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Tax mechanics
The Roth conversion ladder, explained
How the 5-year seasoning rule, gap years, and fill-the-bracket conversions turn pre-tax savings into tax-free money — and why looming RMDs put a deadline on it.
The three 5-year rules of Roth accounts
Contributions, conversions, and inherited Roths each carry their own 5-year clock — which one starts when, which triggers taxes vs. penalties, and the withdrawal ordering that makes ladders work.
Backdoor and mega-backdoor Roth — and the pro-rata trap
How high earners fund Roth accounts past the income limits, why the IRS aggregates all your IRAs when you convert, and the 401(k) features that unlock up to $72,000 (2026).
The RMD bomb: how pre-tax savings become forced income
SECURE 2.0 start ages 73 and 75, the Uniform Lifetime Table, a worked example of forced income growing through your 80s, and how QCDs help defuse it.
RMD exceptions and fine print: still-working, aggregation, Roth 401(k)
Who can delay RMDs while employed, which accounts can pool one withdrawal (IRAs and 403(b)s) and which cannot (401(k)s), the Roth 401(k) exemption since 2024, and the first-year double-RMD trap.
The 0% capital-gains bracket is real: LTCG stacking explained
Long-term gains stack on top of ordinary income and are taxed at 0% up to $98,900 (MFJ, 2026) — how gain harvesting steps up basis for free, and the bump-zone trap.
NUA: the company-stock tax break hiding in your 401(k)
Net unrealized appreciation lets employer stock leave a 401(k) with its growth taxed at capital gains rates instead of ordinary rates — if you satisfy the strict lump-sum rules and avoid the rollover trap.
The Social Security tax torpedo
Provisional income, the 50% and 85% phase-in tiers, and why an IRA withdrawal in the wrong band is taxed at an effective 22.2% or 40.7% — plus how the spike ends.
NIIT: the 3.8% surtax with the frozen threshold
The net investment income tax explained: the lesser-of formula, why Roth conversions expose dividends to it, and how the never-indexed $250k/$200k thresholds reach further every year.
The many MAGIs: one income, five different tests
ACA subsidies, IRMAA, NIIT, IRA deductions, and Roth eligibility each define "modified AGI" differently — what each test adds back, the 2026 thresholds, and which ones are cliffs.
Tax-loss harvesting without wash-sale regret
How harvested losses actually save tax, the 61-day wash-sale window, the IRA trap that destroys a loss permanently, and why retirees in the 0% bracket should harvest gains instead.
Safe-harbor rules: estimated taxes in retirement without penalties
The 90%/100%/110% safe harbors, the four uneven quarterly deadlines, and the §6654(g) quirk that lets a December RMD with withholding retroactively cover the whole year.
State taxes in retirement: the exemptions that change the map
Pennsylvania and Illinois exempt retirement income entirely, Georgia shields $65,000 per person at 65+, nine states have no income tax — and only eight still touch Social Security.
The widow(er)’s penalty: same money, single brackets
Why a survivor’s taxes rise while income falls: halved deductions and brackets, halved IRMAA thresholds, lower Social Security taxability tiers — and the planning window couples have before it happens.
Health & Medicare
The ACA subsidy cliff after 2025
With the enhanced credits expired, subsidies end abruptly at 400% of the poverty level — how the cliff works, what counts as MAGI, and why $1 can cost thousands.
COBRA vs. ACA: bridging health insurance before Medicare
Two very different bridges to 65: COBRA at 102% of the full group premium versus marketplace plans with MAGI-based subsidies — costs, switching traps, and the Medicare handoff.
Working past 65: Medicare, IRMAA, and employer coverage
The 20-employee rule that decides whether you can delay Part B, the HSA six-month lookback trap, and why enrolling during peak earning years triggers IRMAA surcharges.
Medicare late-enrollment penalties: Part B and D forever-fees
Part B costs 10% more per year you delay and Part D 1% per month — both for life, both growing with premiums. The 2026 math, the enrollment windows, and the COBRA trap that starts the meter.
IRMAA: the Medicare surcharge with a two-year memory
Medicare premiums are set by your income from two years earlier — the 2026 tiers, why the boundaries are cliffs, and how a Roth conversion at 63 raises premiums at 65.
Appealing IRMAA: the SSA-44 life-changing-event form
Medicare surcharges are priced from two-year-old income — but retiring, losing a pension, or losing a spouse lets you ask Social Security to use this year instead. What qualifies, and what never does.
The HSA triple advantage — and its inheritance trap
Deduction in, tax-free growth, tax-free medical withdrawals — plus the receipts strategy, Medicare premiums, and the full-taxation cliff when a non-spouse inherits.
Strategy
Monte Carlo vs “the number”: why your plan is a probability
Single-figure targets like 25× spending hide the thing that actually breaks retirements — the order of returns. What a Monte Carlo simulation does, what a success rate means, and what it doesn’t.
Why an 80% 'success rate' leaves millions unspent
Fixed-real spending caps your lifestyle but not your wealth, so the median future dies rich. What the success rate hides, and how guardrails price the surplus back in.
Nominal vs. today’s dollars: the toggle that changes everything
Over 30–60 years, inflation makes nominal charts flatter and real charts honest — why $3M in year 40 buys ~$920k of today’s lifestyle, and when each mode is the right lens.
Fixed vs. guardrails retirement spending
Why probability-of-success planning leaves huge unspent legacies, how Guyton–Klinger cuts and raises work, and the lifestyle-floor question that replaces the success rate.
The bond tent: allocation for sequence-of-returns risk
Why the first years of retirement are the dangerous ones, what happened to 2008 retirees, and the Kitces–Pfau rising equity glidepath that defends against a bad start.
What a 2008-style crash at retirement actually does
Sequence-of-returns risk with real numbers: 2008 by asset class, a worked first-year crash on a 60/40 portfolio, why early crashes hurt and late ones don’t, and the defenses that work.
Asset location: which investments belong in which account
Taxable, pre-tax, and Roth accounts tax growth in three different ways — why bonds usually hide in the 401(k), growth belongs in Roth, and index funds can sit in taxable.
The early-retirement money bridge: Rule of 55, 72(t), Roth basis, and the ladder
Four ways to spend retirement money before 59½ without the 10% penalty — what each span covers, where each one breaks, and how early retirees stack them into a bridge.
The 457(b) quirk: retirement money without the early-withdrawal penalty
Governmental 457(b) plans skip the 10% penalty at any age after you leave the job — plus a separate $24,500 limit on top of a 401(k)/403(b), and the trap that forfeits the exemption.
The Social Security earnings test: claiming early while still working
2026 limits: $1 withheld per $2 earned over $24,480 before FRA, $1 per $3 over $65,160 in the FRA year — and the recomputation at 67 that gives the withheld checks back.
The WEP/GPO repeal: what the Social Security Fairness Act changed
The 2025 law repealed the Windfall Elimination Provision and Government Pension Offset retroactive to January 2024 — who got the $17 billion in back payments, who still needs to apply, and how to update your plan.
QLACs: the annuity that defers RMDs
A qualifying longevity annuity contract pulls up to $210,000 (2026) of IRA or 401(k) money out of the RMD calculation until lifetime payments begin — as late as age 85. How the exclusion works, and what the insurance costs you.
One MAGI budget: why Roth conversions and ACA subsidies fight
Conversions want income recognized in cheap years; subsidies want it low in the same years. How the post-2025 cliff turns a 12% conversion into a 25%+ one — and how to split the budget.
Cliff-riding: why optimizing to $1 under a threshold is fragile
ACA subsidies and IRMAA tiers are cliffs, not slopes — and December fund distributions, corrected 1099s, and unpublished future thresholds make dollar-perfect MAGI plans fail. How to size a safety margin.
Giving & estate
QCDs, donor-advised funds, or appreciated shares: giving tax-efficiently
Cash is the worst asset to donate. How QCDs erase RMD income after 70½, why appreciated shares delete capital gains, and how DAF bunching beats the standard deduction.
Estate and gift tax basics: exclusions, exemptions, and who actually pays
The $19,000 annual exclusion, the $15 million lifetime exemption for 2026, portability, and the carryover-vs-step-up basis wrinkle — plus why recipients never owe the tax and under 1% of estates do.
Give it while you're alive: the tax case for early inheritance
Why the $19,000 annual exclusion, the RMD bomb, and the heirs’ 10-year drain all favor giving earlier — and the basis trap that says which assets to keep until death.
529-to-Roth rollovers: the escape hatch for overfunded college accounts
SECURE 2.0 lets leftover 529 money roll into the beneficiary’s Roth IRA — the $35,000 lifetime cap, the 15-year account clock, the 5-year contribution lookback, and the annual IRA-limit gate.
Inherited retirement accounts and the 10-year rule
Post-SECURE Act rules for non-spouse heirs: the 10-year deadline, when annual RMDs apply in years 1–9, why inherited IRAs can’t be Roth-converted, and bracket-aware draining.
By the numbers (2026)
2026 federal tax brackets and standard deductions, all four filing statuses
Reference tables for tax year 2026: the seven ordinary-income brackets, standard deductions, the 65+ additions and OBBBA senior deduction, and the 0%/15%/20% capital-gains thresholds — for single, MFJ, HoH, and MFS filers.
2026 retirement contribution limits: 401(k), IRA, HSA, and every catch-up
Reference tables for 2026: the $24,500 deferral limit, $8,000 catch-up, the age-60–63 $11,250 super catch-up, the new Roth catch-up rule, IRA and Roth phase-outs, HSA/HDHP figures, and SIMPLE limits.
2026 IRMAA tiers: the complete Medicare surcharge tables
Reference tables for 2026 Medicare IRMAA: Part B and Part D surcharges by MAGI for individual, joint, and the punitive married-filing-separately tables — plus the two-year lookback and what crossing each cliff costs.
2026 ACA numbers: FPL, applicable percentages, and the cliff
Reference tables for 2026 marketplace subsidies: the 2025 poverty guidelines that govern them, the post-expiration applicable percentage schedule, the 400%-FPL cliff by household size, and what one extra dollar costs.
Using the simulator
How to find your maximum sustainable spending
Using Strategy Lab Tool 1 to bisect for the highest fixed real spend that meets your success target — and Tool 1b, which solves for a spending floor instead, because under guardrails the risk moves from running out to lifestyle cuts.
How to model a Roth conversion ladder in Deorbit Plan
A step-by-step walkthrough of fill-the-bracket conversions: picking a bracket top and stop age, guarding the ACA and IRMAA cliffs, and reading the tax, bucket, and RMD charts that show whether the ladder pays off.
How to compare Social Security claiming ages
Claiming at 62 locks in 70% of your benefit; 70 locks in 124%. How to enter your FRA benefit, sweep claim ages against conversion strategies in the Strategy Lab, and read the success-vs-outcome frontier instead of a break-even rule of thumb.
How to stress-test your plan against a 2008 crash
Inject 2008's actual returns into every simulated path — at retirement, at a random year, or a year you fear — with or without the 2009 rebound, and read the success gauge, fan chart, and event markers to see what a worst-case sequence really costs.
Educational content only — not financial, tax, or investment advice.