Q. I plan on taking the standard deduction for my main "W2" job but I was wondering if I can still deduct the expenses for my side job in addition to the standard deduction.
A. Simple answer: yes. But taxes aren't simple. The standard deduction is not "linked" to your W-2. It's you personal deduction. Any expenses associated with your "business" (1099-NEC side job) are deductible in addition to your personal deductions, whether standard deduction or itemized deductions. Business deductions are taken on Schedule C (the same place you report your business income).
Q. Specifically, can I deduct the 22 miles, I drive about twice a week.
A. Simple answer: No. Getting to work is commuting, whether salaried or self employed and commuting is not deductible. But, it depends on timing. If you go directly from your W-2 job to your self employed job, those miles would be deductible. Example: you leave home drive 5 miles to the your W-2 job. When you leave work, you drive 10 miles to your self employment job. At the end of the day you drive 15 miles home. Only the 10 miles between jobs is deductible. The first trip in the morning, from home and the last trip at night back home are considered commuting and are not deductible. Deduct the 10 miles on Schedule C.
Q. When I file with TurboTax (TT) and enter in the 1099-NEC information will it also calculate SS and Medicare tax with the Federal Tax?
A. Yes. TT completes Schedule SE, to pay your SS and Medicare tax. This is known as "Self Employment Tax" (SET).
Q. I also plan to have my main "W2" employer withhold additional money to cover the taxes that I would owe on my side job, just to keep it simple. Is this okay?
A. Yes. Your are correct, that helps keep it simple. You do not need to pay separately each quarter ("estimated tax payments").
