Stop Medicare & IRMAA surprises
A simple readiness check so the premium bump nobody warns you about doesn't cost you $1,000+ a year, silently.
The next 15 years of your money, made clear.
For people over 50: a free, plain-English planner, a Social Security timing tool, and a Medicare checklist — built so you can act on it in an afternoon.
Built for ages 50–72
No upsells in the guide
5-minute signup
Three things that pay you back, year after year.
Time Social Security with confidence
Working-age pensions, WEP & spousal survivors — run the math so the monthly check lasts as long as you do.
A 4% withdrawal rate that actually survives
Bucket your accounts so a bad market year can't permanently shrink the money you need.
3highest-leverage pre-retirement actions
77%potential lifetime SS increase — legal & documented
10fillable checklist items in the PDF
5 minaverage time to fill the opt-in form
Want a second set of eyes on the numbers?
The free planner covers the three worksheets. If you'd like either a one-time written review of your specific numbers or an ongoing planning tool with broader models, the two options below sit at very different prices and time horizons.
Personal Money 50+ Review
A one-time written review of your specific numbers across all three worksheets — done by Bill, delivered as a PDF. You fill in the intake form, get a same-email-back review with named moves 1–3, calendar dates, and the reasoning spelled out.
$47
One-time written review, you own the PDF
See the review →
Ready, Aim, Retire
An ongoing retirement planning tool with scenario modeling — run "what if I retire a year later," test MAGI controls, project spending pressure across decades. You don't link your accounts; it works from the numbers you enter.
See current pricing →
Subscription model · their site & their terms
Check readyaimretire.com →
Which one fits your situation?
The free planner is the worksheets. The $47 review is a written second opinion. Ready, Aim, Retire is an ongoing scenario platform. Side-by-side, the differences line up like this:
| Free 50+ Planner | Personal Money 50+ Review | Ready, Aim, Retire | |
|---|---|---|---|
| Format | Printable PDF you download | Written PDF, delivered by email | Web-based scenario tool |
| Length / scope | ~25–35 pages: three worksheets + 10-item master checklist | One-time written review of your specific numbers | Ongoing — use as life changes; unlimited scenarios |
| Source / author | Bill · Smart Money 50+ | Bill · Smart Money 50+ | Third party · readyaimretire.com |
| What you get | SS timing worksheet · Medicare/IRMAA readiness check · 4% withdrawal math worksheet · 10-item master checklist · print-only re-print toggle | Bill writes up your numbers across the same three worksheets — named moves 1–3, calendar dates, and the reasoning spelled out | Unlimited scenarios · withdrawal strategies · account sequencing · Monte Carlo / Chance of Success · tax modeling across all account types · Social Security collection strategies · spending / inflation budgets |
| Personalization | You fill in your own numbers on the worksheets | Bill runs the math on your specific numbers | You model and stress-test your own numbers in the tool |
| Time required | ~30 minutes first pass | One intake form; review returned by email | Continuous — return when life changes |
| Pairing in the funnel | Optional companion: 5-email welcome series across ~10 days | Standalone review (no auto-renewal) | Standalone subscription (their site, their terms) |
| Refresh cadence | Once a year on the 10-item checklist | One-time — re-order if your situation changes materially | Continuous — re-run scenarios any time |
| Best for | A one-Saturday-afternoon pass on the three basics | Want a second set of eyes without hiring a full advisor | Readers who want to model and re-model over years, not a one-off |
| Cost | Free (email signup) | $47 one-time | See current pricing on readyaimretire.com → |
Pricing & terms for the third option come from readyaimretire.com — check their current pricing rather than relying on this page. Educational content, not financial advice.