Monday Musings: 6 Aspects of the Freelance Life that Revealed My Inner Shark

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When I first learned how to swim, my teacher called me a “guppy.” She didn’t do it as an insult. She did it as a way of encouraging me because she called those that could swim without the use of floating rings or styrofoam noodles “sharks.” Sharks were the masters, the cool kids. In Star Wars terms (happy belated May the Fourth!), guppies were “padawans,” and sharks were “Jedi.”

So on Tuesday, April 18, when I became an independent contractor (a.k.a. freelance online tutor) for Chegg Tutors, I took my first dip into the chilly waters of freelance/self-employment.

And I found myself in those uncharted waters feeling like a guppy swimming with a bunch of sharks again.

Now, I’ve only been at this gig for close to three weeks, so it would be wrong of me to assume that all of my experiences regarding this platform are a complete reflection of the growing freelance economy.

But let me tell you. From what I’ve gone through thus far, the freelance life is…

Something else.

1. It’s cutthroat.

In the freelance life, there’s no steep learning curve. There is no curve. You dive head first, and you’d better know how to tread water. Otherwise, you’ll drown.

Opportunities for work come and go like whack-a-mole. You have to be quick to grab them, or someone else will. Moreover, if you’re new, you’ll likely get passed over in favor of someone with way more experience.

Which presents quite the conundrum: How do you get experience without getting clients, and how do you attract clients without having any experience?

Sometimes, it’s a matter of luck. Sometimes, you’ve just got to pray and hope a client will take a chance on you over someone else.

Scratch that. Prayer of some sort is almost a necessity.

2. It’s addicting.

The freelance life, especially when starting out, is feast-or-famine, snooze-you-lose. And because of that high pace, you might find yourself extremely discouraged, optimistic, or both simultaneously. You might start to think, “I keep replying to these clients, but none of them seem to respond. Maybe I’m not good enough,” or “Maybe if I just wait another few minutes or so, I’ll get the client this time!”

You stare at your computer screen, hoping a potential client will come up. And pretty soon, it’s all you’ll start to think about. How can I get more clients? What can I do to make myself more attractive to them? Should I log in and make myself available more often? Should I take a specialized course so that I can widen my net and attract even more clients?

It’s madness!

But the most maddening part about it isn’t the logic of it all; it’s the emotional part.

3. It’s overwhelming.

Alexander Graham Bell, the inventor of the telephone, says it best on the topic of missed opportunities and failures:

“When one door of happiness closes, another opens; but often we look so long at the closed door that we do not see the one which has been opened for us.”

I can’t tell you how many opportunities I’ve either missed, let go of, or didn’t hear back from on Chegg. The regret, the pain, the frustration — all the cautious excitement, jaded optimism, and silent indignation — The freelance life will bring out all sorts of emotions in you that you didn’t think existed.

But in all the madness and frustration, the freelance life is doing something for me that I didn’t think it would ever do:

It’s teaching me how to be kind and firm with myself at the same time.

4. It’s enlightening.

The freelance life will teach you how to set boundaries. It will teach you how to look at yourself in a critical and honest matter about what you’re doing right and what you can improve. It will teach you how to say yes and no the right way — without any guilt or regret. It will teach you that fear of failure and hesitation are normal and expected, but counterproductive. It will teach you how to roll with the punches, dig deep, and not give up. It will teach you that even if you don’t hit pay dirt and get a client right away, just showing up is enough because every day is a learning experience.

And once you do finally land a client and get paid, it’s one of the greatest confidence boosters in the world.

Don’t get me wrong. There’s a lot of luck involved when landing clients, and there’s a lot that’s out of your control.

But that doesn’t mean all is out of your control. Quite the contrary: So much is in your control.

5. It’s game-changing.

After being on Chegg and not getting clients for a while, I started to wonder if there were other avenues of freelance employment I could take. So, out of curiosity, I made a account.

And not even within a few minutes of setting up my profile and listing my areas of expertise, I get notification after notification of listings — some in Australian dollars, some in Canadian, some in very poor English. But they just kept coming and coming and coming and coming.

And then, it hit me.

All this time, I thought jobs were scarce, few, far, and in between. I thought that by not having an internship or a special certification, I wouldn’t land any job.

But that just wasn’t true. I didn’t have to become an expert; I already was an expert. There are always opportunities out there to help people and get paid for it. So long as there are human beings out there that are struggling with something, I can help them with the exact skill set that I have at this exact moment. And so can you.

Whether you’re a guppy or a shark is irrelevant.

You’re a shark when you say you are.

6. It’s amazing.

The freelance life, in all its frustration and madness, is a life I can get used to. In fact, if I want to be a self-employed, full-time writer, I’ll have to get used to it. I mean, it’s a little harder when you’re a fiction writer, ’cause you’re getting into taste and entertainment and all that.

But that’s okay. I’m growing more comfortable with it. And you can bet if I get a whiff of opportunity, I’ll be there, swimming right after it. ‘Cause I’m a shark.

Are you?

Hey, there! Thanks for reading all the way to the end. I hope you enjoyed this post. If you’re thinking about becoming self-employed or doing some freelance work on the side, go for it! You can do it! If this post helped you make that jump or reinvigorated you, please consider sending some spare change my way so I can write more posts like this one in the future. 

Conversely, if you’d like to become one of the 10,000+ tutors on Chegg, sign up here. For successfully teaching your first lesson, you get paid $20/hour, and I get paid a $10 referral credit. Win-win.

Alright, alright. I heard you. Enough with the ads. I get it. 

But, hey. A shark’s gotta do what a shark’s gotta do. I gotta keep swimming, and I gotta keep hunting. 

And as always, I’ll swim to you in the next post.


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