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Licensed in Nine States · Personal Guidance

Your Social Security & Medicare Roadmap

Make your retirement decisions with a clearer view of how Social Security claiming and Medicare enrollment fit together.

Illustrative scene of the same couple reviewing roadmap questions with Lisa Dillon of Advantage 1
Illustrative image.

Start with the decisions that matter to you

Still working, recently retired, or helping a spouse plan? We help you organize your questions and understand the choices relevant to your household.

Social Security claiming

Review claiming-age choices, working while receiving benefits, and potential spousal, family, and survivor benefits. We discuss how your household goals affect the questions to explore.

Medicare transitions

Review your timing, current employer coverage, prescription needs, and the differences among Original Medicare, Medigap, Part D, and Medicare Advantage.

Income and tax considerations

Identify questions about benefit taxation and Medicare income-related surcharges to discuss with your tax professional. Tax and legal advice should come from your qualified advisors.

Your next steps

Leave with a clearer list of decisions, information to gather, and timing questions to resolve before you apply or change coverage.

What is a Registered Social Security Analyst?

Personalized guidance from Lisa Dillon, RSSA®

Deciding when to claim Social Security is an important retirement decision—but your age is only part of the picture. Your earnings history, plans to continue working, marital history, family needs, and retirement goals can all influence the options worth considering.

As a Registered Social Security Analyst, I have specialized training in Social Security rules and claiming strategies. I help you understand how those rules may apply to your circumstances and compare your options before you make a decision.

At Advantage 1, we begin with your questions and goals. Then we use your Social Security earnings information and planning assumptions to develop a personalized analysis. Together, we review the results so you understand both the opportunities and the trade-offs.

Your circumstances deserve a closer look

Single or still working?

We can compare different claiming ages and explore how continued employment may affect your benefits and retirement timeline.

Married?

We look at the household picture, including each spouse’s earnings record, potential spousal benefits, and survivor considerations.

Divorced or widowed?

Your marital history may create additional claiming options. We can help you understand which questions and eligibility requirements deserve review.

Self-employed or receiving a pension?

We consider how your work history and other retirement income fit into your Social Security decisions.

Navigating disability, children’s benefits, or work outside the United States?

These circumstances can involve additional rules. I can help identify potentially relevant benefits, clarify questions, and recognize when further guidance from Social Security or another specialist is needed.

What will your personalized analysis help you understand?

1. Which benefits may be available

Your review considers more than your own retirement benefit. Depending on your circumstances, spousal, divorced-spouse, survivor, or children’s benefits may also deserve attention.

2. How different claiming dates compare

We compare potential starting dates and explain how claiming earlier or later changes projected monthly and lifetime benefits. The goal is to help you weigh the options against your income needs and priorities.

3. How your assumptions affect the results

An analysis depends on assumptions, including future earnings and longevity. We discuss those assumptions so you understand why a strategy may look favorable—and how changing circumstances could affect the comparison.

4. How your decisions may affect your spouse or family

For couples and families, a claiming decision can have consequences beyond one person’s monthly payment. We consider relevant household and survivor-benefit questions as part of the discussion.

5. What to do next

You receive a written analysis and a personal explanation of the results, along with guidance on relevant eligibility dates, application timing, and how to apply through the Social Security Administration.

A clear process, from questions to next steps

Start with a conversation.

Tell me about your retirement goals, employment plans, family circumstances, and the questions keeping you from moving forward.

Provide your information securely.

I will explain how to obtain your Social Security earnings statement and complete the information needed for your analysis. Never share your Social Security account password or verification codes.

Review your personalized analysis together.

We discuss your claiming options, projected results, assumptions, and trade-offs in plain language.

Leave with a clearer direction.

You will understand the options we reviewed and the next steps to consider. Any analysis fee, service scope, and follow-up support will be explained in writing before work begins.

How does Medicare fit into your Roadmap?

Social Security and Medicare have different enrollment rules and timelines. Starting one does not always mean you should start the other at the same time.

As a licensed insurance broker, I can also help you review Medicare enrollment timing, employer-coverage considerations, and available coverage options as a separate, related service.

Our Social Security and Medicare Roadmap brings these conversations together so you can approach your retirement decisions with greater clarity.

Don’t guess your way into retirement.

Schedule Your Social Security and Medicare Roadmap Consultation

Social Security projections depend on your information, planning assumptions, and applicable rules. Actual results may differ, and no particular benefit amount or outcome is guaranteed. The Social Security Administration determines eligibility and benefits. Advantage 1 Insurance is not affiliated with or endorsed by the Social Security Administration, Medicare, or any government agency.

Let's plan your next step

Personal guidance for people approaching retirement across our nine licensed states.

Schedule a Guidance Call

Educational information only. No specific benefit amount, savings, eligibility, or outcome is guaranteed. Advantage 1 Insurance LLC is an independent insurance agency, not affiliated with or endorsed by the Social Security Administration, Medicare, or any government agency. Calling connects you with a licensed insurance broker. Insurance availability and coverage vary; policy terms govern.

Contact & Your Next Chapter

Licensed for life and health insurance in Florida, Arizona, Illinois, Michigan, North Carolina, New Jersey, Pennsylvania, South Dakota, and Virginia. Insurance products and carrier availability vary by state and ZIP code.

Advantage 1 Insurance LLC · Riverview, Florida · 813-817-3300

Privacy, Insurance Disclosures & Contact Consent · Insurance Compensation & Advisory Fees

Medicare plan availability disclosureWe do not offer every plan available in your area. Currently we represent 24 organizations which offer 136 products in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options. Plan availability varies by state, county, and ZIP code. We help identify options based on your individual needs.