Tax planning checklist

originally published 7/2017, updated 9/3/2022.

Are you paying the lowest tax allowed under the law? Probably not, according to most tax specialists. Use this checklist to help develop some ideas for further exploration and discussion. (The checklist is typically used as part of the second step of three steps in the tax planning process).


_  Structure legal settlements as non-taxable

_  Structure insurance settlements as non-taxable

_  Straddle the tax year

_  Tax-free interest

_  Divorce & separation agreements

_  Recoup basis on retirement annuities

_  Maximize gift income


_  Defer taxes

_  Accelerate expenses

_  Defer income


_  Shift Schedule E expenses to Schedule C as allowed

_  Shift Schedule C income to Schedule E as allowed

Investment Income:

_  Shift investment income to children as allowed

_  Maximize tax-free income in life insurance policy

_  Interest-free Loans

_ Tax-free qualified small business stock sales

Retirement Plan:

_  employer sponsored plan

_  IRA

Miscellaneous Schedule A Deductions:

_  Interest

_  Medical expenses

_  Taxes

_  Contributions

_  Losses

_  Employee expenses


_  Deduct medical insurance

_  Deduct disability insurance

_  Deduct life insurance

_  Deduct long term care insurance

_  Health savings accounts

Tax-Free Benefits:

_  Hospitalization premiums

_  Group life insurance premiums

_  Group legal services premiums

_  Accident and health plans

_  Employee death benefits

_  Merchandise distributed to employees

_  Meals & lodging

_  Employee discounts

_  Workers compensation

_  Cafeteria benefit plans

_  Dependent care assistance plans

_  Employer educational assistance

_  Employee awards

_  Miscellaneous fringe benefits

_  Scholarships and fellowships

_  Gifts, bequests, inheritances

Traditional Tax Shelters:

_  Real estate

_  Real estate partnerships

_  Oil & gas

_  Equipment leasing

_  Single premium life insurance

_ Conservation easement

Innovative Shelters:

_  Family partnerships

_  Family trusts

_  Gift-leaseback

_  Employing family members

_  Voluntary Employee Benefit Associations


_  Earned income credit

_  Credit for health insurance to children

_  Adoption assistance

_  Targeted jobs credit

_  Credit for the elderly or disabled

_  Mortgage credit certificates

_  Child & dependent care credit

_ Small business research and development credit

Related resources

Top ten tax planning strategies

Financial planning data organizer

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