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.
26episodes
Episodes
Newest firstAll episodes
#99: How to Break Out of Your Financial Fishbowl
2d ago00:24:21Tap 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!
2w ago00:29:33Tap 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.
Transcribe →#93: Tax Time Tips: Getting Organized for Retirement and Avoiding Common Filing Mistakes
Mar 200:16:53Tap to summarizeThis 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 TakeawaysTax 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.
Transcribe →#91: Integrating Tax, Lega, and Financial Advice for Better Retirement Outcomes
Feb 1900:26:48Tap to summarizeThis week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland explore a practical dilemma: Should your financial advisor and accountant be the same person? Or does keeping these roles separate offer better outcomes for your retirement planning?Tim and Katie talk through the challenges of managing multiple professional relationships—including how siloed advice can leave clients confused or even missing out on important financial opportunities. Katie shares, “If they're not coordinated, it can get kind of sloppy. And am I getting the best result that I could or should I try to consolidate some of those things and do them all in the same house?”You’ll hear comparisons to other fields—like medicine and landscaping—that reveal the strengths and weaknesses of hyper-specialization versus a coordinated approach. They also address potential concerns over checks and balances, coordination of estate planning, and how their team at PrairieView Wealth & Tax is rethinking what comprehensive service looks like for both individuals and business owners.Plus, Tim and Katie share updates on recent firm growth, including the addition of a Cincinnati office, and introduce ideas for helping clients of all complexities, from tracking rental property liabilities to assisting older adults with day-to-day money management.“Many times we're giving clients tax advice, but we're not executing on that because that wasn't a business we were in. And now, we can just complete the circle,” Katie explains.3 Key TakeawaysLack of coordination between your financial advisor and accountant can lead to missed opportunities and confusion; consolidating services may streamline your planning and execution.Checks and balances sound reassuring, but if your professionals aren’t communicating, you may not be getting the oversight you expect.Comprehensive service can range from straightforward tax compliance for early savers to full-scale financial management for high-net-worth and older clients—including bookkeeping, estate planning, and ongoing reporting.Tune in for practical strategies and insights to make your financial and retirement planning more coordinated—and less stressful.
Transcribe →#92: Navigating Back Taxes and Filing Mistakes for Retirement Readiness
Feb 1600:19:35Tap to summarizeThis week, hosts Tim Regan and Katie Umland tackle a topic that makes many people sweat: what happens if you need to file back taxes, or if you discover errors on your tax return? The conversation begins by normalizing the stress and anxiety many feel about tax delinquency, and moves through practical advice for getting caught up, correcting mistakes, and understanding the real consequences.“There's nothing that is that way, that there's like the dreadful stuff that gets better by waiting,” Tim points out.The hosts explain why the best time to resolve old tax issues is always now, not later, and reassure listeners that accountants are equipped to guide clients through fixing past tax filings, no matter how daunting the paperwork may seem. They also demystify the IRS process for correcting errors, clarifying that most individuals simply receive letters—rarely is there any punitive action unless fraud is involved.Plus, the episode covers the distinctions between “filing an old return” and “back taxes,” why filing for extensions is a common practice for both individuals and businesses, and how to approach amended returns without fear of audits.Tune in for stories, guidance, and encouragement to rip the Band-Aid off and tackle tax concerns head-on.3 Key Takeaways- Filing overdue tax returns is more common than people realize, and addressing them sooner is always easier than waiting.- Mistakes on a tax return typically result in notifications and opportunities to correct, not criminal consequences—unless fraud is involved.- Filing an extension for your return is a common, acceptable practice, but it does not delay tax payments; not filing at all leads to penalties and compounding stress.Click play to learn what to do if you’re behind on taxes or worried about filing errors, and visit pv-wp.com for additional resources and previous episodes.
Transcribe →#90: Avoiding Reckless Decisions: Real-Life Strategies for Pursuing Big Retirement Goals
Jan 1900:34:43Tap to summarizeThis week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland explore the concept of “shattering your fishbowl” – what it means, what it absolutely does not mean, and how to pursue your biggest goals without reckless abandon.Instead of advocating for all-or-nothing risk taking or immediate leaps into the unknown, Tim and Katie help listeners think about measured, methodical ways to push beyond self-imposed limits in life and retirement. They share personal stories and practical examples, including career changes, financial decisions, and even buying real estate or opening a business.“I know that I can accomplish X. Now let’s put together the plan so that I can take the small consistent steps day in and day out to make sure that I accomplish that,” Katie says.Listen in to hear the difference between calculated risk and recklessness, the role of small, consistent actions, and why it’s important to be honest about what you actually want in the next chapter of your life.Click play to hear more, and don’t forget to subscribe for future episodes.3 Key TakeawaysShattering your “fishbowl” isn’t about all-or-nothing moves – it’s about thoughtful, incremental progress toward meaningful goals.Before making big financial decisions, consider the impact on relationships, lifestyle, and long-term well-being.Being clear about what you truly want is crucial; avoiding self-imposed limits allows for more satisfying and realistic retirement planning.Be sure to check out pv-wp.com for more financial planning insights.
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