Navigating Financial Changes in 2026: Retirement, Taxes & Medicare
How Money Works
Craig and Jennifer dive into the key financial updates for 2026 and how they can affect your retirement. They discuss Social Security COLAs, Medicare premium increases, new tax deductions for seniors, and smarter ways to use Roth conversions and catch-up contributions. This episode highlights why proactive tax and income planning matters and how small decisions today can make a big difference in retirement. Here’s some of what we discuss in this episode: 🏥 Healthcare Costs – Rising medical expenses in retirement 💳 Medicare Premiums – How income affects what you pay 🧾 Tax...
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Retirement Sabotage: The Mistakes That Add Up
How Money Works
Most retirement mistakes don’t happen all at once; they happen quietly and over time. In this episode, Craig and Jennifer walk through the most common ways people unknowingly sabotage their retirement, and how to make sure it doesn’t happen to you. Tune in to learn how small, proactive planning choices can protect confidence, income, and peace of mind over the long run. Here’s some of what we discuss in this episode: ⚠️ Retirement Sabotage: Quiet mistakes that compound 📉 Market Volatility: Why reacting hurts long-term plans ⏳ Social Security: Timing decisions with lasting...
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Taking Out the Financial Trash in Your Retirement Plan
How Money Works
As retirement gets closer, the small financial issues you’ve ignored can start to pile up fast. In this episode, Craig walks through the most common “financial trash” people carry into retirement, and how to start the process of cleaning it up. What financial clutter should you clean up before retiring? If you want a clearer, more confident path into retirement, this episode shows where to start. Here’s some of what we discuss in this episode: 🧹 Cash Flow Cleanup: planning income and mortgage payments 💳 Debt & Risk: reducing financial pressure before retirement 💤 Lazy...
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Safeguard Your Legacy: Avoiding Common Errors in Estate Planning
How Money Works
It’s easy to avoid thinking about the realities of aging and the challenges it can bring. But, overlooking the true costs of healthcare and assistance can leave even the best financial plans vulnerable. Jennifer is joined by her son (and financial advisor) Cameron to explore why these risks are so commonly underestimated and what it means for your future security. Are you truly prepared for the hidden costs of growing older? Tune in the find out. Here’s some of what we discuss in this episode: 📛 Designations Matter: why beneficiary forms override your will 💸 Planning for Expenses:...
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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...
info_outlinePlanning for retirement now is not what it used to be. Gone are the days when a pension, Social Security, and personal savings—the three-legged stool—were enough to secure a comfortable retirement. Today, individuals must navigate the intricacies of 401(k)s, IRAs, and other investment accounts that lack the guaranteed income of traditional pensions.
While retirement success might be falling more and more on each individual to plan effectively, it doesn’t mean it’s impossible to accomplish. Craig and Jennifer will dive into the complexities retirees face today and the biggest challenges you’ll need to address within your plan. Learn about the impact of market volatility, the importance of creating a reliable income stream, and how to navigate the challenges of longer life expectancies and rising healthcare costs.
Here’s some of what we discuss in this episode:
- When pensions were common, retirement planning used to be a lot easier.
- The hardest question to answer is often ‘what are your retirement goals?’
- People are living much longer into their retirement.
- The sandwich generation faces a huge strain on their finances.
- Anxiety around the future of Social Security.
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