Jo Whitaker is an AI correspondent; her reporting is reviewed by ADRYENN editors. Reviewed and approved by Adryenn Ashley.
This article is general information, not tax, legal, or financial advice. Tax rules depend on your situation and change often. Figures are for tax year 2026 and were checked on October 15, 2026, on IRS.gov (tax figures) and on CMS.gov, Medicare.gov, and SSA.gov (Medicare figures). Talk to a CPA, Enrolled Agent, or tax attorney before you act.
Your tax bill is not a fixed price
Most people pay whatever the software says. People who plan pay less, legally.
None of this is a loophole. Congress wrote these breaks into the tax code on purpose: to get you saving for retirement, covering health costs, giving to charity, and building a business. Each one comes with rules and paperwork.
The IRS isn’t impressed by creativity. It’s impressed by records.
Each move below covers what it is, who it fits, how to do it right, and the paperwork that keeps it clean. Every dollar figure is the 2026 number from an official source (IRS.gov for taxes; CMS, Medicare.gov, and SSA for Medicare), linked right where it appears.
Start here: the 10-minute triage
- W-2 employee, 50+: Retirement · HSA · Giving
- Self-employed or side business: Business moves · Hiring your kids · Home office
- You or your spouse near RMD age: QCDs · Timing
- Charitably inclined: Giving smarter
- Taxable brokerage account: Tax-loss harvesting
Two terms you’ll see a lot. Adjusted gross income (AGI) is your total income minus certain deductions, such as HSA contributions. Many tax breaks are measured against it. Modified AGI (MAGI) is AGI with a few items added back, and each tax break defines its own version.
Save for retirement, cut taxes now (or later)
Roth or traditional 401(k)?
A traditional 401(k) contribution comes out of your pay before income tax, so it lowers this year’s bill, and you pay tax when you withdraw. A Roth contribution goes in after tax, and qualified withdrawals later come out tax-free.
Traditional tends to fit if you expect a lower bracket in retirement. Roth fits if you expect the same or a higher one. Splitting between the two is a perfectly sane hedge, since nobody knows future tax rates.
For 2026, the employee limit for 401(k), 403(b), most 457 plans, and the federal Thrift Savings Plan is $24,500, Roth and traditional combined, per the IRS (IR-2025-111).
Deadline: December 31. Contributions come out of your paychecks, so raise your election before your last 2026 payday.
Catch-ups: the over-50 bonus round
A catch-up contribution is extra money you can add once you’re 50 or older, on top of the regular limit.
- 50 and older: an extra $8,000 for 2026, for a total of $32,500 (IR-2025-111).
- Turning 60, 61, 62, or 63 in 2026: $11,250 instead of $8,000 (IRS Notice 2025-67). Turning 64? You’re back to $8,000.
Hypothetical example: An employee who turns 61 in 2026 could defer $24,500 + $11,250 = $35,750, if her plan offers the higher catch-up.
The Roth catch-up rule. If your 2025 FICA wages (the Social Security wages on your W-2) from the employer that sponsors your plan topped $150,000, your 2026 catch-ups to that plan must go in as Roth (Notice 2025-67). If your plan has no Roth option, you won’t be able to make catch-ups at all until it adds one. The test counts only FICA wages from that employer. So if you’re self-employed with no W-2 wages from your own business (say, a sole proprietor or partner with a Solo 401(k)), the rule doesn’t apply to you, however much you earned. Pay yourself W-2 wages from an S corp? Those wages count (final regulations, 90 FR 44527). Final IRS rules formally apply in 2027, but plans must follow the requirement in 2026 using a “reasonable, good faith” reading of the law (IR-2025-91). Ask HR how your plan handles the switch, and ask your tax pro whether Roth catch-ups are a good fit for you.
IRAs: your account, your later deadline
- 2026 limit: $7,500, plus a $1,100 catch-up at 50+ (IR-2025-111).
- Roth IRA phase-out: MAGI of $153,000–$168,000 (single) and $242,000–$252,000 (married filing jointly).
- Deducting a traditional IRA if you’re covered by a workplace plan: the deduction phases out at $81,000–$91,000 (single) and $129,000–$149,000 (joint). If only your spouse is covered, it’s $242,000–$252,000 (IR-2025-111).
Deadline: your return’s due date, not counting extensions (Publication 590-A). For most people, that’s mid-April 2027.
If you own a business (the side hustle counts)
Solo 401(k) or SEP IRA?
A Solo 401(k) is a regular 401(k) for an owner with no employees other than a spouse (IRS). You contribute twice. As the employee, you make elective deferrals (pay you choose to set aside) up to $24,500 plus catch-ups. As the employer, you add a profit-sharing contribution.
A SEP IRA (simplified employee pension) takes employer contributions only, into a traditional IRA. If you have staff, you must contribute the same percentage for every eligible employee (IRS).
| Solo 401(k) | SEP IRA | |
|---|---|---|
| Who | Owner with no employees other than a spouse | Any employer, including the self-employed |
| Contributions | Employee deferrals plus employer profit-sharing | Employer only: up to 25% of pay (about 20% of net self-employment earnings for owners) |
| 2026 cap | $72,000 total, plus catch-ups | $72,000; only the first $360,000 of pay counts |
| Catch-ups | $8,000 at 50+; $11,250 at ages 60–63 | None |
| Roth option | If the plan allows | If the provider offers it (SECURE 2.0) |
| Setup deadline | A new plan can be adopted after year-end, up to the business return due date with extensions, for employer contributions. A sole proprietor with no employees can also make first-year employee deferrals if the plan is adopted by the filing deadline without extensions. | Business return due date, with extensions |
| Paperwork | Plan document; Form 5500-EZ once assets reach $250,000 | Form 5305-SEP or provider document; usually no annual IRS filing |
Sources: Notice 2025-67; Publication 560; IRS Solo 401(k) page.
Which wins? With modest profits, a Solo 401(k) usually shelters more, because the employee deferral isn’t a percentage of profit and catch-ups apply. A SEP wins on simplicity: no annual IRS filing and nothing to set up until your extended filing deadline. (A brand-new Solo 401(k) can now be opened after year-end too, but the first-year employee deferral has an earlier, unextended deadline.) If you’ll hire, read the SEP eligibility rules first (IRS SEP FAQs).
Pay your kids. For real work.
Your business pays your child a real wage for real work. The business deducts the wage, and your child pays tax at their own (usually tiny) rate.
Payroll taxes depend on your business structure (IRS: Family help; Publication 15):
– Sole proprietorship, or a partnership owned only by the child’s parents: no Social Security or Medicare tax on a child under 18, and no federal unemployment tax under 21. Income tax withholding rules still apply.
– Corporation (including an S corp) or another partnership: normal payroll taxes, whatever the child’s age.
Empty nest? You can still hire your college-age kid for real work. The Social Security and Medicare break just ends at 18.
Your child’s taxes: For 2026, a dependent’s standard deduction is the greater of $1,350 or earned income plus $450, up to the regular single amount of $16,100 (Rev. Proc. 2025-32). Investment income is a separate matter. A child with more than $2,700 of it may owe the “kiddie tax” at the parent’s rate (Publication 505 (2026)).
Hypothetical example: A sole proprietor pays her 16-year-old $8,000 for documented work. No Social Security or Medicare tax applies. If that’s the teen’s only income, their standard deduction is $8,000 + $450 = $8,450, so no federal income tax. The teen can also fund a Roth IRA with up to their earnings, within the $7,500 limit.
Do it right: age-appropriate work (filing, product photos, social scheduling), market-rate pay, a job description, timesheets, payment by transfer to the child’s own account, and a W-2.
What gets people in trouble: paying a toddler for “modeling,” no timesheets, above-market pay, and money that never reaches the child.
The home office, done right
The space must be used regularly and exclusively for business, and it must be your principal place of business or where you regularly meet clients (IRS). The guest room that hosts your sister at Thanksgiving doesn’t count.
- Simplified method: $5 per square foot, up to 300 square feet, so $1,500 at most. There’s no depreciation to track or recapture (IRS).
- Regular method: the business share of actual costs, including depreciation (a yearly write-off for wear on the building that’s taxed back when you sell), on Form 8829 (Publication 587).
W-2 employees: under current law, you can’t claim it, even if you work from home full-time (IRS).
The HSA: three tax breaks, one account
A health savings account (HSA) pairs with a high-deductible health plan (HDHP). Contributions are deductible, the money grows inside the account, and withdrawals for qualified medical costs aren’t taxed (Publication 969).
2026 numbers (Rev. Proc. 2025-19): you can contribute $4,400 for self-only coverage or $8,750 for family coverage. An HDHP needs a deductible of at least $1,700 / $3,400, with out-of-pocket costs capped at $8,500 / $17,000. If you’re 55 or older, add $1,000 (Publication 969).
New for 2026: bronze and catastrophic individual plans count as HSA-compatible, whether you buy them through the Marketplace or not (IRS; Notice 2026-05). If you buy your own bronze or catastrophic plan, you may have just become eligible.
The Medicare cliff: your limit drops to zero starting the first month you’re enrolled in Medicare, including retroactive coverage (Publication 969). If you sign up after 65, premium-free Part A usually starts up to six months before the month you apply, so Medicare says to stop HSA contributions at least six months before you apply for Medicare or Social Security (Medicare.gov).
Deadline: the April 2027 filing deadline.
Give smarter
What changed for 2026 under the 2025 tax law (the One Big Beautiful Bill Act):
– Standard deduction (the flat amount you subtract instead of listing deductions): $16,100 single, $32,200 joint (IR-2025-103).
– Non-itemizers can now also deduct up to $1,000 of cash gifts to eligible charities ($2,000 joint). Gifts to donor-advised funds don’t count (Publication 6196).
– Itemizers (people who list deductions instead of taking the standard deduction) can deduct only the charitable gifts above 0.5% of AGI (Publication 505 (2026)). In the top 37% bracket, the law also caps the tax benefit of itemized deductions (IR-2025-103).
– SALT cap (state and local taxes): $40,400, reduced once MAGI tops $505,000, but not below $10,000 (IRS).
– 65 or older? A new deduction of up to $6,000 per person (2025–2028), whether or not you itemize, phases out above MAGI of $75,000 ($150,000 joint). You need a valid Social Security number, and married couples must file jointly (IRS). For 2026, that means born before January 2, 1962 (Publication 505 (2026)).
Bunching
Bunching means packing two years of gifts into one so you clear the standard deduction, then taking the standard deduction the next year.
Hypothetical example (married filing jointly, AGI $200,000): They pay $12,000 in SALT and $8,000 in mortgage interest, and they give $10,000 a year. That’s $30,000 itemized, which is under $32,200. Without bunching, they take $32,200 plus the $2,000 non-itemizer deduction each year: $68,400 over two years. If they bunch $20,000 of gifts into 2026, the 0.5% floor trims $1,000, so they itemize $39,000. Then they take $32,200 in 2027: $71,200, or $2,800 more. (The example uses 2026 figures for both years.)
Bunching still works. With the new rules, the payoff is just smaller. Run your own numbers.
Donor-advised funds
A donor-advised fund (DAF) is an account at a sponsoring charity. You deduct the gift when you make it and recommend grants over time. Once you give, the sponsor legally controls the money (IRS). It’s a natural bunching tool. Compare fees.
QCDs (for the 70½ crowd)
A qualified charitable distribution (QCD) moves money directly from your IRA trustee to a charity once you’re 70½. It can’t come from an ongoing SEP or SIMPLE IRA, and it stays out of your income (Publication 590-B). It can also count toward your required minimum distribution (RMD), the yearly withdrawal that starts at 73, or at 75 if you were born in 1960 or later (IRS FAQs; 26 U.S.C. 401(a)(9)(C)(v); proposed regulations, 89 FR 58644). The 2026 limit is $111,000 per person (Notice 2025-67). Donor-advised funds and supporting organizations can’t receive QCDs; the tax code excludes them by name (26 U.S.C. 408(d)(8)(B)(i)). And no double dip: you can’t also deduct a QCD.
Deadline for bunching, DAF gifts, and QCDs: December 31.
Records: you need a written acknowledgment for any gift of $250 or more (Publication 526). Noncash gifts over $500 need Form 8283, and items over $5,000 generally need a qualified appraisal (IRS Topic 506).
Tax-loss harvesting
Sell losing investments in a taxable account to offset gains. If net losses remain, you can deduct up to $3,000 a year against other income ($1,500 married filing separately) and carry the rest forward (Publication 550).
Hypothetical example: $10,000 of losses against $6,000 of gains. That wipes out the gains, takes $3,000 off other income, and carries $1,000 forward.
The wash-sale trap: a wash sale is selling at a loss and buying “substantially identical” stock within 30 days before or after. That includes buying it in your IRA or Roth IRA, or your spouse buying it. The loss is disallowed. Usually it’s just postponed, because it’s added to the cost of the new shares. If the repurchase happened in your IRA, it’s gone for good (Publication 550). Harvesting doesn’t apply inside IRAs or 401(k)s.
Deadline: trade by December 31.
Timing income
- Cash-method businesses count income when it’s received and expenses when they’re paid, so paying deductible bills in December counts for 2026. But under constructive receipt, income counts once it’s credited to your account or available to you. Holding a check doesn’t move it to next year (Publication 538).
- Roth conversions (moving traditional IRA money to a Roth and paying tax now) can make sense in a lower-income year. A conversion also raises your income for the Medicare surcharge two years later (see the next item). Run it by your tax pro.
- Medicare looks back two years. Higher income adds a surcharge called IRMAA to Part B and D premiums. For 2026 premiums, it applied when 2024 MAGI was above $109,000 (individual) or $218,000 (joint). That first tier takes the standard 2026 Part B premium from $202.90 to $284.10 a month (CMS; Medicare.gov). A 2026 income spike shows up in 2028. If your income dropped because of a life-changing event such as retirement, divorce, or a spouse’s death, you can ask Social Security to use your newer, lower income (Form SSA-44) (SSA).
- Estimated taxes: you generally avoid a penalty by paying at least 90% of your 2026 tax or 100% of your 2025 tax. That’s 110% if your 2025 AGI topped $150,000 (Publication 505 (2026)).
Red flags: what not to do
The IRS describes how it picks returns for audit only in general terms (computer screening against “norms” for similar returns, plus related examinations), not the formulas (IRS). So read these as behaviors that invite questions or penalties:
- Paying family for work that isn’t real, at above-market pay, or with no records.
- A home office that isn’t used regularly and exclusively for business.
- 100% business use of the family car with no mileage log. The law requires adequate records (IRS Topic 510).
- Years of losses from what’s really a hobby (IRS).
- Big noncash donations without the appraisal or Form 8283.
- Unreported income, including payments already reported to the IRS on Form 1099-K (IRS). Business income is taxable whether or not a 1099-K arrives.
- Round, guessed numbers instead of records.
- Schemes on the IRS’s 2026 “Dirty Dozen” list, including (IR-2026-30):
- viral social media “tax hacks”
- a bogus “self-employment tax credit”
- inflated “other withholding” to manufacture a bigger refund
- inflated donations through syndicated conservation easements or art
- gifts to fake charities (check the IRS’s Tax Exempt Organization Search before you give)
- “ghost” preparers who won’t sign your return
- Anyone promising to “eliminate” your taxes, a pitch the IRS ties to abusive donation schemes (IR-2026-30), or a preparer who charges a percentage of your refund. The IRS says to avoid preparers who do (IRS Topic 254).
Your December checklist
| Move | Who | Deadline | Keep | Ask your tax pro |
|---|---|---|---|---|
| Max out 401(k) and catch-ups | W-2 employees 50+ | Dec. 31 | Final pay stub | “Must my catch-ups be Roth?” |
| IRA | Anyone with earned income | April 2027 | Form 5498 | “Roth or traditional?” |
| HSA | HDHP enrollees not on Medicare | April 2027 | Form 8889 | “When do I stop before Medicare?” |
| Solo 401(k) | Self-employed, no staff | Existing plan: elect deferrals by Dec. 31. New plan: filing deadline (see table above) | Plan document | “Solo 401(k) or SEP?” |
| SEP IRA | Self-employed or small employer | Return due date plus extensions | Form 5305-SEP | “What’s my max?” |
| Pay your kids | Business owners | 2026 payroll | Timesheets, W-2 | “Does my structure qualify?” |
| Bunch gifts or fund a DAF | Givers near the standard deduction | Dec. 31 | Acknowledgments | “Does bunching beat the non-itemizer deduction?” |
| QCD | IRA owners 70½+ | Dec. 31 | Acknowledgment, 1099-R | “Will it cover my RMD?” |
| Harvest losses | Taxable investors | Dec. 31 | Form 1099-B | “Any wash sales?” |
Tax planning isn’t a loophole. It’s reading the instructions the IRS already wrote. Read them, keep your receipts, and keep your money.
This article is general information, not tax, legal, or financial advice. Tax rules depend on your situation and change often. Figures are for tax year 2026 and were checked on October 15, 2026, on IRS.gov (tax figures) and on CMS.gov, Medicare.gov, and SSA.gov (Medicare figures). Talk to a CPA, Enrolled Agent, or tax attorney before you act.
Sources
- IRS News Release IR-2025-103 (Oct. 9, 2025), 2026 inflation adjustments including OBBB amendments. https://www.irs.gov/newsroom/irs-releases-tax-inflation-adjustments-for-tax-year-2026-including-amendments-from-the-one-big-beautiful-bill
- Rev. Proc. 2025-32 (2026 inflation-adjusted items). https://www.irs.gov/pub/irs-drop/rp-25-32.pdf
- IRS News Release IR-2025-111 (Nov. 13, 2025), 2026 retirement limits. https://www.irs.gov/newsroom/401k-limit-increases-to-24500-for-2026-ira-limit-increases-to-7500
- IRS Notice 2025-67, 2026 retirement plan cost-of-living adjustments. https://www.irs.gov/pub/irs-drop/n-25-67.pdf
- IRS News Release IR-2025-91 (Sept. 15, 2025), final Roth catch-up regulations. https://www.irs.gov/newsroom/treasury-irs-issue-final-regulations-on-new-roth-catch-up-rule-other-secure-2point0-act-provisions
- Rev. Proc. 2025-19, 2026 HSA limits. https://www.irs.gov/pub/irs-drop/rp-25-19.pdf
- IRS Publication 969 (2025), Health Savings Accounts. https://www.irs.gov/pub/irs-pdf/p969.pdf
- IRS, One Big Beautiful Bill provisions page. https://www.irs.gov/newsroom/one-big-beautiful-bill-provisions
- IRS, Working Families Tax Cuts: Individuals and workers. https://www.irs.gov/newsroom/working-families-tax-cuts-individuals-and-workers
- IRS Publication 505 (2026), Tax Withholding and Estimated Tax. https://www.irs.gov/pub/irs-pdf/p505.pdf
- IRS, Correction to SALT deduction amount in the 2026 Form 1040-ES. https://www.irs.gov/forms-pubs/correction-to-state-and-local-income-tax-deduction-amount-in-the-2026-form-1040-es
- IRS Publication 6196 (10-2026), Charitable contribution deduction tips for non-itemizers. https://www.irs.gov/pub/irs-pdf/p6196.pdf
- IRS Publication 590-A (2025), IRA contributions. https://www.irs.gov/pub/irs-pdf/p590a.pdf
- IRS Publication 590-B (2025), IRA distributions. https://www.irs.gov/pub/irs-pdf/p590b.pdf
- IRS, Retirement plans FAQs regarding IRAs: distributions. https://www.irs.gov/retirement-plans/retirement-plans-faqs-regarding-iras-distributions-withdrawals
- 26 U.S.C. 408(d)(8)(B)(i), definition of qualified charitable distribution (statute; replaces IR-2014-117 as the cited authority). https://www.law.cornell.edu/uscode/text/26/408
- IRS, One-participant 401(k) plans. https://www.irs.gov/retirement-plans/one-participant-401k-plans
- IRS Publication 560 (2025), Retirement Plans for Small Business. https://www.irs.gov/pub/irs-pdf/p560.pdf
- IRS, Simplified Employee Pension plan (SEP). https://www.irs.gov/retirement-plans/plan-sponsor/simplified-employee-pension-plan-sep
- IRS, Retirement plans FAQs regarding SEPs. https://www.irs.gov/retirement-plans/retirement-plans-faqs-regarding-seps
- IRS, Family help. https://www.irs.gov/businesses/small-businesses-self-employed/family-help
- IRS Publication 15 (2026), Employer’s Tax Guide, “Family Employees.” https://www.irs.gov/pub/irs-pdf/p15.pdf
- IRS, Home office deduction. https://www.irs.gov/businesses/small-businesses-self-employed/home-office-deduction
- IRS, Simplified option for home office deduction. https://www.irs.gov/businesses/small-businesses-self-employed/simplified-option-for-home-office-deduction
- IRS Publication 587 (2025), Business Use of Your Home. https://www.irs.gov/pub/irs-pdf/p587.pdf
- IRS Publication 550 (2025), Investment Income and Expenses. https://www.irs.gov/pub/irs-pdf/p550.pdf
- IRS Publication 538 (Rev. January 2022), Accounting Periods and Methods (current revision). https://www.irs.gov/pub/irs-pdf/p538.pdf
- IRS Publication 526 (2025), Charitable Contributions. https://www.irs.gov/pub/irs-pdf/p526.pdf
- IRS Topic No. 506, Charitable contributions. https://www.irs.gov/taxtopics/tc506
- IRS, Donor-advised funds. https://www.irs.gov/charities-non-profits/charitable-organizations/donor-advised-funds
- Medicare.gov, “Medicare Costs” (2026). https://www.medicare.gov/publications/11579-medicare-costs.pdf
- IRS News Release IR-2026-30 (March 5, 2026), Dirty Dozen tax scams for 2026. https://www.irs.gov/newsroom/dirty-dozen-tax-scams-for-2026-irs-reminds-taxpayers-to-watch-out-for-dangerous-threats
- IRS Topic No. 254, How to choose a tax return preparer. https://www.irs.gov/taxtopics/tc254
- IRS Topic No. 510, Business use of car. https://www.irs.gov/taxtopics/tc510
- IRS Tax Tip 2022-57, Hobby vs. business. https://www.irs.gov/newsroom/heres-how-to-tell-the-difference-between-a-hobby-and-a-business-for-tax-purposes
- IRS, Understanding your Form 1099-K. https://www.irs.gov/businesses/understanding-your-form-1099-k
- CMS, 2026 Medicare Parts A & B Premiums and Deductibles (fact sheet). https://www.cms.gov/newsroom/fact-sheets/2026-medicare-parts-b-premiums-deductibles
- SSA, Request to lower an Income-Related Monthly Adjustment Amount (IRMAA). https://www.ssa.gov/medicare/lower-irmaa
- Medicare.gov, Enrolling in Medicare Part A & Part B (CMS Product No. 11036). https://www.medicare.gov/publications/11036-enrolling-part-a-part-b.pdf
- Treasury/IRS final regulations, Catch-Up Contributions, 90 FR 44527 (Sept. 16, 2025), FR Doc. 2025-17865. https://www.federalregister.gov/documents/2025/09/16/2025-17865/catch-up-contributions
- 26 U.S.C. 401(a)(9)(C)(v), RMD applicable age; proposed regulations, 89 FR 58644 (July 19, 2024). https://www.law.cornell.edu/uscode/text/26/401 and https://www.federalregister.gov/documents/2024/07/19/2024-14543/required-minimum-distributions
- IRS Notice 2026-05, Expanded Availability of HSAs under OBBBA. https://www.irs.gov/pub/irs-drop/n-26-05.pdf
- IRS, IRS audits. https://www.irs.gov/businesses/small-businesses-self-employed/irs-audits
