Retirement Readiness Podcast

This week on The Retirement Readiness Podcast, Tim Regan and Katie Umland talk about how to know whether a goal is actually worth pursuing—or if you're simply chasing someone else's version of success.

They explore comparison, ambition, outside influence, and the importance of asking yourself the right questions before deciding what needs to change.

3 Key Takeaways

•  Not every goal is worth chasing. 
•  Comparison can make someone else's life look better than your own. 
•  Pay attention to what you're most defensive about—it might be pointing to something worth examining. 

For more resources, visit pv-wp.com, and don’t forget to subscribe for future episodes. 

This week on The Retirement Readiness Podcast, Tim Regan and Katie Umland ask a simple but challenging question: Will you ever feel like you have enough?

From money and retirement to family, faith, and everyday life, they talk about the tension between always pushing for more and knowing when to slow down—and why reaching a certain number doesn’t necessarily mean you’ll feel satisfied. 

3 Key Takeaways

•  More money doesn’t always create a greater sense of “enough.” 
•  Finding balance between striving and being content matters. 
•  Retirement isn’t just about reaching a magical number—it’s about knowing what you actually want your life to look like. 

For more resources, visit pv-wp.com, and don’t forget to subscribe for future episodes.

This week on The Retirement Readiness Podcast, Tim Regan and Katie Umland talk about how to help someone you care about grow—even when they may not be ready to hear it.

From knowing when to speak up to knowing when to give someone space, they explore how honesty, timing, and love can help you have the conversations that matter.

3 Key Takeaways

•  Lead with love, not criticism. 
•  Know your audience and how they communicate. 
•  Sometimes planting a seed is enough—give it time to grow. 

For more resources, visit pv-wp.com, and don’t forget to subscribe for future episodes.

This week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland explore why so many people hesitate just before reaching a major goal.

Whether it's a financial milestone, a career achievement, or a personal dream, it's surprisingly common to experience fear, self-doubt, or the urge to quit when success is within reach. Tim and Katie discuss why this happens, how to recognize it, and practical ways to push through when it matters most.

Click play for an encouraging conversation about overcoming fear, embracing the process, and finishing what you started.

3 Key Takeaways

•  Feeling fear near the finish line is normal—and often a sign you're making progress. 
•  Naming self-doubt can help you overcome it instead of letting it control you. 
•  Growth comes from pushing through discomfort, not avoiding it. 

For more resources, visit pv-wp.com, and don't forget to subscribe for future episodes.

This week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland explore a question many people quietly ask themselves: Should I blow up my life?

From career changes and retirement dreams to redefining success, Tim and Katie discuss how to evaluate major life decisions without chasing an unrealistic fantasy. They explore the tension between financial security, family, purpose, and what it really means to have "enough."

Click play for a thoughtful conversation about making intentional life changes and building a future that aligns with what matters most.

3 Key Takeaways

•  Major life changes should be guided by your values, not just emotions. 
•  Financial freedom is about having choices—not endlessly chasing more. 
•  A meaningful life often comes from intentionally choosing the right challenges. 

For more resources, visit pv-wp.com, and don't forget to subscribe for future episodes.

This week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland share real stories of people whose financial lives changed through intentional decisions and consistent habits.

From overcoming limiting beliefs to finding greater peace and confidence with money, Tim and Katie explore how financial transformation often comes from small, thoughtful changes—not overnight success. Through real-life examples, they show what it looks like to build a life that's aligned with your goals and values.

Click play for an encouraging conversation about the decisions that can lead to lasting financial change.

3 Key Takeaways

•  Financial transformation often begins with small, consistent choices. 
•  Challenging old beliefs can open the door to new opportunities. 
•  Peace of mind comes from aligning your money with your values. 

For more resources, visit pv-wp.com, and don't forget to subscribe for future episodes.

This week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland celebrate the show's 100th episode by exploring a simple but powerful question: What do you want people to say about you on your 100th birthday?

Rather than focusing solely on financial goals, Tim and Katie discuss the importance of starting with the end in mind and thinking about the legacy you want to leave behind. From relationships and personal growth to health and finances, they explore how a long-term perspective can help guide the decisions you make today.

Click play for a thoughtful conversation about living intentionally and building a life you'll be proud to look back on.

3 Key Takeaways

• Starting with your long-term vision can bring greater clarity to today's decisions.
 • A meaningful life is built through more than just financial success.
 • Small choices made consistently over time can shape the legacy you leave behind.

For more resources, visit pv-wp.com, and don’t forget to subscribe for future episodes.

This week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland explore the idea of the “financial fishbowl”—the beliefs, habits, and assumptions about money that shape the way we see the world.

Many of our financial decisions are influenced by experiences we rarely stop to question. Tim and Katie discuss how these invisible boundaries can affect everything from spending and saving to lifestyle choices and long-term goals. They also share why recognizing your fishbowl is the first step toward making more intentional decisions.

Click play for a thought-provoking conversation about challenging financial assumptions and gaining a new perspective on what’s possible.

3 Key Takeaways

• Our financial beliefs are often shaped by the environment and experiences we grew up with.
• Unquestioned assumptions can limit opportunities and influence major life decisions.
• Greater awareness of your “financial fishbowl” can help you make more intentional choices.

For more resources, visit pv-wp.com, and don’t forget to subscribe for future episodes.

This week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland discuss what it means to have financial freedom—and how to use it well.

As your financial situation improves, new questions can arise. Should you spend more, give more, or continue saving? Tim and Katie explore the tension that comes with having options, and how perspective, humility, and intentional decision-making can help guide the way forward.

Click play for a thoughtful conversation on navigating financial freedom and using your money with purpose.

3 Key Takeaways

• Financial freedom creates new decisions—not fewer ones.
 • Perspective and humility help shape how you use your money.
 • Intentional choices lead to greater clarity and confidence.

For more resources, visit pv-wp.com, and don’t forget to subscribe for future episodes.

This week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland discuss the tension between spending, saving, and giving—and how to find the right balance.

As financial situations change, so do the questions around money. Should you enjoy what you’ve built, give more away, or continue to save? Tim and Katie explore why this internal push and pull is so common, and how perspective, humility, and personal values all play a role in making confident decisions.

Click play for a thoughtful conversation on using your money with intention and finding clarity in the balance.

3 Key Takeaways

• Balancing spending, saving, and giving is a natural tension—not a problem to eliminate.
• Perspective and humility play a key role in how you view and use your money.
• Aligning your financial decisions with your values can help bring clarity and confidence.

For more resources, visit pv-wp.com, and don’t forget to subscribe for future episodes.