How do I delicately ask whether or not a part-time job is under-the-table?

Have a friend call and ask for you.

You can’t unless the job is sketchy. The best way to handle this is to offer your services on a Contract Basis and then they pay you and you pay the taxes if you want to. You may get caught, and you may not.

Don’t ask in writing or on voicemail (no trail).

I agree with @missingbite. If you offer your services on a contract basis, then you will have a 1099 form at the end of the year to do your taxes if you choose to… Maybe you could ask in passing which tax forms they will have you fill out, or something to that effect.

But won’t they take my SSN and report that they paid a ‘contractor’ x amount?

@figbash Good question… not sure.

Only if they ask you for a Tax ID number (SS#) or ask you to fill out a 1099. If they don’t, then it would be up to you to report it. Hence, you may get caught but probably not. I am assuming we are talking about jobs that pay a few hundred dollars or so.

The contract idea is wrong. What figbash wants a job with no tax trail. A 1099 is a tax trail and the IRS has the ability to crosscheck them to tax returns. Then you have an audit, penalties and fines.

If you think the job is UTT, then take it. If they hand you a tax form to fill out, just tell them you left the water running and get out. No tax form/no SSN and you should be OK

If a single person pays you more than $600 over the course of the year, they MUST provide you with a 1099.

What type of work are you looking to do?

Ahhh….I see. Thank you. This is helpful!

I just wanted to do some basic odd jobs – maybe small clerical project work, personal assistant work or even a catering gig or two to earn an extra couple of hundred a month. I was hospitalized last year and my medical bills, on top of what was already covered by insurance, ran in excess of 5k and I’m desperately trying to pay it off. I pay more than my fair share in taxes, which on top of my other bills, doesn’t leave a lot for this debt.

~ Not that anyone here would ever dodge taxes of course, but it’s definitely good to know going in to a job what the other side is going to do. I’ve handled it in two ways, both mentioned above, but with a little more information.

If I’m just doing a bit of work, in their offices, like a normal job, I usually just ask if they’ll be providing a 1099. This would mean you’re a contract employee essentially. They’ll report it just like they would for a normal employee but your tax burden is usually even higher than normal W-2 income since the employer doesn’t pay “their half”. Basically you have to get paid a premium to make it worth it, as you noted in the question.

The other way to go is to set up your own business and provide the services that way. The employer becomes a client and simply reports whatever they pay you as an expense. For example, if someone hires a company to repair their copier, they don’t hand that person a tax form, they just pay and write it off on their own taxes. There is a trail, (assuming you invoice) but it’s to a separate entity (your company) and you can write off your expenses as well to reduce the tax burden.

Of course if you don’t mind being fairly obvious with your intent, you can always just look the person in the eye and ask “does the job pay cash?”... most employers understand what’s being said.

Very sorry to hear about the medical bills.

and for what it’s worth, it’s respectable that you’re working to pay them down, good luck with everything

& don’t take a job UTT with somebody who might later run for office or be thinking about getting appointed to a Cabinet post.