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The Index · Topic 02

Tax Planning

How taxes actually work in retirement — 2026 brackets, withdrawal ordering, capital gains, the tax torpedo, QCDs, and the strategies that compound over 20+ years.

18 articlesCurrent SSA · IRS · CMS dataUpdated 2026
Topic 02 · The Index

All Tax Planning articles.

18 published
Tax Planning7 min

Couples Pay 32% Federal Tax on Income Above $394,375 in 2026

Married couples earning $400,000 in 2026 actually pay about 20.1% effective federal tax rate, not 32%, because only income above $394,375 hits the 32% bracket. Understanding this difference could help you save thousands through strategic retirement contributions and income timing.

Tax Planning2 min

Sell at a $10,000 Loss but Buy Back in 29 Days? IRS Says You Owe Tax on $0 Deduction

The wash sale rule's 61-day window can turn your $10,000 investment loss into zero tax deduction, even if you buy back the stock a month later. Understanding this rule could save Maryland retirees thousands in unnecessary taxes.

Tax Planning2 min

The AMT Hits at $133,300 for Couples in 2026

The Alternative Minimum Tax exemption phases out at $133,300 for married couples in 2026, potentially triggering unexpected tax bills for pre-retirees with stock options or other AMT preference items.

Tax Planning2 min

Couples Can Gift $38,000 Per Recipient Tax-Free in 2026

Married couples can gift up to $38,000 per recipient in 2026 without triggering gift taxes, doubling the individual limit and creating powerful wealth transfer opportunities for retirement planning.

Tax Planning2 min

183 Days in California Could Cost You $130,000 in State Taxes

Understanding state tax residency rules is crucial for retirees planning interstate moves. California's 183-day rule and similar state regulations can result in unexpected tax bills exceeding $130,000 for high-income retirees who don't plan carefully.

Tax Planning2 min

At 65+, Your Standard Deduction Jumps to $18,150 for Singles

At 65, your standard deduction increases to $18,150 for singles in 2026, an extra $2,050 that could save $451+ in federal taxes — plus a bonus senior deduction of up to $6,000 through 2028. Understanding when these senior breaks kick in can impact your retirement tax planning significantly.

Tax Planning2 min

$2.8 Million Tax-Free Gain: How Death Resets Capital Gains

The step-up in basis rule can save heirs hundreds of thousands in taxes on inherited assets, making timing crucial for estate planning decisions.

Tax Planning7 min

Convert $29,200 to Roth Annually Without Crossing Into 24% Tax

Strategic Roth conversions up to $29,200 annually can keep some retirees in the 22% tax bracket instead of paying 24%. Learn the 2026 thresholds, timing strategies, and IRMAA considerations that maximize your conversion opportunity.

Tax Planning2 min

SS Maximum Taxable Earnings Jump to $183,000 in 2026

Social Security's maximum taxable earnings will jump to $183,000 in 2026, affecting high earners' take-home pay and retirement credits. Understanding this wage base ceiling is crucial for optimal retirement planning.

Tax Planning2 min

2026 Tax Brackets: A $250,000 Couple Pays 18% Effective Rate

Understanding 2026 tax brackets helps married couples plan smarter retirement moves. A $250,000 household typically pays just 18% effective tax rate, creating opportunities for strategic Roth conversions and tax-efficient withdrawals.

Tax Planning2 min

Married Couples Can Realize $94,050 in Capital Gains Tax-Free

Married couples can harvest up to $94,050 in capital gains completely tax-free in 2026 using the 0% long-term capital gains bracket, creating a powerful annual opportunity to reset investment basis while paying zero tax.

Tax Planning2 min

$105,000 QCD Can Save $23,100 in Taxes at 22% Bracket

Qualified Charitable Distributions can save substantial taxes while fulfilling your Required Minimum Distribution, with couples potentially saving thousands on Medicare premiums by reducing their adjusted gross income.

Tax Planning2 min

6 Months to Retirement: The $1.2M Protection Checklist

Six months before retirement offers a unique window to save over $1 million through strategic tax moves, Roth conversions, and benefit optimization that most retirees completely miss.

Tax Planning3 min

How Poor Tax Planning Cost One Business Owner $1.7 Million

A business owner paid nearly $3 million in taxes after selling his company. Proactive tax planning could have saved $1.7 million. Here is what went wrong.

Tax Planning3 min

How an ESOP Sale Can Help Business Owners Defer Millions in Taxes

Learn how Section 1042 ESOP sales let C-corp owners defer capital gains taxes, preserve company culture, and protect decades of hard work.

Tax Planning3 min

One Big Beautiful Bill: What Retirees Need to Know About Tax Reform

The One Big Beautiful Bill Act reshapes estate planning, tax brackets, and long-term care. Here is what retirees should understand about the new law.

Tax Planning3 min

You Are Paying More in Taxes Than You Think

Taxes may be your biggest expense, and chances are you are overpaying. Learn proactive tax planning moves that can save retirees thousands each year.

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The Tax Planning numbers for 2026.

The thresholds that actually move this part of your plan, kept current and sourced.

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Standard deduction (MFJ)
$32,200
12% bracket tops out (MFJ)
$100,800
Top bracket starts (MFJ)
$768,700
QCD annual limit
$111,000
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