To start: Don’t estimate or pay quarterly taxes like smart people/the law tell you to.
1. Enter 1099-Misc for $30,300 (blogging income, no taxes taken out) into tax prep program.
2. Enter two W-2′s for $2,204.25 (retail income, taxes taken out) into tax prep program.
3. Quit at the part where tax software tells you to start making deductions based on expenses incurred.
4. Because: you need receipts (ha, what receipts?) and perhaps also a professional.
5. But wouldn’t it be nice to get it done now? (Yes.) Maybe you can figure it out.
6. Go back to that part and try to wing it.
7. Get stumped on the first question, about how you claimed expenses on your car last year (“In the first year that you deducted a business expense for this vehicle, did you use the standard mileage rate to determine your deduction?” I HAVE NO IDEA ABOUT THAT ONE, TURBOTAX. Nor do I have any idea where last year’s tax return is so that I might tell you about it).
8. Quit again.
9. File extension.
10. On extension form, estimate taxes owed as $2,000 (wishful thinking?)
11. Don’t pay anything even though you’re supposed to because: With what money? Also: Interest/fees for not paying won’t be much, yet.
12. Make note to call tax professional.
13. Go to bar.