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Solopreneur's 1099 Checklist: Hiring Independent Contractors Simplified

Solopreneur's 1099 Checklist: Hiring Independent Contractors Simplified

Mastering 1099 Forms: Empower Your Solopreneur Journey. Learn what a 1099 form is, why it matters, and how to confidently navigate tax preparation for independent contractors. Unlock the potential of your business with newfound confidence.


As a solopreneur looking to bring on extra help in the form of an independent contractor who wants to make sure you're on top of tax preparation, this article will equip you with the knowledge you need to navigate 1099 forms—from what it is, to how to file it—with confidence. 

If you're like most solopreneurs and small business owners, you've heard of this infamous "1099 form," but you've got some questions, like:

  • What exactly is a 1099 form and how do I fill one out?
  • I'm hiring a new freelancer... do I need a 1099?
  • How do you classify contractors vs. employees?
  • What does it take to be considered an independent contractor by the IRS?

... To name just a few. 

We hear you. And we're here to help. In this article, we'll take a deep dive into everything you need to know about 1099 forms so you're ready to hire an independent contractor with confidence. By the end, you'll know what a 1099 form is, whether or not you need one, and if so—how to fill one out. Let's go!

Please note: What you'll find below is meant to provide general guidance, and we've done our best to cover this topic in detail. However, this is a complex topic, and the information provided here should not be assumed to replace seeking advice from a qualified legal expert. 

First things first: What is a 1099 tax form?

When hiring an independent contractor, you'll need to be well-versed in the 1099-NEC (Nonemployee Compensation). This form is used to report payments of $600 or more made to contractors for their services. Providing this form serves as an important communication to both the contractor and the IRS, documenting the income earned. Depending on your location, you might also need to use a 1099-MISC form for state tax purposes.

Suggested reading: 1099-MISC vs. 1099-NEC: Which One Do You Need?

How do you know if you need to fill out a 1099-NEC form?

If you're a business owner paying a freelancer/independent contractor for their services in exchange for payment in an amount that exceeds $600 during a calendar year, you'll need to fill out a 1099-NEC form. 

Now, while that seems pretty straightforward, the distinction between "employee" and "independent contractor" isn't always cut and dry. So, before we dive further into the intricacies of filling out a 1099 form as a freelancer (or a small business owner hiring one), let's talk about the importance of classification. 

W2 employees vs. 1099 contractors: What's the difference and why does it matter?

As a solopreneur or freelancer, it's essential to grasp the practical distinctions between two fundamental categories of workers: W2 employees and 1099 contractors. These classifications, while seemingly subtle, hold significant implications that extend far beyond mere labels.

W2 Employees: W2 employees are individuals who work in a traditional employer-employee relationship. They are typically subject to greater control and direction from the employer, shaping the nature of their tasks and work hours. Employers provide W2 employees with tools, training, and resources to fulfill their roles effectively. Additionally, employers deduct income taxes, Social Security, and Medicare from their wages, reflecting a sense of structured employment.

1099 Contractors (self-employed): In contrast, 1099 contractors, also known as independent contractors or freelancers, function as self-employed entities. They maintain greater autonomy over their work, setting their own schedules and determining the methods by which they fulfill their responsibilities. Unlike W2 employees, contractors often use their own tools and resources to complete projects. They are responsible for paying their own income taxes, Social Security, and Medicare contributions—a pivotal aspect of their independent status.

Let's look at an example:

Imagine you're a health coach looking to hire someone to help create graphics for your social media content. If you bring on a W2 employee, you would likely set specific work hours, provide training materials and benefits (like health insurance coverage options, paid time off, etc.), and deduct taxes from their wages.

On the other hand, if you decide to collaborate with a 1099 independent contractor, they would have the flexibility to work on their terms, utilizing their tools, and handling their tax obligations. Similarly, independent contractors usually do not receive benefits like health insurance coverage or paid time off—unless specifically negotiated as part of their independent contractor agreement. 

How the IRS determines W-2 employee vs. 1099 independent contractor classification: The 20-Factor Test

The IRS 20-Factor Test is a tool developed by the Internal Revenue Service to gauge the extent of control exerted by a business over a worker. This control is a pivotal factor in distinguishing between an employee and an independent contractor. By dissecting various facets of the working arrangement, the 20-Factor Test brings clarity to the classification decision.

Key factors for consideration

Within the 20-Factor Test, several key factors play a crucial role in shaping the classification determination. As you navigate this assessment, keep these essential elements in mind:

  1. Behavioral Control: How much guidance and direction does the business provide for the worker's tasks? Does the worker have the freedom to choose their methods?

  2. Financial Control: Who supplies the tools and resources necessary for the work? Does the worker hold a substantial financial stake in the arrangement?

  3. Type of Relationship: Is the worker engaged in a project-based or long-term relationship? Are there contracts or benefits involved?

For more on the IRS 20-Factor Test, see this: Independent Contractor (Self-Employed) or Employee (IRS)

The importance of the W2 vs. 1099 distinction

The Internal Revenue Service (IRS) relies on this classification to determine tax requirements for both employers and workers. Proper classification ensures that the appropriate taxes are withheld and reported, safeguarding the financial framework of businesses and individuals alike. Misclassification can lead to substantial penalties and legal consequences, making a clear understanding of these categories crucial.

Understanding this importance is not just a matter of compliance; it's a safeguard against a cascade of potential pitfalls. 

Correct classification protects your business: The classification of workers determines the rights and responsibilities that govern your working relationships. A clear distinction ensures that your business operates within the bounds of the law, upholding the integrity of your enterprise. 

Correct classification helps avoid financial repercussions: Misclassifying workers can lead to legal and financial consequences, creating an avalanche of challenges that threaten the very core of your business. Employing a 1099 contractor as a W2 employee, or vice versa, can trigger a cascade of penalties, including back taxes, fines, and even lawsuits. Such missteps can unravel the financial stability you've worked tirelessly to build, casting shadows over your aspirations of growth.

Correct classification keeps you in right standing with the IRS: Misclassification exposes you to the risk of owing back taxes for Social Security, Medicare, unemployment insurance, and income tax withholdings. Additionally, penalties for non-compliance can be severe, potentially amounting to a percentage of your worker's wages. These financial burdens can erode your resources and impede your business's ability to flourish.

Correct classification helps avoid lawsuits and damages: The repercussions of misclassification extend beyond finances. Workers who are misclassified may be denied crucial benefits such as health insurance, retirement plans, and overtime pay. This can lead to legal disputes, with workers seeking recompense for their rights being denied. Such lawsuits can result in significant damages, sapping your energy, time, and financial stability.

1099 Checklist for small business owners 

You've decided to bring on extra help to grow your business, and you've found an amazing independent contractor who meets your needs? Amazing! As the payer, your role includes accurate reporting of payments and providing the necessary forms to both the IRS and the contractor.

Follow these steps to navigate the process of filling out and filing your 1099-NEC forms with ease:

Step 1: Gather the following information about the independent contractor you are hiring. 

  1. Contractor's full name and address: Ensure you have accurate details for your contractor, as any discrepancies can lead to hiccups in tax reporting.

  2. Taxpayer Identification Number (TIN): This could be the contractor's Social Security Number (SSN) or Employer Identification Number (EIN). Confirm the correct TIN to avoid errors.

  3. Your business information: Provide your business's legal name, address, and TIN to accurately identify the payer.

  4. Payment details: Sum up the total amount paid to the contractor during the tax year. This includes both compensation and any applicable reimbursements.

Step 2: Fill out the 1099 independent contractor form 

  1. Obtain the form: Acquire Form 1099-NEC (Nonemployee Compensation) from the IRS or an authorized distributor. Important: There are two copies of Form 1099: Copy A and Copy B.
    Copy A is submitted to the IRS and used to report what you paid an independent contractor in a calendar year. On Copy B, you report the same information—but you send it to the contractor who completed the work.

  2. Complete payer information: Fill in your business's details in the designated fields. Accurate information is vital for proper tax reporting.

  3. Recipient's information: Enter the contractor's name, address, and Tax Identification Number (TIN). Double-check for accuracy to prevent any issues.

  4. Box 1: Nonemployee compensation: This is where you'll report the total amount paid to the contractor. Be meticulous in your calculations.

  5. Other boxes: Depending on the nature of your contractor relationship, you might need to fill out additional boxes, such as those related to state tax withholding.

  6. Review and validate: Carefully review the completed form to ensure all information is accurate and consistent. Errors can lead to delays in processing.

  7. Accounting for expenses: If you've agreed to reimburse the contractor for specific expenses, ensure these are accurately recorded in the appropriate sections.

  8. Send Copy B of Form 1099-NEC to the contractor who completed the work by January 31.

  9. Send Copy A of Form 1099-NEC to the IRS according to the following dates:
  • January 31: Provide Form 1099-NEC Copy B to contractors. This is also the deadline for filing Form 1099-NEC Copy A with the IRS if you're submitting paper forms.

  • February 28: If you're filing paper forms, this is the deadline for submitting Form 1099-NEC Copy A to the IRS.

  • March 31: This is the deadline for electronically filing Form 1099-NEC Copy A with the IRS. 


As a solopreneur, diving into the world of hiring independent contractors with 1099 forms might seem complex, but this guide has your back. You've learned what a 1099 form is, why it matters, and how to fill it out. Understanding the difference between employees and contractors, and the IRS 20-Factor Test, empowers you to make smart choices.

Remember, accurate paperwork and record-keeping are your allies. By mastering these steps, you're ready to confidently expand your team and achieve your business goals. So, go ahead—embrace the 1099 journey and unlock the potential of your business with newfound confidence.

And as your business grows, we're here to help. Practice's customer relationship management (CRM) platform is designed to assist business owners with storing client data and documents securely. You’ll also gain access to other tools, including document templates, a booking platform, and secure and easy payments—all of which can take some work off your plate and free you up to run your business like a boss. Start your free 7-day trial now.


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