Tips for Working for Yourself

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 who 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 getting paid to sit on your couch 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-foot yacht for a few minutes. Sure, you can charge decent money as a freelancer, but those rates also need to cover all your expenses, including 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, it goes on and on). 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 ’80s), 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’