My situation is as follows; I've been a truck driver since 1994, always as a company driver, with pay and benefits being handled by the company. Sometimes it was good, other times it wasn't. I've been with the same company for over four years now as a company driver, first over-the-road, and now local. The money has been OK, but not great, and the company is slowly sucking any joy out of the job  by means of silly, stifling policies. I have a steady paycheck which isn't as much as I'd like, and since it's basically a salary position, I find myself working longer hours than a lot of other, more whiny, drivers.

I've been offered a position with another company as an OTR driver, but with the caveat that I would be classified as a 1099 contractor, not an employee, and responsible for my own taxes and insurance. This is uncharted territory for me, and a little unsettling, because I'm used to having someone else take care of those things. The job itself sounds like exactly what I want out of an OTR gig, hauling specific products to specific destinations, with a lot of driving in between MI and TX. There is a lot more money to be made at the new job, but I'd have a lot more responsibility in spending/saving/investing it than I ever have before, and that's a little scary.

A big concern is medical insurance, since I'm a Type 2 diabetic who wears glasses, and my current position has medical/dental/vision insurance. The policy isn't great, as it has a high deductible, and most of our yearly medical expenses are paid out of pocket. $160/wk for a family policy that isn't very flexible for two adults and two newly-adult kids is a lot of money. Are HSAs still a thing for people in that situation? I would rather take a job as a jizz-mopper in a dirty bookstore than get on ZeroCare.


Any advice the more learned of Arfcommers can toss my way, the better.

I'm 46 years old and don't have a pot to piss in, due to Mrs. IHJ and I having blended two families after wrenching our children away from their abusive/deadbeat ex-parents. We spent our sweat, blood, and capital on raising a houseful of great kids, now great/fair-to-middling adults, and we have a lot of catching up to do.

One Phrase - Self Employment Tax 12.4%   ...

You will need to earn a fair amount more just to offset the difference in employer paid contributions Vs. you pay it all yourself.

Are you making about 20% more on the new gig?   Are you going to have the discipline to withhold that money for your taxes and make quarterly payments (if needed) so you don't get end of the year tax whacked?

As a 1099 you should be able to expense out a lot of things, (cell phone bills, fuel, repairs, don't know about lodging & meals while on business trips (CPA or Trucker Question)...)

I know you don't like Obama Care, but since it is what it is and is currently the law of the land, consider You may get a tax benefit (you won't pay as much in income taxes - you are not getting FSA money from someone else) with Obama-care / Trump-Care or ????  Don't Care-Care...  and I'd guess you'd most likely need to go to your insurance exchanges to get a decent rate due to your current conditions.

I just left a job and the COBRA coverage for me and my children nearly doubled what I was already paying (and that was painful as it was)...

You need to figure out if you can buy health insurance as a contractor and, if so, how much it will cost you.

If you get past the medical issue and pull the trigger, don't forget to make your quarterly estimated income tax payments.  No one will be withholding for you.  If you don't make your estimated tax payments, you may have to write a big check the following April.  I see a lot of small businesses fuck that up.

I will get the answers to a lot of these questions next Wednesday when I meet with the owner.

Ia disciplined enough to withhold the necessary taxes and so forth, I just haven't had the opportunity due to paying off medical debt for one of our children, as well as student loan debt for me. I'm really tired of just barely getting by, and trucking seems to be the only way I can make more money.

There's a story out there, similar to your situation. I believe it was FedEx that tried to 1099 all of their drivers, and got in trouble for it.

https://www.forbes.com/sites/robertwood/2015/06/16/fedex-settles-driver-mislabeling-case-for-228-million/#2d876835c22e

Being an employee versus an independent contractor isn't an option.  If you aren't an owner/operator, and instead are driving this new company's truck(s), you will most assuredly be an employee.

This. The irs defines this role. Not the employer. At times I've employed more subs on my crews than employees but i follow the irs definitions.

I think if you lease your truck, you then are 1099.   Seems all the truck companies really push their drivers to go "independent" on leases so they can make "big money"...  (or so I've heard...)

Do the math.  Old salary + health insurance + 7.5% more SS and Medicare + vacation pay + downtime will get you to break even. I add these annual amounts up and divide by 2000 hours (50 weeks x 40 hours.) to get an hourly rate. Then give yourself a raise for the risk involved.  If you own your truck, you have to figure those costs in too.

IF you make over 80% of your income from one source, you are an employee in the eyes of the IRS.
I worked into a partnership by being a 1099 contractor and it didn't work out in the beginning.
Paying both sides of SSI sucks.
Buying your own health insurance sucks.

Yeah, I'm figuring that out. The math doesn't work, so I thanked him for the offer, but I'm staying put until something better swims by. Mrs. IHJ got a nice job offer today, so we will see if it works out.


Thanks for the advice, guys.

Unless something changed that im unaware of, you'll not find that 80% definition anywhere in the irs rules.

There is much more to it than a percentage. Ive had many guys that got 99.9% of their income from our company and were subcontractors in every single sense of the word as defined by the irs.