Retirement Readiness Podcast

Tim Regan
  • 5.0 (9)
  • Investing
  • Updated Bimonthly

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.

  1. 5d ago

    Ep 100: What Do You Want People to Say at Your 100th Birthday?

    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.

    33 min

  2. Jun 1

    #99: How to Break Out of Your Financial Fishbowl

    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.

    24 min

  3. May 18

    #98: Financial Freedom Allows For New Decisions!

    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.

    30 min

  4. May 4

    #97: How to Balance Spending, Giving, and Saving Your Money

    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.

    19 min

  5. Apr 20

    #96: How to Have Financial Freedom - The Right Way.

    This 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.

    21 min

  6. Apr 6

    #95: Financial Plan Changes - What Do We Do Now?

    This 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.

    29 min

  7. Mar 16

    #94: Checking In on New Year’s Resolutions: Habits, Goals, and Staying Motivated All Year

    This 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.

    27 min

  8. Mar 2

    #93: Tax Time Tips: Getting Organized for Retirement and Avoiding Common Filing Mistakes

    This week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland  explore the practical side of tax season and what to consider as you start to file your taxes. With paperwork and tax forms arriving in the mail—and sometimes even much later in the year—knowing what to organize and when can feel overwhelming. They walk through which documents matter, what can be ignored, and how taking stock during tax season can double as a valuable “financial spring cleaning” for your overall retirement readiness. “It’s kind of a good opportunity to organize it as you’re organizing it for the accountant, but then organize it for yourself and say, where do I have all this money? And is it doing the best that it could for me?”  Also covered are the benefits of communicating life changes to your accountant, checking for missed opportunities with retirement contributions, and why having a second set of eyes review your return can sometimes uncover valuable errors. The episode also touches on the gap that often exists between basic accounting and comprehensive financial planning. Click play to learn how to approach tax season proactively—and what steps you can take now to set yourself up for next year. 3 Key Takeaways Tax season is a great time to inventory your finances, identify old accounts, and make sure your money is working as hard as it should be for retirement.Life changes like refinancing a home or making charitable contributions can affect your taxes—be sure your accountant knows about anything new from the past year.Reviewing your tax returns with both an accountant and a financial planner can help catch errors and ensure you’re maximizing opportunities for tax savings.For more resources, visit pv-wp.com, and don’t forget to subscribe for future episodes.

    17 min
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Ratings & Reviews

5
out of 5
9 Ratings

About

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.

Information

  • Creator
    Tim Regan
  • Years Active
    2022 - 2026
  • Episodes
    98
  • Rating
    Clean
  • Copyright
    © 2026 Retirement Readiness Podcast
  • Show Website
    Retirement Readiness Podcast

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