Coverage at 65+

Medicare & Healthcare

Choosing the right coverage, avoiding IRMAA surprises, and planning for healthcare costs in retirement.

Articles

Medicare & Healthcare, explained

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Medicare and Healthcare

Medicare and Travel: What’s Covered When You Leave Home

Alt text: A retired couple at an airport gate with luggage, ready to travel, representing Medicare coverage considerations for retirees on the move. Medicare an

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Medicare and Healthcare

Healthcare Costs in Retirement: How to Estimate and Plan for the Unknown

Healthcare Costs in Retirement: How to Estimate and Plan for the Unknown Table of Contents The $315,000 Number — What It Means and What It Doesn’t The Pre-65…

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Medicare and Healthcare

Planning for Long-Term Care Without Insurance

Long-term care insurance isn’t your only option. Here’s how to plan for long-term care without a policy — using an earmarked reserve, home equity, and a clear-e

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Medicare and Healthcare

The Pre-Medicare Gap: Bridging Healthcare Costs Between 60 and 65

Medicare starts at 65 — and for early retirees, the gap between leaving work and that birthday is the most under-discussed problem in retirement planning. Here’

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Medicare and Healthcare

Medicare Savings Programs: Financial Help Most Retirees Don’t Know About

Key Takeaways Four Medicare Savings Programs exist — Qualified Medicare Beneficiary (QMB), Specified Low-Income Medicare Beneficiary (SLMB), Qualifying Individu

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Medicare and Healthcare

IRMAA Explained: The Medicare Surcharge That Catches Retirees Off Guard

Key Takeaways IRMAA is a surcharge on Medicare Part B and Part D premiums that applies to higher-income beneficiaries — and “higher income” starts lower than mo

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Medicare and Healthcare

Medicare Supplement vs. Medicare Advantage: Which Is Right for You?

This is the most common Medicare question I hear: Should I go with a Medicare Supplement plan or Medicare Advantage? The answer depends on how you use healthcar

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Medicare and Healthcare

Understanding Medicare Part D: How to Choose the Right Drug Plan

Understanding Medicare Part D: How to Choose the Right Drug Plan You have spent months figuring out Medicare Part A and Part B. You have chosen between Medicare

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Medicare and Healthcare

Medicare at 65 While Still Working: A Decision Guide

Navigating Medicare while still working at 65? This guide covers employer coverage vs. Medicare, HSA contribution rules, and how to avoid enrollment penalties.

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Medicare and Healthcare

2026 Medicare Changes Every Pre-Retiree Must Know

The 2026 Medicare changes include premium increases, IRMAA adjustments, and a new Part D cap. Here is what every pre-retiree needs to know and do right now.

1 min read →

Where to start

Start free. Go as deep as you want.

Four ways to get your Social Security and retirement decisions right — beginning with the free guide and the free calculator, all the way to the book and the binder.

01Free

The free Social Security guide

The claiming questions most people get wrong — answered in plain English, with the numbers that actually move the decision.

Download it free→

02Free tool

The Social Security calculator

Run your own claiming scenarios in minutes and see what waiting — or filing early — is really worth to you.

Open the calculator→

03$8.99

Social Security Decisions Made Simple

Every claiming decision that matters — spousal, survivor, taxes, the earnings test — in one plain-English place, with current 2026 figures.

See the book→

04Printable

The Just in Case Binder

The printable that lets your spouse find every account, policy, and password — without guessing — when it matters most.

See the binder→

Keep exploring

The other retirement decisions.

Claiming & benefits

Social Security

When to claim, spousal and survivor strategy, the earnings test, taxes on benefits, and the costly mistakes to avoid.

Explore Social Security →

Income & withdrawals

Retirement Planning

Turning a lifetime of savings into a dependable retirement paycheck — sequencing, withdrawals, and an income floor that lasts.

Explore Retirement Planning →

The Now / Soon / Later framework

Bucket Planning

Thomas's signature framework — Now for liquidity, Soon for a guaranteed income floor, Later for growth.

Explore Bucket Planning →

Keep more of it

Tax-Smart Retirement

Roth conversions, withdrawal order, RMDs after 73, and keeping more of every retirement dollar.

Explore Tax-Smart Retirement →

Staying the course

Markets & Investing

Market context for retirees and the psychology of staying invested through volatility.

Explore Markets & Investing →