Tax Planning

Start here: the main guides

Self-employed & business owners

• Accountable Plans for S Corp Owners
  How an accountable plan lets S corp owners get tax-free reimbursement for home office, mileage and phone: the three rules, safe harbor deadlines, plan elements.
• Mileage vs Actual Expenses: How to Deduct a Business Vehicle Comparison
  Compare the 2026 standard mileage rate (72.5 then 76 cents) to actual vehicle expenses: first-year lock-in, heavy SUV limits, recapture and the logs you need.
• PTET Explained: The State Pass-Through Entity Tax SALT Workaround
  Pass-through entity tax (PTET) explained: how the SALT cap workaround works, which entities qualify, who benefits in 2026, the owner credit and common pitfalls.
• S Corp Reasonable Salary: How Much Is Enough?
  How to set a reasonable S corp salary: why the IRS cares, market and many-hats methods, free pay data, how distributions should work and the audit red flags.
• Schedule C Deductions: The Freelancer's Yes, Partly and Nice-Try List Checklist
  A 2026 checklist of Schedule C deductions for freelancers: home office, vehicle, equipment, health insurance, retirement, plus the expenses the IRS rejects.
• Self-Employment Tax: Paying Both Halves, Explained
  How self-employment tax works: the 92.35% rule, the $184,500 Social Security wage base for 2026, the half-SE deduction and legal ways to lower the 15.3% bill.
• Sole Prop vs LLC vs S Corp: What Actually Changes Your Taxes Comparison
  Sole prop vs LLC vs S corp taxes: default treatment, how the S election and reasonable salary work, a 2026 break-even table and the admin costs people forget.
• Tax Identity Theft and the IP PIN
  Protect yourself from tax identity theft with an IRS IP PIN: who qualifies, getting one online or by Form 15227, kids, what to do as a victim, and scams.
• The Form 1099 Field Guide
  A guide to Form 1099s: NEC, MISC, INT, DIV, B, R, K and DA, the new $2,000 NEC threshold, tricky boxes, wrong or missing forms, and a freelancer reconciliation.
• The Home Office Deduction: Your Dining Table Does Not Count
  Claim the home office deduction correctly: exclusive-use rules, the $5-per-square-foot simplified method vs actual expenses, recapture at sale and W-2 limits.
• The Self-Employed Health Insurance Deduction, Untangled
  Who can claim the self-employed health insurance deduction in 2026: subsidized-plan rule, S corp shareholder steps, the ACA credit circular math and examples.
• When Does an S Corp Election Pay Off?
  Calculate S corp break-even for 2026: payroll tax savings formula, real costs, state taxes, the QBI deduction offset and an example table by profit level.

Family, kids & estate

• AOTC vs Lifetime Learning Credit: Which Education Credit Fits in 2026
  Compare the 2026 American Opportunity Tax Credit (up to $2,500) and Lifetime Learning Credit (up to $2,000): eligibility, phaseouts and coordinating with a 529.
• Child Tax Credit 2026: Amount, Refundability, SSN Rules and Phaseouts
  The 2026 child tax credit is $2,200 per child with $1,700 refundable. Learn the age and SSN rules, the $200k/$400k phaseout and planning moves that protect it.
• Custodial Roth IRA for Kids: Earned Income, Limits and Documentation
  How a custodial Roth IRA works for kids in 2026: the earned income rule, the $7,500 limit, documenting babysitting and family jobs, and withdrawals.
• Dependent Care FSA vs Child and Dependent Care Credit in 2026 Comparison
  Compare the 2026 dependent care FSA ($7,500 limit) with the dependent care credit (20% to 50%). See which saves more at your income and how to combine them.
• Divorce Tax Planning: What the Decree Misses
  Divorce tax rules in 2026: filing status, post-2018 alimony, who claims the kids, tax-free property transfers, QDROs, the home, and after-tax asset math.
• Estate Tax Basics: The 2026 Exemption, Portability and Who Actually Pays
  Estate tax basics for 2026: the $15 million federal exemption, portability for married couples, state estate and inheritance taxes, and simple planning steps.
• Gift Tax Annual Exclusion 2026: $19,000 Per Person and When to File Form 709
  The 2026 gift tax annual exclusion is $19,000 per recipient. See the $15 million lifetime exemption, when Form 709 is due, gift splitting and 529 superfunding.
• Revocable Living Trusts and Taxes: What Changes (Nothing, Mostly)
  A revocable living trust changes almost nothing about your taxes while you are alive. See grantor trust status, probate vs tax, the EIN after death and step-up.
• Step-Up in Basis: How Inherited Assets Lose Their Capital Gains
  How step-up in basis works at death, why community property gets a double step-up, which assets to hold until death and why gifting low-basis assets backfires.
• Tax Checklist for a New Baby Checklist
  A 2026 new-baby tax checklist: get the SSN, claim the $2,200 child tax credit, choose dependent care FSA vs credit, raise HSA limits, and open a Trump Account.
• Tax Planning After a Spouse Dies
  Tax steps after a spouse dies: the final joint return, surviving spouse status, step-up in basis, inherited IRAs, the home sale window, portability, and IRMAA.
• Tax Strategies With Kids: Credits, 529s, Custodial Roths and Hiring Your Kids
  Every 2026 tax break for parents in one place: child and care credits, 529 plans, custodial Roth IRAs, Trump accounts and hiring your kids in a family business.
• The Nanny Tax: Household Employees, Explained
  Nanny tax rules for 2026: who is a household employee, the $3,000 FICA and $1,000 FUTA thresholds, what to withhold, Schedule H, W-2s, and tax breaks.
• Trump Accounts for Kids: $1,000 Seed, $5,000 Limit and How They Compare
  Trump accounts explained: who gets the $1,000 seed, the $5,000 yearly limit, $2,500 employer contributions, investment rules, and how they compare with 529s.

Capital gains & investments

• Crypto Taxes: The Property Rules, Explained
  How crypto is taxed in 2026: taxable events, gains and basis, new Form 1099-DA reporting, staking income, losses and wash sale status, with a worked example.
• ESPP Taxes Without the Headache
  How qualified ESPP shares are taxed: qualifying vs disqualifying dispositions, ordinary income math, the Form 1099-B basis trap, and when holding is worth it.
• Investment Interest Expense, Explained
  How the investment interest deduction works: what counts, the net investment income limit, the qualified dividend election, Form 4952, and carryforwards.
• Roth Conversions While You Still Have a Paycheck
  Plan Roth conversions while working: why low-income years matter, measuring 2026 bracket room, timing, paying tax from outside the IRA and the pro-rata trap.
• RSU Taxes: Vest, Withholding, Basis and Selling
  How RSUs are taxed at vest and at sale, why 22% withholding falls short, the zero cost basis trap on Form 1099-B, and a four-year worked example for 2026.
• Short-Term vs Long-Term Capital Gains: Why Day 366 Matters Comparison
  Short-term vs long-term capital gains for 2026: how to count the holding period, rate differences, wash sale interplay, examples and planning around day 366.
• Specific Lot Identification: Pick Which Shares You Sell and Save
  Specific lot identification explained: FIFO vs average cost vs spec ID, how to set it at your broker, HIFO strategy, mutual fund rules and a worked example.
• Tax Diversification: Why Your Account Mix Matters
  Tax diversification explained: the four account types, why your mix matters for brackets and benefit cliffs, how to build it, Roth conversions, and withdrawals.
• Tax-Loss Harvesting Mistakes to Avoid Checklist
  Avoid tax-loss harvesting mistakes: wash sales across IRAs and spouse accounts, dividend reinvestment traps, short vs long-term errors, state rules and fixes.
• The $3,000 Capital Loss Limit and the Netting Rules
  How the $3,000 capital loss limit works: the netting order, short vs long-term character, indefinite carryforwards, wash sales, and a three-year worked example.
• The Wash Sale Rule: 30 Days, IRAs, Spouses and Other Traps
  The wash sale rule explained: the 61-day window, substantially identical securities, IRA and spouse purchases, basis adjustments and worked examples for 2026.

IRS, deadlines & paperwork

• Estimated Tax Payments: Safe Harbors, 2026 Deadlines and How to Avoid Penalties
  Who must pay estimated tax, the 90%, 100% and 110% safe harbors, the 2026 quarterly due dates, the annualized method and how to pay online without penalties.
• Got an IRS Notice? What Each Common Letter Means
  Decode common IRS notices: CP2000 underreporting proposals, CP14 balance due, the CP501 to CP504 reminders, Letter 5071C identity checks, and how to respond.
• How Long to Keep Tax Records Checklist
  How long to keep tax records: the 3, 6 and 7-year rules, basis records to keep until you sell, documents to keep forever, and what you can safely shred.
• How to Amend a Tax Return (1040-X)
  When and how to amend a tax return with Form 1040-X: what needs amending, the 3-year refund deadline, e-filing, state amendments and refund processing times.
• IRS Audit: What to Expect and How to Prepare
  What happens in an IRS audit: mail, office and field exams, what draws attention, how to organize documents, your rights and the statute of limitations.
• IRS Penalties: Failure to File, Pay and Estimate
  How IRS penalties work: late filing (5%/month), late payment (0.5%), estimated tax and accuracy penalties, interest, and relief via First Time Abate.
• Tax Extensions: What They Do and Don't Do
  What a tax extension really does: Form 4868 moves filing to October 15 but not payment. Penalty rates, the 90% rule, disaster relief and who should extend.
• Tax Planning Calendar: What to Do Each Month Checklist
  A month-by-month tax planning calendar for 2027: estimated tax dates, filing deadlines, IRA and HSA cutoffs, mid-year reviews and the December 31 moves.
• Tax Software vs. a CPA: An Honest Comparison Comparison
  Tax software vs a CPA or enrolled agent: what each does well, credentials, free filing options, preparer red flags, and a decision guide by tax situation.
• Year-End Tax Planning Checklist Checklist
  A 2026 year-end tax checklist: project your bracket, max 401(k) and HSA limits, Roth conversions, loss harvesting, new charitable rules and business moves.

Deductions & credits

• Car Loan Interest Deduction: New Rules
  The new car loan interest deduction for 2025-2028: up to $10,000 for new U.S.-assembled vehicles, loan date rules, the $100,000 phaseout and what it saves.
• Charitable Deduction Rules Starting 2026: Non-Itemizer Deduction and 0.5% Floor
  Charitable deduction rules for 2026: the $1,000/$2,000 non-itemizer deduction, the 0.5% of AGI floor, the 35% cap for top earners and how to plan around them.
• Deduction Bunching: How to Itemize Every Other Year and Win
  Deduction bunching for 2026: what you can bunch, pairing it with a donor-advised fund, the new 0.5% charity floor, a worked example and a timing calendar.
• Donor-Advised Funds: The Simple Way to Bunch Gifts and Give Stock
  Donor-advised funds explained: how a DAF works, 2026 deduction limits and new floor, gifting appreciated stock, fees and sponsors, and a worked example.
• Itemize or Take the Standard Deduction? How to Decide in 2026 Comparison
  Itemize or take the standard deduction in 2026? Standard amounts, common itemized items, the $40,400 SALT cap, break-even math and when bunching beats both.
• Medical Expense Deduction: How the 7.5% Floor Really Works
  The medical expense deduction for 2026: the 7.5% AGI floor, what counts, bunching surgeries, long-term care premium limits, and a worked example with real math.
• Mortgage Interest Deduction: Limits, HELOCs and Refinances
  Mortgage interest deduction for 2026: the permanent $750,000 limit, HELOC rules, points, PMI, refinances, and the itemizing test, with two worked examples.
• No Tax on Tips and Overtime: How the Deductions Really Work
  How the no tax on tips and overtime deductions work for 2025-2028: who qualifies, the $25,000 and $12,500 caps, phaseouts, payroll taxes and how to claim.
• Qualified Charitable Distributions: The Best Charity Move After 70½
  Qualified charitable distributions explained: the 70½ age rule, $111,000 limit for 2026, satisfying RMDs, reporting on Form 1040 and the mistakes to avoid.
• SALT Cap Planning: The $40,400 Cap, the Phasedown and What to Do
  SALT cap planning for 2026: the $40,400 cap, the 30% phasedown above $505,000 MAGI, who benefits, PTET workarounds, payment timing and the 2030 sunset.
• The $6,000 Senior Deduction: Who Gets It
  The $6,000 senior deduction for 2025-2028: who qualifies at 65+, the 6% phaseout above $75,000 MAGI, and how it stacks with the standard deduction.
• The 2025 Tax Law (OBBBA): What Changed for Individuals
  What the 2025 tax law (OBBBA) changed: permanent brackets, new tips, overtime, car loan and senior deductions, the higher SALT cap and expired energy credits.

Brackets, rates & filing basics

• A Year-Round Tax Checklist for Retirees Checklist
  A year-round 2026 tax checklist for retirees: withholding, RMDs, QCDs, the $6,000 senior deduction, Social Security taxation, IRMAA and fall Roth conversions.
• AGI vs MAGI, Without the Headache
  AGI vs MAGI explained: what lowers AGI, how Roth, ACA, IRMAA and NIIT each define MAGI, the 2026 thresholds that use them, and levers to manage the numbers.
• AMT in 2026: Who Still Pays the Alternative Minimum Tax (and Why)
  Alternative minimum tax for 2026: exemption $140,200 joint, phaseout from $1 million, ISO and private activity bond triggers, AMT credit and a worked example.
• Big Refund or Small Balance Due? How to Aim Your Withholding
  A big tax refund is a 0% loan to the IRS. Learn the underpayment penalty safe harbors, the withholding target zone and how to fix your W-4 mid-year in 2026.
• Filing Status: Single, HOH, MFJ, MFS Explained
  How to choose a filing status: single, married filing jointly or separately, head of household or surviving spouse, with 2026 deductions and brackets.
• Gambling Taxes and the New 90% Loss Rule
  How gambling is taxed in 2026: all winnings are income, W-2G and withholding basics, the new 90% loss limit, why itemizing matters, and the records you need.
• Hidden Marginal Tax Rates: Phaseouts, Cliffs and the Tax Torpedo
  Hidden marginal tax rates in 2026: phaseouts, credit cliffs, the Social Security tax torpedo, IRMAA and ACA cliffs, and how they stack, with a worked example.
• How Bonuses Are Taxed (and Why It Looks Worse)
  Bonuses are not taxed at a special rate. Learn 2026 supplemental withholding (22% and 37%), FICA, and moves like 401(k) deferrals, with a $30,000 example.
• How to Fill Out a W-4 Without Owing or Overpaying
  A step-by-step guide to the Form W-4: filing status, two-job households, credits for kids, extra withholding, a mid-year checkup and a worked 2026 example.
• How to Read Your Form 1040 (Beyond the Refund)
  A plain-English walkthrough of Form 1040: income lines, AGI, deductions, taxable income, credits and payments, and how to find effective and marginal rates.
• Marginal vs Effective Tax Rate: The Difference That Drives Decisions
  Marginal vs effective tax rate explained with 2026 brackets: why a raise never costs you money, a full worked example, and which rate to use for each decision.
• State Income Tax Planning for Real Humans
  State income tax planning: no-tax states, residency and domicile audits, working across state lines, retirement income, the 2026 SALT cap, PTET, and moving.
• Tax Checklist for Buying a Home Checklist
  A 2026 home-buying tax checklist: whether you will itemize, points and closing costs, IRA down payment rules, mortgage insurance, basis and ended credits.
• Tax Checklist for Starting a New Job Checklist
  A 2026 tax checklist for a new job: W-4 withholding, 401(k) limits across employers, HSA and FSA elections, equity pay, and Social Security refunds.
• Taxes on Unemployment and Severance Pay
  How unemployment and severance pay are taxed, withholding traps, ACA and COBRA tradeoffs, retirement moves, and tax planning in a low-income layoff year.
• The Foreign Earned Income Exclusion, Explained
  The 2026 foreign earned income exclusion of $132,900: who qualifies, the 330-day test, housing exclusion, stacking, FEIE vs the foreign tax credit, and FBAR.
• Traditional vs. Roth vs. taxable: the tax map Comparison
  How traditional, Roth and taxable accounts are taxed going in, growing, coming out and passing to heirs, with 2026 limits, early access and a worked example.
• When Married Filing Separately Saves Money
  When married filing separately saves money: lost credits and deductions, medical and student loan cases, liability protection and community property rules.

Calculators

• Deduction bunching calculator Calculator
  Compare giving every year with bunching several years of gifts into one, using the 2026 standard deduction, 0.5% AGI floor and non-itemizer charity deduction.
• Estimated tax payment calculator Calculator
  Free 2026 estimated tax calculator: find the safe harbor amount (90% of this year or 100%/110% of last year), what you still owe and each quarterly payment.
• Marginal tax rate calculator Calculator
  Free 2026 marginal tax rate calculator: your bracket, your true marginal rate on extra income with capital gains stacking and NIIT, plus your effective rate.
• S corp savings calculator Calculator
  Estimate 2026 S corp tax savings: compare sole prop self-employment tax with payroll tax on a reasonable salary, minus the extra costs of running an S corp.
• Self-employment tax calculator Calculator
  Free 2026 self-employment tax calculator: 92.35% of profit, 12.4% Social Security up to $184,500, 2.9% Medicare, the deductible half and Additional Medicare.

More tools: all calculators.