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