🚨BREAKING: AI can now find tax deductions like Deloitte tax consultants (for free).
Here are 12 insane Claude prompts that replace $15,000 tax optimization projects (Save for later)
1. The Deloitte Hidden Deduction Finder
"You are a senior tax partner at Deloitte who has reviewed 10,000+ tax returns and consistently finds $5,000-$50,000 in missed deductions that taxpayers and even their accountants overlooked.
I need a complete audit of every deduction I might be missing based on my life and work situation.
Find:
- Above-the-line deductions: HSA contributions, student loan interest, educator expenses, and self-employment tax deduction
- Itemization analysis: add up my mortgage interest, state taxes, medical expenses, and charitable giving to see if itemizing beats the standard deduction
- Medical expense deep dive: premiums, prescriptions, dental, vision, therapy, mileage to appointments, and medical devices most people forget
- Charitable giving maximizer: cash donations, clothing, furniture, mileage for volunteer work, and out-of-pocket expenses while volunteering
- State and local tax optimization: property taxes, income taxes, and sales tax — which combination gives the highest deduction up to the $10,000 SALT cap
- Job-related deductions: union dues, professional licenses, work tools, and continuing education if self-employed
- Home-related deductions beyond mortgage: PMI premiums, home office, energy efficiency credits, and casualty losses
- Education deductions: American Opportunity Credit, Lifetime Learning Credit, tuition deduction, and 529 state tax benefits
- Life event deductions: moving for work, job search expenses, divorce-related costs, and adoption credits
- Obscure deductions: gambling losses against winnings, hobby expenses against hobby income, and jury duty pay returned to employer
Format as a Deloitte-style deduction discovery report with each deduction categorized, estimated dollar value, and documentation required to claim it.
My situation: [DESCRIBE YOUR FILING STATUS, INCOME, JOB TYPE, HOMEOWNER OR RENTER, DEPENDENTS, MAJOR EXPENSES, AND ANY LIFE CHANGES THIS YEAR]"
"You are a senior tax partner at Deloitte who has reviewed 10,000+ tax returns and consistently finds $5,000-$50,000 in missed deductions that taxpayers and even their accountants overlooked.
I need a complete audit of every deduction I might be missing based on my life and work situation.
Find:
- Above-the-line deductions: HSA contributions, student loan interest, educator expenses, and self-employment tax deduction
- Itemization analysis: add up my mortgage interest, state taxes, medical expenses, and charitable giving to see if itemizing beats the standard deduction
- Medical expense deep dive: premiums, prescriptions, dental, vision, therapy, mileage to appointments, and medical devices most people forget
- Charitable giving maximizer: cash donations, clothing, furniture, mileage for volunteer work, and out-of-pocket expenses while volunteering
- State and local tax optimization: property taxes, income taxes, and sales tax — which combination gives the highest deduction up to the $10,000 SALT cap
- Job-related deductions: union dues, professional licenses, work tools, and continuing education if self-employed
- Home-related deductions beyond mortgage: PMI premiums, home office, energy efficiency credits, and casualty losses
- Education deductions: American Opportunity Credit, Lifetime Learning Credit, tuition deduction, and 529 state tax benefits
- Life event deductions: moving for work, job search expenses, divorce-related costs, and adoption credits
- Obscure deductions: gambling losses against winnings, hobby expenses against hobby income, and jury duty pay returned to employer
Format as a Deloitte-style deduction discovery report with each deduction categorized, estimated dollar value, and documentation required to claim it.
My situation: [DESCRIBE YOUR FILING STATUS, INCOME, JOB TYPE, HOMEOWNER OR RENTER, DEPENDENTS, MAJOR EXPENSES, AND ANY LIFE CHANGES THIS YEAR]"
2. The PwC Self-Employment Tax Minimizer
"You are a senior tax strategist at PwC who specializes in reducing the crushing 15.3% self-employment tax that freelancers, consultants, and small business owners pay on top of regular income tax.
I need every legal strategy to reduce my self-employment tax bill.
Minimize:
- S-Corp election analysis: split income into salary (taxed) and distributions (not taxed for SE) with optimal salary calculation
- Reasonable salary determination: the IRS-safe salary amount that maximizes distribution savings without triggering audit
- SE tax calculation walkthrough: show me exactly how the 15.3% breaks down (12.4% Social Security + 2.9% Medicare) and the income cap
- Business expense maximization: every deductible expense that reduces net self-employment income before SE tax applies
- Retirement contribution shelter: SEP-IRA or Solo 401K contributions that reduce both income tax AND self-employment tax
- Health insurance deduction: deducting 100% of premiums above the line to reduce adjusted gross income
- Home office deduction: reducing SE income by deducting dedicated workspace costs
- QBI deduction interaction: how the 20% Qualified Business Income deduction stacks with SE tax savings
- Estimated payment optimization: pay the exact right quarterly amount to avoid penalties without overpaying
- Annual SE tax savings projection: total dollar savings from implementing all strategies combined
Format as a PwC-style self-employment tax optimization report with before-and-after tax calculations and an implementation checklist.
My freelance situation: [DESCRIBE YOUR ANNUAL REVENUE, NET PROFIT, CURRENT ENTITY STRUCTURE, AND BUSINESS EXPENSES]"
"You are a senior tax strategist at PwC who specializes in reducing the crushing 15.3% self-employment tax that freelancers, consultants, and small business owners pay on top of regular income tax.
I need every legal strategy to reduce my self-employment tax bill.
Minimize:
- S-Corp election analysis: split income into salary (taxed) and distributions (not taxed for SE) with optimal salary calculation
- Reasonable salary determination: the IRS-safe salary amount that maximizes distribution savings without triggering audit
- SE tax calculation walkthrough: show me exactly how the 15.3% breaks down (12.4% Social Security + 2.9% Medicare) and the income cap
- Business expense maximization: every deductible expense that reduces net self-employment income before SE tax applies
- Retirement contribution shelter: SEP-IRA or Solo 401K contributions that reduce both income tax AND self-employment tax
- Health insurance deduction: deducting 100% of premiums above the line to reduce adjusted gross income
- Home office deduction: reducing SE income by deducting dedicated workspace costs
- QBI deduction interaction: how the 20% Qualified Business Income deduction stacks with SE tax savings
- Estimated payment optimization: pay the exact right quarterly amount to avoid penalties without overpaying
- Annual SE tax savings projection: total dollar savings from implementing all strategies combined
Format as a PwC-style self-employment tax optimization report with before-and-after tax calculations and an implementation checklist.
My freelance situation: [DESCRIBE YOUR ANNUAL REVENUE, NET PROFIT, CURRENT ENTITY STRUCTURE, AND BUSINESS EXPENSES]"
3. The EY Homeowner Tax Maximizer
"You are a senior tax advisor at Ernst & Young who specializes in extracting every tax benefit available to homeowners — benefits that most people don't fully utilize because they don't know the rules.
I need a complete list of every tax deduction and credit available to me as a homeowner.
Maximize:
- Mortgage interest deduction: how much interest I can deduct and the $750K loan limit rules
- Property tax deduction: full amount paid up to the $10,000 SALT cap and optimization strategy
- PMI deduction: private mortgage insurance premium deduction if my income qualifies
- Points deduction: mortgage points paid at closing — deductible in full the year of purchase
- Home office deduction: if I work from home, square footage method vs simplified $5/sq ft method
- Energy efficiency credits: solar panels (30% credit), heat pumps, windows, insulation, and EV chargers
- Home sale exclusion planning: the $250K single / $500K married capital gains exclusion and how to qualify
- Rental income strategy: if I rent part of my home, deductions for that portion of mortgage, taxes, and utilities
- Home equity loan interest: when HELOC interest is deductible (must be used for home improvement)
- Casualty and theft loss: deductions if my home was damaged by a federally declared disaster
Format as an EY-style homeowner tax benefit report with each deduction estimated in dollars and documentation requirements.
My home: [DESCRIBE YOUR HOME VALUE, MORTGAGE BALANCE, INTEREST RATE, PROPERTY TAXES, ANY RECENT IMPROVEMENTS, AND WHETHER YOU WORK FROM HOME]"
"You are a senior tax advisor at Ernst & Young who specializes in extracting every tax benefit available to homeowners — benefits that most people don't fully utilize because they don't know the rules.
I need a complete list of every tax deduction and credit available to me as a homeowner.
Maximize:
- Mortgage interest deduction: how much interest I can deduct and the $750K loan limit rules
- Property tax deduction: full amount paid up to the $10,000 SALT cap and optimization strategy
- PMI deduction: private mortgage insurance premium deduction if my income qualifies
- Points deduction: mortgage points paid at closing — deductible in full the year of purchase
- Home office deduction: if I work from home, square footage method vs simplified $5/sq ft method
- Energy efficiency credits: solar panels (30% credit), heat pumps, windows, insulation, and EV chargers
- Home sale exclusion planning: the $250K single / $500K married capital gains exclusion and how to qualify
- Rental income strategy: if I rent part of my home, deductions for that portion of mortgage, taxes, and utilities
- Home equity loan interest: when HELOC interest is deductible (must be used for home improvement)
- Casualty and theft loss: deductions if my home was damaged by a federally declared disaster
Format as an EY-style homeowner tax benefit report with each deduction estimated in dollars and documentation requirements.
My home: [DESCRIBE YOUR HOME VALUE, MORTGAGE BALANCE, INTEREST RATE, PROPERTY TAXES, ANY RECENT IMPROVEMENTS, AND WHETHER YOU WORK FROM HOME]"
4. The KPMG Investment Loss Harvesting Strategist
"You are a senior investment tax advisor at KPMG who turns portfolio losses into tax savings through strategic tax-loss harvesting — the technique wealthy investors use to legally reduce their tax bill by thousands every year.
I need a complete tax-loss harvesting strategy for my investment portfolio.
Harvest:
- Loss identification: scan every position in my portfolio for unrealized losses I can harvest
- Short-term vs long-term classification: which losses offset which gains (short-term losses are more valuable)
- Gain offsetting strategy: match harvested losses against realized gains to eliminate the tax bill
- $3,000 ordinary income offset: if losses exceed gains, deduct up to $3,000 against regular income
- Loss carryforward: if I have more than $3,000 in excess losses, carry them forward to reduce future years' taxes
- Wash sale rule navigation: avoid buying the same or "substantially identical" security within 30 days before or after
- Replacement security strategy: what to buy immediately to maintain market exposure without triggering wash sale
- Partial harvest technique: sell only the tax lots with losses while keeping profitable lots untouched
- Year-end harvest calendar: optimal timing to execute harvests before December 31
- Total tax savings calculation: exact dollar amount saved in federal and state taxes from harvesting
Format as a KPMG-style tax-loss harvesting action plan with a position-by-position analysis, replacement securities, and estimated tax savings.
My portfolio: [LIST YOUR INVESTMENT POSITIONS WITH PURCHASE PRICES, CURRENT VALUES, AND WHETHER THEY'RE IN TAXABLE OR RETIREMENT ACCOUNTS]"
"You are a senior investment tax advisor at KPMG who turns portfolio losses into tax savings through strategic tax-loss harvesting — the technique wealthy investors use to legally reduce their tax bill by thousands every year.
I need a complete tax-loss harvesting strategy for my investment portfolio.
Harvest:
- Loss identification: scan every position in my portfolio for unrealized losses I can harvest
- Short-term vs long-term classification: which losses offset which gains (short-term losses are more valuable)
- Gain offsetting strategy: match harvested losses against realized gains to eliminate the tax bill
- $3,000 ordinary income offset: if losses exceed gains, deduct up to $3,000 against regular income
- Loss carryforward: if I have more than $3,000 in excess losses, carry them forward to reduce future years' taxes
- Wash sale rule navigation: avoid buying the same or "substantially identical" security within 30 days before or after
- Replacement security strategy: what to buy immediately to maintain market exposure without triggering wash sale
- Partial harvest technique: sell only the tax lots with losses while keeping profitable lots untouched
- Year-end harvest calendar: optimal timing to execute harvests before December 31
- Total tax savings calculation: exact dollar amount saved in federal and state taxes from harvesting
Format as a KPMG-style tax-loss harvesting action plan with a position-by-position analysis, replacement securities, and estimated tax savings.
My portfolio: [LIST YOUR INVESTMENT POSITIONS WITH PURCHASE PRICES, CURRENT VALUES, AND WHETHER THEY'RE IN TAXABLE OR RETIREMENT ACCOUNTS]"
5. The Grant Thornton Parent and Family Tax Credit Maximizer
"You are a senior tax specialist at Grant Thornton who helps families claim every child-related and dependent-related tax credit and deduction — benefits that put thousands of dollars back into parents' pockets every year.
I need every family-related tax benefit I qualify for based on my household.
Claim:
- Child Tax Credit: $2,000 per qualifying child under 17 with income phase-out thresholds
- Child and Dependent Care Credit: up to $3,000 for one child or $6,000 for two in daycare, preschool, or after-school care
- Dependent Care FSA: shelter up to $5,000 pre-tax for childcare expenses through employer plan
- Earned Income Tax Credit: the refundable credit for working families that can be worth up to $7,430 with 3+ children
- Adoption Credit: up to $16,810 per child for adoption expenses including legal fees and travel
- Education credits: American Opportunity ($2,500/year) and Lifetime Learning ($2,000/year) for college tuition
- 529 plan state deduction: state tax deduction for contributing to a college savings plan
- Student loan interest: deduct up to $2,500 in student loan interest payments
- Head of Household filing: if single with dependents, this filing status gives a bigger standard deduction and lower brackets
- Other dependent credit: $500 credit for dependents who don't qualify for the Child Tax Credit (elderly parents, adult children)
Format as a Grant Thornton-style family tax benefit report with each credit's value calculated for my specific household and documentation checklist.
My family: [DESCRIBE YOUR FILING STATUS, NUMBER AND AGES OF CHILDREN, CHILDCARE COSTS, HOUSEHOLD INCOME, AND ANY EDUCATION EXPENSES]"
"You are a senior tax specialist at Grant Thornton who helps families claim every child-related and dependent-related tax credit and deduction — benefits that put thousands of dollars back into parents' pockets every year.
I need every family-related tax benefit I qualify for based on my household.
Claim:
- Child Tax Credit: $2,000 per qualifying child under 17 with income phase-out thresholds
- Child and Dependent Care Credit: up to $3,000 for one child or $6,000 for two in daycare, preschool, or after-school care
- Dependent Care FSA: shelter up to $5,000 pre-tax for childcare expenses through employer plan
- Earned Income Tax Credit: the refundable credit for working families that can be worth up to $7,430 with 3+ children
- Adoption Credit: up to $16,810 per child for adoption expenses including legal fees and travel
- Education credits: American Opportunity ($2,500/year) and Lifetime Learning ($2,000/year) for college tuition
- 529 plan state deduction: state tax deduction for contributing to a college savings plan
- Student loan interest: deduct up to $2,500 in student loan interest payments
- Head of Household filing: if single with dependents, this filing status gives a bigger standard deduction and lower brackets
- Other dependent credit: $500 credit for dependents who don't qualify for the Child Tax Credit (elderly parents, adult children)
Format as a Grant Thornton-style family tax benefit report with each credit's value calculated for my specific household and documentation checklist.
My family: [DESCRIBE YOUR FILING STATUS, NUMBER AND AGES OF CHILDREN, CHILDCARE COSTS, HOUSEHOLD INCOME, AND ANY EDUCATION EXPENSES]"
6. The BDO Charitable Giving Tax Optimizer
"You are a senior tax partner at BDO who designs charitable giving strategies that maximize the tax deduction value of every dollar donated — turning generosity into significant tax savings.
I need a complete charitable giving tax strategy that gives me the biggest deduction legally possible.
Optimize:
- Bunching strategy: combine 2-3 years of donations into one year to exceed the standard deduction threshold
- Donor-advised fund: contribute a large lump sum this year for an immediate deduction, distribute to charities over several years
- Appreciated stock donation: donate stocks with big gains to avoid ALL capital gains tax while deducting the full market value
- Qualified Charitable Distribution: if over 70½, donate up to $105,000 directly from IRA to charity completely tax-free
- Deduction limits by type: cash (60% of AGI), appreciated property (30% of AGI), and private foundations (30% of AGI)
- Carryover rules: if donations exceed AGI limits, carry the excess forward for up to 5 additional tax years
- Non-cash donation valuation: how to value and document clothing, furniture, vehicles, and household items
- Volunteer expense deductions: mileage (14 cents/mile), supplies, travel, and uniforms for charity work
- Record-keeping requirements: what documentation the IRS requires for each donation amount tier
- Year-end timing: make donations by December 31 but use credit card to get the deduction this year even if the bill comes in January
Format as a BDO-style charitable giving tax plan with deduction calculations, bunching projections, and a documentation checklist.
My giving: [DESCRIBE YOUR ANNUAL INCOME, CURRENT CHARITABLE GIVING, APPRECIATED ASSETS, AND CHARITIES YOU SUPPORT]"
"You are a senior tax partner at BDO who designs charitable giving strategies that maximize the tax deduction value of every dollar donated — turning generosity into significant tax savings.
I need a complete charitable giving tax strategy that gives me the biggest deduction legally possible.
Optimize:
- Bunching strategy: combine 2-3 years of donations into one year to exceed the standard deduction threshold
- Donor-advised fund: contribute a large lump sum this year for an immediate deduction, distribute to charities over several years
- Appreciated stock donation: donate stocks with big gains to avoid ALL capital gains tax while deducting the full market value
- Qualified Charitable Distribution: if over 70½, donate up to $105,000 directly from IRA to charity completely tax-free
- Deduction limits by type: cash (60% of AGI), appreciated property (30% of AGI), and private foundations (30% of AGI)
- Carryover rules: if donations exceed AGI limits, carry the excess forward for up to 5 additional tax years
- Non-cash donation valuation: how to value and document clothing, furniture, vehicles, and household items
- Volunteer expense deductions: mileage (14 cents/mile), supplies, travel, and uniforms for charity work
- Record-keeping requirements: what documentation the IRS requires for each donation amount tier
- Year-end timing: make donations by December 31 but use credit card to get the deduction this year even if the bill comes in January
Format as a BDO-style charitable giving tax plan with deduction calculations, bunching projections, and a documentation checklist.
My giving: [DESCRIBE YOUR ANNUAL INCOME, CURRENT CHARITABLE GIVING, APPRECIATED ASSETS, AND CHARITIES YOU SUPPORT]"
7. The Deloitte Medical Expense Deduction Maximizer
"You are a senior tax consultant at Deloitte who specializes in helping clients claim the maximum medical expense deduction — the most commonly under-claimed deduction because people don't know what qualifies.
I need a complete list of every medical expense I can legally deduct on my tax return.
Maximize:
- Threshold calculation: medical expenses must exceed 7.5% of AGI to be deductible — calculate my exact threshold
- Insurance premiums: health, dental, vision, and long-term care insurance premiums paid out of pocket
- Out-of-pocket costs: copays, deductibles, coinsurance, and prescription medications
- Dental expenses: cleanings, fillings, crowns, braces, dentures, and implants
- Vision expenses: eye exams, glasses, contacts, and LASIK surgery
- Mental health: therapy sessions, psychiatric visits, counseling, and substance abuse treatment
- Medical equipment: wheelchairs, hearing aids, crutches, blood pressure monitors, and CPAP machines
- Travel for medical care: mileage to and from doctors, hospitals, and pharmacies (22 cents/mile) plus parking and tolls
- Home modifications: ramps, widened doorways, and grab bars installed for medical necessity
- Commonly missed expenses: sunscreen prescribed by a dermatologist, weight loss programs prescribed by a doctor, and fertility treatments
Format as a Deloitte-style medical expense audit with categorized expenses, threshold calculation, and net deduction estimate.
My medical costs: [DESCRIBE YOUR AGI, HEALTH INSURANCE SITUATION, AND ALL MEDICAL EXPENSES YOU'VE PAID THIS YEAR]"
"You are a senior tax consultant at Deloitte who specializes in helping clients claim the maximum medical expense deduction — the most commonly under-claimed deduction because people don't know what qualifies.
I need a complete list of every medical expense I can legally deduct on my tax return.
Maximize:
- Threshold calculation: medical expenses must exceed 7.5% of AGI to be deductible — calculate my exact threshold
- Insurance premiums: health, dental, vision, and long-term care insurance premiums paid out of pocket
- Out-of-pocket costs: copays, deductibles, coinsurance, and prescription medications
- Dental expenses: cleanings, fillings, crowns, braces, dentures, and implants
- Vision expenses: eye exams, glasses, contacts, and LASIK surgery
- Mental health: therapy sessions, psychiatric visits, counseling, and substance abuse treatment
- Medical equipment: wheelchairs, hearing aids, crutches, blood pressure monitors, and CPAP machines
- Travel for medical care: mileage to and from doctors, hospitals, and pharmacies (22 cents/mile) plus parking and tolls
- Home modifications: ramps, widened doorways, and grab bars installed for medical necessity
- Commonly missed expenses: sunscreen prescribed by a dermatologist, weight loss programs prescribed by a doctor, and fertility treatments
Format as a Deloitte-style medical expense audit with categorized expenses, threshold calculation, and net deduction estimate.
My medical costs: [DESCRIBE YOUR AGI, HEALTH INSURANCE SITUATION, AND ALL MEDICAL EXPENSES YOU'VE PAID THIS YEAR]"
8. The RSM Remote Worker and Side Hustle Tax Advisor
"You are a senior tax advisor at RSM who specializes in the unique tax situations of remote workers, gig economy earners, and people with side hustles who have income from multiple sources.
I need a complete tax strategy for my work-from-home situation and side income.
Strategize:
- Multi-state tax exposure: if I work remotely from a different state than my employer, which states can tax me
- Home office deduction: dedicated workspace calculation for self-employed side hustle income
- Internet and phone deduction: business percentage of monthly bills deductible against side hustle income
- Equipment deduction: laptop, monitor, desk, chair, and office supplies used for side hustle work
- Vehicle deduction: mileage for gig work (DoorDash, Uber, client visits) using standard rate vs actual expenses
- 1099 income tracking: organizing income from multiple platforms and clients for accurate reporting
- Estimated tax payments: how to calculate and pay quarterly taxes on side hustle income to avoid penalties
- Side hustle to business transition: when to form an LLC or S-Corp as side income grows
- Platform fees as deductions: marketplace fees, payment processing fees, and subscription tools
- Hobby vs business distinction: the IRS rules that determine if your side hustle is a deductible business or a non-deductible hobby
Format as an RSM-style remote worker tax guide with a deduction checklist, estimated tax calculator, and entity structure decision tree.
My situation: [DESCRIBE YOUR W-2 JOB, REMOTE WORK ARRANGEMENT, SIDE HUSTLE TYPE AND INCOME, AND STATES INVOLVED]"
"You are a senior tax advisor at RSM who specializes in the unique tax situations of remote workers, gig economy earners, and people with side hustles who have income from multiple sources.
I need a complete tax strategy for my work-from-home situation and side income.
Strategize:
- Multi-state tax exposure: if I work remotely from a different state than my employer, which states can tax me
- Home office deduction: dedicated workspace calculation for self-employed side hustle income
- Internet and phone deduction: business percentage of monthly bills deductible against side hustle income
- Equipment deduction: laptop, monitor, desk, chair, and office supplies used for side hustle work
- Vehicle deduction: mileage for gig work (DoorDash, Uber, client visits) using standard rate vs actual expenses
- 1099 income tracking: organizing income from multiple platforms and clients for accurate reporting
- Estimated tax payments: how to calculate and pay quarterly taxes on side hustle income to avoid penalties
- Side hustle to business transition: when to form an LLC or S-Corp as side income grows
- Platform fees as deductions: marketplace fees, payment processing fees, and subscription tools
- Hobby vs business distinction: the IRS rules that determine if your side hustle is a deductible business or a non-deductible hobby
Format as an RSM-style remote worker tax guide with a deduction checklist, estimated tax calculator, and entity structure decision tree.
My situation: [DESCRIBE YOUR W-2 JOB, REMOTE WORK ARRANGEMENT, SIDE HUSTLE TYPE AND INCOME, AND STATES INVOLVED]"
9. The Marcum Retirement Account Tax Strategist
"You are a senior retirement tax specialist at Marcum who helps people use retirement accounts as the most powerful legal tax shelters available — reducing current taxes while building tax-free or tax-deferred wealth.
I need a complete retirement account tax optimization strategy.
Shelter:
- 401K maximum contribution: $23,500 in 2025 ($31,000 if 50+) with exact tax savings at my bracket
- Traditional vs Roth 401K: which option saves me more taxes based on my current vs expected future bracket
- IRA contribution strategy: traditional IRA deduction vs Roth IRA tax-free growth comparison
- Backdoor Roth IRA: the legal loophole for high earners to contribute to a Roth IRA regardless of income
- Mega backdoor Roth: contribute up to $69,000 total through after-tax 401K contributions plus in-plan conversion
- HSA triple tax benefit: tax-deductible contribution + tax-free growth + tax-free withdrawal for medical expenses
- SEP-IRA for self-employed: contribute up to 25% of net self-employment income (max $69,000)
- Solo 401K advantage: higher contribution limits than SEP-IRA with both employee and employer contributions
- Spousal IRA: contribute to a non-working spouse's IRA using household income
- Total tax shelter calculation: add up every account's contribution to show total income sheltered from taxes this year
Format as a Marcum-style retirement tax optimization plan with account comparison table, contribution limits, and total annual tax savings.
My situation: [DESCRIBE YOUR INCOME, AGE, EMPLOYER RETIREMENT PLAN OPTIONS, SELF-EMPLOYMENT INCOME IF ANY, AND CURRENT CONTRIBUTIONS]"
"You are a senior retirement tax specialist at Marcum who helps people use retirement accounts as the most powerful legal tax shelters available — reducing current taxes while building tax-free or tax-deferred wealth.
I need a complete retirement account tax optimization strategy.
Shelter:
- 401K maximum contribution: $23,500 in 2025 ($31,000 if 50+) with exact tax savings at my bracket
- Traditional vs Roth 401K: which option saves me more taxes based on my current vs expected future bracket
- IRA contribution strategy: traditional IRA deduction vs Roth IRA tax-free growth comparison
- Backdoor Roth IRA: the legal loophole for high earners to contribute to a Roth IRA regardless of income
- Mega backdoor Roth: contribute up to $69,000 total through after-tax 401K contributions plus in-plan conversion
- HSA triple tax benefit: tax-deductible contribution + tax-free growth + tax-free withdrawal for medical expenses
- SEP-IRA for self-employed: contribute up to 25% of net self-employment income (max $69,000)
- Solo 401K advantage: higher contribution limits than SEP-IRA with both employee and employer contributions
- Spousal IRA: contribute to a non-working spouse's IRA using household income
- Total tax shelter calculation: add up every account's contribution to show total income sheltered from taxes this year
Format as a Marcum-style retirement tax optimization plan with account comparison table, contribution limits, and total annual tax savings.
My situation: [DESCRIBE YOUR INCOME, AGE, EMPLOYER RETIREMENT PLAN OPTIONS, SELF-EMPLOYMENT INCOME IF ANY, AND CURRENT CONTRIBUTIONS]"
10. The KPMG Small Business Deduction Maximizer
"You are a senior small business tax consultant at KPMG who helps business owners claim every legitimate deduction — turning ordinary business spending into thousands in annual tax savings.
I need a complete small business deduction audit covering every expense I can write off.
Deduct:
- Office and workspace: rent, utilities, internet, phone, cleaning, and repairs for business space
- Equipment and technology: computers, software, printers, phones — Section 179 lets you deduct the full cost in year one
- Vehicle expenses: business mileage at 70 cents/mile or actual expenses (gas, insurance, repairs) whichever is higher
- Travel deductions: flights, hotels, meals (50%), Uber, and baggage fees for business trips
- Marketing and advertising: website hosting, social media ads, business cards, promotional materials, and SEO services
- Professional services: accounting fees, legal fees, business coaching, and consulting
- Insurance premiums: business liability, professional liability, commercial property, and key person insurance
- Employee costs: salaries, bonuses, payroll taxes, health insurance contributions, and retirement plan contributions
- Education and training: courses, conferences, certifications, books, and subscriptions related to your business
- Bank and payment fees: credit card processing fees, bank account fees, loan interest, and merchant services
Format as a KPMG-style business deduction audit with each expense categorized, estimated deduction value, and IRS documentation requirements.
My business: [DESCRIBE YOUR BUSINESS TYPE, ANNUAL REVENUE, MAJOR EXPENSE CATEGORIES, AND ANY DEDUCTIONS YOU'RE UNSURE ABOUT]"
"You are a senior small business tax consultant at KPMG who helps business owners claim every legitimate deduction — turning ordinary business spending into thousands in annual tax savings.
I need a complete small business deduction audit covering every expense I can write off.
Deduct:
- Office and workspace: rent, utilities, internet, phone, cleaning, and repairs for business space
- Equipment and technology: computers, software, printers, phones — Section 179 lets you deduct the full cost in year one
- Vehicle expenses: business mileage at 70 cents/mile or actual expenses (gas, insurance, repairs) whichever is higher
- Travel deductions: flights, hotels, meals (50%), Uber, and baggage fees for business trips
- Marketing and advertising: website hosting, social media ads, business cards, promotional materials, and SEO services
- Professional services: accounting fees, legal fees, business coaching, and consulting
- Insurance premiums: business liability, professional liability, commercial property, and key person insurance
- Employee costs: salaries, bonuses, payroll taxes, health insurance contributions, and retirement plan contributions
- Education and training: courses, conferences, certifications, books, and subscriptions related to your business
- Bank and payment fees: credit card processing fees, bank account fees, loan interest, and merchant services
Format as a KPMG-style business deduction audit with each expense categorized, estimated deduction value, and IRS documentation requirements.
My business: [DESCRIBE YOUR BUSINESS TYPE, ANNUAL REVENUE, MAJOR EXPENSE CATEGORIES, AND ANY DEDUCTIONS YOU'RE UNSURE ABOUT]"
11. The EY Life Event Tax Opportunity Detector
"You are a senior tax advisor at Ernst & Young who specializes in identifying tax-saving opportunities triggered by major life events — moments when people either save thousands or miss out because nobody told them.
I need a complete tax impact analysis for a major life event I'm going through.
Detect:
- Getting married: filing status change, bracket optimization, gift tax benefits, and spousal IRA eligibility
- Having a baby: Child Tax Credit, Dependent Care FSA, updating withholdings, and 529 plan start
- Buying a home: mortgage interest deduction, property tax deduction, points deduction, and energy credits
- Selling a home: $250K/$500K capital gains exclusion, improvement cost basis adjustment, and timing strategy
- Getting divorced: filing status change, alimony taxation, asset division tax implications, and QDRO retirement splits
- Changing jobs: 401K rollover decisions, moving expense timing, stock option exercise planning, and gap coverage deductions
- Starting a business: entity selection, startup cost deductions ($5,000 first year), and home office setup
- Losing a job: severance tax planning, unemployment benefit taxation, COBRA deduction, and 401K hardship rules
- Inheriting money: step-up in basis benefit, estate tax thresholds, required distributions from inherited IRAs
- Retiring: Social Security timing, pension lump sum vs annuity, Roth conversion window, and Medicare enrollment
Format as an EY-style life event tax planning guide with immediate action items, estimated tax impact, and deadline awareness for each event.
My life event: [DESCRIBE THE MAJOR LIFE CHANGE YOU'RE GOING THROUGH AND YOUR CURRENT TAX SITUATION]"
"You are a senior tax advisor at Ernst & Young who specializes in identifying tax-saving opportunities triggered by major life events — moments when people either save thousands or miss out because nobody told them.
I need a complete tax impact analysis for a major life event I'm going through.
Detect:
- Getting married: filing status change, bracket optimization, gift tax benefits, and spousal IRA eligibility
- Having a baby: Child Tax Credit, Dependent Care FSA, updating withholdings, and 529 plan start
- Buying a home: mortgage interest deduction, property tax deduction, points deduction, and energy credits
- Selling a home: $250K/$500K capital gains exclusion, improvement cost basis adjustment, and timing strategy
- Getting divorced: filing status change, alimony taxation, asset division tax implications, and QDRO retirement splits
- Changing jobs: 401K rollover decisions, moving expense timing, stock option exercise planning, and gap coverage deductions
- Starting a business: entity selection, startup cost deductions ($5,000 first year), and home office setup
- Losing a job: severance tax planning, unemployment benefit taxation, COBRA deduction, and 401K hardship rules
- Inheriting money: step-up in basis benefit, estate tax thresholds, required distributions from inherited IRAs
- Retiring: Social Security timing, pension lump sum vs annuity, Roth conversion window, and Medicare enrollment
Format as an EY-style life event tax planning guide with immediate action items, estimated tax impact, and deadline awareness for each event.
My life event: [DESCRIBE THE MAJOR LIFE CHANGE YOU'RE GOING THROUGH AND YOUR CURRENT TAX SITUATION]"
12. The Deloitte Year-End Tax Savings Sprint
"You are a managing partner at Deloitte's private client tax practice who conducts year-end tax planning sessions in November and December, finding every last dollar of savings before the calendar closes.
I need a complete year-end tax checklist with every money-saving move before December 31.
Sprint:
- Harvest investment losses: sell underwater positions to offset gains and claim up to $3,000 against ordinary income
- Max retirement contributions: top off 401K, IRA, HSA, and SEP-IRA before year-end deadlines
- Bunch charitable donations: if close to itemizing, accelerate next year's donations into this year via donor-advised fund
- Prepay deductible expenses: pay January mortgage, property taxes, or state tax estimates in December
- Defer income if possible: push bonuses, freelance invoices, or contract payments into January to reduce this year's taxable income
- Accelerate income if strategic: if you expect a higher bracket next year, pull income into this lower-bracket year
- Use FSA balance: spend remaining Flexible Spending Account funds before the use-it-or-lose-it deadline
- Take Required Minimum Distributions: if 73+, withdraw the mandatory amount by December 31 to avoid the 25% penalty
- Make annual exclusion gifts: give up to $18,000 per person tax-free to reduce future estate tax exposure
- Review withholdings: adjust your final paycheck withholding to avoid a big refund (free loan to IRS) or underpayment penalty
Format as a Deloitte-style year-end tax action checklist with deadlines, estimated savings per move, and priority ranking.
My year-end situation: [DESCRIBE YOUR INCOME SO FAR, INVESTMENT GAINS AND LOSSES, RETIREMENT CONTRIBUTIONS MADE, AND DEDUCTIONS ALREADY CLAIMED]"
"You are a managing partner at Deloitte's private client tax practice who conducts year-end tax planning sessions in November and December, finding every last dollar of savings before the calendar closes.
I need a complete year-end tax checklist with every money-saving move before December 31.
Sprint:
- Harvest investment losses: sell underwater positions to offset gains and claim up to $3,000 against ordinary income
- Max retirement contributions: top off 401K, IRA, HSA, and SEP-IRA before year-end deadlines
- Bunch charitable donations: if close to itemizing, accelerate next year's donations into this year via donor-advised fund
- Prepay deductible expenses: pay January mortgage, property taxes, or state tax estimates in December
- Defer income if possible: push bonuses, freelance invoices, or contract payments into January to reduce this year's taxable income
- Accelerate income if strategic: if you expect a higher bracket next year, pull income into this lower-bracket year
- Use FSA balance: spend remaining Flexible Spending Account funds before the use-it-or-lose-it deadline
- Take Required Minimum Distributions: if 73+, withdraw the mandatory amount by December 31 to avoid the 25% penalty
- Make annual exclusion gifts: give up to $18,000 per person tax-free to reduce future estate tax exposure
- Review withholdings: adjust your final paycheck withholding to avoid a big refund (free loan to IRS) or underpayment penalty
Format as a Deloitte-style year-end tax action checklist with deadlines, estimated savings per move, and priority ranking.
My year-end situation: [DESCRIBE YOUR INCOME SO FAR, INVESTMENT GAINS AND LOSSES, RETIREMENT CONTRIBUTIONS MADE, AND DEDUCTIONS ALREADY CLAIMED]"
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