Articles
Deeper dives on retirement-planning topics that don’t fit neatly inside a calculator — the mechanics, the tradeoffs, and the strategies people actually use. See the About page for who writes these and how they’re sourced.
August 10, 2026
The Net Investment Income Tax (NIIT): History, Purpose, and How to Avoid It
A 3.8% surtax on investment income that's applied above a threshold frozen since 2013. Here's where NIIT came from, exactly how it's calculated, and the legitimate ways to manage your way around it.
August 9, 2026
Deferred Compensation Plans: 401(k), 403(b), 457(b), and 409A Compared
401(k), 403(b), and 457(b) plans all defer pay and taxes the same basic way, but which one you can use depends entirely on your employer's sector — and Section 409A is a different animal altogether. Here's how each works and where they diverge.
August 3, 2026
The Widow's Penalty: How Taxes Jump When a Spouse Dies
Household income barely changes when a spouse dies, but the tax and Medicare-premium thresholds it runs through roughly cut in half overnight. Here's why the squeeze happens, and what can be done about it before it hits.
August 3, 2026
Long-Term Care: Self-Insuring vs. LTC Insurance vs. Hybrid Policies
There are really only three ways to handle the cost of long-term care: pay out of savings, transfer the risk to an insurer, or use a hybrid policy that pays out either way. Here's how each works, and who each one actually fits.
August 2, 2026
The 4% Rule: Its Origin, How It's Changed, and Its Link to Shiller CAPE
A worst-case backtest from 1994 became the default retirement rule of thumb. Here's where the 4% actually came from, how it's been revised since, and what Shiller CAPE has to do with it.
August 2, 2026
Backdoor and Mega Backdoor Roth Conversions: How They Work and Who They're For
Roth IRAs phase out at higher incomes, but two IRS-sanctioned workarounds — the backdoor Roth and the mega backdoor Roth — let high earners get money into Roth accounts anyway. Here's how each works, and where they trip people up.
August 2, 2026
Inherited IRAs and the SECURE Act's 10-Year Rule
The stretch IRA is gone for most beneficiaries, replaced by a 10-year deadline — and as of 2024's final IRS regulations, whether you owe annual withdrawals inside that window depends on a detail most people miss.
August 2, 2026
QLACs: Using an Annuity to Delay RMDs
A QLAC is the one retirement-account asset that gets excluded from your RMD calculation entirely, in exchange for guaranteed income that doesn't start until later — here's how it works and the trade-offs involved.
August 2, 2026
Health Insurance Before Medicare: ACA Subsidies and the Retirement Bridge Years
Retiring before 65 means bridging the gap to Medicare, usually with an ACA marketplace plan — and with the enhanced subsidies expired and the 400% FPL cliff back for 2026, how you time your income now has real financial consequences.
August 2, 2026
Reverse Mortgages (HECMs): Turning Home Equity Into Retirement Income
For many retirees, home equity is the largest asset that never shows up in a portfolio balance. Here's how a HECM converts it into spendable cash — and what it costs to do so.
July 20, 2026
SEPP and 72(t): Accessing Retirement Money Early Without the Penalty
A SEPP lets you draw from an IRA or 401(k) before 59½ without the 10% penalty — in exchange for locking into a rigid, formula-determined payment schedule for years. Here's how the math works and what breaks it.
July 20, 2026
Dynamic Withdrawal Strategies: Adapting Retirement Spending to the Market
A fixed withdrawal ignores what the market just did. Here's how guardrails, downturn cuts, and other dynamic spending rules let retirement withdrawals flex with the portfolio instead — and which one fits which kind of market.
July 20, 2026
Social Security, Explained: How It Works, Its History, and Its Future
Social Security isn't a personal savings account — it's a pay-as-you-go system funded by today's payroll taxes. Here's how it actually works, how it got here, and what the Trustees' own numbers say about its future.
July 20, 2026
HSAs: The Triple Tax Advantage, Who Qualifies, and How Much You Can Contribute
An HSA is the only account that deducts contributions, grows tax-free, and lets qualified withdrawals out tax-free too — but only if you're enrolled in a qualifying high-deductible health plan. Here's how eligibility and the limits actually work.
July 20, 2026
Roth IRA vs. Roth 401(k): What They Are, Their History, and How They Differ
Both tax the money going in and let it grow tax-free forever after — but a Roth IRA and a Roth 401(k) differ on almost everything else, from who can use one to how much you can put in. Here's the full comparison, and the history behind each.
July 16, 2026
Qualified Charitable Distributions: A Tax-Free Way to Satisfy Your RMD
Give directly from an IRA to charity and the money never counts as taxable income at all — a better result than a deduction, and one that can zero out some or all of your RMD.
July 16, 2026
Roth Conversions: What They Are and How to Strategize Them
Converting shifts when you pay tax, not whether you pay it. Here are the main strategies for deciding how much to convert, and when — from bracket-filling to timing conversions around market dips.
July 16, 2026
Sequence of Returns Risk: Why the Order of Returns Matters More Than the Average
Two retirees can see the exact same average return over 30 years and end up in completely different places, purely because of the order those returns arrived in. Here's why, and how to hedge against it.
July 13, 2026
When to Claim Social Security: A Breakeven Analysis
Claiming early locks in a smaller check for longer; waiting locks in a bigger check for less time. Here's the actual math behind that trade-off — and why the math isn't the whole story.
July 13, 2026
Required Minimum Distributions, Explained
Once you hit your RMD age, the IRS stops letting your pre-tax accounts grow tax-deferred forever. Here's exactly how the withdrawal is calculated and what your options are.
July 13, 2026
Net Unrealized Appreciation (NUA): The 401(k) Tax Break Most People Never Use
A narrow rule for a specific situation — appreciated company stock inside a 401(k) — that can turn a big ordinary-income tax bill into a long-term capital gains one, if you do it correctly.
July 13, 2026
The Rule of 55: Tapping Your 401(k) Early Without the Penalty
Leave your job at 55 or later and the 10% early-withdrawal penalty on that employer's 401(k) disappears — but only under specific conditions, and only until you roll the money somewhere else.
July 13, 2026
Glide Path Strategies: How Your Allocation Should Change Over Time
Target-date funds made glide paths mainstream, but the idea — gradually shifting from stocks to bonds as retirement nears — has more nuance to it than "get safer as you age."