Should you report gross total amount made through the year or separately enter every jobs payment. Selfemployed side jobs income less than 5,000

The amount of your gross income should be totaled on your calculator before you enter that number into TurboTax.

As stated by @fanfare, you should report the total amount made throughout the year on your Schedule C, rather than separately entering every job you completed. 

In addition, please follow these steps below to start your Schedule C:

1. Open your return.
2. Search schedule c with the magnifying glass tool on the top of the page.
3. Go to the Jump to schedule c link in the search results. 
4. Answer Yes to the page titled, Did you have any self-employment income or expenses?
5. Follow the on-screen instructions.
6. On the page titled Let's enter the income for your work, click on Other self-employed income under Common Income.
7. Enter your total amount of income.
8. Follow the on-screen instructions.

@arodmcg