Trucker CFO

Tax Season is Coming...

By Colton Lawrence - The Trucker CFO
Posted Nov 25th 2022 8:00AM

Are You Ready? Do You Have Questions?

Now that Thanksgiving is in our side-view mirrors, the countdown to the end of the year and the next seasons on the calendar are getting closer. When looking at our Trucker CFO day planner, the holiday season is always followed by tax season. As you might imagine, we work throughout the year to be prepared for tax season and the questions we most often hear heading into this point on the calendar.

For the latest episode of the Trucker CFO Podcast, I reached out to our Trucker CFO Team to have them list the most common questions that come up at this time of year through the emails we receive, calls to our office and chat sessions on our website. Through this edition of the Trucker CFO Podcast, we address 10 of the most frequently asked questions we receive as we enter tax season.

I would like to invite you to listen as we have an in-depth discussion on the following 10 questions:

  1. Is this deductible?
  2. I was talking to my friend who is also a trucker, and his accountant lets him write off everything… Why don’t you?
  3. I always get a refund. Why is that I owe so much?
  4. Do I have to pay estimated taxes?
  5. Do I pay taxes from my business or personal account?
  6. When should I incorporate?
  7. When should I make an S-Corp election?
  8. Can I change/transfer my LLC from one state to another?
  9. I want, or need, W2 income from my LLC, my Sole Proprietorship or my Partnership. Can I do that?
  10. How do I structure my income to avoid levies, garnishments, and child support payments?

As we note in the podcast, every person’s tax situation is unique to that individual. There are some points within these questions that are clear cut. As you’ll hear, with the question of what is deductible as an example, it depends on a number of factors.

When it comes to your business operation and making tax deductions, it must meet the criteria of being ordinary and being necessary. Expenses that are ordinary and necessary for one business owner may not be the same as they are for another business owner. There can be gray areas when it comes to what would be allowed as a deduction for your business, and we cite some examples within the podcast.

Of course, what we shared here within the blog on deductions is a small portion of what we explored as we worked our way through this list. Our goal in sharing this podcast with you is to highlight how we approach answering your questions. We want to help you in your preparation efforts as tax season approaches.

Maybe you have asked some of the same questions on our list. Maybe you are having to consider these questions for the first time. In either case, now is a good time to be thinking about and asking the questions we have shared here. One of the best ways to prepare for the upcoming tax season is to have good information in hand.

As we share during the podcast, our team at Trucker CFO believes that there is no stupid question. Over the years, our team has been asked all kinds of things. Our approach is very simple. We are going to take the time to respectfully look at and answer your question. We understand the regulations and the laws involved with taxes, and we will always give you a straight answer.

Once we get into tax season, you will no doubt see countless offers related to handling your tax returns. If you are in trucking, especially if you own a trucking business, you should keep in mind that trucking is a unique industry. When it comes to working with tax returns of people and businesses in this industry, you really need a resource that understands the complexities of trucking.

At Trucker CFO, the answers we provide to your questions are not just coming off the cuff. What we are sharing with everyone who works with us and contacts us is the product of many years of experience working with truck drivers and years of experience working with the IRS on audits. We are responding to the questions people may have as it pertains to truck driver tax returns and small trucking business operations.

No one has seen it all when it comes to taxes, but our team worked with clients on a wide range of tax, accounting and business situations. We are always ready for the next question. For now, the questions of the moment are this: Are you ready for the upcoming tax season? Do you have questions that need answers?

Now is the time to ask your questions and our Trucker CFO is ready to help. If you would like to learn more about Trucker CFO, please visit us at