Welcome to Questioning Your Cents where you can get real-world, pragmatic tax & financial advice for business owners, entrepreneurs and independent contractors.

We are your hosts, Kevin Molen and Charles Steinmetz. Our job is to help educate you on how to manage your money and save on taxes. In this episode, we discuss self-employment, side jobs and how they are taxed.

Important Points:

Side jobs, Self-employment, MLM, temporary or contract workers

Real estate agents, Law enforcement extra jobs and truck drivers often times fall into these categories

Do you have to report small side job cash on your tax return?

What is a 1099-K and what is it used for?

When do you need to begin claiming your income?

How do I correctly track my income and expenses?

1099-NEC vs 1099-MISC

When do you need to issue a 1099 to a worker?

How do business expenses work for side gigs?

What do ordinary and necessary mean for business expenses?

Security extra job and law enforcement deductions

Why are tax deductions like Web MD?

Facts and circumstances determine what is tax deductible?

Can I deduct expenses as a W2 employee?

What happened to the form 2106? Unreimbursed employee expenses

How is side income taxed?

What are estimated tax payments? Are they the same as quarterly payments?

How do underpayment penalties work?

Do I have to file taxes quarterly on self-employment income?

Comfort Zone:

Is Social Security taxed?

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