Retirement, Legacy, and the Big Conversations Families Avoid

Retirement planning is rarely just about numbers. It is about confidence, preparation, and knowing the work you put in will support the life you want to live.

On this episode of Retire Well with Josh Bretl, Josh and Mark Elliott explore how thoughtful planning, clear communication, and proactive decisions can help retirees feel more secure about both their income and their legacy.

A Lesson from the Gymnastics Floor

Josh opens the show with a personal story about his daughter Maggie competing in her first gymnastics meet. After months of preparation, hard work, and uncertainty, she finally had the chance to perform on her own. The outcome was not about winning every event. It was about pride, effort, and enjoying the experience.

Josh explains that retirement works much the same way. People spend decades saving, planning, and worrying about the future. When retirement finally arrives, the goal is not perfection. It is confidence. Knowing you prepared properly allows you to enjoy the moment instead of fearing it.

Why Families Avoid Legacy Conversations

The conversation then turns to inheritance and legacy planning. While most people agree these discussions are important, many families avoid them entirely. Josh explains that this often stems from uncertainty, discomfort, or fear of making promises that may not come true.

Josh outlines a simple framework he uses with clients to clarify these decisions. Before legacy planning even enters the picture, retirees must address two foundational areas.

• Lifestyle. Understanding how much it truly costs to live the life you want.
• Contingencies. Preparing for the what if scenarios, including healthcare, longevity, and unexpected expenses.

Only after those needs are addressed does legacy become relevant. If money remains after lifestyle and contingencies are funded, retirees can decide how they want that legacy to be handled. Clear communication helps families avoid confusion and unnecessary stress.

The New Reality of Retirement Income

In the second half of the show, Josh and Mark focus on the challenges modern retirees face. Traditional pensions have largely disappeared, longevity is increasing, and inflation continues to erode purchasing power over time. As a result, retirees are more dependent than ever on their own savings to generate income.

Josh explains that retirement planning is ultimately income planning. Knowing where income comes from, how it grows, and how it is taxed plays a major role in long term confidence. Decisions around withdrawals, tax strategies, and asset structure can have a meaningful impact on how long savings last.