Social Security timing, Medicare enrollment, and how you draw down savings all have deadlines — and getting them wrong can cost you thousands. Lumeway helps you understand your options and avoid the common mistakes.
Estimate your Social Security benefits at different claiming ages. Review every retirement account you have. Research Medicare options so you're not deciding under pressure later.
Decide your Social Security claiming strategy. Build a detailed retirement budget with healthcare, taxes, and inflation. Plan for the insurance gap if retiring before 65.
Enroll during your Initial Enrollment Period — missing it triggers permanent late penalties. Choose between Original Medicare and Medicare Advantage. Review Part D drug plans for your specific medications.
Start Required Minimum Distributions at 73. Update your estate plan. Track actual spending against your budget. Your Lumeway dashboard tracks every deadline.
Critical deadlines
Starts 3 months before you turn 65 and ends 3 months after. Missing this window triggers a late enrollment penalty that increases your Part B premium by 10% for every 12 months you were eligible but didn't enroll — and it's permanent.
Benefits are reduced ~30% if you claim at 62. Full benefits at 67 (for most). Delayed credits of 8% per year if you wait until 70. Once you claim, you can only undo it within 12 months.
RMDs from 401k and traditional IRA accounts must begin by April 1 of the year after you turn 73. The penalty for missing an RMD is 25% of the amount you should have withdrawn.
This is your annual window to switch Medicare Advantage plans, change from Advantage to Original (or vice versa), and change Part D drug plans. Review your plan every year — formularies and costs change.
If you have a pension, you'll need to choose a payout option (lump sum vs. annuity, single life vs. joint survivor). This is often irrevocable — take your time and consult a financial advisor.
The year you retire is often the best time for Roth conversions, tax-loss harvesting, and other strategies. Work with a CPA or tax advisor before year-end.
Trusted resources
Estimate your Social Security benefits, apply online, and learn about claiming strategies.
ssa.gov/benefits/retirement →Official Medicare enrollment, plan comparison tool, and coverage information.
medicare.gov →Retirement planning calculators, guides, and resources for every stage.
aarp.org/retirement →Independent federal guide to retirement planning, avoiding scams, and managing your money.
consumerfinance.gov →Your retirement dashboard
Organized guidance built for exactly this moment — so you can start this chapter with confidence.
Your personal dashboard
Track every step in one place
Checklists, in-depth guides, a resource directory, and a glossary of terms — all organized around your specific situation.
See all dashboard features →See it in action
Start with a free conversation — Lumeway walks you through your situation step by step. Then track everything in your personal dashboard: deadlines, documents, activity log, and state-specific resources.
Lumeway helps you navigate Medicare, Social Security, and your retirement plan with confidence — so you can focus on what matters.
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