Are You Really
Ready for Retirement?
47 essential questions every American 50+ should be able to answer — covering Medicare, Social Security, retirement income, life insurance, estate planning, and more.
- Know exactly which Medicare plan is right for you
- Discover the optimal time to claim Social Security
- Find out if your retirement income will actually last
- Identify estate planning gaps before they cost your family
- Score yourself across 8 critical planning areas
Prepared by Rodney Cummings, RSSA® · Legacy Wealth Services · No spam, ever.
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What's Inside
8 Critical Areas Every Retiree Must Address
The checklist walks you through each planning area with specific action items, common mistakes to avoid, and Rodney's expert insights.
Medicare Planning
Enrollment windows, Advantage vs. Supplement, Part D, IRMAA, and annual review checklist
Social Security Strategy
Optimal claiming age, spousal benefits, taxation, and the breakeven analysis most people skip
Retirement Income
Income sources, sequence-of-return risk, RMDs, FIAs, and the Go-Go/Slow-Go/No-Go framework
Life Insurance Review
Policy reviews, lapsing term policies, life settlements, final expense, and beneficiary audit
Estate Planning
Wills, trusts, power of attorney, healthcare directives, and family communication checklist
Annuities & Safe Growth
Fixed Index Annuities, guaranteed income, CD alternatives, and surrender period review
Final Expense Planning
Funeral costs, burial preferences, final expense insurance, and family notification plan
Beneficiary Review
Life insurance, IRAs, 401ks, contingent beneficiaries, and common designation mistakes
How Do You Stack Up?
Score Yourself on 47 Planning Items
After completing the checklist, you'll know exactly where you stand — and where to focus first.
You're well-prepared. A quick review with Rodney can identify any remaining gaps and confirm your plan is solid.
You've made progress, but there are meaningful gaps that could cost you later. Let's build a plan to close them.
Significant planning gaps exist. A conversation with Rodney now — not later — can prevent costly and irreversible mistakes.
About Your Guide
Rodney Cummings, RSSA®
Founder, Legacy Wealth Services · Independent Retirement Advisor
After 40+ years in a combination of business and financial services, Rodney has helped hundreds of Americans navigate the complex decisions that define retirement — Medicare, Social Security, income planning, life insurance, and legacy protection. As a Registered Social Security Analyst (RSSA®), he specializes in helping clients ages 61+ identify the optimal time to begin taking Social Security benefits, a decision that can be worth tens of thousands of dollars over a lifetime.
Rodney works with 50+ carriers and is licensed in 25+ states, which means he gives advice based on what's right for you — not what pays the highest commission.
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Takes 2 minutes to get. Could save you thousands. No obligation — just clarity about where you stand.
Legacy Wealth Services is not affiliated with or endorsed by Medicare, CMS, the Social Security Administration, or any government agency. This checklist is for educational purposes only and does not constitute tax, legal, investment, or personalized insurance advice. Plan availability, benefits, and eligibility vary by state, carrier, age, health status, and individual circumstances. Consult with a licensed professional before making coverage decisions. © 2026 Legacy Wealth Services. All rights reserved.