Retirement. For decades, it may have seemed like a distant dream. Now, it’s just around the corner. The final five years before you leave your job are a critical time. The decisions you make now will shape your financial security and lifestyle for the next 20, 30, or even 40 years. This period isn’t about panic; it’s about purpose. It’s the time to move from accumulating wealth to creating a lasting, reliable income stream.

Think of these next five years as your “glide path” to a successful retirement. It’s a structured approach to transition smoothly from your working life to your retired life. This checklist is designed to guide you, year by year, through the most important financial steps. We’ll cover everything from creating a vision and managing debt to navigating Social Security and understanding your healthcare options. Let’s walk through this journey together, one step at a time.