🌅 Retirement

Retirement Planning Guide

Retirement brings big decisions — when to claim Social Security, how to handle Medicare, what to do with your savings. Lumeway helps you understand your options and avoid costly mistakes.

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See rules specific to your state:

What to expect

A timeline of what
needs to happen

Each phase has specific tasks and deadlines. Lumeway helps you stay on track so nothing falls through the cracks.

1–2 years before

Plan and project

  • Estimate your Social Security benefits at different claiming ages (use ssa.gov/myaccount)
  • Review all retirement accounts: 401k, IRA, pension, brokerage accounts
  • Meet with a fee-only financial advisor to stress-test your retirement plan
  • Research Medicare options so you're not making decisions under pressure
6–12 months before

Make key decisions

  • Decide your Social Security claiming strategy (62 = reduced, 67 = full, 70 = maximum)
  • Create a detailed retirement budget — include healthcare, taxes, and inflation
  • Plan for the health insurance gap if retiring before 65 (COBRA, marketplace, or spouse's plan)
  • Notify your employer and understand your final benefits (unused PTO, pension election, retiree benefits)
3 months before 65

Medicare enrollment

  • Enroll in Medicare during your Initial Enrollment Period (starts 3 months before your 65th birthday)
  • Choose between Original Medicare (Parts A & B) and Medicare Advantage (Part C)
  • Evaluate Medigap supplemental plans if choosing Original Medicare
  • Review Part D prescription drug plans — compare formularies for your specific medications
After retirement

Manage and adjust

  • Begin Required Minimum Distributions (RMDs) from retirement accounts at age 73
  • Review and update your estate plan (will, trust, power of attorney, healthcare directive)
  • Track actual spending vs. your budget for the first year — adjust as needed
  • Consider long-term care insurance or planning if not already in place

Critical deadlines

Don't miss these
time-sensitive steps

7-month window
Medicare Initial Enrollment Period

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.

Age 62 / 67 / 70
Social Security claiming decision

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.

Age 73
Required Minimum Distributions

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.

Oct 15 – Dec 7
Medicare open enrollment

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.

Varies
Pension election deadline

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.

Year of retirement
Tax planning window

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.

You
I'm turning 64 next month and thinking about retirement. I'm not sure when to start Social Security.
L
That's one of the biggest financial decisions you'll make — and there's no one-size-fits-all answer. A few things help me give better guidance: do you have other retirement savings like a 401k or IRA?
You
I have a 401k with about $350,000 and a small pension.
L
That's a solid foundation. Here's the key tradeoff with Social Security: claiming at 62 gives you smaller checks sooner, while waiting until 70 gives you about 77% more per month. With a 401k and pension as a bridge, you may be able to delay Social Security and lock in a higher lifetime benefit. But it depends on your monthly expenses, health, and other factors.
You
I hadn't thought about using my 401k as a bridge. How does that work?
L
The idea is to live off 401k withdrawals from 65–70 while your Social Security benefit grows at 8% per year. Meanwhile, at 65 you'll enroll in Medicare so healthcare is covered. Want me to map out what that timeline would look like for you?

See it in action

See how Lumeway helps

Try Lumeway's guidance navigator -- it walks you through each step of your transition. Plus, track everything in your personal dashboard.

Start a free conversation → Explore dashboard features

National resources

Trusted organizations
that can help

🏛️
SSA.gov Retirement

Estimate your Social Security benefits, apply online, and learn about claiming strategies.

ssa.gov/benefits/retirement →
🏥
Medicare.gov

Official Medicare enrollment, plan comparison tool, and coverage information.

medicare.gov →
📊
AARP Retirement

Retirement planning calculators, guides, and resources for every stage.

aarp.org/retirement →
💰
Consumer Financial Protection Bureau

Independent federal guide to retirement planning, avoiding scams, and managing your money.

consumerfinance.gov →

Common questions

Frequently asked
questions

Quick answers to help you understand what to expect and what to prioritize.

You can claim as early as 62 (with a roughly 30% reduction), at your full retirement age of 66–67 (for most), or delay until 70 (earning about 8% more per year you wait). The best age depends on your health, other income sources, and whether you need the money now versus later. Lumeway can walk you through the tradeoffs →
Enroll during your Initial Enrollment Period, which starts 3 months before you turn 65 and ends 3 months after. You can enroll at Medicare.gov or your local Social Security office. If you miss this window, you face permanent late enrollment penalties.
Original Medicare (Parts A & B) is the federal program that covers hospital and medical services — you can see any provider that accepts Medicare. Medicare Advantage (Part C) is a private plan alternative that often includes extra benefits (dental, vision) but restricts you to a provider network.
Required Minimum Distributions 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.
The years between retirement and age 73 (when RMDs start) can be an ideal window for Roth conversions, especially if you're in a lower tax bracket. But the right strategy depends on your individual circumstances — consult a CPA or financial advisor before making this decision.
If you retire before 65, you'll need bridge coverage — COBRA (up to 18 months), a marketplace plan, retiree benefits (if your employer offers them), or a spouse's plan. At 65, Medicare becomes your primary coverage regardless of other insurance.

Ready to make the most
of what's next?

Lumeway helps you navigate Medicare, Social Security, and your retirement plan with confidence — so you can focus on what matters.

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