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The Reality Of Being A Full-Time Freelancer

Workin' Girl

So, you're sitting at your desk scrolling through Instagram with stealth-like precision, and you come across a successful entrepreneur.


Maybe she's leaving a yoga class, mat tucked adorably under her arm with a green juice in hand or perhaps she's all smiles with her passport raised to the sky heading on a sponsored vacation. She's got it made, you think. Living her best life, answering to no one, able to explore, come and go as she pleases.

You decide enough is enough---you, too, dream of freedom. After all, working for yourself will be the answer to all of your problems, right?

Girl. Listen.

This life? This "stress free" freelancing life? It ain't for everybody. Let us debunk the myth that a career as an entrepreneur is the end all be all, or equivalent to going from Mariah Carey's Glitter album to her Emancipation of Mimi comeback together, shall we?

Being The HBIC Isn't Easy

First things first, the fish rots from the head. And, SURPRISE, you're now the head. What I mean by this is that until now, you've spent most of your life having a set of predetermined guidelines to follow to ensure the ease at which you're able to succeed. There's a start time, a list of job duties, a built-in break time, an embedded assessment system in the form of monthly meetings, bonuses, a steady paycheck, and, everyone's favorite, a clear time to clock out.

In short, there is a simplicity that comes with having things mapped out for you every day. That completely disappears when you're working for yourself (more on this phrase later). There is no one to bcc when things need fixing, nor is there a clear start or end time to your workday. For many freelancers, learning how to set your own "company policies," boundaries, expectations, and/or schedule is more daunting than freeing, at times. Can you work from home in your pajamas while D'Angelo's Voodoo album plays in the background and collect money without leaving your bed? Yes.

But you can also spend your time doing nothing productive for a whole day with no one to answer to---and this is where many entrepreneurs get (and stay!) stuck. Can you discipline yourself to get results when there's no one to hold you accountable but the person in the mirror? This isn't rhetorical. This is perhaps the most important question you can ask yourself and the one you HAVE to answer honestlybefore you tell your boss to kiss you where the sun don't shine, and you sail off into the CEO sunset.

Every Coin Matters

Then, there's the matter of money.

Oh, yes. Although there are few things as satisfying than the first time you get paid to do exactly what you want to do---you only eat what you catch when you're the HBIC. As a freelancer, every coin matters because there is no guarantee that the coins will keep coming. See, the thing about not having one steady job is that you must always be thinking a few months ahead in order to keep your financial well from drying up.

When you factor in the freelancer's tendency to accept much less than what they're worth and the chance that someone may drag their feet on cutting the check---the idea of knowing where your money is coming from weekly, biweekly or monthly doesn't seem all that bad now, does it? And there is absolutely nothing wrong with not wanting to give yourself a mini heart attack on the first of every month when you try to map out what you have left for the next 30 days. Tons of entrepreneurs will tell you about how they made a dollar out of 15 cents but very few will admit that they just wish they'd had the damn dollar in the first place.

The Truth About Working For Yourself

So, we've covered self-discipline, money, and accountability but how about the phrase: "I want to work for myself"?

Here's the brutal truth: in a country built on capitalism, you'll always need to appeal to someone else in order to get paid.

When you make the switch from a 9-5 to the dance of professional side hustling, what happens is that you go from having one boss to a whole lot of bosses. Whether you're now answering to clients, the people who consume your art or customers who buy your products; the idea of complete autonomy of your time, decisions and abilities is false. You are going to have to juggle the expectations of total strangers while you navigate the demands of being in charge.

And if you think after hours emails are annoying from a single source, consider the stream of emails from different people on different time-zones about different projects…Jesus wept, ok? The only sure thing when working "for yourself" is that you'll be overworked and have less free time than you ever did punching a clock.

There is no magic wand that comes with entrepreneurship that turns your life into a 24-hour social media victory lap.

You will fail.

You will go underpaid at best and unpaid at worst.

There will be days where staying in bed to do nothing will be, at once, too expensive and yet the only thing that can get you through the week.

You will question every decision you make from a million different angles. Hell, you'll even envy the normalcy of a "regular" job. But as Jim Carrey once said: you can fail at something you don't want to do, so there's no harm in taking a gamble on something you really love.

I am here to tell you that ultimately how you choose to live your life must depend on a 100% honest evaluation of yourself and not on what others believe makes you a success.

Some will suggest that you jump off the boat of the traditional 9-5 so that you can walk on the proverbial waters of self-employment. I say, there's nothing wrong with staying on that boat and making it peacefully to shore---ain't no sense in messing up a good pair of shoes walking in someone else's footsteps, sis.

But if your reason for staying onboard is because you fear you won't be able to swim---have faith that you'll be just fine and keep swimming.

Featured image by Thought Catalog on Unsplash

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When I was ten, my Sunday school teacher put on a brief performance in class that included some of the boys standing in front of the classroom while she stood in front of them holding a heart shaped box of chocolate. One by one, she tells each boy to come and bite a piece of candy and then place the remainder back into the box. After the last boy, she gave the box of now mangled chocolate over to the other Sunday school teacher — who happened to be her real husband — who made a comically puzzled face. She told us that the lesson to be gleaned from this was that if you give your heart away to too many people, once you find “the one,” that your heart would be too damaged. The lesson wasn’t explicitly about sex but the implication was clearly present.

That memory came back to me after a flier went viral last week, advertising an abstinence event titled The Close Your Legs Tour with the specific target demo of teen girls came across my Twitter timeline. The event was met with derision online. Writer, artist, and professor Ashon Crawley said: “We have to refuse shame. it is not yours to hold. legs open or not.” Writer and theologian Candice Marie Benbow said on her Twitter: “Any event where 12-17-year-old girls are being told to ‘keep their legs closed’ is a space where purity culture is being reinforced.”

“Purity culture,” as Benbow referenced, is a culture that teaches primarily girls and women that their value is to be found in their ability to stay chaste and “pure”–as in, non-sexual–for both God and their future husbands.

I grew up in an explicitly evangelical house and church, where I was taught virginity was the best gift a girl can hold on to until she got married. I fortunately never wore a purity ring or had a ceremony where I promised my father I wouldn’t have pre-marital sex. I certainly never even thought of having my hymen examined and the certificate handed over to my father on my wedding day as “proof” that I kept my promise. But the culture was always present. A few years after that chocolate-flavored indoctrination, I was introduced to the fabled car anecdote. “Boys don’t like girls who have been test-driven,” as it goes.

And I believed it for a long time. That to be loved and to be desired by men, it was only right for me to deny myself my own basic human desires, in the hopes of one day meeting a man that would fill all of my fantasies — romantically and sexually. Even if it meant denying my queerness, or even if it meant ignoring how being the only Black and fat girl in a predominantly white Christian space often had me watch all the white girls have their first boyfriends while I didn’t. Something they don’t tell you about purity culture – and that it took me years to learn and unlearn myself – is that there are bodies that are deemed inherently sinful and vulgar. That purity is about the desire to see girls and women shrink themselves, make themselves meek for men.

Purity culture isn’t unlike rape culture which tells young girls in so many ways that their worth can only be found through their bodies. Whether it be through promiscuity or chastity, young girls are instructed on what to do with their bodies before they’ve had time to figure themselves out, separate from a patriarchal lens. That their needs are secondary to that of the men and boys in their lives.

It took me a while —after leaving the church and unlearning the toxic ideals around purity culture rooted in anti-Blackness, fatphobia, heteropatriarchy, and queerphobia — to embrace my body, my sexuality, and my queerness as something that was not only not sinful or dirty, but actually in line with the vision God has over my life. Our bodies don't stop being our temples depending on who we do or who we don’t let in, and our worth isn’t dependent on the width of our legs at any given point.

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