Retire With Confidence: Your Essential Retirement Planning Checklist

A practical guide to reduce financial stress and create clarity as retirement approaches

Why Retirement Planning Still Feels Stressful

Most people believe they have a retirement plan—but many still feel uneasy about money.

According to Fidelity’s 2026 New Year’s Financial Resolutions Study, 71% of people say they have a plan, yet 31% describe their relationship with money as stressful.

That disconnect often comes from unanswered questions, unclear priorities, and plans that haven’t been tested against real-world retirement risks.

What This Retirement Checklist Helps You Do

• Clarify what you want retirement to look like—and what it will cost
• Identify income sources and understand how each is taxed
• Plan for healthcare, longevity, and market uncertainty
• Stress-test your plan before key retirement decisions
• Create confidence around spending, taxes, and legacy planning

Inside the Retirement Checklist

• Defining your retirement vision and values
• Estimating retirement expenses (needs, wants, wishes)
• Reviewing income sources and withdrawal strategies
• Managing taxes before and during retirement
• Healthcare and long-term care planning
• Protecting your plan from market and life risks
• Legacy and estate planning considerations

Who This Guide Is Designed For

This checklist is designed for individuals and couples approaching retirement who want clarity, structure, and peace of mind—without relying on guesswork or assumptions.

Start Reducing Stress and Planning With Confidence

A plan shouldn’t just exist—it should help you feel confident about the decisions ahead. This checklist gives you a clear framework to organize your thoughts, identify gaps, and approach retirement with greater peace of mind.