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 Deductions – New charitable and senior deduction rules

📈 Catch-Up Savings – Expanded contribution limits for older workers

🧠 Tax Strategy – Planning withdrawals before retirement begins

📜 Secure Act 2.0 – Roth rules changing retirement contributions

Contact Maestro Wealth:

Web: https://maestrowealth.com/

Email: info@maestrowealth.com

Phone: 336-448-1086

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 impact

💼 Job Assumptions: When work ends sooner than expected

🎯 Financial Strategy: Replacing hope with structure

Contact Maestro Wealth:

Web: https://maestrowealth.com/

Email: info@maestrowealth.com

Phone: 336-448-1086

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 Money: cash losing ground due to inflation

🏦 Pension Choices: evaluating pension versus lump sum decisions

🏢 Life Changes: navigating company sales and job transitions

Contact Maestro Wealth:

Web: https://maestrowealth.com/

Email: info@maestrowealth.com

Phone: 336-448-1086

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: the danger of ignoring future healthcare and long-term care costs

🔄 Update Your Heirs: outdated beneficiaries that send assets to the wrong person

🏡 Don't Gift Too Soon: tax traps when transferring property while alive

🤝 Avoid Family Conflict: how communication prevents litigation

Contact Maestro Wealth:

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

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

Phone: 336-448-1086

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: why counting on future money is risky

😨 Market Fear: handling volatility without making emotional mistakes

📊 Smart Strategies: financial planning and investment fundamentals

Contact Maestro Wealth:

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

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

Phone: 336-448-1086

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 Planning: coordinating taxes, income, and estate goals

🔁 Adapting to Change: adjusting your plan as life evolves

💰 Tax Strategies: keeping more of what you've earned

Contact Maestro Wealth:

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

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

Phone: 336-448-1086

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 can navigate those bumps without losing sight of your goal.

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

🗺️ Decide your retirement destination before you hit the road

💰 Know what the trip will cost and how you'll pay for it

🛣️ Map your route: income, risk, and tax planning

🚧 Be ready for roadblocks like healthcare or market surprises

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

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

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 most people start getting serious about retirement and we want to make sure you know where to focus. We won't sugarcoat the fact that there's a lot to plan for, but we'll also offer a clear process that helps you step into retirement with confidence.

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

🎯 Decide what matters most before you retire

📊 Know your numbers: income, expenses, and gaps

🏥 Prepare for healthcare and long-term care costs

📈 Build inflation into your plan so your lifestyle keeps up

🔄 Expect change and create flexibility in your retirement strategy

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

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