Need to Know Tax › Tax Planning Strategies
The series
Tax Planning Strategies
“Anyone may so arrange his affairs that his taxes shall be as low as possible; he is not bound to choose that pattern which will best pay the Treasury.”
— Judge Learned Hand, Helvering v. Gregory, 1934
There is no cure for income tax. These are the strategies that work.
By Charles Trautman, EA
The Tax Shop · Lone Tree, Colorado · Reviewed October 16, 2026
Everyone wants to pay less tax. Most of what is sold under that heading is either illegal, imaginary, or built for someone else’s situation. What actually works is a shorter list than the internet suggests, it is written down in the Code and the regulations, and nearly all of it depends on who you are: a strategy that saves a retiree $4,000 does nothing for a family with toddlers, and the reverse.
So this series is organized by who you are. Ten pages, nine for a stage of life or a kind of income and one for the whole family across generations, each with eight to ten strategies: what it is, the 2026 figure, the condition that makes it hold up, and the full article where the detail lives. At the end of each page, the costs and risks: what the strategy costs or risks, and where one strategy reduces another. Choose your page. Most households belong to two or three.
Families with children
The child tax credit and the Trump account, day camp and the FSA, head of household, the earned income credit, state credits, a teenager on the payroll, the kiddie tax, 529s, adoption, and the W-4.
Students and the parents paying for college
The American Opportunity Credit four times, making room for it before the 529 pays, scholarships allocated to room and board, grandparent 529s under the new FAFSA, loans, and whose return the student goes on.
Homeowners
The exclusion used more than once, the two windows after a move or a death, the refinance, PMI again, bunching, 14 days tax-free, converting to a rental, the 1031 route, and state property tax breaks.
Investors
The 0% bracket, harvesting without a wash, holding past a year, asset location, employer stock and the NUA election, options and RSUs, giving stock instead of cash, QSBS, the 3.8% line, and the step-up.
The self-employed and small business owners
Your own retirement plan, the S election at the right income, keeping QBI, hiring family, the home office, the 6,000-pound line, the HSA, the state PTE election, timing across December 31, and the paperwork that keeps the rest.
People within ten years of retirement
Catch-ups including the new one at 60, the Roth conversion window, the 55 rule, Social Security timing, the IRMAA lookback, the HSA until Medicare, NUA, pension or lump sum, and how your state taxes retirement income.
Retirees
Giving from the IRA, staying under the senior deduction line, gains at 0%, the order to spend accounts, RMD timing and December withholding, beneficiaries after the ten-year rule, conversions after 73, the medical deduction, long-term care, and the state side of retirement income.
The widowed and the divorced
The last joint year and the two after, the house inside the window, recording the step-up, the spousal IRA decision, converting while the brackets are still joint, the QDRO, the children, Form SSA-44, and the state side of pensions and the homestead.
Higher earners
Every deferral, the backdoor and mega backdoor Roth, bunching into a donor-advised fund, the PTE election, entity and salary, the cash balance plan, real estate and the professional route, QSBS and opportunity zones, charitable tools, and the cliffs.
Tax planning by generations
Grandparents, parents and children on one plan: the $19,000 exclusion and direct tuition, what to give and what to hold for the step-up, QCDs, converting for the heirs, front-loading a 529, filling the parents’ pre-tax accounts, the child on the payroll, the Trump account deposit, the custodial Roth, and the kiddie tax.
On this page
What Counts as a Strategy
Three tests. It has to be legal, which means it is in the Code, the regulations, a revenue procedure, or a case the IRS lost, and each page names which one. It has to be worth doing, which means it saves more than it costs in fees, risk, or lost flexibility for a typical household in that group; a strategy that saves $300 and costs an appraisal is not on these pages. And it has to be something you can actually do, this year or next, with the income and assets you have; a strategy that requires owning a business is on the business owners’ page, not the retirees’.
What is not here: anything that depends on the IRS not noticing, anything that requires a promoter, anything with the word “secret” in it, and the captive insurance, conservation easement, and micro-captive arrangements that the IRS lists as abusive every year. If a strategy you have been offered isn’t on these pages, ask whoever is selling it why, before signing.
Strategies That No Longer Work
People ask about these every season. They were real once; the 2017 act suspended them and the 2025 act made the suspension permanent.
- Unreimbursed employee expenses, including the home office for employees, union dues, tools, and work travel. Gone. The employer has to reimburse under an accountable plan.
- Moving expenses, except for active-duty military under orders.
- Investment advisory fees, tax preparation fees, and safe deposit boxes as itemized deductions.
- Alimony deductions for agreements signed after 2018.
- The personal exemption, replaced by the larger standard deduction and the child credit.
- Home equity interest on money not spent on the home.
- Casualty losses outside a federally declared disaster.
- The stretch IRA for most non-spouse beneficiaries, replaced by the ten-year rule in 2020.
- Recharacterizing a Roth conversion after the fact.
- Residential energy and electric vehicle credits, which ended during 2025 under the 2025 act; see Energy Credits That Ended.
When Each Strategy Happens
April is too late for almost all of this. The return filed in April reports a year that is over; the strategies on these pages are applied in the year itself, and most of them in its last six weeks, when the year’s income is nearly known and there is still time to act. The decisions that belong in November and December: the retirement plan contribution, the Roth conversion amount, gains and losses to harvest, the charitable bunching, the vehicle or equipment purchase, the state PTE payment, the RMD withholding, and what gets invoiced in January. The decisions that belong at a life event: a new job (the W-4), a retirement (the window), a death (the step-up, the IRA, SSA-44), a divorce (the house, the QDRO, the children), a sale (the exclusion, the exchange). The decisions that belong at open enrollment: the HSA, the dependent care FSA, the 401(k) percentage and the Roth option.
The organizer and the 2027 tax calendar list the dates. A December conversation with whoever prepares your return is worth more than the April one.
Your State Runs Through Most of It
In most states with an income tax, the state return starts from federal adjusted gross income, so every federal strategy that reduces AGI (the retirement plan contribution, the HSA, harvesting a loss, the QCD) saves state tax too, and every strategy that works below AGI (itemizing, bunching, the QBI deduction, the senior deduction) often saves nothing at the state level. What your state exempts, which credits it offers and whether it has a pass-through entity election differ from state to state and appear in the Tennessee side box of the relevant articles. Full treatment: the Tennessee articles.
Costs and risks
- Each strategy gives the 2026 figure; figures change every year and the pages are revised each January
- Items marked (verify) are being confirmed against the primary source before the figures freeze in December
- Costs and risks are the costs and risks of each strategy, and the places where one strategy reduces another
- Nothing here is advice for a particular person; the right figure depends on the whole return, which is why every page ends by pointing you to whoever prepares yours
Questions people ask
Which page should I read?
The one that describes your biggest source of income or your current stage: a W-2 couple with children starts with Families; a couple at 60 starts with Near Retirement and Investors; a business owner starts with Self-Employed and, above $400,000, Higher Earners. Most households belong to two pages.
Are these strategies risky?
No. Each one is in the Code, the regulations, or a case the IRS lost, and each page names the authority. The risk in most of them is documentation: a log that wasn’t kept, an election that wasn’t attached, a form that wasn’t filed. The costs and risks on each page say where that is.
Can my preparer just do these for me?
The ones that live on the return, yes, as part of preparing it. The ones that require a decision during the year (how much to convert, what to buy, what to give) need a short meeting in November or December with the year-to-date numbers. That meeting is usually the most valuable hour of the tax year.
Why is there nothing here about deducting my commute, my clothes, or my lunch?
Because none of those is deductible, and it is better to hear it here than on examination. Commuting is personal; work clothes are deductible only if unsuitable for ordinary wear; meals are deductible at 50% only for business travel or a business meeting with a documented purpose. The strategies on these pages are the ones that hold up.
Where to start
Pick your page, read the ten, and mark the ones you aren’t doing. Then take the list to whoever prepares your return before December. Most households find three or four that apply, one of which they had never heard of, and a December conversation turns the list into numbers. The tax code is not going to get simpler. The strategies are how you live with it.
Written by Charles Trautman, EA, editor · Need to Know Tax, Lone Tree, Colorado
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