness to seek mentors can shape not only your work but how you live a life of abundance, generosity, and purpose.
  
  

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To learn more, check out more episodes of the Retirement Readiness Podcast or visit www.pv-wp.com. And remember: your Two Comma Life® is within reach.

This week on The Retirement Readiness Podcast, Tim Regan is joined by his daughter and PrairieView’s Head of Marketing, Maddy Regan, for a conversation rooted in personal growth, generational influence, and the lessons found in Tim’s upcoming book, “Shatter Your Fishbowl: Live your Two Comma Life”. Together, they explore what it means to “shatter your fishbowls” - the self-imposed boundaries that hold us back - and the ripple effect these breakthroughs can have for families and beyond.

Tim reflects on his early career challenges, including supporting a young family while navigating an uncertain income, and the mindset shifts that eventually enabled him to achieve goals he once thought impossible. Maddy shares her own experience, explaining how her father’s willingness to break through his own “fishbowls” empowered her to approach law school - and life’s new challenges - with confidence. As Tim puts it: “Your ceiling always becomes your floor.”

The episode also touches on the importance of recognizing both visible and invisible support systems, understanding privilege, and how each generation can launch the next to greater heights. Plus, Tim and Maddy offer resources for listeners interested in leaning deeper into their purpose and confronting their own self-doubt.

Tune in to hear a candid family discussion on breaking boundaries and helping others do the same!

3 Key Takeaways

• Our own personal breakthroughs (“shattering fishbowls”) often have a ripple effect, empowering those around us to expand their horizons, too.
• Recognizing and acknowledging the support and resources we receive can broaden our empathy and understanding for others with different challenges.
• “Your ceiling always becomes your floor” - once you overcome a limitation, it becomes the new baseline for your life and those who come after you.

“As we all have some level of self doubt…once you break through them, you never go down. That now is your minimum acceptable.” - Tim Regan

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To learn more, check out more episodes of the Retirement Readiness Podcast or visit www.pv-wp.com. And remember: your Two Comma Life® is within reach.

This week on The Retirement Readiness Podcast, Tim Regan and Katie Umland dive into a topic that impacts every financial decision we make—stress.

When life throws unexpected changes your way, from downsizing your home to helping adult children financially, the line between strategy and stress can blur. Tim and Katie break down how to prepare before the pressure hits, so you’re not making emotional decisions when the stakes are high.

Through real client stories and personal insight, they explore why planning ahead is one of the most powerful ways to take ownership of your financial journey. You’ll hear how simple mindset shifts—and intentional conversations—can help you navigate your next life crossroad with clarity and calm.

They also explore the connection between stress, decision fatigue, and confidence, offering practical ways to shift from reactive to proactive thinking when it comes to your money and your life.

Whether you're facing a big transition or just want to avoid the “spinout” when the next one comes, this episode is packed with guidance on how to lead with strategy instead of stress.

3 Key Takeaways:

• Big decisions are inevitable—but stress doesn’t have to be. Planning ahead is key.
• Strategy gives you something to fall back on when life feels overwhelming.
• Aligning your financial choices with your values brings clarity and confidence.

Listen in for a thoughtful discussion on how to turn stress into strategy—and visit www.pv-wp.com for resources to help you navigate what’s next.

This week on The Retirement Readiness Podcast, Tim Regan and Katie Umland take a step back from dollars and cents to ask: How do you really define wealth? 

Drawing from both personal stories and client experiences, Tim and Katie explore the ways wealth can mean much more than just a bank balance—from health and relationships to intentional living and finding time for what matters most.

Tim shares the story of two funerals—one for a wealthy benefactor, held in a nearly empty room, and one for a janitor, filled to the brim with people whose lives he’d touched—to ask what truly contributes to a rich and meaningful life. Katie and Tim discuss the stress that can come from both having too little and too much money, and how wealth is best measured across all aspects of life: physical health, relationships, time, and even spirituality.

“Your bank account, yes—but it’s also all these other things,” Tim says. They also talk about how your definition of wealth may evolve over time, yet core values like connection and purpose tend to remain constant.

Whether you’re wrestling with budgeting for convenience during a hectic season of life, or thinking about legacy and lifelong health, this episode will help you take a more intentional approach to building true wealth.

3 Key Takeaways

- Wealth isn’t just about money—it includes your health, relationships, and overall well-being.

- Your definition of wealth changes as you move through life, but your core values often stay the same.

- Being intentional and regularly evaluating all areas of your life can help you build the kind of wealth that matters most to you.

Listen in for a thoughtful conversation on redefining wealth, and visit www.pv-wp.com for more resources.

This week, Tim Regan and Katie Umland take a lighter approach on the Retirement Readiness Podcast as they explore the ins and outs of road trips in retirement. With summer on the horizon, Tim and Katie discuss why the freedom that comes with retirement is the perfect opportunity to rediscover the classic American road trip—whether it’s a weekend getaway, a cross-country adventure, or something in between.

Drawing from their own experiences and stories from clients, they cover how travel styles shift in retirement, options for planning road trips (from fully spontaneous to professionally arranged), and the unique memories created by embracing both the expected and the unexpected. “You never talk about the trip that went perfectly. You always talk about the trip fondly... those kinds of things,” Tim shares.

The conversation also touches on RV living, group travel, train journeys, and how travel can evolve into a meaningful way to connect with family and create new traditions during the retirement years.

Tune in for practical advice, personal anecdotes, and inspiration for making the most of your post-career freedom—on the road and beyond.

3 Key Takeaways

• Retirement opens up a new world of travel possibilities, from impromptu weekend outings to month-long adventures you may never have considered before.
• There’s no single “right” way to plan a road trip: some prefer the flexibility of no reservations, and others feel more comfortable with a detailed itinerary or hiring a travel planner.
• Road trips can create lasting memories and become vehicles (literally and figuratively) for family bonding and expanding your horizons in retirement.

Give this episode a listen and discover how to craft your perfect road trip in retirement—whether you’re seeking adventure, connection, or just a change of scenery.

This week on The Retirement Readiness Podcast, Tim Regan welcomes Laura Rudzinski, a 31-year veteran of her company and long-time participant in its employee stock ownership plan (ESOP). Together, they explore what it really means to be an employee-owner, how an ESOP can play a unique role in retirement readiness, and the key planning considerations for those participating in such plans.

Laura shares her experience with her company’s transition to an ESOP 20 years ago, the impact it’s had on her and her family’s financial future, and the practical pros and cons of having a significant portion of retirement wealth tied to a single company. Tim and Laura also discuss the importance of transparency, risk management, and what it’s like to make retirement decisions when you’re both an employee and an owner.

“Every day that I'm working, I'm thinking to myself, I'm helping myself by helping our clients grow—you know, you're helping yourself be able to grow your wealth,” Laura explains.

Whether you’re already part of an ESOP, considering joining one, or just looking for ways to strengthen your retirement strategy, this episode offers a candid look at how employee ownership can shape not just your retirement, but your mindset at work.

3 Key Takeaways

1. ESOPs can create significant wealth for employees, but come with unique risks and considerations, especially the concentration of assets in one company’s stock.
2. Transparency and annual valuations play a critical role in the ESOP experience, affecting both engagement at work and retirement planning.
3. Actively participating in an ESOP—and seeking expert advice—can help employees make the most of this unique benefit and tailor their financial plan accordingly.

Listen in for a practical, first-hand perspective on ESOPs and retirement planning, and be sure to explore our past episodes for more insights.

This week, Tim Regan and Katie Umland explore the realities of semi-retired life—a stage where you’re “kind of working, you’re kind of retired” and figuring out how to make it work for you. They discuss common reasons people choose part-time or consulting work in retirement, from financial necessity and personal interests to simply needing something to do outside the home.

Tim and Katie candidly reflect on the challenges and opportunities this lifestyle presents, emphasizing the importance of intention when designing your retirement years. As Katie notes, “If you’re gonna fill it with something, be intentional about what you’re filling it with. Don’t let your day get filled.” The conversation covers making a list of what you enjoy (and what you don’t), weighing domestic roles alongside work, and practical strategies for blending part-time income with Social Security and future financial security.

Whether you’re concerned about losing purpose after leaving full-time work, worried about navigating part-time pay and taxes, or simply looking for ideas on how to create a more fulfilling retired life, this episode lays out thoughtful steps for making the transition.

3 Key Takeaways

1. Semi-retirement is most successful when you intentionally design both your work and personal life around activities you value, rather than just letting your calendar fill up by default.
2. The transition to consulting or part-time roles often has a narrow window of opportunity—so if you’re considering this path, it’s important to act while your industry experience and network are still fresh.
3. Understanding how part-time work interacts with retirement benefits, like Social Security, is critical—working with an advisor can help you avoid unexpected pitfalls and optimize your financial plan.

Tune in for stories, practical tips, and a discussion on how building the right retirement lifestyle starts with knowing yourself—and making a plan that matches your vision. Don’t forget to check out more episodes and resources at pv-wp.com!

In this episode of The Retirement Readiness Podcast, Tim Regan and Katie Umland explore the critical transition from wealth accumulation to wealth distribution in retirement. They tackle the often daunting task of structuring investments to ensure your financial strategy sustains you through retirement, and Tim equates it to mountain climbing: “You would use different tools, different strategies to climb up the mountain than you would use coming back down."

Together, Tim and Katie discuss practical strategies that retirees can implement to avoid riding the stock market roller coaster. They delve into the importance of managing the order of returns and suggest innovative approaches to maintain financial stability, such as structuring income in different pools and utilizing home equity lines of credit wisely.

Plus, hear about the personal anecdotes that illustrate these concepts and make financial planning relatable, including tales of family budget debates and the unexpected life changes of children growing up.

Click play to uncover insights and strategies that can transform your retirement planning approach. Visit pv-wp.com for more resources, and don’t forget to explore our library of previous episodes!

3 Key Takeaways:

1. It’s crucial to match your investment strategy to your life stage, transitioning from wealth accumulation to wealth sustainability in retirement.
2. Implementing a bucket system can provide financial security, ensuring core expenses are met irrespective of market fluctuations.
3. Home equity lines of credit offer flexibility and peace of mind, allowing for strategic financial decisions without immediately impacting your primary investments.

In this episode of The Retirement Readiness Podcast, we're addressing a critical concern for retirees: how to navigate economic downturns once you've left the workforce. Hosts Katie Umland and Tim Regan engage in a candid discussion about the strategies retirees can employ to protect their financial security during turbulent market conditions.

"Once you hit retirement age, I lose all of my ability to flex…because I don't have income coming in anymore that I can recover with," Tim explains, emphasizing the importance of preemptive financial planning before a downturn occurs.

Tim and Katie delve into the significance of diversifying one's portfolio, not just in stocks but across risk categories to ensure resilience against market fluctuations. They introduce the concept of the "bucket" strategy, a method that can provide retirees with a structured withdrawal plan to maintain steady income without panic selling during market lows.

The episode stresses the role of a financial advisor as a critical partner in this journey, offering guidance tailored to individual circumstances. Plus, the hosts share insights on differentiating between mere market noise and genuine downturns, equipping listeners with the knowledge to remain calm and stick to their plans.

Whether you're facing your first market correction in retirement or looking to refine your wealth management strategies, tune in for practical advice and peace of mind.

3 Key Takeaways:

• It's vital to have a structured plan for market downturns, including a well-diversified portfolio and a strategy like the "bucket" approach.
• Economic downturns are inevitable, but with the right financial planning and advisory support, retirees can confidently weather the storm.
• Relying on a financial advisor can help set alarms for necessary adjustments, ensuring a stable financial footing without constant monitoring.

Join us in this episode for valuable tips on safeguarding your retirement lifestyle amidst economic uncertainties. Be sure to explore our previous episodes for more insights! 

In this week's episode, hosts Katie Umland and Tim Regan explore the nuanced challenges faced by the sandwich generation, those individuals caught between supporting their children and caring for aging parents. How do you balance the responsibilities of two generations? What are the financial implications, and how can you prepare for what's often an unpredictable but inevitable situation?

"Every dollar can only be spent once," Tim reminds us, emphasizing the importance of intentional and proactive financial decision-making. The discussion dives into scenarios where familial assumptions can lead to unexpected complications if not addressed early on. Whether it's deciding on living arrangements for aging parents or managing financial support for adult children, these conversations require clear communication and planning.

Plus, the hosts share insights into the emotional and financial dynamics of moving parents closer for care, addressing the historical differences between now and previous generations when it comes to family support.

3 Key Takeaways:

• Being part of the sandwich generation requires carefully balancing time and resources between caring for aging parents and supporting children.
• Open communication and setting clear expectations with family members about care and financial support can prevent conflicts and misunderstandings.
• Being intentional about financial decisions means recognizing that every dollar spent in one area is a dollar not available elsewhere, highlighting the need for prioritization and planning.

Join Tim and Katie as they unpack these dynamics to better prepare for the responsibilities that come with being part of the sandwich generation, and don't forget to explore our previous episodes for more insights!