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
#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.
Transcribe →#89: Should You Pay Off Debt Before Retirement? Navigating Interest Rates and Loans
Jan 500:45:45Tap to summarizeThis week on The Retirement Readiness Podcast, hosts Tim Regan and Katie Umland tackle a topic that’s relevant at every life stage: interest rates—how they work, when to finance a purchase, and how to make smarter borrowing decisions. From buying a first TV on a college budget to considering a mortgage payoff in retirement, Tim Regan and Katie Umland break down the basic concepts and address common misconceptions about borrowing, tax deductions, and credit scores.“Whenever you’re going to borrow money, there’s a number of things that I kind of like to think through,” Katie Umland says. “The first one is recognize that if you have to borrow money and there is an interest rate associated with it, you just increased the purchase price by a lot.”Listen as they walk through real-life examples of common borrowing decisions—from cars to student loans—and offer practical rules of thumb to help you decide when financing makes sense, and when it doesn’t. Plus, Tim Regan and Katie Umland discuss the emotional side of debt, strategies for getting organized, and how interest rates can affect everything from home buying to your grocery delivery bill.Click play to learn more, and visit pv-wp.com for additional resources.3 Key TakeawaysBefore financing any purchase, determine whether it’s out of necessity or choice, and always do the math to understand the real cost.To efficiently pay off debt, prioritize payments on the highest interest rate balances first, and stay organized with a clear list of what you owe.Interest rates and their impact on everything from mortgages to car loans start with how banks assess risk and set rates—your credit score matters.Be sure to check out pv-wp.com for more financial planning insights.
Transcribe →#88: Should You Choose Roth or Traditional Contributions for Your 401k?
Dec 1500:07:51Tap to summarizeThis week, Tim Regan is joined by guest host Kaitlyn Hedger, head of the Kickstart program at PrairieView Wealth & Tax Advisors, for a practical discussion on how proactive tax planning can make a difference in your long-term financial journey.Many people think tax time is just about tallying up last year’s numbers and filing with your accountant. But Kaitlyn explains why true tax planning should start long before the calendar year wraps up—and how aligning your tax decisions with personal goals can help you avoid missed opportunities and unnecessary penalties.“It has to take place before then,” Kaitlyn says about tax planning, “because otherwise if you wait until January 1st, you might miss the boat for some tax credits or benefits.”Tim and Kaitlyn cover common questions about tax deferral, Roth choices, 401(k) contributions, and even saving for milestones like a first home or your child’s college education. They highlight the unique approach of the Kickstart program, which aims to understand your life goals—not just your income—and how regular check-ins can help you stay ahead of changes in your personal situation and tax law.Listen in for a refresher on what proactive tax planning looks like, whether you’re just starting out or revisiting your strategy as life circumstances shift.3 Key Takeaways:Effective tax planning is proactive, not just reactive—waiting until tax season can lead to missed opportunities.The best tax strategies are goal-oriented and tailored to your specific life plans, not just tax minimization.Regular, ongoing reviews are vital, as both tax laws and personal situations can change from year to year.For more insights on financial planning and the Kickstart program, visit pv-wp.com, and be sure to check out previous episodes of the Retirement Readiness Podcast
Transcribe →#87: Kickstarting Your Financial Future: Investment Strategies Explained
Dec 100:07:40Tap to summarizeThis week on The Retirement Readiness Podcast, Tim Regan and Kaitlyn Hedger dive into the essentials of investment management for early-career professionals. If you’ve wondered how to get started with investing, what “investment management” really means, or whether you need a big bankroll to work with a financial advisor, this episode has practical answers.Tim and Kaitlyn break down common misconceptions—like the idea that investing is only for people with large portfolios—and explain how investment management starts with understanding your goals: Are you saving for a house, kids’ college, or retirement? “Step one is figuring out what you actually have,” they emphasize, underscoring the importance of taking inventory and aligning investments to specific goals and timelines.They also discuss the difference between investing and speculating, how to balance “play money” with a disciplined investment plan, and why building the right “money set”—a clear mindset and strategy for each goal—is the foundation for long-term financial success.Quote from the episode:“We see investment management as breaking down what the heck these investments even are—what we should be in, what we should be considering, and what’s available to you. That’s the biggest piece.”Tune in to learn how the Kickstart Program helps young professionals take the guesswork out of investing, and how thoughtful, goal-oriented decisions today can put you on track for your two-comma life.3 Key TakeawaysYou don’t need a large amount of money to start investing; everyone can benefit from guidance that aligns investments with personal goals.Investment strategies—and risk tolerance—should be tailored to specific goals, like buying a home soon versus saving for retirement decades away.Taking inventory of your current accounts and understanding your options is the first step toward building a methodical and intentional investment plan.Listen now, and be sure to visit pvwp.com for more resources or subscribe to the Retirement Readiness Podcast on your preferred platform.
Transcribe →#86: Kickstarting Your Financial Future: Estate Planning Tips for Ages 25 to 35
Nov 1800:11:07Tap to summarizeThis week on The Retirement Readiness Podcast, Tim Regan and Kaitlyn Hedger take a closer look at estate planning for young professionals—an often-overlooked but essential step in building a secure financial future. Kaitlyn, head of Prairieview’s Kickstart program, joins Tim to break down why creating an estate plan matters, even if you’re just starting out in your career or raising young kids.They discuss the real reasons to set up wills, financial and healthcare powers of attorney, and living wills long before retirement age. Kaitlyn explains, “No one wants to have these conversations, but lack of planning in that area can really cause a lot of chaos for your family members or your loved ones in general.”You’ll also hear about common questions clients have, the difference between a will and a trust, and why naming guardians for kids and being clear on your legacy is so important.Looking out for your loved ones isn’t just about life insurance or saving for college—it’s also about making sure your legal documents are up to date, so your wishes are known and followed.Press play for practical guidance on starting your estate plan today, and learn about the built-in support available through the Kickstart program.3 Key Takeaways- Estate planning isn’t just for the elderly; having a will, powers of attorney, and a living will is crucial for anyone—especially parents of young children.- Without an estate plan, decisions about your assets and dependents may be made by the courts, which could be at odds with your wishes.- Working with an advisor through Prairie View’s Kickstart program can help make the estate planning process less overwhelming by providing guidance and connections to legal resources.For more resources, visit PVWP.com, and remember to subscribe to the Retirement Readiness Podcast on your favorite platform.
Transcribe →#85: Understanding 401k, HSA, and More for Retirement Readiness in Your 20s and 30s
Nov 300:10:44Tap to summarizeThis week on The Retirement Readiness Podcast, hosts Tim Regan and Kaitlyn Hedger zoom in on an essential step for early-career professionals: understanding and maximizing your employer benefits. Whether you’re just starting your career or already navigating the complexities of health insurance and retirement plans, Tim and Kaitlyn break down what you really need to know about making the most of what your workplace offers.Kaitlyn, leader of the Kickstart program and a financial advisor at Prairie View Wealth, joins Tim to walk through common questions and overlooked opportunities—from choosing the right health insurance to deciding what to do with old 401(k) accounts. “With your employer benefits…you might be leaving money on the table if you’re not taking part in these benefits,” Kaitlyn explains.They cover topics such as what to do if you don’t plan to stay with a job long-term, how to avoid gaps in your financial plan, and why it’s worth the effort to review your benefits package—even if it means finally digging that email out of your inbox. Plus, they share practical steps, like using Prairie View’s online tools and checklists, to stay organized along the way.Tune in to boost your benefits knowledge and take actionable steps towards your own “2 comma life.”3 Key TakeawaysYour employer benefits are a significant part of your compensation—understanding them can help you avoid leaving money on the table.Enrolling in your 401(k), even if you don’t plan to stay at your current job long-term, is an important step since your account goes with you.Regularly reviewing and organizing your benefits (like health insurance, life insurance, and retirement accounts) helps you spot and close any gaps in your financial plan.Want more guidance? Visit pv-wp.com for resources and previous episodes, and don’t forget to subscribe to The Retirement Readiness Podcast.
Transcribe →#84: Shatter Your Fishbowl: Recognizing and Overcoming Self-Limiting Beliefs
Oct 2000:25:28Tap to summarizeIn this episode, hosts Tim and Maddy Regan invite listeners into a candid conversation about “fishbowls”—the limiting beliefs and perceptions that keep us from living our fullest lives, both financially and personally. Throughout the discussion, Tim reflects on transforming his own perceptions over time, sharing how reframing moments of scarcity into sources of growth is foundational to living what he calls a “two comma life.” As he puts it, “Usually, the thing that I’m most scared of doing or dreading the most is the thing I need to do the most.”The hosts also offer practical advice for listeners hoping to identify and break through their own limiting beliefs—whether they stem from childhood memories, recent experiences, or simply a general sense of fear or uncertainty.Click play for a thoughtful look at how personal narrative, mindset shifts, and faith intersect on the path to retirement readiness.3 Key TakeawaysLimiting beliefs (“fishbowls”) often stem from formative life experiences, and shifting your perception of these events is key to personal and financial growth.“Shattering your fishbowl” applies to all areas of life, not just money—taking action often starts with identifying the moments or feelings that hold you back.The path to living with abundance is gradual and individual, but it begins with the confidence to believe, “If somebody else has already done it, so can you.”Want more guidance? Visit pv-wp.com for resources and previous episodes, and don’t forget to subscribe to The Retirement Readiness Podcast
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