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!

On this episode of The Retirement Readiness Podcast, Katie Umland and Tim Regan explore the complexities of planning for retirement and estate management in blended families. They delve into the unique challenges and considerations blended families face when trying to ensure a fair and smooth transition of assets across their family structures.

From understanding the dynamics of a family where "everything is ours" to addressing scenarios where individual asset maintenance is key, Katie and Tim outline strategies for effective communication and planning. As Tim poignantly observes, "You have to be intentional with how you plan for that."

Join them as they discuss practical strategies for integrating both emotional and logical perspectives into your planning. They also touch on Prairie View's recent developments, including the launch of Purview Tax, dedicated to providing proactive tax advice.

3 Key Takeaways:

1. Blended families, especially those formed later in life with established individual assets, benefit from intentional planning and clear expectations.
2. Establishing clear communication with all family members involved, including adult children, can help prevent misunderstandings and ensure everyone is aligned with estate plans.
3. Retirement and estate planning should be approached as a phase-oriented strategy, where flexibility and forward-thinking can help integrate both individual and collective family goals.

This week, we're tackling an important question for those approaching retirement: How do you know when it's time to move, and what should you consider during this life transition? Hosts Tim Regan and Katie Umland delve into the complexities of moving in retirement, from deciding whether to downsize to contemplating a move to a retirement community.

Many clients have grand plans to downsize their homes, imagining a significant financial windfall, but it doesn't always work out that way. Their discussion highlights how lifestyle factors often outweigh financial considerations, underscoring the importance of aligning your living situation with your retirement goals and family needs.

Key points include:

• The reality of downsizing: smaller spaces often come with higher expectations and costs.
• The emotional aspect of moving: how nostalgia and family memories can impact the decision to sell a long-time home.
• The stages of moving in retirement: from bigger homes to independent living facilities and eventually, possibly assisted living.

"You live in a house to support the lifestyle that you want."

3 Key Takeaways:

1. Downsizing does not always result in a financial windfall due to increased expectations for quality and amenities in a new home.
2. When considering a move, weigh the emotional and lifestyle benefits as heavily as financial ones.
3. Planning for retirement housing involves assessing different stages of life, from maintaining a larger family home to transitioning to independent living and eventually assisted living if needed.

Click play to hear practical advice on aligning your retirement lifestyle with your housing choices, and check out our previous episodes for more retirement planning insights!