#85: The Freelancer's Dilemma

HUMOR

Tired of clocking in every day for The Man? Fed up with exchanging your best hours for the boring stability of a biweekly check? Dreaming of kicking corporate life to the curb and going freelance?

Been there. Doing that.

Freelancing is all fun and games when it’s in your mind’s eye. Think of the flexible schedule! The marvelous lack of middle managers! Not a mandatory team bonding activity in sight!

In reality, freelancing comes with its own unique challenges. Let’s break them down, so you think twice before dreaming of labor — even the freelance kind.

The Freelancer’s Dilemma

Expectation: I’ll have so much more free time! Hello, hobbies! Hello, sunshine!

Reality: Welcome to your company of one, in which you, and only you, comprise the marketing, sales, analytics, human resources, communications, creative, strategy, IT, and c-suite teams! You’ll definitely have more time as soon as you build your website and find your clients and do your assigned projects and advertise your services and ensure your staff is paid and…should I go on?

Expectation: I’ll never have to deal with annoying coworkers!

Reality: Sure, you’ll no longer have to deal with the odd big personality. Because you’ll be dealing with no other personalities at all. Just you. Alone. All the time. Likely in your empty apartment. On your computer. Alone. Did I already say alone? It’s worth repeating. And might I float the idea that without others as a buffer, you are the most annoying coworker of all?

Expectation: Bye-bye, bad bosses!

Reality: Ever had your old boss call you a lazy piece of shit and question whether you’re even worthy of love? Well, your new boss will. Even if she never says it out loud, you’ll know. Because she’s in your head. Because she’s you.

Expectation: Financial freedom!

Reality: So you ordered The 4-Hour Workweek on Amazon and watched the five-figure month entrepreneur TikTok videos — super! You’re well on your way to eating microwaved ramen for dinner while you play P.I. hunting down the client from four months ago who is late on paying you the $67.83 you rightfully earned. (Don’t forget to squirrel 33% of that away for the taxes you’ll be paying out of pocket! If you ever even get the money that is.)

Expectation: I won’t be a cog in the machine!

Reality: No sir, you absolutely will not. Instead, you’ll be the harried troll squatting under the machine grinding morning, noon, and night to afford even a crumb of a cog’s salary to simply stay alive. Suck it, machine!

Expectation: I’ll do whatever I want!

Reality: You totally will. I mean, until rent is due. Then we’ll see.

From one freelancer to maybe-one-day another, good luck! You will most certainly need it.

ily bye,

Ariana