Podcast
Retirement Readiness Podcast
Hosted by Tim Regan · EN
Retirement readiness is a phrase that can be defined differently by everyone, but we believe that it involves the idea of living with purpose. If you’ve ever wondered if it’s possible to find purpose in retirement, this show is for you. Please see https://prairieviewwealthpartners.com/disclosures/ for important disclosures.
30episodes
Episodes
Newest firstAll episodes
#103: Why We Get Scared When Success Is Close
1w ago00:23:10Tap to summarizeThis 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.
Transcribe →#102: Is It Time to Blow Up Your Life Plan?
4w ago00:40:17Tap to summarizeThis 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.
Transcribe →#101: Real Stories of Financial Transformation
Jun 2900:31:27Tap to summarizeThis 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.
Transcribe →#100: What Do You Want People to Say at Your 100th Birthday?
Jun 1800:32:48Tap to summarizeThis 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.
Transcribe →#99: How to Break Out of Your Financial Fishbowl
Jun 100:24:21Tap to summarizeThis 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.
Transcribe →#98: Financial Freedom Allows For New Decisions!
May 1800:29:33Tap to summarizeThis 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.
Transcribe →#97: How to Balance Spending, Giving, and Saving Your Money
May 400:18:48Tap to summarizeThis 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.
Transcribe →#96: How to Have Financial Freedom - The Right Way.
Apr 2000:21:19Tap to summarizeThis week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland discuss the tension many people feel between enjoying their money and staying humble.As wealth grows, so can uncertainty—should you spend, save, or give more? Tim and Katie explore why this tension exists and how aligning your decisions with your values can help bring clarity and confidence.Click play for a thoughtful conversation on making intentional financial decisions without guilt.3 Key Takeaways• Feeling tension around spending and saving is common—and worth addressing.• Clarity comes from understanding your values, not chasing a perfect balance.• Confidence with money grows when your decisions align with what matters most.For more resources, visit pv-wp.com, and don’t forget to subscribe for future episodes.
Transcribe →#95: Financial Plan Changes - What Do We Do Now?
Apr 600:28:42Tap to summarizeThis week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland discuss what happens when life doesn’t go according to plan—and how to navigate those moments with confidence.From unexpected family changes to shifting financial priorities, even the best plans can take a turn. Tim and Katie share why having clear core principles can help guide decisions, how to stay flexible when circumstances change, and the importance of communication when working through these challenges together.Click play for a practical conversation on handling life’s curveballs and staying aligned with what matters most.3 Key Takeaways• Life doesn’t always go as planned—flexibility is key.• Core principles can help guide decisions during uncertain times.• Communication and perspective lead to better outcomes.For more resources, visit pv-wp.com, and don’t forget to subscribe for future episodes.
Transcribe →#94: Checking In on New Year’s Resolutions: Habits, Goals, and Staying Motivated All Year
Mar 1600:27:29Tap to summarizeThis week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland take a mid-quarter pause to check in on their New Year’s resolutions and the habits that help turn big goals into lasting progress.It’s easy to start the year with excitement and a long list of things you want to accomplish—but staying consistent once the initial motivation fades can be the real challenge. Tim and Katie discuss the importance of revisiting goals throughout the year, focusing on small daily habits rather than just outcomes, and recognizing the progress you’ve already made along the way.The conversation also explores the difference between focusing on the “gap” versus the “gain”—a concept that reminds us to measure how far we’ve come rather than only looking at how far we still have to go. From writing goals down and creating reminders to finding accountability and building better routines, they share practical ways to stay on track even when life gets busy.Click play for a thoughtful discussion about goal-setting, motivation, and why taking time to reflect on your progress can help you stay focused on what matters most.3 Key Takeaways• Checking in on your goals early in the year helps you adjust course and stay motivated before the year slips by.• Focusing on daily habits—rather than just big outcomes—can make long-term goals much easier to achieve.• Measuring progress by how far you’ve come (“the gain”) instead of only what’s left to accomplish (“the gap”) can keep you encouraged and moving forward.For more resources, visit pv-wp.com, and don’t forget to subscribe for future episodes.
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