Fall is one of the busiest seasons in the transportation industry. From hauling grain during harvest to keeping shelves stocked for the holiday rush, seasonal work opportunities are everywhere. For many drivers, these short-term gigs are a great way to earn extra income, test out new routes, or even get a foot in the door with a new carrier.

But before you hit the road for that temporary assignment, it’s important to understand how seasonal driving jobs can impact your taxes. Short-term work might last only a few weeks, but it can have long-term effects on your tax return.

W-2 vs. 1099: How Your Work Is Reported

Not all seasonal jobs are the same when it comes to taxes.

  • W-2 Employee Jobs: If the company hires you as an employee, they’ll typically withhold federal and state taxes from your paycheck. This means your tax bill may already be partly covered by the time you file.
  • 1099 Independent Contractor Jobs: Many short-term gigs treat drivers as independent contractors. In this case, you’ll receive a Form 1099 at the end of the year, and no taxes are withheld. That means you’re responsible for covering income and self-employment taxes on your own.

Knowing which category you fall into is the first step to planning ahead.

Why Self-Employment Taxes Can Sneak Up on You

If you’re paid on a 1099, you’re not just responsible for regular income taxes—you also owe self-employment taxes, which cover Social Security and Medicare contributions. These can add up quickly if you’re not prepared.

A smart move is to set aside a percentage of each paycheck (often 25–30%) to cover your eventual tax bill. That way, seasonal work doesn’t turn into an April surprise.

Don’t Forget About Estimated Taxes

If your seasonal earnings push your income higher than expected, you may need to adjust your quarterly estimated tax payments. Missing or underpaying these can result in penalties. Even if the work only lasts a few months, the IRS still expects you to pay as you go.

Deductions Still Apply (Even for Short-Term Work)

Just because the work is seasonal doesn’t mean you lose out on valuable deductions. If you’re self-employed (an independent contractor), you may be able to deduct ordinary and necessary business expenses, as long as they are directly related to the work you do and you keep accurate records.

Strategic Benefits of Seasonal Work

Seasonal jobs don’t just provide extra income—they can also help you plan smarter financially. For example:

  • Use seasonal earnings to catch up on quarterly estimated taxes.
  • Put extra income toward retirement contributions or HSAs, which also lower your taxable income.
  • Try out independent contracting without committing full-time, giving you insight into how taxes work as a 1099 driver.

With a little planning, seasonal work can help you build long-term financial stability.

Seasonal driving jobs can be a great opportunity to earn more during busy times of the year. But even short-term work comes with tax responsibilities that shouldn’t be overlooked. Understanding how your income is reported, planning for self-employment taxes, and tracking deductions will help ensure those extra paychecks stay profitable.

At Abacus!, we specialize in helping transportation professionals navigate taxes year-round. Whether you’re driving full-time or just picking up seasonal work, we’ll help you make smarter decisions so you can keep more of what you earn.