How Money Works: Planning, Fables, and Real-Life Finance
How Money Works
The stories we believe about money often shape our choices more than the numbers do. In this episode, Craig and Jennifer explores these “financial fables,” using real-life situations to reveal how hidden beliefs influence the way people plan. The team also tackles listener questions and offers smart portfolio strategies to balance risk and reward at every life stage. Here’s some of what we discuss in this episode: 📘 Financial Fables: classic stories that reveal modern money lessons 🎓 Student Loan Decisions: balancing generosity with retirement readiness 🏡 Inheritance Reality:...
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You Made It to Retirement… Now Don’t Screw It Up!
How Money Works
You’ve worked for decades, saved diligently, and finally reached retirement, now comes the hard part: not screwing it up. Craig and Jennifer share the most common post-retirement mistakes people make and explain why having a solid, flexible plan is far more important than a collection of accounts or hot stock tips. Once you’ve already won the race, don’t jump back in. Here’s some of what we discuss in this episode: 🏗️ Build a Strong Foundation: secure income before chasing returns 💡 New Opportunities: evaluating investments with clarity, not emotion 🧩 Comprehensive...
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The Retirement Road Trip: Don’t Drive Without a Plan
How Money Works
Most people will spend hours planning a vacation: researching routes, mapping stops, and budgeting for the trip. But when it comes to retirement, many people set off without a roadmap. Today we’ll use the great American road trip as a powerful analogy for planning the retirement journey. Craig and Jennifer break down the essentials: knowing your destination, calculating the cost of the trip, and choosing the right route to get there. Just like with travel, unexpected detours will pop up, like health issues, market downturns, or surprise expenses. With a clear plan and the right guide, you...
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The 10-Year Retirement Countdown: Ages 55–65
How Money Works
The decade between 55 and 65 is one of the most critical stretches in your financial life. It’s the runway leading into retirement, and the choices you make in these years can set the tone for the decades that follow. In this episode, Craig and Jennifer break down the key decisions that every pre-retiree needs to think about before taking the leap. Today, you’ll hear how to decide what really matters in retirement, why “knowing your numbers” is more important than ever, and how healthcare costs often surprise people who assume Medicare will cover everything. This decade is one where...
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Harder Than It Looks: Retirement Planning’s Hidden Challenges
How Money Works
Some financial decisions appear simple on the surface until you start working through the details. In this episode, Craig and Jennifer break down common areas of retirement planning that are harder than they look and explain why professional guidance makes all the difference. Each of these areas can feel overwhelming if you’re going it alone, but with the right plan, they don’t have to be. They start with Social Security, where the choice of when to file isn’t just about picking an age, it’s about understanding penalties, income limits, and how benefits fit into your larger income...
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Misconceptions That Put Business Owners at Risk
How Money Works
Owning a business can be one of the best wealth-building opportunities, but it also comes with unique challenges, especially when it’s time to think about retirement. Too many business owners assume their company alone will carry them through, but as Craig and Jennifer explain, that’s often a dangerous misconception. In this episode, they share common myths business owners believe and the risks of relying solely on a business for future security. They discuss why saving outside your business matters, how to think about retirement plans like SEPs and 401(k)s, and why things like HSAs and...
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Are You Wealthier Than You Think?
How Money Works
Could you be wealthier than you think once all your accounts and assets are tallied? In this episode, Craig and Jennifer explore the surprising ways your financial standing might be stronger than you realize. But first, they kick things off with a mid-year business owner checklist, covering everything from retirement plan reviews to tax strategies, cash flow, and succession planning. Then, you’ll hear real-world examples of why emergency funds matter, how saving consistently builds long-term wealth, and why even small contributions add up over time. The message? Building wealth comes from...
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Redefining “Safe Money:” The Truth About Cash, CDs, and Risk
How Money Works
Everyone talks about “safe money,” but what does it actually mean and how much should you have? In this episode, Craig and Jennifer unpack the overused (and often misunderstood) concept of safe money. They explain what it really means to keep your money protected from loss, why liquidity is often more important than growth, and how safe money fits into the bigger picture of your financial plan, especially in retirement. You’ll hear why some clients are sitting on $300k+ in cash or CDs and not realizing how little they’re actually keeping after taxes and inflation. Plus, Craig and...
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The 5 Financial Pain Points You Can’t Ignore
How Money Works
When it comes to retirement, most people have a few lingering fears, but some concerns come up time and again. In this episode, Craig and Jennifer break down the biggest pain points they hear from clients and explain what you can actually do about them. From running out of money to the anxiety of market crashes, this episode explores the emotional (and very real) weight of uncertainty. Craig shares how failing to run the numbers leads to unnecessary fear, while Jennifer outlines why taxes, healthcare costs, and long-term care are often overlooked until it’s too late. They also talk about a...
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The Five People You Meet Before Retirement
How Money Works
In the book The Five People You Meet in Heaven, each person the main character meets help him understand his life in a new way. Today, Craig and Jennifer talk about the five people you should meet before retirement, people who can guide your next chapter and help you retire with confidence, and purpose. After all, retirement isn’t just about money, it’s about strategy, mindset, and having the right people in your corner. Craig and Jennifer reveal the essential allies you’ll want by your side before you retire, people who can help you avoid costly missteps, protect what you’ve built,...
info_outlineRetirement planning isn’t always a smooth ride, and sometimes it can feel more like spinning a wheel or picking a mystery box. In this playful but practical episode, Craig and Jennifer turn retirement planning into a game show, using iconic formats like The Price is Right and Are You Smarter Than a Fifth Grader? to unpack the real-life financial decisions people face every day.
Underneath the fun lies serious wisdom. Craig and Jennifer discuss why focusing only on “the pile of money” misses the bigger picture, how the timing of your pension or Social Security benefits can make or break your plan, and why cash flow, not just account balances, is what truly matters. You’ll also hear their take on simplifying your strategy so it works for you in real life, and not just on paper.
Here’s some of what we discuss in this episode:
🎯 Why your “magic number” might be misleading
🏦 The real cost of pre-tax retirement savings
🧮 Social Security timing tricks that boost payouts
🧠 How to simplify your plan
🧾 What game shows can teach us about income planning
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