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RetiPilot gives you free, easy-to-use planning tools and clear, jargon-free education, so you can approach retirement with a plan instead of a guess.
Within about five years of retirement? Work through our free step-by-step checklist, the same framework advisors walk clients through.
Answer your biggest retirement questions
Start with your readiness score, then go deeper on the decisions that shape your income.
Retirement Readiness
See whether you are on track with a personalized readiness score — the best place to start.
Get your score →Social Security Optimizer
Compare claiming ages and find the timing that fits your plan.
Open tool →Healthcare Cost Estimator
Project Medicare premiums, IRMAA surcharges, and lifetime healthcare costs.
Open tool →Roth Conversion
Estimate the long-term tax impact of converting before required distributions begin.
Open tool →Latest from RetiPilot

The Backdoor Roth IRA — and the Pro-Rata Trap
High earners locked out of Roth contributions can still fund one through a two-step move. It works beautifully — unless an old IRA quietly triggers the pro-rata rule.
Jul 1, 2026 · 6 min read
Medicare Enrollment Windows: The Deadlines That Can Cost You
Medicare's most expensive mistakes aren't about picking the wrong plan — they're about missing a window. Some penalties last for life, and some choices can't be undone.
Jun 29, 2026 · 5 min read
Medigap vs. Medicare Advantage: How to Choose
Turning 65 hands you one of retirement's biggest decisions: Original Medicare with a Medigap supplement, or a Medicare Advantage plan. Getting it right the first time matters.
Jun 25, 2026 · 8 min readWebinars built on research from the industry’s leading firms
In each session, our team pairs a presentation from Vanguard, Capital Group, or Allianz with our own planning expertise. You get the research the largest firms in the industry produce, applied by professionals to the decisions in front of you.
“Roth Conversions: Is It Right for You?”
“Will Social Security Be There for Me?”
Watch the sessions →Featuring presentations from“Market Volatility in Mid-Term Election Years”
Watch the sessions →Featuring presentations from“Building an Income Plan That Lasts”
Watch the sessions →Presentation materials are sourced from these firms and used for educational purposes. RetiPilot is independent and is not affiliated with, sponsored by, or endorsed by them.
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