Complete Guide to Tax Filing

My friend Sarah owns a marketing consultancy in Denver. Last tax season, three freelancers had worked for her—a copywriter she'd paid $2,400, a web developer who got $8,500, and a photographer she'd hired for $1,200. Her accountant sent a quote: $45 per form. Simple math: $135 she hadn't budgeted for.

"Isn't there a cheaper way?" she texted me one night.

There is. And it costs exactly nothing if you're willing to navigate the right systems.

Small business owner? Side hustle runner? You can send 1099 forms straight to the IRS without spending a dollar. The government built its own filing platform years ago. Certain commercial companies offer limited freebies too. The tricky part? Knowing which tool fits your situation and steering clear of the upgrade screens that pop up at every turn.

I'm about to show you the whole process, including the errors that trigger penalty notices.

When You're Required to File a 1099 Form

You hit filing requirements once you've paid someone who isn't on your payroll. Paid that freelance photographer $600 or more last calendar year? Time for a 1099-NEC.

The specifics depend heavily on what kind of payment you made.

Payment types carry different dollar triggers: Services require $600. Royalties? Just $10 activates filing. Withheld backup withholding from a check? File it regardless of the amount. Rent payments of $600+ to your office landlord need a 1099-MISC. Each scenario has peculiarities worth understanding.

The people who receive these forms: Independent ...