Retirement Readiness Podcast

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. Throu...

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 behi...

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...

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 ca...

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,...

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 thoughtfu...

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 ci...

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 Kat...

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 taki...

This 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 c...

This 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. “Ther...

This 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...

This 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 commo...

This 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 sh...

This 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 miscon...

This 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. Th...

This 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 w...

In 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 wh...

This episode of The Retirement Readiness Podcast features hosts Tim Regan and Kaitlyn Hedger taking a closer look at what it means to kickstart your financial life in your mid-twenties to mid-thirties. Kaitlyn, an advisor and head of the Kickstart program at Prairie View Wealth Partners, joins Tim for a practical conversation on why budgeting and cash flow management is a crucial next step after s...

In this episode of The Retirement Readiness Podcast, Tim Regan is joined by his daughter and Prairie View’s Head of Marketing, Maddy Regan, for a candid conversation about their recently launched book and how it’s designed to help readers live their Two Comma Life®. Together, Tim and Maddy discuss the unique format of the book—which blends story, practical advice, and workbook sections—and why it’...

This week on The Retirement Readiness Podcast, guest host Kaitlyn Hedger joins Tim Regan to break down the first and most crucial step of PrairieView Wealth’s Kickstart program: goal setting and planning. Designed for young professionals just starting their financial journey or looking to refine their path, the Kickstart program guides clients through a structured series of steps—including employe...

On this episode of The Retirement Readiness Podcast, Tim Regan welcomes back his daughter, Maddy Reagan as they further the conversation of Tim’s book, "Shatter Your Fishbowl: Live Your Two Comma Life®." Together, they share the story behind the book’s creation, what inspired Tim to turn years of family lessons into a manuscript, and how the writing process unfolded. Tim and Maddy talk a...

This week, Tim Regan is joined by guest host Kaitlyn Hedger, Associate Wealth Partner at PrairieView Wealth & Tax Partners and lead of the new Financial Kickstart Program. Together, they explore the unique financial planning needs of early career professionals and explain why financial guidance shouldn't wait until you’re “rich.” In this episode, Kaitlyn outlines how the Financial Kicksta...

This week on The Retirement Readiness Podcast, Tim Regan is joined by his daughter and PrairieView’s Head of Marketing, Maddy Regan, for a conversation rooted in personal growth, generational influence, and the lessons found in Tim’s upcoming book, “Shatter Your Fishbowl: Live your Two Comma Life” . Together, they explore what it means to “shatter your fishbowls” - the self-imposed boundaries that...

This week on The Retirement Readiness Podcast, Tim Regan and Katie Umland dive into a topic that impacts every financial decision we make—stress. When life throws unexpected changes your way, from downsizing your home to helping adult children financially, the line between strategy and stress can blur. Tim and Katie break down how to prepare before the pressure hits, so you’re not making emotional...