Medicare and Social Security, explained plainly — before you decide.
Answer a few questions about your health, income, and work history. Get a personalized, plain-English plan for when to enroll and when to claim, with your exact dates. Not just a number.
No insurance sales. Your key dates are free. See a sample report.
Widowed? Get your survivor benefit timing right.
You can start a survivor benefit as early as 60, or wait for the full amount. You can take one benefit first and switch to the other later, but you never get both. The order you choose changes what you collect for the rest of your life.
Educational, not advice. No insurance sales. See a sample report.
Married? Plan your Social Security as a couple.
A spousal benefit can be up to half of your spouse's full amount, but it can't start until they file, and it stops growing at full retirement age. When the higher earner starts also sets what the surviving spouse gets for life. The order you both choose changes your income for decades.
Educational, not advice. No insurance sales. See a sample couple's report.
Most people making Medicare and Social Security decisions are leaving tens of thousands of dollars on the table — not because they're careless, but because the system is genuinely confusing.
Three steps, in order
Each step depends on the one before it. This is the actual sequence, not a menu.
Answer 7 questions
Your birth month and year, work status, coverage, doctors, prescriptions, income bracket, and what matters most to you. Takes about ten minutes.
Get your plain-English plan
Not a score. A written explanation of what to do, in what order, and why, with your exact sign-up and claiming dates. Add the estimate from your Social Security statement to see the dollar difference between your options.
Take it further, if you want
If you'd like to talk it through, book a one-on-one call with a Waypoint specialist who will walk through your plan with you. Entirely optional. The plan is yours either way.
What we are, and aren't
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Educational, not advice
Everything you get is general information to help you understand your options. It is not financial, insurance, or legal advice.
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No insurance sales, ever
We aren't a licensed insurance agent or carrier. We don't sell plans and don't earn carrier commissions.
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Plain language, no fine print games
If a term matters, we explain it. If something's uncertain, we say so.
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You choose what happens next
A call with a Waypoint specialist is offered, never automatic, and always your choice.
How we make money
Your key dates are free. We make money when you choose a paid custom report or a one-on-one call.
We don't sell insurance, we don't earn commissions from any plan or carrier, and we don't take referral fees.
You are never charged unless you choose to buy, and there's no obligation to do anything beyond the free key dates.
Two ways to get your plan
Get a full custom report, or talk it through on a live call. Not ready to pay? Your key dates are free, just below.
Full custom report
Your exact Medicare sign-up dates, which Medicare path fits your doctors and prescriptions, and what each Social Security start date pays, in plain English. Saved to a link and emailed to you.
One-on-one call
A live call with a Waypoint specialist to walk through your full situation (spouse, income, health, timing) and get direct answers to your specific questions. Already bought the report? Your $49 counts toward the call.
Card payments are processed securely by Stripe. We never see or store your card number.
Not ready to pay? Get your key dates free.
Your key dates, free
Tell us your birth month and year. See your Medicare sign-up window and your Social Security start dates right away.
Turn these dates into a plan
- Which Medicare path fits your doctors and prescriptions
- What each Social Security start date pays you in dollars, and the break-even age
- If you're married, what the surviving spouse would receive
- If you're widowed, whether to take your survivor benefit or your own first
- Your next 30 days, step by step
Let's find your timing
Seven questions. Nothing here is shared unless you choose to share it at the end.
Your report is saved at this link.
You're set.
Thanks. We've received your details.
Educational information only. Waypoint provides general educational information about Medicare and Social Security and does not constitute financial, insurance, or legal advice. Waypoint is not a licensed insurance agent, broker, or financial advisor, and does not sell insurance plans. For advice specific to your situation, consult a licensed professional, the Social Security Administration, or your State Health Insurance Assistance Program (SHIP).