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!