Getting a 1099??

No need to file quarterly. You will pay a small amount of interest, on the amount owed, when you file.

 

interest and a small penalty, except on the first year of self employment. You will AT LEAST pay the 15% self employment tax. With that many kids, I doubt you’ll pay more than 10% income tax, probably just a few %.

you need medical and long term disability insurance.

 

Whoa there, the deductions have to exceed the standard deduction and then itemized them, which means keeping receipts.

Keep 30% for taxes,

As for being a contractor, there has to be a contract for that to exist, otherwise you are an employee.

 

Many years ago a friend of mine worked for a guy that was leased to landstar. It was a 1099 gig he paid for his own fuel, booked his own loads, and ran the truck like it was his. After a year he had a really good idea about how much he could afford and what real expenses were. For him it was OO with training wheels.

 

This is painting with a very broad brush, and I'll point out up front I know zilch about where you're going to work.

1099 places that take on people that have no other options often care about you even less than a mega. HOS, overweight, poor equipment, whatever, they don't care. It's not like the people they hire can walk across the street for another job. It is very possible to leave one of those places worse off than when you started. I'm not saying you shouldn't do it, but don't expect a magic pony ride back to employability. If that's a word.

 

If you are Self Employed, Social Security and Medicare alone are going to be 15.6% Better plan on at least 10 to cover State and Federal taxes. Put away a minimum of 25% per check. Is your family on Medicaid? You don't even want to think of the cost of medical insurance for a family of 7. If you don't pay your taxes quarterly (estimated in advance) there will be some IRS penalties to pay. Good luck!

 

The point of paying quarterly is it wont be as much of a burden cost wise at the end of the year.