I claim exempt and then cheat.

It's not a bad gig and I plan on it when I retire. If it looks like you are going to do it, shoot me a PM.

Withhold as much as possible then lie your ass off come tax time.

Never was brave enough to cheat on my taxes

FYP

Tax time makes me cry.

By far the most depressing thing about being self employed. Drought, Risk Exposure, Stress, uncertainty all suck, but paying that tax bill is awful. Terrible. Hate it.

Oh. And Gaz. I run an estimate in November and see what I need to do from a tax strategy standpoint. The IRS does allow cash based accounting so that is a huge plus to my industry.

I get 1099's... Sucks to pay taxes on those

Yessir. My guess is you have a better shot of getting back your SS and Medicare taxes than I do.

BOHICA?

I make several large donations to charity each month. My taxes go to them

The interest lost by giving the govt a "free loan" is miniscule. All in all, the pain in writing $1000 check or whatever all at once in April is more than the pain in knowing I gave up a tiny bit of interest over the year.

I try not to give them any more than I need to, my issue is that I'm a moving target at tax time. Some years I'm writing a check, some I'm getting some back.

Either way...it always feels like I'm working too many days and too many hours to pay "my fair share" while so many get a "refund" without paying in.

I have no choice but to over-withhold. My income is relatively volatile and the risk of paying a penalty for underpayment is greater than the interest cost of overwithholding.

I let them earn interest on my money...I like getting a return every February or March.