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 less-discussed struggle: the fear of walking away from a steady paycheck and into the unknown. And if you think simply stashing money in CDs is a safe bet, it’s time to rethink your plan. Today, we unpack how certain strategies can backfire and what to do instead.

Here’s some of what we discuss in this episode:

💸 The #1 fear most retirees won’t admit

🏥 What long-term care actually costs—and who pays for it

💀 Death, taxes, and the rollercoaster of retirement

💡 Why doing nothing is the riskiest plan of all

📉 How market crashes can drain your nest egg faster than you think

Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/

Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

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, and design a future that fits your life. You’ll also meet the “bonus sixth person,” a relationship that may just bring the most lasting fulfillment of all. If you're looking to retire on your terms, don’t miss this insightful episode.

Here’s some of what we discuss in this episode:

🧭 Why you may want a retirement income specialist

📜 Estate planning mistakes you definitely want to avoid

📋 How insurance planning prevents retirement surprises

💸 Differences between tax planning and tax preparation

🏋️‍♂️ The role a fitness instructor plays in retirement vitality

Contact Maestro Wealth:

Web: https://maestrowealth.com/

Email: info@maestrowealth.com

Phone: 336-448-1086

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 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

Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/

Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

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 a complex life transition. With decades of experience, Craig and Jennifer guide you through the truth behind the myths, and the smarter steps you can take now to protect your lifestyle and legacy.

Here’s some of what we discuss in this episode:

💼 Why most business owners don’t really retire

🧾 Is a financial analysis just as good as a plan?

🛑 Why “my spouse will be fine” could be a costly assumption

🧠 Learn from others' financial mistakes, without living them yourself

⚖️ Debunking common “rules” and what to consider instead

Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/

Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

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 volatility in real dollars (not just percentages), and what questions to ask if you're worried about whether your plan can hold up. Plus, Craig explains how sensitivity analysis helps you stress-test your portfolio so you can stop guessing and start planning with clarity.

Here’s some of what we discuss in this episode:

📉 Why the worst reaction to market drops is overreaction

🧺 How “bucketing” your money may protect your peace of mind

🧠 Why emotional investors often derail their own plans

📊 What a sensitivity analysis tells you about your portfolio

💵 The real danger of needing money from volatile investments

Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/

Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

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 drops, and why risk, volatility, and media noise don’t have to define your retirement. You’ll also hear a powerful real-world example of how sequence-of-return risk can derail a plan and what to do instead.

Here’s some of what we discuss in this episode:

📉 The real risk of retiring during a downturn

📊 Understanding the risk in your portfolio

🧠 Control what you can and ignore the noise

🛡️ Real-world strategies for building a resilient income plan

Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/

Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

When it comes to your financial future, a few bad assumptions can lead to costly mistakes. In this episode, Craig and Jennifer break down some of the most common (and dangerous) misconceptions people have about retirement planning.

We’ll discuss why a Roth IRA is an account—not an investment, the truth about delaying Social Security benefits, and why assuming your pension lump sum is always the best option might not work for you. We’ll also talk about the implications of tax brackets and how tax laws could shift dramatically if the Tax Cuts and Jobs Act (TCJA) expires.

With more than 30 years working with clients, we can help you make more informed financial decisions and avoid bad assumptions with your retirement plan.

Here’s some of what we discuss in this episode:

🔍 Roth IRA Misunderstanding – It’s not an investment; it’s a tax wrapper

📈 Social Security Timing – Delaying isn’t always the best answer

💼 Pension Decisions – Lump sum vs. lifetime payments: What’s the right move?

📉 Bond Risks – Rising rates can hurt your portfolio more than you think

Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/

Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin

Ever wonder what other people talk about with their financial advisors? A new survey of nearly 400 experienced advisors reveals the biggest concerns, challenges, and financial goals their clients are facing today. In this episode, Craig and Jennifer Moser break down the results and compare the findings to what we see at Maestro Wealth Advisors.

We’ll unpack insights on why 52% of clients are primarily focused on retirement planning, what higher-net-worth families often overlook (like estate planning!), and how to build reliable income streams that don’t collapse in a market downturn. You'll also learn why outliving your money, healthcare costs, and supporting both aging parents and adult children are becoming top financial concerns.

Here’s some of what we discuss in this episode:

📜 Estate plans are often outdated (or nonexistent!)

💸 Most people worry about outliving their money—even millionaires

🏥 Healthcare costs are underestimated but potentially devastating

👪 The “sandwich generation” is real—supporting parents and kids impacts retirement

🔄 Retirement is a dollar amount, not an age—planning brings confidence

Check out the survey: https://www.fa-mag.com/news/retirement-planning-survey-2024-80450.html

Get additional financial resources: https://maestrowealth.com/how-money-works-podcast/

Schedule a meeting: https://timetoseemaestrowealth.as.me/ReadytoBegin