Tax Year Prior to 2020: How do I file my taxes using both a W-2 & a 1099 from 2 different jobs?

Since you are paid with a 1099-MISC as an Independent Contractor (for one of your jobs), you will file a Schedule C as a self-employed person.  (This is true as long as you have not taken any steps to become a corporation or are not a multi-member LLC.)  Your W-2 income is reported as Personal Income and your 1099-MISC is Business income.

The Schedule C will flow onto your individual income tax return (Form 1040) and be netted with other personal income and expenses.

Also, you will need to use the TurboTax Self-Employed version if using the online software.

How to get to the area to enter your business expenses :   While inside the software and working on your return, type Schedule C in the Search at the top of the screen (you may see a magnifying glass there).  There will be a popup that says Jump to Schedule C.  Select that to get to the general area.

You can use your own name and address for the business, if you don't have a business name.  And, there is no need for an EIN when it asks for that, if you don't have one. 

Follow through all the areas in the Business section of the TurboTax software and it will provide you with a lot of assistance. You'll notice blue links that have more information and details about the particular sections that will be extremely helpful. 

Also, this link may be helpful to you IRS Small Business Help Center .