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,...
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What Game Shows Teach Us About Retirement
How Money Works
Retirement 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...
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Retirement Mythbusters: Debunking the Biggest Financial Lies
How Money Works
Retirement planning comes with no shortage of conventional wisdom, but how much of it is actually true? In this eye-opening episode, Craig and Jennifer go full-on mythbusters mode to take down some of the most common financial planning myths that could seriously derail your future. From the illusion of simplicity ("all I need is a will") to dangerous assumptions about income, inheritance, and investment strategies, they expose how outdated thinking can cost you, sometimes for generations. It’s a candid look at what real planning requires, especially if you’re a business owner or navigating...
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What to Do When Markets Get Messy
How Money Works
When the market takes a dip—or just feels unpredictable—it’s natural to want to do something. But when it comes to your retirement plan, sometimes the smartest move is actually to pause. In this episode, Craig and Jennifer share a calm, methodical approach to navigating difficult markets without panicking, overreacting, or making costly mistakes. Tune in if you’ve been looking at your portfolio lately and wondering, “What should I do now?” You’ll learn why the duo recommends a “bucketing” strategy to separate near-term needs from long-term growth, how to think about...
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Should You Retire During a Volatile Market?
How Money Works
Plenty of people have concerns about stock market volatility, a potential recession on the horizon, and fears for the economy right now. Retiring in a down market can feel like stepping onto a shaky bridge, but with the right structure, it doesn’t have to be. In this episode, Craig and Cameron unpack strategies for financial stability and peace of mind- like smart diversification and tuning out the media noise- even when the headlines are shouting panic. They cover how to build a resilient portfolio using the “three-bucket” strategy, how to plan for consistent income even if the market...
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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