Retirement Check 101™ — Know Your Plan

76 articles across 13 topics:

Limits & Rules

• 2026 IRS Retirement Contribution Limits: The Complete Guide
  Every 2026 IRS retirement contribution limit in one place — 401(k), IRA, HSA, SEP, SIMPLE, 457(b), and the new SECURE 2.0 super catch-up for ages 60–63.
• SECURE 2.0 Super Catch-Up (Ages 60–63): An Extra $3,250 You Probably Missed
  Starting in 2026, savers ages 60, 61, 62, and 63 can contribute an extra $11,250 catch-up to their 401(k), 403(b), or 457(b) instead of the standard $8,000.
• The 415(c) Annual Additions Limit, Explained
  IRC §415(c) sets the master ceiling on everything that flows into a defined-contribution plan in a single year — $72,000 in 2026. Here is what it covers, what it doesn't, and why it controls every mega backdoor Roth calculation.
• HSA Contribution Limits and the 55+ Catch-Up
  Every 2026 HSA contribution limit — self-only, family, the $1,000 catch-up — plus the eligibility rules and the Medicare trap that ends contributions early.
• RMD Rules After SECURE 2.0
  Required minimum distribution rules as they stand for 2026: starting age, the Uniform Lifetime Table, the still-working exception, the SECURE 2.0 excise-tax cut, and the inherited-IRA annual-RMD rule now fully in force.
• The Mandatory Roth Catch-Up Starting 2026
  SECURE 2.0 §603 forces high earners (FICA wages above $150,000) to take their age-50+ catch-up contributions as Roth starting January 1, 2026. The mechanics, the two-year delay, and the planning moves before year-end 2026.
• FICA Wage Base and How It Drives Plan Limits
  The Social Security wage base ($184,500 for 2026) is the OASDI cap — and the quiet anchor for nearly every other retirement-plan limit in the Internal Revenue Code. Here is how the linkages work and the math on a $400,000 earner.
• Compensation Limits That Cap Employer Contributions
  Above $360,000 of salary, your employer's retirement plan has to pretend you don't earn another dollar — the IRC §401(a)(17) compensation limit. Here is what it does, why it exists, and how it eats your match.

Strategies

• Mega Backdoor Roth: How High Earners Save Up to $47,500 More Per Year
  The mega backdoor Roth lets high earners contribute up to $47,500 of after-tax money to a 401(k) and convert it to Roth — tax-free growth for life.
• HSA: The Only Triple Tax-Advantaged Account in the Tax Code
  A Health Savings Account is the only account where contributions, growth, and qualified withdrawals are all tax-free. Here is how to use one as a stealth retirement account.
• Backdoor Roth IRA: Step-by-Step for High Earners
  A clean four-step walkthrough of the backdoor Roth IRA, the pro-rata rule trap, and how to avoid the tax mistake that wrecks most do-it-yourself attempts.
• The Roth Conversion Ladder: Early Retirement Without the Penalty
  A Roth conversion ladder turns pre-tax retirement money into spendable cash before age 59½ without the 10% early-withdrawal penalty. Step-by-step mechanics, a worked example, and the five-year clock you can't skip.
• Asset Location: Which Accounts Hold Which Investments
  Asset allocation is what you own. Asset location is which account each asset lives in. Done right it adds 0.25% to 0.75% of after-tax return per year, with no extra risk.
• Tax-Loss Harvesting and the IRA Wash-Sale Trap
  Tax-loss harvesting offsets gains and up to $3,000 of ordinary income per year — but only in taxable accounts. Buy the replacement security in an IRA and Rev. Rul. 2008-5 erases the loss permanently.
• Qualified Charitable Distributions (QCDs) From Your IRA
  A QCD moves up to $111,000 (2026) directly from your IRA to a charity, satisfies your RMD, and never appears in your taxable income. The most efficient giving tool the tax code offers retirees 70½ and older.
• Net Unrealized Appreciation (NUA) on Company Stock
  IRC §402(e)(4) converts decades of growth on employer stock held in a 401(k) from ordinary income to long-term capital gains — but only if you execute the lump-sum distribution exactly right. The mechanic and the four conditions, with a worked example.
• 72(t) Substantially Equal Periodic Payments
  IRC §72(t)(2)(A)(iv) lets you tap an IRA before 59½ without the 10% penalty by taking a fixed schedule for at least five years. Methods, the modification trap, the carve-out technique, and Notice 2022-6 in plain English.
• Bunching Charitable Giving with a Donor-Advised Fund
  OBBBA made the doubled standard deduction permanent. For most households, charitable giving no longer produces a federal benefit unless it is bunched. The DAF makes bunching painless — here is the arithmetic.

History

• A Brief History of Retirement: From Augustan Rome to OBBBA
  Retirement as we know it is a 150-year-old invention built by accident, by war, and by political compromise on three continents. An executive-summary history of how today's IRS rules came to be what they are.
• How IRS Retirement Limits Have Changed: 2017–2026
  A ten-year grid of every major IRS retirement limit — 401(k), IRA, HSA, compensation caps, the estate exemption, and top tax rates — plus the story of the laws and inflation surges that moved them.

Self-Employed

• Solo 401(k) vs. SEP IRA: Which Should the Self-Employed Choose?
  Solo 401(k) vs. SEP IRA compared head-to-head: contribution limits, Roth availability, loans, paperwork, and the income level where each one wins.
• Cash Balance Plans for High-Earning Professionals
  A cash balance plan is a hybrid defined-benefit plan that lets a 55-year-old physician or partner contribute $200,000+ per year on top of a 401(k). The mechanics, the actuarial assumptions, and when the numbers actually justify the cost.
• Defined Benefit Plans: When the Numbers Make Sense
  Traditional DB plans let owner-only businesses fund six-figure annual contributions targeting a fixed retirement income. When DB beats cash balance, when both beat a SEP, and the funding obligation that surprises new sponsors.
• S-Corp vs Sole Prop: Impact on Retirement Savings
  The same $200,000 of business profit funds very different retirement contribution caps depending on entity choice. The 25% W-2 rule for S-Corps, the ~20% net-SE rule for sole props, and where the break-even sits.
• SIMPLE IRA Basics for Small Business Owners
  The SIMPLE IRA gives small employers a 401(k)-lite: $17,000 deferral, mandatory employer contribution, no nondiscrimination testing. Why it fits some businesses, why it disqualifies others, and the two-year withdrawal trap.
• Solo 401(k) Mechanics for One-Person Businesses
  The Solo 401(k) is the highest-contribution retirement plan available to a one-person business. Two contribution sources, the $72,000 cap, Roth option, loan provision, and the rule that disqualifies you the moment you hire an eligible employee.
• Adding a Spouse to Your Solo 401(k)
  A spouse who works in the business can double the household's Solo 401(k) capacity — up to $140,000 of combined contributions (or more with catch-ups). The W-2 versus K-1 distinction, the reasonable-compensation requirement, and the plan-document fix to enable spousal participation.

Employer Plans

• How a 401(k) Actually Works
  The 401(k) is the dominant private-sector retirement vehicle in America — built on a 1978 statutory accident. The mechanics, the nondiscrimination tests, and the safe harbor that lets HCEs max out.
• 403(b) Plans for Nonprofit and School Workers
  The 403(b) is the 401(k)'s cousin for nonprofits, public schools, and churches. Same $24,500 deferral limit, similar mechanics — plus a 15-year service catch-up no other plan offers.
• 457(b) Plans and Why They Stack
  The 457(b) carries its own $24,500 deferral limit that does not coordinate with the 401(k) or 403(b). For public-sector workers with both, that means $47,000 of pre-tax deferral per year. Plus the unique pre-59½ access rules.
• Employer Match Math: Don't Leave Money on the Table
  Match formulas, true-up provisions, the front-loading trap, and the SECURE 2.0 student-loan match. The mechanics of the most valuable employee benefit most people misunderstand.
• Vesting Schedules and What Happens When You Leave
  Cliff vs graded vesting, immediate vesting for safe-harbor contributions, and how to time a job change so you don't forfeit thousands in unvested employer match.
• After-Tax 401(k) Contributions and In-Plan Roth Conversions
  The mega backdoor Roth lives or dies on two plan-document provisions: (1) after-tax contributions allowed and (2) in-plan Roth conversions or in-service rollovers permitted. Mechanics, the $40,000+ headroom math, and the questions to ask HR.

IRAs

• Traditional vs Roth IRA: How to Choose
  The choice between Traditional and Roth depends on one variable — your tax rate now versus your tax rate in retirement. Here is the math, the contribution rules, and why most high earners should do both.
• IRA Deductibility Phaseouts by Filing Status
  Every Traditional and Roth IRA phaseout range for 2026, plus how MFS gets caught in the $0–$10,000 trap and what to do when one spouse is covered by a workplace plan and the other is not.
• Spousal IRAs for Non-Earning Partners
  IRC §219(c) lets a working spouse fund an IRA for a non-earning spouse — the only place in the tax code where someone with no income can fund their own retirement account. Mechanics, deduction rules, and the higher phaseout the non-covered spouse enjoys.
• Inherited IRA Rules After the SECURE Act
  The 10-year rule, the five categories of eligible designated beneficiaries who escape it, and the July 2024 final regulations that confirm annual RMDs are required during the 10-year window — fully enforced starting in 2026.
• Rollover IRAs vs Direct Transfers
  A direct trustee-to-trustee transfer is always safe. An indirect 60-day rollover triggers 20% withholding from a 401(k), the one-rollover-per-year IRA rule, and the chance to miss the deadline entirely. When to use which.
• The Pro-Rata Rule and Why It Matters for Backdoor Roths
  IRC §408(d)(2) requires every IRA distribution and conversion to be partly basis and partly pre-tax money — pro rata across all your Traditional, SEP, and SIMPLE IRAs. The rule that ruins most backdoor Roths and three legitimate ways around it.

Social Security

• When to Claim Social Security: Age 62, 67, or 70
  Claiming at 62 cuts your benefit by 30%; claiming at 70 increases it by 24%. The breakeven math, the survivor-benefit consideration, and why the optimal claim age is almost never 62.
• Spousal and Survivor Benefits, Explained
  Spousal benefits pay up to 50% of the worker's PIA; survivor benefits pay 100%. The rules on when each starts, the divorce-spouse claim, and the often-misunderstood interaction between your own benefit and a spousal benefit.
• Working While Collecting: The Earnings Test
  Claim Social Security before FRA and your benefit is reduced by $1 for every $2 of earnings above $24,480 (2026). The mechanic, the special year-of-FRA rule, and why most of the reduction comes back as a higher benefit later.
• Taxation of Social Security Benefits
  Up to 85% of Social Security can be subject to federal income tax once your provisional income crosses $25K/$32K. The two-tier threshold mechanism, the cliff effect, and the planning moves to keep benefits below the tax line.
• WEP and GPO Repeal: What Changed in 2026
  The Social Security Fairness Act, signed January 5, 2025, eliminated the Windfall Elimination Provision and the Government Pension Offset retroactive to January 2024. Who benefits, how much, and what the SSA back-pay process looks like.
• How Inflation Adjustments (COLA) Work
  Social Security's annual Cost-of-Living Adjustment is set by a CPI-W formula written into the 1972 amendments. How the number is computed, the third-quarter measurement window, and why the COLA you receive often understates your actual retiree inflation.

Medicare & Healthcare

• Medicare Enrollment Basics: Parts A, B, C, and D
  The 7-month Initial Enrollment Period around age 65, the four parts of Medicare, the late-enrollment penalties that last forever, and how Medicare coordinates with employer coverage past 65.
• IRMAA Brackets and the Two-Year Lookback
  Income-Related Monthly Adjustment Amounts add up to $487/month to your 2026 Medicare Part B premium, plus a Part D surcharge — based on MAGI from two years earlier. Bracket table, the cliff problem, and the appeal you can file after a 'life-changing event.'
• Transitioning from an HSA to Medicare
  Medicare enrollment ends HSA contributions. The six-month Part A retroactive trap, the timing of your last contribution, and what to do with the HSA balance after 65.
• Long-Term Care Planning Without Long-Term Care Insurance
  Traditional LTC insurance is increasingly unobtainable and unaffordable. Self-funding, hybrid life/LTC policies, the HSA stockpile, and the Medicaid-planning rules that actually still work in 2026.
• Coordinating Marketplace Coverage with Early Retirement
  Retire before 65 and the ACA marketplace is the bridge to Medicare. The premium tax credit math, MAGI sensitivity, and why a Roth conversion in the wrong year can cost you $20,000 of subsidy.

Withdrawals & RMDs

• The 4% Rule Revisited
  Bill Bengen's 1994 study said a 4% initial withdrawal indexed for inflation survived every 30-year period in U.S. history. The Trinity Study confirmed it. Three decades on, what the rule actually says, what it doesn't, and how to use it without abusing it.
• Sequence-of-Returns Risk in Early Retirement
  Two retirees with identical 30-year average returns can have wildly different outcomes if the bad years come first. Why the first five years of retirement matter disproportionately, and what to do about it.
• Bucket Strategies for Drawing Down Accounts
  The classic three-bucket approach: 1–2 years in cash, 3–10 years in bonds, 10+ years in equities. Why it psychologically works even when it doesn't strictly mathematically dominate, and how to refill the buckets.
• Roth Conversions in Retirement
  The window between retirement and Social Security or RMDs is the most efficient time to convert Traditional IRA dollars to Roth. The bracket-filling math, IRMAA awareness, and why the gap years are worth more than the conversion itself.
• RMD Planning to Reduce Lifetime Taxes
  RMDs are not a tax problem in any given year — they are a 30-year tax problem. Pre-RMD conversions, QCDs, donor-advised funds, and the surviving-spouse compression that makes the second-spouse tax bill the worst.
• Order of Withdrawal: Taxable, Tax-Deferred, Tax-Free
  The textbook order — taxable first, tax-deferred second, Roth last — is right only on average. The dynamic withdrawal approach that fills brackets each year usually beats the textbook by tens of thousands over a 30-year retirement.

Estate Planning

• Federal Estate and Gift Tax After OBBBA: The Permanent $15M Exemption
  The One Big Beautiful Bill Act made the elevated federal estate and gift tax exemption permanent and raised it to $15M per person beginning 2026. What that changes — and what it doesn't.
• Beneficiary Designations: The Most Overlooked Estate Document
  Beneficiary designations on retirement accounts and life insurance override your will. Why they are the most common, most expensive estate-planning error — and how to audit them.
• Trusts as IRA Beneficiaries: See-Through Rules and the 10-Year Trap
  Naming a trust as IRA beneficiary requires meeting the Treas. Reg. §1.401(a)(9)-4 see-through requirements — and post-SECURE the rules interact with the 10-year payout in counterintuitive ways.
• Step-Up in Basis Under §1014 and Why It Drives Asset Location
  Internal Revenue Code §1014 erases unrealized capital gains at death. Understanding which assets receive step-up — and which do not — determines where wealth should be held during life.
• GRATs, SLATs, and Other Advanced Transfer Strategies
  Grantor retained annuity trusts, spousal lifetime access trusts, and intentionally defective grantor trusts — the mechanics of moving appreciation out of a taxable estate at minimal gift cost.
• Charitable Lead and Charitable Remainder Trusts
  CLTs send the income stream to charity and the remainder to family; CRTs do the reverse. Both work the §7520 rate to compress gift values and defer capital gains.

State & Local

• California Nonconformity to Federal Retirement Rules
  California does not conform to several major federal retirement and tax provisions. HSAs are taxable, mental health surtax adds 1%, and OBBBA conformity is selective. A practical map for California residents.
• State Income Tax Map for Retirees
  How each state treats retirement income — pensions, Social Security, IRA withdrawals, and capital gains. A practical map for retirees considering relocation.
• Domicile Planning Before You Retire
  Changing domicile from a high-tax to a low-tax state requires more than a moving van. The mechanics of severing residency, surviving an audit, and getting the timing right around Roth conversions and large gains.
• States That Do Not Tax Social Security Benefits
  Forty-one states and DC fully exempt Social Security from state income tax. The nine that still tax it — and how their rules differ.

Special Situations

• Divorce and Retirement Accounts: Qualified Domestic Relations Orders
  A QDRO is the only mechanism to divide a qualified retirement plan in divorce without triggering tax or early-withdrawal penalty. The drafting, the timing, and the most common failures.
• Foreign Accounts: FBAR and FATCA Reporting
  U.S. taxpayers with foreign financial accounts face two parallel reporting regimes — FinCEN Form 114 (FBAR) and IRS Form 8938 (FATCA). The thresholds, the deadlines, and the brutal penalties for noncompliance.
• Disability and Early Access to Retirement Funds
  Internal Revenue Code §72(t)(2)(A)(iii) waives the 10% early-withdrawal penalty for disability. The definition is stricter than Social Security's, the documentation matters, and SECURE 2.0 added new exceptions.
• Federal Employees: TSP and FERS Basics
  The federal Thrift Savings Plan and Federal Employees Retirement System produce one of the strongest retirement packages in U.S. employment — if used correctly. Match math, fund selection, and the FERS supplement.
• Military Retirement and the Blended Retirement System
  The Blended Retirement System combines a 20-year pension at a reduced multiplier with a Thrift Savings Plan match. The 12-year continuation pay decision, the lump-sum option, and how reserve service counts.

High Net Worth

• QSBS §1202 Family Stacking
  Internal Revenue Code §1202 excludes up to $10M (or 10× basis) of gain on qualified small business stock — per shareholder, per issuer. Multiple non-grantor trusts can multiply the exclusion; OBBBA preserved and expanded the provision.
• Conservation Easements: Risk and Reward
  Internal Revenue Code §170(h) allows a charitable deduction for the donation of a qualified conservation easement. The economics, the syndicated-easement crackdown, and what survives.
• Family Limited Partnerships and Discount Planning
  An FLP holds family assets in a partnership where senior generations retain control and junior generations receive discounted limited-partnership interests. The valuation discounts, the §2036 traps, and what survived OBBBA.
• Private Placement Life Insurance for High Earners
  Private placement life insurance wraps a customized investment portfolio inside a §7702 life insurance contract — providing tax-free internal compounding and tax-free death benefit. The economics, the §817 diversification rules, and when it works.
• Charitable Lead Trusts for Concentrated Wealth
  A zeroed-out CLAT funded with concentrated low-basis stock can transfer the entire appreciation above the §7520 hurdle to family with no gift tax — while satisfying philanthropic commitments along the way.