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7 Tweets That Perfectly Express Common #FreelancerProblems

By Brandi Neal

freelancer problems

If you freelance for a living like me, or you have a side hustle, then you know that while there are tons of benefits to being your own boss, sometimes it can feel like pushing a rock up a hill. There’s multiple 1099s, payment processing systems, and deadlines to manage. You have to buy your own health insurance, chase down your money, and working from home can be lonely AF. Sometimes, you go days at a time where the Amazon delivery person is the only other human you see, you start talking to your pets like they’re going to answer you back, and your laundry no longer consists of any actual clothes.


What’s more, your friends and family think being a freelancer means that you are always free. Whether it be airport runs, a shoulder to cry on, or walking their dog, some people just don’t understand that you are actually working, and no, you do not have two hours to spare to pick up aunt Gladys to the airport and take her to Old Country Buffet. Because you have deadlines, and if you don’t work, you don’t get paid. If you can relate, then these tweets about the frustrations of being a freelancer will make you feel more understood than you ever have in your life.

Saying "Yes" When You Should Say "No"

When you freelance for a living, it can be hard to say no when a client offers you work, especially if it’s been a dry couple of months, and you’re so desperate you’ve considered selling fruit at intersections to pay your rent. However, the second you say yes to one project, you get offered five more. And, everyone needs them completed yesterday. While it’s a good problem to have, freelancing is feast or famine, and when it’s feast you probably wish you could clone yourself like those “sestras” on Orphan Black.

Spending More Time Trying To Get Paid Than Working

While these days a lot of places use automated direct-deposit payment systems, some companies still cut paper checks like it’s 1999, and these companies tend to be hella disorganized. There’s one person processing invoices, and they live in Alaska and only work for two hours on Wednesday. I am not exaggerating even a little bit when I say I have spent more time trying to get my paper checks than I spent doing the work.

Emails to the clients go unanswered because that person in Alaska is experiencing an internet outage, or you get a “check’s in the mail” response. What’s more, it seems like the company that takes the longest to pay you also owes you the most money, which basically turns you into a bill collector. If I wanted to be a bill collector Karen, I would have been a bill collector. Hey, at least you know you can always fall back on your bill collector skills during the lean times because everyone owes someone money, and you know how to get them to fork it over.

Procrastination Is An Art Form,Despite Having Eleventy-Million Deadlines

Whoever coined the phrase, “if it weren’t for the last minute, nothing would get done” was definitely a freelancer. Most freelancers and side hustlers I know have the cleanest houses, the best Spotify playlists, and have marathoned everything on Netflix. Why? Because we like to avoid doing our work so much that outsiders might think we actually enjoy having an ax hanging over our heads. Seriously, if you need your house cleaned, ask a freelancer with a looming deadline. Why do we torture ourselves like this? If I knew the answer I wouldn’t be on season 11 of Criminal Minds, which I just started watching last month.

Three Words: What Are Clothes?

Freelancers can have a sad wardrobe. My work uniform consists of yoga pants, sneakers, and a black tank top. I have about 30 of these shirts so I can wear one every day. However, I once had an early morning video conference call, which I dressed appropriately for – from the waist up. During the call, my dog started barking and I got up from my chair to shush her. The problem? I forgot that I wasn’t wearing any pants. Oops.

There Are So Many Emails

I have serious email anxiety. It’s so bad that I have a permanent out-of-office reply explaining to people when I will respond to their messages so they don’t email me again. If you juggle multiple clients, your inbox probably looks like an overflowing trash can that you just don’t have time to empty. After awhile, that trash can starts to smell and attract flies, and you chastise yourself for not emptying it sooner.

In order to reduce the stress of seeing emails coming in on my phone, I turned off the notifications and then put my two email accounts in a folder that I call “shit show.” I set aside specific times to check email each day, and then I tune it out because it’s the only way for me to avoid hyperventilating. Making sure that doesn’t happen is a priority because my ACA health insurance has a high ER copay.

Taking A Vacation Is NOT Relaxing

Freelancers don’t get vacation time. We’re literally always working because when we don’t work, we don’t get paid. If by some miracle we’ve saved up enough money to go on a trip and unplug for a few days, fear sets in. What am I missing? Will I remember how to [insert your craft here] when I get back? Why did I go on this vacation? I am so stressed out (promptly raids the mini bar and curls up on the bed in the fetal position). Was that vacation worth it? Because you’re likely going to have to pick up extra work to pay that mini-bar bill, it probably wasn’t.

Happy Hour Is Kind Of Sad...

OK, it’s really sad. One of the benefits of having an actual job in a real office is being able to head to happy hour with your coworkers. Even if you don’t like them that much, sometimes it’s good to be out in public around other humans who understand just how annoying Linda in HR can be. Happy hour for freelancers might include drinking wine right out of the bottle while eating a frozen burrito while sitting on your sofa/office.

You probably get these items delivered by using an app because you’re buried under deadlines and haven’t left the house in a week. Seriously, once I had my groceries delivered and ordered food off another app at the same time. The delivery people ran into each other in the elevator and were confused when they realized they were both coming to my place. Yeah, I ordered that pizza and that bag of groceries with two bottles of wine, so what? Maybe I am a freelance shut-in, but hey, at least my house is clean.

Share your freelancer frustrations in the comments below – it’s a great way to avoid that looming deadline.

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