David Morris

By: David Morris on November 29th, 2023

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Key Considerations for Freight Agents During Tax Season [2023 Update]

Industry News | Agency Ownership | Business Advice | Logistics | Transportation | Best Practices | Freight Management | Freight Broker

Most of us attempt to file taxes accurately to stay in Uncle Sam's good graces. In the world of freight brokerages and freight agents, small business reigns and contracted workers are common. This presents its own set of tax-related challenges, which is why many in the industry enlist the help of a certified public accountant.

uncle-sam-taxesWhile this post is not designed to provide specific tax advice, it does cover common tax scenarios that freight agency owners and independent contractors experience during a fiscal year. Whether you are just starting, transitioning to a new opportunity, or have been in the business for decades, use this information to help alleviate your tax burdens.   

Getting Started: Create a System

According to the IRS, the average taxpayer spends 13 hours every year on their taxes. Some organizations put the number higher (up to 54 hours per taxpayer). Either way, the average American worker and small business owner commit a lot of time to paperwork and tax filing preparations. That's incentive enough to ensure you have a reliable system to help you streamline those tasks. 

Paying taxes is like studying for an exam. By planning and staying organized throughout the year, you'll save yourself hours of scrambling to find receipts and documents in the lead-up to your tax payment deadline. 

Engaging a tax advisor well before you owe taxes will help you understand which receipts and documents to track and file throughout the year. Creating a filing system or purchasing (and using) tax software will help cut down on hours of work leading up to tax deadlines. And yes, we mean deadlines (plural)—more on quarterly tax payments later.  

Your Employment Classification: 1099 or W-2

If you're referred to as a 1099 or W-2, you haven't become a Star Wars droid. Those classifications refer to the tax forms different workers must complete for payroll deductions. Here's a quick snapshot:


Unless you own a freight brokerage, you are likely an independent agency owner or a subcontractor. In either case, the IRS considers you self-employed. This type of worker reports income using the IRS Form 1099-NEC.

As an independent consultant, you must also complete an IRS Form W-9, which collects your contact information and taxpayer ID or Social Security number. Your signature indicates that you are aware of the tax status you hold with your company. 

Considerations for Small Business Owners 

Independent contractors can also be small business owners. You get the option to create a business structure that influences your day-to-day operations, taxes, and how much of your assets are at risk. Business structures are designed to give you the right balance of legal protections and tax benefits. 

You may have heard of the varying types of business structures, including – but not limited to – sole proprietorship, limited liability corporation (LLC), S-Corp, and C-Corp. Choices can be mind-boggling.

Connect with your tax consultant or attorney to help you decide the best structure for your business. Our agent recruiting team is also available to answer any general questions you might have about becoming a new agent. 

Bookkeeping and Tax Deductions

Taxes are paid on income earned. You can reduce the amount of income taxes you owe by claiming deductions (or "write-offs") available to you or your small business.


Essentially, deductions lower your tax bill. But they need to fit the IRS criteria for a tax deduction. Sometimes, those expenses are directly related to running a business, while others are more personal deductions. This list from Bench.co outlines the most common deductions available to small businesses. Still, Armstrong recommends consulting with your tax advisor or CPA before claiming a deduction on your tax return. 

Be prepared to keep meticulous records! More on audits below. 

Writing Off Startup Costs

You may have heard that initial startup expenses related to small businesses can be tax-deductible. Yes, but the IRS only allows you to deduct up to $5,000 in business startup costs and up to $5,000 in organizational costs if your total startup costs are $50,000 or less. One of the benefits of freight agency ownership is the low overall startup costs – all you need is a home office, a computer, a phone, and an internet connection, and you are ready to begin. So, be sure to check with a tax professional before deducting any initial startup expenses. 

Paying Taxes on Commissions

Independent freight agents typically earn all of their income on commissions – payments you receive in exchange for accomplishing a specific goal, making a sale, or completing a transaction. At Armstrong, our agent owners earn up to 75% commissions in addition to a new agent bonus. You will need to report your commissions annually. A reputable tax advisor can show you where and how to document your commissions. 

Paying Taxes Quarterly

It's easy to focus on April 15th as "Tax Day." Unfortunately, it's a common misconception that the IRS accepts lump-sum payments at year-end. If you are an independent contractor or self-employed worker, you must file quarterly taxes. Unlike W-2 workers whose employers withhold income taxes, there is no automatic withholding method for independent contractors' income. Figuring out your quarterly tax payments can be challenging, but it's essential. If you avoid them, you'll be hit with a considerable fee come tax time. This TurboTax post reviews truths, myths, and scheduling guidelines associated with quarterly tax payments. Check with a tax professional to ensure you understand your quarterly payment schedule and the estimated amount owed. 

Failure to Pay

What happens if you fail to file your taxes by a scheduled deadline? Or if you incorrectly allocate tax funds elsewhere? Don't assume that you can wait for the next deadline to approach. Your outstanding tax bill will not go away, be forgotten, or be forgiven. Instead, find counsel from someone qualified to discuss your tax options. The IRS provides information on their website under the "Need More Time to Pay?" section.  


Avoiding Common Audit Pitfalls

Going through an audit requires a lot of extra time and effort, which can be costly to any business. To avoid some of the most common audit pitfalls, be mindful of: 

  • Estimations for expenses or mileage. Keeping track of every mile driven and drop of gas purchased can be a nuisance. But large round numbers – like 30,000 miles driven, of which 50% were business-related – are red flags to the IRS and a quick way to get yourself audited. Instead, get in the habit of routinely tracking your expenses. 
  • "Miscellaneous" deductions. You may come across an expense that doesn't fit into any other category, in which case you can classify it as "miscellaneous." However, use this designation sparingly. Try to avoid routinely recording large transactions in the miscellaneous category. 
  • Home office deductions. Whether you are new to working from home or have used a home office for years, there are strict rules about who is eligible to claim a deduction. You might also be surprised to find out how much of your home office space you can claim. This IRS link will help you navigate the rules around home office deductions. 

Want to Learn More? 

There are so many benefits to being an independent agent owner. You can make your hours, work at your own pace, and take control of the commissions you earn. Of course, there are responsibilities, too, and taxes are one of them. 

The easiest way to navigate your tax responsibilities is to ask for help. Working with a CPA or other certified tax professional can help you ensure you've got every base covered. 

Partnering with Armstrong gives independent agent owners access to unparalleled back-office support, allowing you to stay organized and focus on what you do best – running your business. If you're interested in an opportunity with Armstrong, connect with us today, and one of our agent recruiters will be in touch!


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About David Morris

Operating as Armstrong’s Chief Financial Officer, David is responsible for Armstrong’s finance activities and oversees multiple finance, accounting, and legal departments. He is an accounting, finance, and financial reporting expert, specializing in financial analysis, auditing, and internal controls.