U.S. Self-Employment Income and Taxes

WHAT'S IN THIS ARTICLE
Overview Self Employment Income | Constructive Receipt Doctrine | EIN | Estimated Tax Payments | Business Entities | Standard Mileage Rates | Standard Mileage FAQ | Deemed Depreciation Rates | Meals & Entertainment

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Published November 2010  |  Revised December 19, 2024

As a small business owner in the U.S., it's wise to understand how self-employment income works. If you have self-employment income, it means you need to become familiar with IRS tax compliance requirements and rules ... to avoid getting into deep dodo.

As a sole proprietor, you also need to be aware that you must pay self-employment tax on your net earnings. This chat provides the basic information you need to get you started on the right foot.

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Self-Employment Series

As a small business owner in the U.S., it's critical to understand how self-employment income works. Here's a brief overview:

1. Definition: Self-employment income is the earnings you receive from a trade or business in which you actively participate. This includes income from sole proprietorships, partnerships, and some types of corporations where you're actively involved in the management.
2. Reporting: You'll report your self-employment income on Schedule C (Form 1040), where you'll list your income and deductible expenses to determine your net profit or loss. This net amount is what you'll use to calculate your self-employment taxes.
3. Self-Employment Tax: You're responsible for paying self-employment taxes, which cover Social Security and Medicare. The self-employment tax rate is currently 15.3% of your net earnings (12.4% for Social Security and 2.9% for Medicare).
4. Deductions: One key advantage of self-employment is the ability to deduct allowable business-related expenses. These can include office supplies, vehicle expenses, travel expenses, home office deductions, and more. These deductions reduce your taxable income and, consequently, your tax liability.
5. Estimated Taxes: Because you're self-employed, taxes aren't withheld from your self-employment income as they would be with a regular paycheck. Instead, you may need to make quarterly estimated tax payments to cover your federal income tax and self-employment tax.
6. Record Keeping: It's crucial to maintain good records of all your business transactions. This helps ensure you can support the self-employment income and deductions you report and makes tax filing easier. This is absolutely necessary if you want to pass any future income tax audits.
7. Retirement Plans: As a self-employed individual, you have access to certain retirement plans that can provide tax advantages, such as a SEP IRA, SIMPLE IRA, or Solo 401(k).
8. Health Insurance: You can deduct health insurance premiums as an adjustment to income, which can lower your overall tax bill.

Remember, tax laws can be complex, and it's always a good idea to consult with a tax professional who can provide advice tailored to your specific situation and ensure you're complying with all tax requirements. This chat is just to give you some talking points to discuss with your accountant about your self-employment income.

It is important for a small business owner to understand the concept of 'the tax law doctrine of constructive receipt', as it pertains to how self-employment income is reported and taxed if your business uses the cash-basis accounting method.

Tax Law Doctrine of Constructive Receipt (Treasury Regulation 1.451-2(a))

This is a tax principle used primarily in cash-basis accounting, which affects how income is recognized. Under this doctrine, income is considered received when it is credited to an individual's account, set apart, or otherwise made available to be drawn upon, even if it's not actually in hand. Essentially, it's about when you have control over the money.

The doctrine of constructive receipts is defined in the regulations but was conceived by the courts to test realization of income. It prevents a cash basis taxpayer from selecting the year in which income will be reported. Its purpose is to prevent tax avoidance.*

This concept is essential for cash-basis taxpayers to understand so as to prevent them from arbitrarily deferring income recognition (and thus taxes) to a future tax year. Constructive receipt of self-employment income ensures that income is recognized and taxed in the year it is made available, not necessarily when it is actually received or cashed.

Why It Matters:

1. Timing of Income: Understanding this doctrine helps you recognize when income should be declared. It affects the tax year in which income is reported, which can impact your tax planning and cash flow management.
2. Cash vs. Accrual Basis: Many small businesses use the cash basis of accounting, which aligns with the constructive receipt doctrine (but not GAAP). If income is made accessible to you, it's considered received.
   
   Here's an IRS example:  "If the postal service tries to deliver a check to you on the last day of the tax year but you are not at home to receive it, you must include the amount in your income for that tax year.  If the check was mailed so that it could not possibly reach you until after the end of the tax year, and you could not otherwise get the funds before the end of the year, you include the amount in your income for the next year." 
3. Tax Planning: Awareness of when income is constructively received allows you to plan effectively for tax obligations, potentially deferring income or accelerating expenses to optimize tax positions.
4. Avoiding Penalties: Misreporting income due to a misunderstanding of this concept can lead to penalties and interest. Properly understanding constructive receipt ensures compliance with tax regulations.
5. Revenue Recognition: Knowing when to recognize income under this doctrine ensures accurate financial reporting, which is vital for analyzing the business’s performance and attracting potential investors or lenders.

For these reasons, being familiar with the doctrine of constructive receipt is crucial for managing your business finances and tax responsibilities effectively. It’s often beneficial to consult with a CPA or tax professional to ensure a thorough understanding and proper application of this concept in your specific business context.

Audit Ready 

When accounting for self-employment income, it is important to understand the constructive receipt principle.

Under the doctrine of constructive receipts, cash basis taxpayers (as opposed to accrual basis taxpayers) are generally not permitted to receive/write postdated or predated cheques. This is because the most significant aspect of constructive receipt is related to actual control over the funds by the end of the tax year. If you have control over those funds before the year ends, they may be considered income in that year, regardless of the date on the check. Courts have generally emphasized access to funds over the notation of the date.

*Source: Barriers to the application of the constructive receipt doctrine by Knight, Lee, G, Knight, Ray A. published in Tax Executive on January 1, 1989

References: Legislative Commission on Pensions and Retirement - BackGround Information on Constructive Receipt Federal Income Taxation Problem;  IRS What is Taxable and Nontaxable Income?

As a small business owner, it's important to clarify the doctrine of constructive receipt and how it relates to accounting practices.

Constructive Receipt

The doctrine of constructive receipt is a tax principle used primarily in cash-basis accounting, which affects how income is recognized. Under this doctrine, income is taxable when it is credited to your account or made available to you without restriction, regardless of whether you physically receive the payment. Cash-basis accounting is not GAAP.

• Constructive Receipt and Checks: If you receive a check before the end of the tax year but choose not to cash it until the following year, it is generally considered to be income in the year it was received, due to constructive receipt. The same concept applies to postdated checks; if you have control over the funds, they are considered received.

GAAP Accounting

Generally Accepted Accounting Principles (GAAP) are used in accrual-basis accounting, which is different from cash-basis accounting.

• Accrual Accounting: Under GAAP, income is recognized when earned, regardless of when payment is received. Constructive receipt is not a concept used in GAAP; instead, GAAP focuses on when the obligation to perform (i.e., deliver goods or services) has been fulfilled.

Practical Considerations for Your Business

1. Cash Basis vs. Accrual Basis: Determine whether your small business is using cash-basis or accrual-basis accounting, as this will dictate how income is recognized.
2. Postdated Checks: While you might be able to delay accounting for income with postdated checks under specific circumstances, consult your tax advisor to understand any legal implications for your tax liabilities.
3. Consult a Professional: Because these accounting principles can have significant tax implications, especially regarding year-end tax planning, it’s prudent to work with a CPA who can provide guidance tailored to your specific circumstances.

Takeaway

• Constructive receipt doesn't pertain to GAAP but primarily concerns tax reporting and cash-basis accounting. Understanding these principles is essential for accurately managing your business finances and ensuring compliance with tax laws.
• For tax purposes, for businesses using  cash-basis accounting, a cheque is constructively received when it is delivered to the taxpayer ... not when it is cashed.

As a small business owner, it's important to understand the subtle distinctions of constructive receipt and the situations where it might not apply. Here are some restrictions or limitations on the doctrine of constructive receipt:

1. Substantial Limitations or Restrictions: Self-employment income is not constructively received if there are substantial limitations or restrictions on the taxpayer's control over the receipt of the income. This means that if there are conditions or requirements that need to be met before the taxpayer can actually access the funds, the income would not be considered constructively received until those conditions are satisfied.
2. No Physical Receipt: If the taxpayer does not have physical control over the funds or the ability to access them freely and without restrictions by the end of the tax year, the income is not deemed constructively received. For example, if the funds are in an account that is not accessible without a penalty or are held by a third party with a restriction on release, this can delay recognition of income.
3. Payment Contingencies or Unresolved Conditions: If there are unresolved contingencies on the payment, such as requirements for the completion of additional work or significant unresolved conditions that need to be satisfied before the taxpayer has the right to receive the income, then constructive receipt does not apply. This could include scenarios where a performance obligation must be completed, or approval from a third party is required before the funds can be accessed.

These limitations ensure that constructive receipt is applied fairly, recognizing income when it is genuinely available to the taxpayer and not merely when expected or owed. If you're experiencing  situations where this might be the case, discuss the issue with your CPA so s/he can provide tailored guidance based on your business's circumstances.

This is the method used to pay income taxes on income not subject to withholding taxes ... i.e. your self-employment income.

You need to pay estimated taxes four times if your expected tax is $1,000 or more in 2024 after subtracting withholdings and credits ... AND you expect your withholding and refundable credits to be less than the smaller of:

1. 90% of your taxes to be shown on your 2025 return ... OR
2. 100% of your taxes to be shown on your 2024 return which must cover 12 months.

You may be charged a penalty if you don't pay enough tax by each due date. If you like smoothing out your cash flow over the year, you can setup monthly payments on EFTPS instead of the four required payments.

It's important to note that while you file and pay quarterly, the four periods do not fall every three months. See the table below for how the tax periods are divided.

IRS Form 1040-ES is a worksheet that can help you calculate your estimated payment.

Tax Type	Tax Period	Form to be Filed	Filing AND Payment Deadline
1st Tax Installment (3 months)	Jan-Mar	1040-ES pay thru EFTPS	April 15
2nd Tax Installment (2 months)	Apr-May	1040-ES pay thru EFTPS	June 15
3rd Tax Installment (3 months)	Jun-Aug	1040-ES pay thru EFTPS	September 15
4th Tax Installment (4 months)	Sep-Dec	1040-ES pay thru EFTPS	January 15 next year*
Annual Est. Payment Farmers, Fishermen	Jan-Dec	1040-ES	January 15 next year

If the 15th falls on a Saturday or Sunday, the filing date and payment move to the Monday.

*You don't need to pay the January 15 estimated tax payment if you file your 2024 tax return with taxes due by January 31, 2025. However, if you do need to make a payment, best practice is review your estimated earnings and payments made to date. Adjust your fourth payment to ensure you aren't under paying or over paying your tax. IF you choose to write a cheque rather pay online through EFTPS ... although why you would choose this payment method is beyond me ... the cheque is made payable to United States Treasury.

See the IRS Estimated Taxes Guide for more small business information on estimated taxes located on their website by entering "Estimated Taxes" into the search box. The IRS website path is Home> File> Business and Self-employed> Small business and self-employed> Business taxes> Estimated Taxes.

There is also a good small business tax information article on Estimated Tax 101 at https://fairmark.com/general-taxation/estimated-tax/estimated-tax-101/. It walks you through the process and explains how to decide what is the best way for you to calculate your estimated taxes.

Source: Notice IR-2024-312, IR-2023-239, IR-2022-234, IR 2021-251, IR 2020-279, IR 2019-215
Normally released sometime in December each year; updated December 19, 2024

December 19, 2024 --- The 2025 standard mileage rates were increased by 3 cents to 70 cents per mile driven for business use. 2026 mileage rates are expected to be released in December, 2025.

June 9, 2022 --- In a rare event, the 2022 standard mileage rates were changed midyear to help alleviate the burden of rising costs. 2023 mileage rates are expected to be released in December, 2022.

Earning self-employment income often requires business travel. The IRS allows employees and self-employed individuals to use a standard mileage rate. Here are the mileage rates allowed by IRS.

Table below is cents / mile

Year	Business Miles Driven***	Moving / Relocation Purposes	Medical Purposes	Charitable Services
2025	70.0*	21.0**	21.0	14.0
2024	67.0*	21.0**	21.0	14.0
2023	65.5*	22.0**	22.0	14.0
2022 Jul-Dec	62.5*	22.0**	22.0	14.0
2022 Jan-Jun	58.5*	18.0**	18.0	14.0
2021	56.0*	16.0**	16.0	14.0
2020	57.5*	17.0**	17.0	14.0
2019	58.0*	20.0**	20.0	14.0
2018	54.5*	18.0**	18.0	14.0
2017	53.5	17.0	17.0	14.0
2016	54.0	19.0	19.0	14.0
2015	57.5	23.0	23.0	14.0
2014	56.0	23.5	23.5	14.0
2013	56.5	24.0	24.0	14.0
2012	55.5	23.0	23.0	14.0
2011 Jul-Dec	55.5	23.5	23.5	14.0
2011 Jan-Jun	51.0	19.0	19.0	14.0

Standard Mileage Rates Notes

*Suspension of Miscellaneous Itemized Deductions:
The Tax Cuts and Jobs Act (TCJA) suspended miscellaneous itemized deductions for the tax years 2018 through 2025. Exceptions to this suspension include:

• Members of a reserve component of the U.S. Armed Forces,
• State or local government officials compensated on a fee basis,
• Certain performing artists.

See Notice 2019-2 and Notice 2018-42 (modifies Notice 2018-03) for more information.

**Repeal of Moving Expense Deduction:
The TCJA also repealed the moving expense deduction for most individual taxpayers during the same period (2018-2025). The exception is for members of the U.S. Armed Forces on active duty moving pursuant to a military order.

See Notice 2019-2 and Notice 2018-42 (modifies Notice 2018-03) for more information.

*** 1. Mileage Log Requirement:
Maintaining a mileage log is necessary to substantiate the number of miles driven for business purposes. It's important to maintain accurate records of the business miles driven each year as well as keep track of how the standard mileage rate's deemed depreciation may affect your vehicle's basis.

*** 2. Restrictions on Business Standard Mileage Rate:
You cannot use the business standard mileage rate under the following circumstances:

• For vehicles used for hire,
• For more than four vehicles used simultaneously,
• If a Section 179 deduction has been taken for that vehicle,
• After using any depreciation method under MACRS for that vehicle.

The business standard mileage rate applies to cars, vans, pickups, and panel trucks.

*** 3. Additional Deductible Expenses:
While you cannot deduct actual vehicle operating costs with the standard mileage rate, you can deduct:

• Parking fees and tolls related to business,
• The business portion of interest on vehicle loans,
• The business portion of any local or state personal property tax on the vehicle.

Other Notes:

Actual Vehicle Expenses Method:
You always have the option of calculating the actual costs of using your vehicle rather than using the standard mileage rates. Tracking these expenses can be time-consuming, but it may lead to a larger deduction if your vehicle is expensive to operate.

This method allows you to deduct the actual costs of operating your vehicle for business purposes. It includes expenses such as gas, oil, repairs, tires, insurance, registration fees, licenses, and depreciation (or lease payments).

You can choose the method that provides the larger deduction but once you opt for the actual expenses method, you must stick to it for as long as you use that vehicle for business purposes. If you start with the mileage method, you can later switch to actual costs if deemed beneficial, given that the switch complies with certain IRS rules.

Standard Mileage Rate Information:
Historical mileage rates can typically be found on the IRS website. Key in 'standard mileage rates' into the IRS search box to locate it.

Additional Resources:
For more detailed information, IRS Publication 463, Travel, Entertainment, Gift, and Car Expenses, would be helpful.

Takeaway:
The standard mileage rates method is a simpler method (than the actual costs method) where you multiply the number of business miles driven by the IRS standard mileage rate to determine your deduction. It is typically more beneficial if your vehicle operating costs are low, as it simplifies the record-keeping and provides a straightforward calculation.

As a small business owner in the U.S., handling meals and entertainment expenses correctly is crucial for tax purposes. It is a frequently audited area, so it is important to know the rules. It is a bit complex, so here's a detailed breakdown:

General Rules

1. Ordinary and Necessary Expense (Sec. 162(a)): For a meal or entertainment expense to be deductible, it needs to be ordinary (common and accepted in your trade or business) and necessary (helpful and appropriate for your business). 
2. Business Purpose (Sec. 274(a) and Notice 87-23): There must be a clear business purpose for the expense, and it needs to be directly related to the active operations of your business.

Meals have strict deductibility requirements

1. Business Discussion: A deductible meal must involve either a business discussion during the meal or directly before or after it. Keep records of the nature of the discussion. (Sec. 274(a) and Notice 87-23)
   
2. 50% Deduction Limitation (Sec. 274(n)(1)): Generally, you can deduct 50% of the cost of business meals if the expense is ordinary, necessary, and was not lavish or extravagant (Sec. 274(k)).
3. Taxes and Tips Included in a Meal Receipt: When calculating the total cost of a meal for deduction purposes, you may include taxes and tips as part of the meal expense. These costs are part of the ordinary expense incurred during a business meal and are subject to the same deduction limitations as the meal itself (e.g., 50% unless an exception applies).
4. Parking: Amounts paid for parking at a restaurant are subject to the 50% limit.
5. Substantiation Requirement (Sec. 274(d)): Substantiation means you must provide adequate evidence to support the deduction of meal expenses. This substantiation requirement ensures that each meal expense is legitimate and connected to business activities, allowing it to qualify as a deductible expense under the tax code. It involves detailed record-keeping. Typically, you need to keep receipts, and the documentation should include:
      (i) Amount: The cost of the meal;
      (ii) Time and Date: When the meal took place;
      (iii) Location: Where the meal was consumed;
      (iv) Business Purpose: A brief explanation of the business reason for the meal, such as the topics discussed or the nature of the meeting; and
      (v) Attendees: The names of the individuals who attended the meal and their relationship to the business.
   
6. Taxpayer’s Presence Requirement (Sec. 274(k)): For a meal expense to be deductible, the taxpayer or a representative of the taxpayer (such as an employee or an authorized agent) must be present at the meal.
   
   This requirement was put in place to ensure that the meal actually has a business purpose. The presence of the taxpayer or their representative indicates active involvement in the meal as part of conducting business, not just providing a meal for an unrelated party.
   
   Keeping thorough records and staying organized are key aspects of meeting the substantiation and presence requirements.
   
7. Exceptions 100% Deductibility: Certain meal expenses are exempt from the 50% disallowance and can be 100% deductible such as meals provided for the convenience of the employer or those related to recreational or social activities primarily for ordinary employees. See 'Disallowance Rules' below for further details.
8. 100% Deduction (Temporary COVID-19 Relief): Under the 2021 Consolidated Appropriations Act passed for COVID-19 relief, there is a temporary allowance for a 100% deduction on business meals provided by a restaurant for expenses paid or incurred in 2021 and 2022. This was a temporary measure.
9. Restaurants Only: To take advantage of the 100% deduction (if applicable), meals must be from a restaurant, defined as businesses that prepare and sell food/drinks to retail customers for immediate consumption.

Entertainment is generally are fully nondeductible

1. Definition: For tax purposes, "entertainment" generally refers to any activity or an item that provides amusement or recreational enjoyment. Historically, the IRS definition included a wide range of activities. However, recent tax reforms have further clarified what qualifies or doesn't qualify as deductible entertainment expenses.
   
   Entertainment Definition Pre-Tax 2017 Cuts and Jobs Act
   In the past, the definition covered:
      (i) Activities such as nightclubs, cocktail lounges, theaters, country clubs, golf and athletic clubs, sporting events, and similar venues.
      (ii) It also included the costs related to the provision of entertainment such as tickets, greens fees, transportation, lodging (if necessary), and any other costs attributable to entertainment.
   
   Changes Post-Tax Cuts and Jobs Act (2017)
   Under the Tax Cuts and Jobs Act (TCJA) of 2017, the deduction for entertainment, amusement, or recreation expenses has generally been eliminated. This means that most expenses that would fit into the "entertainment" category can no longer be deducted from your business taxes. However, there is an allowance for meals, as meal expenses that are directly related to the taxpayer’s business activities can still be 50% deductible under certain circumstances.
   
   Key Entertainment Considerations
   Exception for Meals: The cost of meals associated with entertaining clients or stakeholders may still be deductible at 50%, as long as business is conducted during the meal and proper documentation is provided.
   Entertainment Facilities: Expenditures related to owning or operating facilities for entertainment purposes are not deductible.
   
   Takeaway
   Prior to 2017, 'entertainment' was a broad category. The Tax Cuts and Jobs Act narrowed the scope considerably for deductible expenses, primarily removing the deduction for most entertainment activities. Always keep detailed and organized records.
2. Non-Deductible: Under the Tax Cuts and Jobs Act of 2017, entertainment expenses are generally non-deductible. This includes activities considered amusement, entertainment, or recreation.
3. Exceptions: Certain expenses incurred for the benefit of ordinary employees (like holiday parties) might be fully deductible, but these are specific and should be verified they are allowable deductions. (Regs. Sec. 1.274-12(c)(2) (iii)). The Tax Advisor explains that "Free food and beverages provided in a break room available to all employees do not qualify and will be subject to the 50% disallowance rule (Regs. Sec. 1.274-12(c)(2)(iii)(B)(3))."
4. Business Meals During Entertainment: If you provide meals during an entertainment event, only the meals can be deductible—subject to the 50% limit—and not the entertainment portion. These should be separately listed or invoiced to ensure clarity.
5. Non-Deductible Expenses:
   (i) Lavish or Extravagant: Meals or entertainment considered lavish or extravagant are non-deductible.
   (ii) Club Memberships: Dues for social, athletic, or sporting clubs are non-deductible.

Disallowance Rules

1. Documentation: Maintain proper documentation, including receipts, the amount spent, date, location, business purpose, and those in attendance for all meals and entertainment expenses. The IRS requires adequate records to substantiate deductions.
2. Substantiation: Ensure you provide substantive evidence if audited. This includes invoices, receipts, and a record of the business purpose.
3. 50% Deduction Limitation (Sec. 274(n)(1)): Only 50% of otherwise allowable meal expenses are deductible as business expenses.
4. Transportation costs: The cost of traveling to and from the meal are not subject to the 50% disallowance rules unless the business owner uses the per diem method for travel expenses.

Disallowance Rules Exceptions

1. Certain Meal Expenses: Certain meal expenses are exempt from the 50% disallowance and are 100% deductible. These exceptions typically include:
      (i) Meals provided on the business premises to employees for the employer's convenience may qualify for full deductibility.
      (ii) Meals associated with substantial business meetings including company-wide trainings, or conferences at which business matters are discussed may qualify.
      (iii) Certain minimal (minor) fringe benefits, such as snacks provided in a break room, are fully deductible. This is referred to as 'De Minimis Fringe Benefits' (Sec. 132(e)).
      (iv) If a business fully reimburses an employee for meal expenses incurred on its behalf, and the business treats the amount as reimbursed under an accountable plan, the business may be able to fully deduct these meals.
      (v) Meals associated with a qualifying charitable sporting event may also be fully deductible.
      (vi) Meals made on the business premises of the Taxpayer that are provided to employees on-site, like cafeteria meals for staff used to facilitate meetings or gatherings pertinent to work matters. (Sec. 132(e)(2))
2. Non-Employee Compensation: Non-employee prizes and awards are generally treated as compensation to the recipient and should be reported on Form 1099-NEC if they exceed $600. They might be considered 100% deductible for the business as promotional expenses or prizes if directly connected to a business activity, but it's crucial to ensure proper reporting and classification.
3. Client Related Expenses: Expenses that are billed to clients can potentially be 100% deductible to the extent that they are ordinary and necessary business expenses. If meals or entertainment expenses are billed, it's important to keep detailed records to substantiate the business purpose and client association. When billing clients, ensure these items are properly documented and align with the client's contractual agreements. The client is then subject to the 50% disallowance rule.
4. Advertising and Promotion: Expenses incurred for advertising or promoting your business, including promotional meals or entertainment directly related to your business activities, can often be 100% deductible. However, meals and entertainment need to comply with related deductible rules, especially considering expenses intended for client goodwill must adhere to IRS requirements to qualify for deduction. For example, the promotion must be for the general public and not by 'invitation only' gathering.

Additional Considerations

1. State Tax Treatment: Some states may handle the deduction of meals and entertainment expenses differently than the federal rules, so check your state's specific tax regulations.
2. Review Changes Annually: Tax laws can change; stay informed each year, either directly or through a tax professional like a CPA, is prudent.

If you're unsure of how to apply these rules to your situation, consulting with a CPA, who understands the specifics of your business, can provide tailored guidance. A good guide to read is The Tax Advisor's November 1, 2023 Case Study by Patrick L. Young titled, 'Navigating around limits on meals and entertainment'. He includes examples such as a business meal with a client, a business meal with an employee, costs subject to the 50% disallowance, disallowance of meal expenses incurred while traveling as well as food and beverages at an entertainment event.

No one said earning self-employment income would be easy. This is a frequently audited area so know the rules.

If you made it this far, I think you've earned a nice, hot cup of tea. :o) 

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