I have to pay what!? - The First Years of Self-Employed Taxes

This was the year!
You took the bold step of making your side hustle your day job.
You had a decent year; you may not want to live on the income you made for very long, but you made it. Pat yourself on the back, raise a glass—you are a bonafide entrepreneur. Welcome to the club!

That was yesterday; then you filed your taxes.
I remember this day well... "I have to pay what!?"
If you have been an employee all your life, you likely have grown to expect a tax return, not to have to return your hard-earned money to the government. You may have even expected to pay a certain sum—after all, everyone has to pay taxes—but hoped that your other deductions would offset enough that it wouldn't hurt too much. We can't help it; not everything in our minds makes the switch from employee to business owner in one, or even a few years.

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