Independent Contractor or Employee? A Wise Choice Will Pay Dividends

Brian J. Massimino • June 30, 2021
A man in a suit and white shirt is walking down a sidewalk.


For many early-stage businesses, it makes sense to utilize independent contractors rather than full-time employees. While it may seem simple to distinguish an independent contractor from an employee, the line is not as clear as it seems. Proactive businesses are aware of the distinction and take steps to maintain that distinction.


Courts and various governmental agencies (federal, state, and local) that regulate and determine worker status tend to construe independent contractor status narrowly. If they determine you have misclassified a worker, your business may be liable for back wages, overtime pay, employee benefits, disability, worker’s compensation, tax and insurance obligations, and possibly civil monetary penalties.


This question is even more prevalent with the rise of the gig economy, which has grown rapidly during the COVID-19 pandemic allowing technology to help serve those who were able to work from home. The gig economy includes independent contractors who do freelancing, temporary jobs, and project-based jobs.

 

Courts and agencies consider different factors when determining a worker’s status, but there is not a bright-line rule. Generally, each test examines the employer’s level of control over the worker. Since this is the case, certain factors are regularly used to distinguish independent contractors from employees. There are three simple questions to ask to differentiate between the two:



  1. What is the precise role of this person going to be? Are they professional staff or support staff?
  2. Where and how are they working? Are they coming into an office, or do they work somewhere of their own choosing?
  3. How are you paying them? By the hour, by project, by availability, some other way?


You can better determine whether a worker is an independent contractor or an employee based on the following characteristics. When viewed this way, the distinction can be clearer:


Independent Contractors:

  • Often not vested with institutional knowledge and history
  • Contract to be paid for a specific project
  • Have discretion over where, how, and when they work
  • Are responsible for their own tax obligations


Employees:

  • Rely on institutional knowledge and history to perform job functions
  • Are paid set wages and employed continuously
  • Are directed by their employer as to where, how, and when they work
  • Have their employer meet their tax obligations


It should also be noted that workers who perform a key, or controlling, function for your business, such as C-suite executive functions, should be classified as employees and not independent contractors.


Lavelle Law can review your employment relationships to help determine if your workers are independent contractors or employees. We can also assist with negotiating and documenting agreements between your business and independent contractors.


If you would like more information on this subject, or other matters relating to Entrepreneurial Law, contact attorney Brian Massimino at Lavelle Law at 312-332-7555 or via email at bmassimino@lavellelaw.com.

More News & Resources

Lavelle Law News and Events

IRS Issues Guidance on Trump Accounts Established Under the Working Families Tax Cuts
By Timothy M. Hughes December 10, 2025
The Department of the Treasury and the Internal Revenue Service recently issued a notice announcing upcoming regulations and providing guidance regarding Trump Accounts, which are a new type of individual retirement account (IRA) for eligible children.
Consider this two-part test when finding the right attorney or law firm.
By Kerry M. Lavelle December 9, 2025
How do you choose the right attorney or law firm for your needs? Attorney Kerry Lavelle has refined his answer to this common question into a clear, two-part test - one that helps individuals and businesses identify legal representation that is both highly competent and truly client-focused.
IL Condominium Law: Updates, HOA Strategies, & Financing Insights - a presentation recording
November 24, 2025
Daday and Kish discussed the essentials of Illinois condominium and common interest community association law. The presentation highlighted recent legal updates impacting HOA operations and addressed key issues in collections and safeguarding the financial interests of the association.
Understanding Grandparent Visitation Rights in Illinois
By Elizabeth C. Thompson November 19, 2025
While Illinois law recognizes that grandparents can play a vital role in a child’s life, it also strongly defers to the rights of parents. A grandparent seeking visitation must overcome a high legal threshold and demonstrate that denial of contact would likely harm the child’s well-being.
Behind the Scenes of Our 2025 Food Drive Delivery Day!
By Lavelle Law Charities November 17, 2025
The 2025 Lavelle Law Charities Food Drive wrapped up excitingly on October 24, 2025! After weeks of heartfelt community giving, Lavelle Law team members personally delivered an enormous haul to the Schaumburg Township Food Pantry.
Impact of Partial Government Shutdown on IRS – Day 41
By Timothy M. Hughes November 10, 2025
Impact of Partial Government Shutdown on IRS – Day 41: Due to the current lapse in appropriations, IRS operations are limited. However, the underlying tax law remains in effect, and all taxpayers must continue to meet their tax obligations as normal.
$65 Million Sale of Business - Lavelle Law Success Story
By Business Law October 29, 2025
$65 Million Sale of Business – a Lavelle Law Success Story. We were able to effectively negotiate the terms of a complex sale in a manner that enabled both buyer and seller to achieve their objectives.
Free Event. Learn the nuts and bolts of Illinois condominium law.
By Stephen G. Daday and Robyn K. Kish October 27, 2025
Explore the nuts and bolts of condominium law and gain actionable strategies to navigate today’s condominium and HOA challenges in Illinois.
New law provides expanded protection for Illinois residents, increasing key debtor exemptions.
By Timothy M. Hughes October 15, 2025
The Illinois General Assembly enacted Public Act 1738, amending several provisions of the Illinois Code of Civil Procedure to raise debtor exemption limits effective 1.1.26. The new law provides expanded protection for residents, marking the most significant increase to the state’s exemption statutes in over a decade.
Be proactive and put your home in a trust to avoid the time, hassle, and expense of probate court.
By Heather A. McCollum October 13, 2025
A crucial estate planning tool that many people in Illinois overlook is putting their home in a trust. Placing your house in a revocable trust offers multiple benefits. It avoids probate, which can save your family time and money after your death.
More Posts