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 honestly before 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.

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