Got Questions? We've Got Answers!
Find clear answers to common questions about Medicare, life insurance, retirement planning, and preparing for your appointment. If you don’t see what you’re looking for, reach out and we’ll be glad to help.
This checklist is for Medicare appointments. To help make our meeting efficient, stress-free, and productive, please review the section below that best describes where you are in your Medicare journey. If you don’t have everything listed, that’s okay. We’ll work with what you have.
(You may still be working or covered by a group health plan)
Please bring:
- Current group health insurance card
- Employer or retiree health coverage information (premiums, deductibles, and max out-of-pocket details, plus your HR contact or benefits summary if available)
- Your SSA.gov account login, in case we need to apply for Medicare Part A. If you don’t have one, we can create it together during the appointment
- Photo ID
This helps us determine whether enrolling in Medicare now makes sense, or whether delaying is the better option for you.
Please bring:
- Your SSA.gov account login, to apply for Medicare Part A and B. If you don’t have one, we can create it together during the appointment
- Driver’s license or photo ID
- Current insurance card (if applicable)
- A list of the doctors you want to keep (primary care and specialists)
- Your current medications (name and dosage if available)
- Your preferred pharmacy (CVS, Walgreens, and so on)
- Bank routing and account number, for setting up premium payments
We may complete your Medicare enrollment during this appointment.
Please bring:
- Medicare card
- Current insurance cards (Medicare Supplement or Medicare Advantage plan, if applicable)
- A list of the doctors you want to keep (primary care and specialists)
- Your current medications (name and dosage if available)
- Your preferred pharmacy
- Any questions or concerns you’d like to review
Some appointments may involve secure online enrollment or electronic signatures. Please make sure you have your phone or tablet handy so you can access emails and text messages during our meeting.
It’s best to start about three months before you turn 65, which is when your Initial Enrollment Period begins. Planning early helps you avoid late-enrollment penalties and gives you time to compare your options without feeling rushed. If you’re still working past 65, we can help you decide whether to enroll now or delay.
Original Medicare (Parts A and B) is the federal program that covers hospital and medical care, and you can pair it with a separate drug plan and a supplement. Medicare Advantage (Part C) is an all-in-one alternative offered through private carriers that often bundles medical, drug, and extra benefits into a single plan. We’ll walk you through the tradeoffs so you can choose what fits your care and budget.
It depends on your situation. A Medicare Supplement (Medigap) plan helps cover the out-of-pocket costs that Original Medicare leaves behind, like deductibles and coinsurance. Whether it makes sense for you comes down to your health needs, budget, and how you want to receive care. We’ll help you weigh it against your other options.
Part D plans help cover the cost of your prescriptions and are offered through private carriers. Each plan has its own list of covered drugs and pharmacy network, so the right plan depends on the specific medications you take. We compare plans based on your prescriptions to help you find the best fit.
Yes. Medicare gives you specific windows to make changes, including the Annual Enrollment Period each fall and certain Special Enrollment Periods triggered by life events. We keep in touch and review your coverage each year so you can adjust if a better option becomes available.
There can be. Enrolling late in Part B or Part D without other qualifying coverage can lead to lifelong penalties added to your premiums. This is exactly why we help you understand your enrollment windows, so you never miss an important deadline.
There’s no single best plan, only the best plan for you. We look at your doctors, prescriptions, budget, and how you like to receive care, then compare options across many carriers to find the one that fits. Because we’re independent, our recommendation is based on your needs, not any one company’s interests.
Yes. Our educational events are completely free and no-pressure. You’re welcome to come, learn, and ask questions with no cost and no obligation to enroll in anything.
If anyone depends on your income, or you want to cover final expenses and avoid leaving costs to your family, life insurance is worth considering. It provides a financial safety net so your loved ones are protected during a difficult time. We help you figure out whether you need it and how much makes sense.
Term life covers you for a set period, like 10, 20, or 30 years, and is usually the most affordable option for temporary needs. Permanent life, such as whole life or universal life, covers you for life and can build cash value over time. We explain both so you can choose what fits your goals and budget.
It depends on your income, debts, family situation, and what you want the policy to accomplish. Some people want enough to cover final expenses, others want to replace years of income or leave a legacy. We help you land on a coverage amount that fits your needs without paying for more than you need.
Yes. Many people hold more than one policy to cover different needs, for example a term policy for income replacement during working years plus a smaller permanent policy for final expenses. We can help you structure coverage that layers well together.
In most cases, yes. Standard life insurance policies cover death from nearly all causes, including accidents, once the policy is in force. Some policies also offer accidental death riders that provide additional benefits. We’ll make sure you understand exactly what your policy covers.
It starts with understanding your goals, your budget, and who you’re protecting. As independent brokers, we compare options across many top-rated carriers and explain the differences in plain language, so you can choose with confidence rather than guesswork.
It’s often more affordable than people expect, especially term coverage and when you’re in good health. Your premium depends on factors like age, health, coverage amount, and policy type. We shop multiple carriers to find you quality coverage at a price that works.
Often, yes. Many policies allow adjustments over time, such as converting term to permanent coverage or updating beneficiaries. We’re here to review your coverage as your life changes and help you make updates when needed.
The best time is as early as possible, but it’s never too late to make a meaningful difference. Whether you’re decades away or approaching retirement soon, we help you organize what you have and build a strategy focused on stability and income for the years ahead.
It depends on your lifestyle, expenses, and the kind of retirement you envision. We help you look at your income sources, savings, and future needs to build a clearer picture of what comfortable looks like for you specifically.
Social Security is a government benefit based on your work history that provides guaranteed income in retirement. Retirement savings plans, like 401(k)s and IRAs, are accounts you build over your working years. Most people rely on a combination of both, and we help you understand how the pieces fit together.
There are strategies designed to reduce your exposure to market downturns while still supporting steady growth, including certain annuity-based options. We help you evaluate approaches that protect what you’ve built while keeping your long-term goals on track.
It depends on where you are in your journey. Earlier on, growth often takes priority, while closer to and during retirement the focus usually shifts toward reliable income and protecting your savings. We help you strike the right balance for your stage of life.
Yes. Starting late means we’re more intentional about your strategy, but a thoughtful plan can still make a real difference. We meet you where you are and focus on the moves that matter most for your situation.
A significant one. Products like annuities can provide guaranteed income, and life and long-term care coverage protect your savings from unexpected costs. Insurance-based strategies are often a key piece of a well-rounded retirement plan, and they’re a core part of how we help.
Absolutely. When you work with us, you get a team that oversees your entire plan from start to finish, backed by the strength of our partnership with Lasting Mark Retirement. You have one relationship and one point of contact, with the expertise of a full team behind your plan.

