High-Income Tax Planning Questions to Discuss With Your CPA

A higher income can make tax planning more complex. It does not make every deduction available or every popular strategy suitable. Before moving money, selling investments or changing a business structure, bring your CPA the facts, the tax year and the decision you are considering.

Useful planning starts with questions you can answer together throughout the year.

1. Which retirement contributions are available to me?

Ask which plans you can use, which contribution limits apply for the relevant year and whether you qualify for catch-up contributions. Limits change, and employer plans can have their own rules.

A contribution limit and a deduction are different questions. Ask how your income, filing status, workplace plan coverage and choice of account affect eligibility, deductions and taxation. Roth contributions do not provide the same current deduction as an eligible deductible traditional contribution.

If you are considering a Roth conversion, ask your CPA to assess the tax consequences using all relevant IRA balances and your circumstances before proceeding. Do not assume an indirect contribution or conversion is automatically tax-free.

Use the IRS's current annual limits as a reference, then confirm how the rules apply to you: IRS source 1  IRS source 2 

2. Am I eligible to contribute to a health savings account?

An HSA can offer tax advantages, but having a health plan with a large deductible is not enough by itself to establish eligibility. Ask your CPA to review eligible coverage, other coverage, Medicare enrollment, dependency status and applicable contribution limits before contributing. Ask which expenses qualify for tax-free distributions and what records to retain.

IRS reference: IRS source 3 

3. What would selling an investment change?

A sale can create a gain or a loss. Ask your CPA to model how capital gains and losses interact, consider holding periods and review wash-sale rules before implementing a loss-harvesting strategy. Investment decisions should also fit your investment objectives.

When net capital losses exceed gains, the deduction against other income is generally limited to the lesser of the net loss or $3,000, or $1,500 if married filing separately. Remaining eligible losses may carry forward. Have your CPA confirm the calculation rather than treating the headline amount as an automatic deduction.

IRS references: IRS source 4  IRS source 5 

4. What must be true for a charitable contribution deduction?

Ask whether the organization and contribution qualify, which substantiation is required, whether you will itemize and which limits apply for the year. Cash, appreciated assets and donor-advised fund contributions can have different consequences.

Do not assume a donation produces a dollar-for-dollar tax saving or that a gift of appreciated property always has the same result. Review the proposed gift before transferring the asset.

IRS reference: IRS source 6 

5. Which business expenses are deductible, and what evidence do I need?

Bring actual expenses and records. Ask your CPA to distinguish business and personal costs, identify applicable limitations and establish documentation requirements.

Entertainment expenses are generally nondeductible, subject to specific exceptions. Eligible business meals have separate requirements and limitations. Reasonableness alone does not make an expense deductible.

Family compensation, home-office costs and a change in entity structure also need individual analysis. Paying a relative or changing an entity does not automatically reduce the family's total tax. Ask which rules apply to the actual work, compensation, ownership and business facts.

IRS reference: IRS source 7 

6. Which property decisions need specialist review before I act?

Ask your CPA to assess the property, intended use, ownership, timing and records before relying on depreciation, an exchange or any other tax treatment. A real-estate investment is not automatically a tax shelter. Coordinate with the appropriate legal, investment and other professionals when the decision requires their expertise.

7. What should we revisit during the year?

Agree on when to review income changes, estimated payments, investment activity and business decisions. Ask what information your CPA needs, who owns each next step and which dates matter.

Your business and your life keep moving. Your planning should keep up.

Talk with Cachet

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This article provides general educational questions, not individualized tax, legal or investment advice. Applicable rules, eligibility and outcomes depend on the facts and the tax year.

Originally published December 9, 2025. Updated October 1, 2026 to correct geographic metadata, remove outdated retirement figures and clarify the limits of general tax guidance. No CPA review is claimed.