Buckle up for The Retirement Roadtrip!

In this episode of Retirement Roadtrip, we tackle the ripple effects of tariffs, the rising cost of goods, and the often-overlooked realities of Medicare. Greg and Tom break down why retirement planning isn’t just about your portfolio, it’s also about healthcare, hidden costs, and knowing what decisions will follow you for decades.

From navigating the Medicare alphabet soup to understanding IRMAA and the difference between skilled care and long-term care, this episode clears up the confusion and helps you plan smarter, whether you're nearing retirement or helping someone who is.

In this episode of Retirement Roadtrip, we tackle market drops, emotional decisions, and how to make smart moves with Social Security and Medicare. After a rough market week fueled by tariff talk and economic fear, Greg and Tom get real about what investors should (and shouldn’t) do next. They also break down the often misunderstood rules around filing for Social Security, spousal benefits, Medicare enrollment, and how to protect your income in retirement.

Whether you're 23 and panicking, or 65 and confused about healthcare, this episode clears the fog and helps you move forward with confidence.

In this episode of Retirement Roadtrip, we tackle the topic of tariffs, economic fear, and how investors can remain confident through uncertain times. With recent headlines stirring anxiety about trade policy and consumer confidence, Greg and Tom break down what tariffs really mean, how history can help us put things into perspective, and what steps you can take to protect your financial future. Whether you're worried about market volatility or trying to make smart moves near retirement, this episode offers clarity and encouragement when the headlines feel overwhelming.

In this episode of Retirement Roadtrip, we explore the ins and outs of real estate investing, including five key ways investors can generate wealth. While many consider real estate an alternative investment, it offers unique advantages that can provide long-term financial security. Whether you're a seasoned investor or just getting started, this episode will help you understand the fundamental principles of real estate investing and how to maximize returns.

In this episode, we explore the biggest pitfalls retirees face and how to navigate them with confidence. Retirement isn’t just about having enough money—it’s about having a plan for how you’ll spend your time, maintain your purpose, and adapt as your needs change. We break down the three phases of retirement, common mistakes to avoid, and practical strategies to ensure a fulfilling and financially secure retirement. From testing your retirement lifestyle before making big commitments to finding meaningful ways to stay engaged, this episode will help you map out a smoother road ahead.

In this episode, we explore how to prepare for retirement beyond just finances. We discuss the emotional and practical aspects of retirement, sharing personal stories, key strategies, and tips on finding purpose in this new phase of life. From the importance of 'practicing' retirement to staying engaged through volunteering or part-time work, this episode provides valuable insights for retirees looking to navigate their journey with confidence.

In this episode, we will explore the often-overlooked but essential topic of insurance in retirement. We’ll guide you through the four key types of insurance—health, disability, life, and long-term care—highlighting their importance in crafting a robust financial plan. Along the way, we’ll debunk common myths that keep people from getting the coverage they need and share real-life scenarios to illustrate the critical role insurance plays in protecting your loved ones and your legacy. Whether you’re just starting to think about retirement or already planning the details, this episode will equip you with actionable advice to secure your financial future with confidence.

In this episode, we will explore the often-overlooked but essential topic of insurance in retirement. We’ll guide you through the four key types of insurance—health, disability, life, and long-term care—highlighting their importance in crafting a robust financial plan. Along the way, we’ll debunk common myths that keep people from getting the coverage they need and share real-life scenarios to illustrate the critical role insurance plays in protecting your loved ones and your legacy. Whether you’re just starting to think about retirement or already planning the details, this episode will equip you with actionable advice to secure your financial future with confidence.

In this episode, hosts Tom and Greg map out the 12 essential steps of a successful retirement plan. They provide listeners with a comprehensive guide to navigating the complexities of retirement, sharing practical strategies and valuable insights to ensure financial security and peace of mind. Topics include building an emergency fund, understanding estate planning, evaluating insurance needs, creating a comprehensive retirement plan, managing portfolio and asset allocation, navigating Social Security and Medicare, planning for distributions, employing bucket planning strategies, exploring advanced tax planning, utilizing smart special strategies, and embracing the importance of giving in retirement.

In this episode explore the timeless principle of giving and its profound impact on both personal fulfillment and financial planning. As the holiday season unfolds, they share inspiring stories, practical strategies, and actionable advice on how generosity can lead to a richer and more purposeful retirement.

Whether you’re curious about the tax benefits of charitable giving or looking for inspiration to make a difference, this episode provides a roadmap for giving more and receiving even greater rewards in return.