Why Freelancing Sucks

(But Doesn’t Have To)

As a freelancing consultant, you have a degree of flexibility that can be enviable by your “regular working hours” friends. You are your own boss, and you work on your own schedule (kind of). You’re living the dream.

But if you’re considering leaving your 9–5 for the “gig economy” or are already freelancing and want to commiserate, here’s some things that really suck about being a freelancer. And, of course, some solutions, because let’s be honest, setting your hours and choosing your projects is pretty great.

Health insurance.

Hello, $400/month premium, how are you? Not helping anyone’s budget, that’s for sure. And, on top of that, most “affordable” monthly plans have extremely costly out-of-pocket expenses. Buying your own individual health insurance without the benefit of company coverage is expensive — and confusing.

Solution: Get as informed as possible and shop plans to find the best one for you. This Step-By-Step Guide by the Freelancers Union can help with choosing the best health insurance. Also, this article — the 7 Do’s and Don’ts for Freelancers Buying Health Insurance — includes links and important information about your health care.


As a freelancer, no longer are your taxes done for you, neatly spelled out on your pay stub, with the amounts automatically withheld for Social Security, Medicare, and state and federal taxes. Now, if you make over $400, you’re responsible to pay those bills yourself.

Solution: Use Track, a smart application that does your taxes for you. Anytime you get paid, Track will give you an option to save and will even help pay your quarterly tax owed to the IRS. And, you’ll get a weekly pay stub so you can monitor your progress.

Bonus tip: Make sure when you’re negotiating your compensation that you account for your additional self-employed expenses like taxes and health care. (Read More in “Treat Yourself Like A Business”)

Tracking Expenses.

Calculating expenses is both a positive and a negative of being self-employed. On the plus side, you can save money by deducting qualified business expenses like your home office and mileage driven for business purposes. Tracking these expenses on a regular basis can be tedious, time-consuming — and personal accounting probably isn’t what’s paying your bills).

Solution: Be meticulous about your bookkeeping to satisfy the IRS with your deductions. One of the most common tax deductions that self-employed taxpayers can claim is their auto expenses. Using a tool like MileIQ will tally your mileage for you in an easy-to-use app, without adding to your workload.

Yoga pants.

Why would anyone put on anything else? Oh yeah, because most people wake up, get dressed and go to work. As a freelancer working from home, it’s easy to just put on sweatpants and shuffle over to the home office.

But you know it may have gone too far when you’re embarrassed to answer the door, even when it’s just a delivery person. (We’ve all been there). While there’s nothing wrong with wearing workout clothes all day (even without actually exercising), it is important to put yourself in the most productive mindset that will set you up for success.

Solution: Commit to a morning routine that helps you feel productive, positive and ready for the day. Finish your morning routine before your dive into work (or you’ll get sucked in and find yourself in sweatpants, without your teeth brushed…still…at 4pm.)

Always Hustling.

Being paid as a contractor means that money doesn’t flow in as regularly. Companies are late in paying, or maybe work is slower one month to the next. As a result, when you’re self-employed, your “free” time, doesn’t feel free.

Solution: Save money to account for the ebb and flow of business. Also, polish up your negotiating skills to make sure you’re getting paid enough for what you’re worth, and finally, make sure to set aside “you time”. Every day can be a hustle, but there is a time to put your computer and phone away and be in the moment, for yourself, your family and friends.

Have you had other problems you’ve faced as a freelancer? Or some solutions you’ve found?

Share in the comments below!