Tax Planning Prompts That Actually Save You Money

Decide itemize vs standard deduction. Filing status: [describe]. Standard: $[amount]. Potential itemized: mortgage interest [$], SALT capped at $10K, charitable [$], medical >7.5% AGI. Include: math comparison, bunching strategy if close, year-over-year planning.

Optimize charitable giving. Annual giving: $[amount]. Filing: [describe]. Income: $[amount]. Include: cash vs appreciated stock (best!), DAF (donor-advised fund) for bunching, QCDs from IRA post-70.5, AGI limits (60% cash, 30% stock), carry-forward 5 years.

Scan for tax credits I may miss. Family: [describe]. Kids: [ages]. Income: $[X]. Activities: [describe]. Include: Child Tax Credit, Child Care Credit, Saver's Credit, Earned Income Credit, Lifetime Learning Credit, Residential Clean Energy Credit, retirement contribution credits.

Qualify for home office deduction. Self-employed / W-2: [which]. Office details: [sq ft of home office, total sq ft]. Include: simplified ($5/sq ft up to $1500) vs regular method, actual expenses (% of utilities, insurance, depreciation), W-2 employee can't claim (post-2018), audit risks.

Plan capital gains for year. Short-term (under 1yr) gains: $[X]. Long-term gains: $[Y]. Income: $[Z]. Include: LTCG brackets (0%, 15%, 20%), harvesting gains at 0% bracket, timing sales across years, offsetting with losses, state tax impact.

Roth conversion strategy. Traditional IRA: $[amount]. Current tax bracket: [X]. Retirement bracket expected: [Y]. Income this year: $[Z]. Include: amount to convert (fill bracket without bumping), tax bill source, 5-year rule, Medicare IRMAA impact if 63+.

Tax-loss harvesting plan. Portfolio: [current losses]. Include: specific candidates to sell, wash sale rules, replacement securities (30+ day similar not identical), $3K annual limit against income, unlimited vs gains, carry-forward.

Mega Backdoor Roth feasibility. Employer 401k: [describe options — after-tax contributions allowed? in-service conversion?]. Current contributions: [describe]. Include: eligibility check, contribution amount possible ($46K above 401k limit), conversion to Roth IRA mechanics, step-by-step.

Self-employment tax strategy. Business income: $[amount]. Structure: [sole prop, LLC, S-Corp]. Include: S-Corp election break-even (~$60K net), reasonable salary rule, SEP-IRA vs Solo 401k, deductible business expenses checklist, quarterly estimated taxes.

Set up Solo 401k for self-employed. Business income: $[amount]. Include: contribution limits ($23K employee + 25% employer, up to $69K total), Roth option availability, Mega Backdoor option, plan administrator (Fidelity, Schwab, ETrade), deadline requirements.

Scan business deductions. Business: [describe]. Include: home office, mileage (67 cents/mile 2026), half of SE tax, health insurance premiums, retirement contributions, business meals (50%), software + subscriptions, professional development, equipment (Section 179).

Calculate quarterly estimated taxes. Self-employment income: $[amount]. Other income: $[Y]. Deductions: [describe]. Include: federal + state estimates, safe harbor (100/110% prior year), penalty avoidance, quarterly payment schedule, automation setup.

Maximize HSA tax strategy. Current HSA: $[X]. Contribution limit: $[Y]. Include: pre-tax contribution, investment growth tax-free, tax-free withdrawal for medical, pay medical out-of-pocket + save receipts, after 65 penalty-free for anything.

529 plan tax strategy. Kids: [ages]. State: [X]. Include: state tax deduction for contributions (varies by state), federal tax-free growth, qualified education expenses, Secure Act 2.0 leftover → Roth IRA conversion, overfunding risk.

December tax move checklist. Current situation: [describe]. Include: max 401k, HSA, FSA, tax-loss harvesting, charitable giving, estimated tax true-up, Roth conversions before year-end, required minimum distributions if 73+, bunching strategies.