After Tax · Tax Playbook
Tax Playbook: 97 strategies that keep more of your money
Every strategy below is explained in plain English: what it is, who it is good for, and where to learn more. Educational only — not tax advice. Tax law is personal and it changes; check with your tax pro before acting on anything here.
Keep more of each paycheck (20)
- 529 plans — and the Roth rollover
A 529 is a savings jar for college: the money grows tax-free, and many states give you a tax break for putting money in. Leftover … - Max out pre-tax retirement accounts
Put money in a 401(k) before taxes are taken out, and you skip paying tax on it this year. In 2026 you can put in up to $24,500 — … - Backdoor Roth IRA
Make too much money for a Roth IRA? There's a legal workaround: put money in a regular IRA without taking a tax deduction, then mo… - Mega backdoor Roth
Some 401(k) plans let you put in extra after-tax money — far more than the normal limit — and then slide it into the Roth side of … - HSA: the triple tax break
An HSA is the only account with three tax breaks in one: money goes in tax-free, grows tax-free, and comes out tax-free when you s… - Solo 401(k) for side gigs
If you run your own business, you can save for retirement as both boss and worker. In 2026 you can put in up to $24,500 as the wor… - The 457(b) double-dip
If your employer offers both a 457(b) and a 401(k) or 403(b), you get two separate savings limits. Each plan lets you save up to $… - Spousal IRAs
A couple filing taxes together can each save in their own IRA, even if only one spouse works. Each person can put in $7,500 in 202… - The Saver's Credit
If you save for retirement and earn a modest income, the IRS can cut your tax bill. You can get a credit worth 10% to 50% of up to… - FSAs: spend pre-tax
An FSA lets you set aside part of your paycheck before taxes to pay for care. In 2026 a dependent care FSA covers up to $7,500 of … - RSU withholding: beat the 22% trap
When your RSUs vest, the share value counts as pay on your W-2. Your employer withholds a flat 22%, but if you are in the 32% or 3… - ESPP: hold for the qualifying sale
An ESPP lets you buy your company's stock at a discount, often 15%. If you hold the shares at least 2 years from the offering date… - ISO exercises: watch the AMT
When you exercise incentive stock options and hold the shares, you owe no regular tax at that moment. But the bargain element — th… - NUA: cheaper tax on company stock in your 401(k)
If your 401(k) holds a lot of your own company's stock, you can get a tax break when you leave — instead of rolling the shares int… - Deferred comp: skip tax now, pay later (maybe less)
A deferred comp plan lets you skip pay now and take it later, usually at retirement. A CFO earning $800,000 who defers $200,000 a … - Rule of 55: tap the 401(k) early, skip the 10% penalty
Leave your job in or after the year you turn 55, and you can take money from that employer's 401(k) without the usual 10% early pe… - Never leave the 401(k) match
Many jobs match part of what you put in your 401(k). That is free money. If you earn $60,000 and your job matches half of the firs… - Student-loan payments can earn the 401(k) match
Some jobs now match your student-loan payments with money in your 401(k). Your boss does not pay your loan — the money goes into y… - Roth or traditional 401(k)?
Traditional 401(k) money lowers your tax bill today, but you pay tax later. Roth 401(k) money is taxed today, and you usually pay … - Run the HSA through payroll
Put your HSA money through your paycheck instead of from your bank account. Paycheck deposits skip Social Security and Medicare ta…
Investment tax wins (37)
- 1031 exchanges
Sell a rental property and use the money to buy another one, and the tax on your profit waits — potentially forever. Do it again a… - Municipal bonds
When cities and states borrow money, the interest they pay you is free from federal tax (and often state tax too). The rate looks … - I Bonds
I Bonds are U.S. government savings bonds that keep up with inflation, so your money doesn't lose buying power. You don't pay fede… - Tax-loss harvesting
If one investment lost money, sell it and use the loss to cancel out tax on an investment that made money — dollar for dollar. You… - Direct indexing & tax-managed SMAs
Instead of buying one fund holding 500 stocks, you buy the 500 stocks yourself. Then whenever some dip, you sell the losers and bu… - Asset location
It's not just what you own, it's where you keep it. Bonds (taxed heavily) go in retirement accounts; stocks (taxed lightly) go in … - QSBS: exclude millions in gains
Own stock in a small startup? Hold it 5 years and you could pay zero federal tax when you sell — on up to $15 million of profit. H… - Opportunity Zone funds
Sold something for a big profit? Reinvest that profit in neighborhoods the government wants to develop and you can put off paying … - Tax-gain harvesting
In 2026, a single filer with under $49,450 in taxable income pays 0% on long-term capital gains. So if you sell a stock you have h… - Treasuries skip state tax
Treasury bonds and bills are taxed by the federal government, but your state cannot tax the interest. That helps most in states wi… - Buying Treasuries at a discount
Some bonds sell for less than face value, and that price gap is called a discount. If the gap is bigger than the cutoff, the IRS t… - TIPS: the phantom-income catch
TIPS raise their principal when prices rise, which protects your buying power. But you owe federal tax on that rise each year, eve… - ETFs dodge surprise tax bills
A mutual fund can send you a taxable gain even when you sold nothing. If it sends a $20,000 gain and your rate is 15%, that can me… - Qualified dividends
Qualified dividends use the lower 0%, 15%, or 20% tax rates. You usually must hold the stock for more than 60 days around the divi… - The step-up at death
At death, an heir usually starts with the asset's value on that date. If stock cost $20,000 but is worth $100,000 at death, the ol… - Installment sales
Take payments for a property or business over several years, and the gain can be taxed over those years too. A $300,000 gain paid … - Crypto's wash-sale loophole
The IRS treats crypto as property, not as a stock. That means you can sell crypto at a $20,000 loss and buy it back right away wit… - The 83(b) election
An 83(b) election lets you pay tax on restricted stock at its value on the grant date, not its value as it vests. You must file wi… - The short-term rental loophole
This is an aggressive strategy, so work with a tax professional. If guests stay seven days or fewer on average and you truly run t… - Cost segregation studies
A rental building is normally depreciated over 27.5 years for housing or 39 years for commercial buildings. A cost segregation stu… - DSTs: 1031 without the landlord hassle
You sell your rental and buy a share of a DST instead of another building, and the IRS counts your share as real estate, so the ta… - Private placement life insurance
Very rich investors can put investments like hedge funds inside a custom life insurance policy. The money inside grows without yea… - Hold international funds in taxable
International funds pay taxes to other countries, and you can get a credit for that tax — but only in a regular taxable account. I… - REITs belong in retirement accounts
Most REIT payouts are taxed like your paycheck, not like regular stock dividends. A $2,000 REIT payout in the 24% bracket costs ab… - EE Bonds double in 20 years
EE Bonds are a deal from the US government: buy one and it will be worth double in 20 years. Put in $1,000 and it becomes $2,000, … - Borrow with box spreads
Sometimes you can borrow money through the stock market instead of a bank. You place one options trade called a box spread, and it… - Sell shares instead of taking the coupon
When a fund pays you cash, the IRS taxes almost all of it that same year. But if you let the money keep growing and sell a little … - Let it compound: defer your taxes
Every dollar you pay in taxes today is a dollar that cannot grow for you. If you let your gains build up untaxed and pay the tax o… - Watch the 3.8% NIIT tripwire
High earners can pay an extra 3.8% tax on investment income called the Net Investment Income Tax. It kicks in when your income pas… - Buy, borrow, die
Instead of selling winning stocks and paying tax, wealthy investors borrow against them for spending money — loan proceeds are not… - Diversify a concentrated stock position without selling
If one stock is most of your money, selling it means a huge tax bill — Section 351 lets you swap it into a new fund without paying… - Return of capital: the tax bill that waits
Some payouts are return of capital — you are just getting your own money back, so you owe zero tax today, and your cost basis simp… - Stash cash in T-bills, not a money market fund
When a money market fund pays you, every dollar shows up on that year's tax return. A T-bill works differently: you buy it cheap, … - Buy total return, not yield
A bond fund is a faucet: every payout is taxed that same year at ordinary income rates, even though about 90% of it just gets rein… - The 0.2% that costs Californians thousands
Treasury income is usually free from state tax. But California, New York, and Connecticut only let a fund pass that break to you i… - Deferred beats muni beats taxable
Munis pay less but you keep it all: 3.5% muni means 3.5% in your pocket. Taxable bonds pay more — 4.8% — but if you pay 33% tax ev… - Do not buy a mutual fund's December tax bill
Every December, mutual funds must pay out the gains their managers made that year — often 5% to 15% of the fund's value, sometimes…
Giving, strategically (9)
- Donor-advised funds & bunching
Instead of giving a little to charity every year, give several years' worth all at once into a donor-advised fund — like a charita… - Donate appreciated stock
Own stock that shot up? Give the shares themselves to charity instead of selling first. You get to deduct what they're worth today… - Charitable remainder trusts
Put investments that grew a lot into a special trust. The trust pays you income for the rest of your life, you get a tax deduction… - Donate your RMD (QCDs)
Once you're 70½, you can send up to $111,000 a year straight from your IRA to a charity. The money is never taxed, and it still co… - Charitable lead trusts
A charitable lead trust is the flip of a charitable remainder trust. You put assets in, and the charity gets yearly payments for a… - Gifting to kids (kiddie tax)
You can give investments to your kids through a UTMA or UGMA custodial account, but there's a catch called the kiddie tax. For 202… - Charitable gift annuities
You give cash or stock to a charity, and it pays you a fixed amount every year for life (or for two lives). You get a partial tax … - Donate business stock
Donate your private company shares directly to a charity before any sale is final, and you can skip paying capital-gains tax on th… - Private foundations
A private foundation is your own charitable fund that you control — but it must give away about 5% of its investment assets every …
Business owners (12)
- S-corp election
Self-employed and profitable (roughly $80,000+/year)? Elect S-corp tax treatment: pay yourself a fair salary, and take the rest as… - Hire your kids
Hire your own kids in the family business and their pay is a tax deduction for you. Keep it under the standard deduction (about $1… - The 20% QBI deduction
Run a small business? You may get to ignore 20% of your profit for tax purposes — earn $100,000, pay tax on $80,000. Congress made… - Dodge the SALT cap (PTET)
The feds cap your state-tax write-off at $40,400 in 2026. But 36 states let your S-corp or partnership pay the state tax itself — … - Bonus depreciation & Section 179
A $100,000 work truck is usually written off a little each year. In 2026, 100% bonus depreciation lets your business deduct the wh… - The Augusta Rule
Rent your home out for 14 days or fewer in a year and the rent is tax-free — you don't even report it. That's the 'Augusta Rule,' … - Self-employed health insurance
If you work for yourself, you can deduct 100% of what you pay for health, dental, and vision insurance — Medicare premiums count t… - Hire your spouse
Hiring your spouse as a real employee lets you deduct their pay like any other wage, and it can unlock a second solo 401(k) for th… - Cash balance pension plans
A cash balance plan is a type of retirement pension that lets older business owners stash far more pre-tax money than a 401(k). Ar… - Real estate professional status
Rental losses normally can only offset rental income — not your salary. But if you log 750+ hours a year in real estate work AND i… - The home-office deduction, simplified
If you are self-employed, you can deduct part of your home as an office. The easy way: $5 per square foot, up to 300 square feet —… - The R&D tax credit
If your small business builds new products or software, the R&D tax credit can wipe out your employer payroll tax — up to $500,000…
Big life moves (19)
- Roth conversions in low-income years
In a year your income is low — a gap year, early retirement — move money from your pre-tax retirement account into a Roth and pay … - Move to a lower-tax state
Moving from a high-tax state like California to Texas or Florida can save five figures a year in state income tax at high incomes … - Annual gifts & the lifetime exemption
In 2026 you can give anyone $19,000 a year ($38,000 per couple) with no tax paperwork. And over your lifetime you can pass on up t… - Bunch medical expenses
You can only deduct medical bills that are more than 7.5% of your income — say you earn $100,000, so the first $7,500 of bills giv… - IRMAA: keep Medicare premiums down
When you turn 65, Medicare checks your income from two years ago. For 2026, if that income is over $109,000 (single) or $218,000 (… - Roth IRAs for kids
A child with a real job can have a Roth IRA. In 2026 you can put in up to $7,500, or less if the child earned less than that. The … - ABLE accounts
An ABLE account is a special savings account for people with disabilities. Money in it grows with no tax, and if you get SSI, up t… - 529 superfunding
You can put five years of gifts into a 529 college account all at once. In 2026 that means $95,000 from one person or $190,000 fro… - Education tax credits
The American Opportunity Credit can cut your taxes by up to $2,500 per college student per year, for the first four years of colle… - Child Tax Credit
In 2026 the Child Tax Credit is $2,200 for each child under 17. Two kids means up to $4,400 off your tax bill, and up to $1,700 pe… - Shrink tax on Social Security
The IRS adds up your "combined income" — your other income plus half your Social Security check. Keep it under $25,000 single or $… - Roth conversion ladders
Each year you move a slice of your pre-tax IRA or 401(k) into a Roth and pay tax on it that year — for example, a $40,000 conversi… - SLATs and grantor trusts
One spouse gifts assets into an irrevocable trust for the other, using the $15 million per-person 2026 gift and estate tax exempti… - Coverdell ESAs
You can put up to $2,000 per child per year into a Coverdell ESA — that limit is per child, not per person contributing. The money… - The 10-year inherited IRA rule
Most people who inherit an IRA from a parent must empty it by December 31 of the tenth year after the death. If the owner had alre… - Prove you really moved
California doesn't use a simple day count — it decides where you live from your whole life: homes, family, work, doctors, banks, l… - 72(t): retire early without the penalty
Pulling money from an IRA or 401(k) before age 59½ usually costs a 10% penalty on top of regular income tax. The 72(t) rule lets y… - Know your marginal tax rate
Your marginal tax rate is the tax on your next dollar of pay, not the average across everything you earned. That average — your ef… - Trump Accounts: a head start for your kid
On July 4, 2026, a brand-new kids' savings account opened for business. Kids born from 2025 through 2028 can get a free one-time $…
Educational summary, not tax advice. Limits and rules change — confirm current law with your tax adviser.