What Is The Deal With 1099 Trucking Jobs? Is There A Catch?

I've ran with a small company for a little bit that was 1099, the company owned the truck, paid all the expenses. Nothing came out of my pocket, just like a normal W2 job. The only thing that was different in my eyes was no benefits and I had to do taxes; I didn't stay there too long, as I stopped driving after I was rear-ended in my personal vehicle... A friend I made back in CDL school 4 years ago messaged me about how he is running his own operation now. And has a few trucks, told me I could work for him when I get my CDL again if I want. Guarantees me $1500 a week and home once a week. What am I missing about these types of jobs? Are there certain questions I should be asking? Like insurance policies or anything like that at all? They almost seem too good to be true, and I feel like I am missing the catch.

Hi Harvest,

I was just self employed in the mortgage industry so I can tell you that you need to squirrel extra money away for taxes . As a 1099 contractor you are considered self employed and are responsible for both shares of your social security tax (normally the employer pays half in a W-2 situation). Save any receipts that could be considered business expenses and be prepared to hire a CPA to file a Schedule C tax return for the tax year.

Please note that If you stay on this path and want to buy a house, you may not qualify for a home mortgage until you have 2 years of self employed income taxes with adequate usable income. Typically expenses like depreciation and depletion can be added back BUT if you have a really creative accountant, it may impact your ability to buy a home (if it matters at all to you)

TurboTax Self Employed Tax Center

Hope this helps and best of success!

Hi Harvest,

I was just self employed in the mortgage industry so I can tell you that you need to squirrel extra money away for taxes . As a 1099 contractor you are considered self employed and are responsible for both shares of your social security tax (normally the employer pays half in a W-2 situation). Save any receipts that could be considered business expenses and be prepared to hire a CPA to file a Schedule C tax return for the tax year.

Please note that If you stay on this path and want to buy a house, you may not qualify for a home mortgage until you have 2 years of self employed income taxes with adequate usable income. Typically expenses like depreciation and depletion can be added back BUT if you have a really creative accountant, it may impact your ability to buy a home (if it matters at all to you)

TurboTax Self Employed Tax Center

Hope this helps and best of success!

Thanks, yeah I knew about the tax situation. And saving any and all receipts to write off as much as possible. But I wonder about insurance and everything else. Like are their specific questions I should be asking before I am hired on?

You also will end up paying a high tax rate. I want to say 3.5% but don’t quote me on percentage.

How about hiring on with a reputable established company that does things legally (not an illegal 1099 company) instead of jumping on the first shiny object that sounds good? Benefits, no quarterly taxes, 401K possible, workers comp., paid vacation, solid maintenance plans, established customer freight, etc. Anything there sound like it makes more sense?

I often wonder if we're getting through to you after the past couple years on here, Harvest. You are active for a few weeks, disappear to another job for awhile, then come back with "well that didn't work out". Repeat.

How much solid advice do you require? There are no shortcuts to becoming a successful driver. Repeat that ten times each day until it sinks in.

How about hiring on with a reputable established company that does things legally (not an illegal 1099 company) instead of jumping on the first shiny object that sounds good? Benefits, no quarterly taxes, 401K possible, workers comp., paid vacation, solid maintenance plans, established customer freight, etc. Anything there sound like it makes more sense?

I often wonder if we're getting through to you after the past couple years on here, Harvest. You are active for a few weeks, disappear to another job for awhile, then come back with "well that didn't work out". Repeat.

How much solid advice do you require? There are no shortcuts to becoming a successful driver. Repeat that ten times each day until it sinks in.

Literally just asking about what the downsides are. It could also be solid information for anyone else that has been offered such a position. So what is illegal about it? I was just genuinely curious, if I did not care, I wouldn't be asking on this site at all.

They are not paying taxes nor workers compensation payments as an employer with a driver driving their trucks. Many don't even carry insurance for the vehicle, cargo, property, or the driver. You cannot be classified as an employee when operating their equipment, unless it is a lease, which at that point is a sub contractor. These 1099 companies are circumventing the law and literally cheating on their taxes.

They are not paying taxes nor workers compensation payments as an employer with a driver driving their trucks. Many don't even carry insurance for the vehicle, cargo, property, or the driver. You cannot be classified as an employee when operating their equipment, unless it is a lease, which at that point is a sub contractor. These 1099 companies are circumventing the law and literally cheating on their taxes.

So those are the questions I need to ask if I even consider hearing about his offer. I did not seek this employment, I was messaged by him directly. I am not looking for shortcuts in this career, however, when someone offers me employment claiming to pay $1500 a week, I am going to look into it. And part of looking into it is asking people that are knowledgeable on the matter here. Claiming I am looking for shortcuts is a very broad statement that is honestly insulting. I am only active on this site when I am seeking information.

Low bars are always easily reached. Good luck wherever you end up next Harvest.

Edit to my above post, I meant to say a higher tax rate. 3.5% higher but don’t quote on percentage.