Freelancing Myths Exposed

08/20/2015 04:31 pm ET Updated Aug 19, 2016

I feel like I've been hired by Dateline to write this exposé (related: if you are a Dateline producer, have your people call my people - we'll do lunch).

Time and time again I hear from folks who are freelance-curious (nothing wrong exploring new lifestyles) that think working for yourself amounts to a walk in the park. Literally, more walks in the park than actual work.

Let me break it down for you and bring your dreams of money-fights back to reality...

MYTH #1 - You can work from home in your underwear!
Reality: The only reason you're working at home in your underwear is because you're so busy you haven't had time to get dressed...in four days. And now, your mother is coming over to visit and you also realize that you haven't done dishes or even bathed in the last four days either.

MYTH #2 - All freelancers make a ton of money!
Reality: Hold off on buying that 157-ft yacht for a few minutes. Sure, you can charge decent money as a freelancer, but those rates also need to cover ALL your expenses like MacBooks, iMacs, iPhones, Apple Watches, and even a few non-Apple products (like software, tattoos, a desk, a chair, an Internet connection, website hosting, a mailing list, etc, etc, etc). You also need to think about insurance, savings and investing, and paying a large chunk of your hard-earned cash money to the government.

MYTH #3 - No more bosses means no more stresses!
Reality: Know how you get hired by clients who give you money and expect work? Well, those people are your new bosses. And instead of having one boss, you've now got ALL OF THE BOSSES. They all want your time, your attention and for you to reply to their 14 emails right now. Even though you're your own boss (think Mona from that show in the 80's), you still have to answer to a lot of other people.

MYTH #4 - You now have free time all the time!
Reality: Sure, technically you can brush off work on a Wednesday to day-drink in your underwear and binge on Netflix. Really though, if you aren't working, you aren't making money. Which is why most freelancers will work more than 40-hours a week to avoid working 40-hours a week for someone else.

MYTH #5 - Your work can't even be considered work anymore because it's so awesome to do!
Reality: Until someone monetizes Netflix-binging as a career, working for yourself still means a whole lot of work. Especially in the beginning, you'll have to work harder than ever because you aren't just responsible for doing the work, you're also responsible for FINDING the work. That takes time. Sometimes a METRIC TON of time. Seriously though, someone please find a way that I can monetize binge-watching TV series on Netflix...

MYTH #6 - No more red tape or corporate bureaucracy!
Reality: All the administrativia that goes with working for a company will now be replaced with you having to do ALL OF THE JOBS. Payroll, accounting, legal, sales, marketing, and project management...all on top of the work you are getting hired to do.

MYTH #7 - Now you can be that lone wolf you've always wanted to be!
Reality: Loners and introverts can be drawn to freelancing, with visions of sitting alone all day, listening to Sigur Rós, and not having to talk to anyone. Unfortunately clients like to communicate with you, and building your brand/awareness of your services requires lots and lots of connecting. You can't just sit in your fortress of solitude and watch streams of workflow your way.

MYTH #8 - Freelancing is great for people when you can't hold down a job!
Reality: Many folks are drawn to freelancing because they don't want to work for the WOMAN, MAN or ROBOT OVERLORD. But if you're too flaky to hold down a job, then you're going to be way too flaky to work for yourself. There won't be anyone looking over your shoulder to make sure the work is getting done. There'll just be pissed off clients who don't want to pay you because you bailed on the deadlines they gave you.

MYTH #9 - All you need is a website!
Reality: Too many new freelancers think that their portfolio website is a money-printing machine. All you need to do is set it up and watch the money roll in! This couldn't be further from the truth--if the right people aren't finding your website, trusting your work and understanding the problem that your services solve--your site will sit, collect dust and never be Google's BFF.

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Don't get me wrong, working for yourself can amount to the most awesome and rewarding choice you'll ever make. But only if you do it right (and by "do it right" I mean, "put a shit-ton of work into it").

Working for yourself can amount to the most awesome and rewarding choice you'll ever make.

And now back to writing more articles in my underwear, while day-drinking on my 157-ft private yacht...