Insights & Resources

Retirement Income & Strategy

Turning savings into a paycheck is a different problem from building the savings in the first place. These articles cover Social Security claiming, required minimum distributions, Medicare and IRMAA, withdrawal order, and sequence risk, with the tradeoffs laid out so the decisions make sense on their own terms.

Medigap vs. Medicare Advantage

Retirement Income & Strategy

Medigap vs. Medicare Advantage: The Decision You Only Get to Make Once

Medigap vs. Medicare Advantage is not an annual choice. One path is easy to leave and hard to re-enter. The 2026 costs, the switching rules, and how to decide.

Jim Crider, CFP®
18 min readSep 1, 2026

Medicare Enrollment Timing

Retirement Income & Strategy

Medicare Enrollment Timing: The Windows, the Penalties, and the Traps That Follow You for Life

The Medicare enrollment windows explained: the 7-month IEP, the 8-month special period, lifetime late penalties, and the retroactive Part A trap.

Jim Crider, CFP®
13 min readAug 24, 2026

Long-Term Care Funding

Retirement Income & Strategy

Long-Term Care Funding: Self-Insure, Traditional, or Hybrid, and Which Dollars Should Pay

The three ways to fund long-term care, the tax mechanics that change which dollars should pay, and why doing nothing is also a plan.

Jim Crider, CFP®
12 min readAug 11, 2026

Pension Lump Sum or Annuity

Retirement Income & Strategy

Pension Lump Sum or Annuity: How to Compare Two Offers That Are Not Comparable

The hurdle rate your lump sum must earn, what inflation does to a fixed pension, and why the plan's funded status belongs in the decision.

Jim Crider, CFP®
21 min readAug 7, 2026

ACA Subsidies in Early Retirement

Retirement Income & Strategy

ACA Subsidies in Early Retirement: Living With the 400% Cliff

How marketplace premium subsidies work in 2026, what counts toward MAGI, the restored 400% FPL cliff, and how early retirees plan income around it.

Jim Crider, CFP®
11 min readAug 4, 2026

Inheriting an IRA: The 10-Year Rule

Retirement Income & Strategy

Inheriting an IRA: How the 10-Year Rule Works and When to Withdraw

Who gets the 10-year rule, who can still stretch, the annual RMD twist, spousal choices, and how to time inherited IRA withdrawals.

Jim Crider, CFP®
16 min readJul 30, 2026

Sequence-of-Returns Risk

Retirement Income & Strategy

Sequence-of-Returns Risk: Why the Order of Market Returns Matters More Than the Average

Two retirees earn the same average return and retire into opposite outcomes. How sequence-of-returns risk works, why it cuts both ways, and how we manage it.

Jim Crider, CFP®
17 min readJul 2, 2026

Required Minimum Distributions in 2026

Retirement Income & Strategy

Required Minimum Distributions in 2026: The Complete Guide to RMDs, the Taxes They Trigger, and How to Plan Around Them

How RMDs work under SECURE 2.0 in 2026 — the age-73/75 rules, the calculation, the taxes a large distribution triggers (IRMAA, Social Security, the widow's penalty), and the planning levers: Roth conversions, QCDs, QLACs, and inherited-IRA rules.

Jim Crider, CFP®
18 min readJun 29, 2026

The Retirement Gap Years

Retirement Income & Strategy

The Retirement "Gap Years": The Richest Tax-Planning Window Most People Sleep Through

The low-income window between retiring and RMDs is the richest tax-planning opportunity most people miss. How to use the gap years in 2026 — Roth conversions, QCDs, and the guardrails.

Jim Crider, CFP®
14 min readJun 19, 2026

Retirement Withdrawal Sequencing

Retirement Income & Strategy

Retirement Withdrawal Sequencing: Which Account Do You Tap First?

The "spend taxable first" rule is only half the answer. How to sequence retirement withdrawals across account types in 2026 to minimize lifetime taxes — not just this year's.

Jim Crider, CFP®
12 min readJun 18, 2026

The Social Security Tax Torpedo

Retirement Income & Strategy

The Social Security Tax Torpedo: Why Your Next Dollar of Retirement Income Can Be Taxed at 40% or More

Why each extra dollar of retirement income can be taxed at 40%+ — how the Social Security "tax torpedo" works in 2026, who it hits, and how to plan around it.

Jim Crider, CFP®
12 min readJun 17, 2026

The Widow’s Tax Penalty

Retirement Income & Strategy

The Widow’s Tax Penalty: Why Losing a Spouse Can Raise Your Tax Rate on the Same Income

When one spouse dies, the survivor often keeps most of the household income but loses half the brackets, half the standard deduction, and faces steeper Medicare surcharges. Here’s the mechanics of the widow’s tax penalty — and the planning window that exists before it hits.

Jim Crider, CFP®
15 min readJun 3, 2026

IRMAA in 2026

Retirement Income & Strategy

IRMAA in 2026: The Medicare Surcharge You Can Plan Around — If You See It Coming

How Medicare's IRMAA surcharges work in 2026, the income brackets that trigger them, and the multi-year planning moves that keep high-income households from paying more than they must.

Jim Crider, CFP®
13 min readMay 29, 2026

When to Claim Social Security

Retirement Income & Strategy

When to Claim Social Security: Five Questions the Break-Even Calculation Doesn’t Answer

The break-even chart answers one narrow question. Here are five it doesn’t ask — and why those questions matter more for your retirement.

Jim Crider, CFP®
22 min readMay 23, 2026

Social Security for Couples

Retirement Income & Strategy

Social Security Claiming Strategies for Married Couples: A Framework for the Decision Behind the Decision

Social Security claiming for married couples isn't one decision — it's two decisions plus a third about survivor protection. Here are five questions that determine the right strategy for your household.

Jim Crider, CFP®
24 min readApr 29, 2026