Free · Educational · 10 minutes

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 — not just a number.

No insurance sales. No cost. We'll show you exactly how we make money before you share anything.

The decisions are all about timing
62Earliest Social Security — smallest monthly check
65Medicare eligibility begins — enrollment window opens
66–67Full retirement age — varies by birth year
70Social Security maxes out — no reason to wait past this

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.

How it works

Three steps, in order

Each step depends on the one before it — this is the actual sequence, not a menu.

01

Answer 7 questions

Your age, work status, coverage, doctors, prescriptions, income bracket, and what matters most to you. Takes about ten minutes.

02

Get your plain-English plan

Not a score. Not a calculator output. A written explanation of what to do, in what order, and why — including the dollar difference between your options where it's known.

03

Take it further, if you want

If you'd like help acting on it, we can introduce you to a licensed advisor. Entirely optional — the plan is yours either way.

Trust, spelled out

What we are, and aren't

  • Educational, not advice

    Everything you get is general information to help you understand your options — not financial, insurance, or legal advice.

  • No insurance sales, ever

    We aren't a licensed insurance agent or carrier. We don't sell plans and don't earn carrier commissions.

  • Plain language, no fine print games

    If a term matters, we explain it. If something's uncertain, we say so.

  • You choose what happens next

    Introduction to a licensed advisor is offered, never automatic, and always your call.

How we make money

Waypoint is free to use. If you ask to be connected with a licensed Medicare advisor after receiving your plan, we may be paid a referral fee by that advisor for the introduction.

We do not offer every Medicare plan available in your area. Any advisor you're introduced to will tell you which plans and carriers they represent.

You'll never be connected to anyone without saying yes first, and there's no obligation to move forward at all.

Your plan

Let's find your timing

Seven questions. Nothing here is shared unless you choose to share it at the end.

QUESTION 1 OF 7

What's your age — and your spouse's, if that applies?

QUESTION 2 OF 7

Are you currently working, or retired?

QUESTION 3 OF 7

Do you have employer health coverage now, or in the next 12 months?

QUESTION 4 OF 7

Do you have specific doctors you want to keep seeing?

QUESTION 5 OF 7

What prescriptions do you take regularly?

Type each one and press Enter. General names are fine — this stays general, not a full medication list.

QUESTION 6 OF 7

Approximate household income last year?

This only affects whether an income-related surcharge applies — a broad range is enough.

QUESTION 7 OF 7

What matters most to you in this decision?

Putting your plan together…

You're set.

Your plan is on its way.

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).