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Should I Quit My Job to Be a Freelancer?

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So you wanna quit your job, huh? Drawn by the allure of…

Being your own boss?

Calling your own shots?

Working from your couch in your Snuggie?



In February 2013, I was in your shoes. Unable to face another day filled with dread at the prospect of my desk job, I turned in my two weeks’ notice to my supervisor. I told her I was doing it to to start my own business.

I was 22 years old.

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    That was my first job.

    I had no idea what I was doing.

    Fast forward three months, and I was pawning my grandmother’s diamond ring just to get $180 in extra cash to be able to make rent the next day.

    For weeks, I did things like sell junk on Craigslist to try to scrape together what I could.

    While I’ve come a LONG way since those days, I want to address a question I get asked a LOT: Should I quit my job to be a freelancer and/or start my own business?

    Having done that myself, here’s my honest opinion:

    Should I quit my job to be a freelancer_ My honest advice after freelancing full-time since 2013.

    Should I Quit My Job to Be a Freelancer?

    No. Don’t do it. I’m serious.

    Consider these things:

    Your desk job gives you a steady paycheck.

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    Oh, how I miss those! Lemme tell ya something: As a freelancer, it’s common to have what’s called Net-30 terms. That means you get paid up to THIRTY DAYS AFTER you did the work! I know, bizarre. But it’s commonplace in the freelance world.

    As a blogger, many affiliate programs don’t pay out for 30, 60, sometimes 90 days AFTER you made the sale.

    So, as an entrepreneur, you constantly are waiting on a paycheck. Sometimes, it doesn’t come and you have to hunt down the client. I’ve never had that happen to me, but it DOES happen.

    And benefits.

    Say bye bye to paying only $30 a month for your health insurance, which is subsidized by your employer. I currently pay $495 a MONTH for my own health and dental insurance. I paid more last year.

    The “bright side” is that as of of 2017’s tax filing, self-employed people were allowed to deduct payments made for their own health insurance.

    And coworkers (though you think you don’t like them now).

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    I kid you not, the first two weeks of starting my business, I sank into depression. I could hardly get out of bed in the morning because…no one was expecting me to. I no longer had a boss (except myself). I no longer had coworkers. I no longer had an office I had to be at. And that type of freedom paralyzed me.

    And the EASIEST tax structure ever!

    When you work for an employer, they withhold taxes for you, and all you do come April 15 is plug in your W2 info and bam! Taxes filed.

    As a freelancer, however, you now have a Schedule C where you have to report all your business income and expenses. Also, you now have to submit estimated tax payments every quarter. Your taxes become more complicated, which is why you should hire an accountant if you’re a freelancer.

    Running your own business means everything is on YOU.

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    Unhappy customer? You get to deal with it!

    Came down with the flu? You still need to work because no one can take over for you!

    Taxes? ALL ON YOU. You pay them now! When you’re an employee, your employer takes care of much of your taxes AND withholds taxes for you. As a freelancer, you must now pay Self-Employment Tax.

    Being a freelancer means everyone will question whether you have a “real job.”

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    Ughhhh I hate this one SO MUCH. But you know that annoying question “What do you do?” Now, it’s, like, ten times more annoying because if you mention “freelance” anything, you’ll get dubious stares or awkward questions like “So…do you plan to get a real job?”

    Working from home means everyone will wonder if you actually do any work at all.

    “Hey, since you’re home anyway, could you go pick up my dog from the groomers at 3?”

    Get ready to hear LOTS of requests like that! While working from home is AWESOME (sweatpants all day, er’day!), outsiders will NOT understand that you are in your “office” and actually ARE working.

    Just watch this:

    Wait—As a Full-Time Freelancer and Self-Employed Person, Why Am I Saying All This?

    Because I know the people who are truly ready to quit their jobs are the ones who responded to everything I just said with, “F*** you! I’m doing it anyway!”

    If what I said scared you away, then you’re not ready. You need a life of stability, and that’s something entrepreneurship cannot offer you.

    If, however, what I said lit a fire in you and made you more determined than ever to make your freelance dream come true, more power to you!