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I Started Freelancing Full Time 18 Months Ago. Here’s The Expectation Vs. Reality



Welcome to the start of our Side Hustle Diaries series which is meant to take an inside look at women who are dabbling in or diving head first into working for themselves. Over the course of the series, Brandi will be sharing her experiences every month while weekly we also highlight other women interested in sharing their side hustle stories. For more info or if you'd like to participate click here.

While I have freelanced my entire career, I’ve always kept a full-time gig — until now. Eighteen months ago I left my corporate marketing job and jumped into the abyss of a full-time freelance career. In my previous job, I was managing more than 1,000 deliverables a year with no permanent staff. And, because I already have a chronic pain condition, and suffer from both anxiety and depression, five years of working 24/7 in a toxic environment took its toll. At one point I had a migraine every day for two months. It got so bad that I thought I had a brain tumor. When my MRI came back clean, my neurologist was pretty direct with me. “Your migraines are from stress,” she said. “You need to learn how to manage the stress of your job, or you need to find a different one.” In that job, work-life balance was not encouraged, and I didn’t see any realistic way to make my job less stressful. I worked from home, and I was working so much that I got my groceries and meals delivered. Hardly ever leaving my apartment made me even more isolated and miserable.

What’s more, I would regularly wake up to more than 200 emails every day at 6 a.m. This led to a string of morning panic attacks in which I started every day shaking and crying. I told myself: “This is no way to live. This is a way to die.” However, knowing something and doing something about it are two different things, but I eventually gave my notice when I finally realized that I was staying in a job that made me miserable because I was afraid I wouldn’t be able to make it on my own. Even though I ashamed that was I was knowingly keeping a job that was making me sick, I was so beaten down at that point that I doubted that I had what it takes to be successful, even though all evidence pointed to the contrary. This was a common theme for most women who worked at this company. What’s more, for someone whose identity is firmly tied to being a writer, realizing that I hadn’t published anything in more than a year came as a big blow.


At that moment, I knew I had to stop letting fear dictate my decisions for both my health and my happiness, and I resigned from my high-salaried job with the fancy title. In order to remain true to myself, the only choice for me was to leave. I didn’t have any clients, any current clips, and I had no idea how I was going to make it work. But, one thing I learned at my last full-time gig is that while money can buy you a lot of stuff, and it can buy you security, it cannot buy happiness. Same? I’m here to tell you that even when you feel like you’re stuck in a tunnel, there is light on both sides. And, you’ll eventually get out of the dark and twisty downward spiral if you choose a path that allows you to feel good about what you’re doing every single day. That being said, before you give your notice, it’s important to know that it’s not called a hustle for nothin'.

Freelance Life Expectations Vs. Reality


Making your side hustle your main hustle doesn’t happen like magic, and it sometimes feels akin to jumping off of a cliff every single day. If you’re miserable in your 9-to-5, it’s easy to get caught up in the romance of being your own boss, only accepting work that you like, and working from home in your pajamas. I recommend planning your escape from corporate drudgery better than I did by getting started while you still have that secure job so you don’t have to cash out your 401k (like me). And, before you quit your day job, it’s also important to know some of the expectations versus realities of freelancing, because it’s not for everyone.

Expectation: Being Your Own Boss Is Totally Boss


It’s true that being your own boss is A-M-A-Z-I-N-G because you can do whatever you want whenever you want and no one cares. You can take long lunches, create a schedule that works for you, make your own website, and promote yourself on social media like the boss you are. However, being your own boss also means that the only person who is going to make sure you get your work done is you. Basically, you have to boss yourself around and hold yourself accountable because, you guessed it, no one else cares.


Reality: Being Your Own Boss Is Hard AF


As a freelancer, you have to play every role in your little company of one. This includes getting your own health insurance (hello Affordable Care Act) and managing and tracking your expenses. Taxes go from a simple W2 to a barrage of 1099s. And, you’re probably going to owe the IRS versus the other way around. The good news is that if you start to bring in the bucks you can eventually outsource some of this stuff. What’s more, while you do have deadlines, you are the only one responsible for getting your work done. And, nine times out of 10, you are also the only person preventing yourself from doing said work. Truth? It’s kind of weird to reprimand yourself.

Expectation: Working From Home Is Where It’s At


If your current job involves a frustrating commute, annoying co-workers, and an uninspiring office, working from home might sound like a dream come true. You can get up whenever you feel like it, skip that shower, forgo the makeup, work in your pajamas, and listen to Lady Gaga as loud as you want. You’ll also probably have the cleanest apartment in the city because one way freelancers distract themselves from deadlines is by cleaning, reorganizing their closets, cooking, and basically by engaging in every other distracting activity you can imagine. However, I will admit that I love, love, love working from home, and I can’t imagine ever going back to an office. But, it’s not without its pitfalls.

Reality: Working From Home Is Lonely


I’ll be the first to admit that I love working alone. I’m a hardcore introvert and not being surrounded by people to distract me is one of the things I appreciate the most about working from home. It’s also one of the things I loathe. But, why? Well my friendlies, let me tell you what working from home really looks like. Your laundry does not include any actual clothes. No, you don’t work naked, but eventually, you’ll realize that you’re only washing yoga pants and sweatshirts because why get dressed up when you’re the only one there? You also don’t have that built-in-after-work social circle, and happy hour can become pretty sad when you’re pouring that glass of wine for one. If you have pets, you might find yourself carrying on conversations with them like they’re people. If they start answering you back it’s time to get up and go for a walk. One way to combat the work-from-home blues is to get a co-working space or commit to working in a coffee shop a few days a week.


Expectation: You’re Going To Have A Ton Of Free Time


One of the most attractive things about working from home is being able to make your own schedule. This means it’s easier to take vacations, meet up with friends or family during the day, and basically work when you want. If you wake up feeling meh, you can close your computer and opt for a hike instead of filling orders for your Etsy store or writing that article you owed your editor last week. Sounds totally boss, right? Unfortunately, it’s not that easy.

While Carrie Bradshaw made working from home look glamorous AF on Sex and the City, her situation is not realistic. Who are these people getting paid enough to live in New York City and buy $40,000 worth of shoes by only writing one column a week? I’ll let you in on a little secret. These people do not exist in 2017. While the internet has made freelancing a lot more accessible, it also means that a lot more people are doing it, and the competition is fierce.


Reality: It Might Feel Like You’re Working 24/7

When you’re first getting started as a freelancer, especially if you intend on doing it full time, you’re going to be working a lot. Whether you’re a writer, a career coach, a meditation teacher, or you’re opening an Etsy store, it’s a hardcore hustle to get people to hire you or to buy your products. This means you might accept less money than you normally would until you find your footing. What’s more, while you can take a vacay whenever you want, there is no vacation pay. Not working means not getting paid. When you’re a newbie, you also might be reluctant to turn down work you don’t really love because you never know when you’ll get another client. When I started, I went from not writing any stories for more than a year to writing more than three-to-six a day. I wrote my ass off, and 18 months later I am finally starting to bring in more money than I am spending by securing one regular part-time gig and myriad freelance clients. In order to do this, I usually work six days a week. But, I don’t work eight hours every day, and I still feel like I have more free time than I had at my full-time job.


Expectation & Reality: Freelance Life Is Way Better Than 9-to-5 Life


If I haven’t scared you away yet, despite everything I just warned you about – if you can deal with the uncertainty – freelance life is so much more rewarding than being a 9-to-5er. While you might work more in the beginning, and you have to master that whole being-your-own-boss and remembering-to-shower thing, you get to do something you love, which gives your work a kind of purpose that you can’t get working for someone else. You’re investing in yourself and your future, and you’re telling yourself that you are worth it. You deserve to be happy. Let’s be honest, you’re likely going to spend eleventy-million hours of your life working, and having a fulfilling career is the very least you deserve.

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