The 500 Hats of Freelancer Cubbins

This post was originally for my column, “Freelance by Lauren,” on the now defunct DIY Writing: A Writer’s Bucket List.

Illustration by Ramiro Roman
Illustration by Ramiro Roman

The title of this article is a Dr. Seuss reference — partly because I wanted to lighten things up before we got into the nitty-gritty details of the many, many duties you’ll be taking on in your life as a freelancer… But also because I really liked Seuss’The 500 Hats of Bartholomew Cubbins as a child. Perhaps even more than Bartholomew and the Oobleck! (Don’t judge).

Taking on the numerous hats a freelancer must wear can be a little scary. I know. But it’s less scary when you know what you’re getting yourself into ahead of time.

That’s exactly why I’m here: To make things less scary for you.

So, take a deep breath. Let it out slowly. And let’s take a look at some of the caps you’ll be donning:

The Boss’ Top Hat

This is the hat most of us wistfully daydream about when we first imagine going freelance — the chance to be your own boss. Yes! [Insert in-the-air fist pump here].

And it’s true. You’ll be wearing the Boss Hat. You’ll be the one calling the shots and making the rules. And that’s a great feeling to have.

The Employee’s Cap

But you’re not only the boss, you’re the employee. Not only do you get to choose the projects and make the rules with your Boss Hat, but you also have to make sure said projects are completed and said rules are followed, via your Employee Cap.

In other words, you get to choose the work; but, you also have to do the work.

Also, unlike a “normal” employee, freelance employees don’t get paid holidays, sick leave, retirement funds, or health insurance.

The Co-Worker’s Fez

You know how I said you’re the employee? Well, you’re the sole employee. For those of us who are used to having other people to chat with at work (co-workers), this can be daunting. The freelancer’s life is one made up of large chunks of isolation.

Becoming your own co-worker can be a hard thing to get used to. This particular “hat” can feel uncomfortable the first time you wear it.

The Professor’s Mortarboard

Once you take on the freelance lifestyle as your own, it’ll become up to you to keep your skills up-to-date.Here’s something I say every chance we get: NEVER STOP LEARNING!


Never stop updating your skills and honing your craft. NEVER!

Mentors will come and go. Classes will start and end. But it’ll be up to you to find those mentors; seek out those classes; read those books, blogs, and magazines in your field … And it’s up to YOU to apply what you learned to your career.

You know what that means? That means your number one teacher is you.

The Assistant’s Bonnet

Some freelancers choose to outsource this particular “hat” to a virtual (or in-person) assistant; however, most of us — especially in the beginning stages of our careers — don’t.

That means you’re going to be in charge of your own scheduling, keeping up with deadlines, conducting interviews, taking calls, answering emails, and making coffee.

The Customer Service Stetson

If you’re getting into freelancing because you’re tired of dealing with “the public”, you’re in for a nasty surprise with this one.

You most certainly do have to interact with the public! Who do you think your clients are? 😉

Working with people is a huge part of this job. They’re the people you’re providing your services for! And they’re also the people you’ll have to strive to satisfy when things go awry.

The Accountant’s Visor

Unlike a “normal” employee’s, taxes will not be taken out of your paychecks when you’re a freelancer.

Does that mean you don’t have to pay taxes?

HA! Oh, I wish!

No; it just means you’re the one who has to keep track of how much of each paycheck to set aside. So make sure you save accordingly.

The Marketer’s Boater

You might be thinking, “But, Lauren! I’m a writer and/or editor. I’m not a sales person.” And I hear you. Loud and clear! But, uh, guess what? You are a sales person now!

The Field of Dreams’ “Build it and they will come” mentality has become a bit of a plague in this business — so much that it’s a cliché at this point.

Bottom line: It just doesn’t work that way.

If you want clients, you have to sell.

But, don’t worry; marketing and self-promotion can be fun! It can be a great new experience and an energizing way to put your skills into action.

The Bill Collector’s Fedora

Back in the “normal” world, when a customer didn’t want to pay, you could hand them over to your manager. Or a collection agency. Or whoever else was in charge of these dirty dealings.

Now that you’re running the show, if a client doesn’t pay up in a timely manner, it’ll be up to you to break their kneecaps. Er…I mean…ask them politely, yet firmly, to heed your mutual contract and pay you your dues!

The Supplies & IT Derby

If you’ve ever worked at an office job, you may have taken all the pens, paper, staplers, files, clips, printer ink, desks, and chairs for granted. You’re going to feel this “hat” in your wallet-carrying region. Because it’s now up to you to provide all your own office supplies.

And, no, you won’t be reimbursed — at least not in full.

You’ll also be in charge of obtaining and maintaining your own technical equipment — namely, your computer and your website. So be sure you back up your files!

The Janitor’s Beanie

A clean work area is a happy, productive work area. And it’s up to you to clean it.

One of the skills every freelancer must have, no matter what field they’re in, is organization.

Organizational skills don’t come naturally to everyone. To be honest, I was so piss-poor at organization when I was in seventh grade that I was literally forced to stay after school every Monday and attend Organization Class.

That class was normally an elective. For me, it was a punishment for my sloppy locker habits.

If I told that story to anyone who’s known me post-1990s, they’d think I was joking. I’m a total neat-freak now. I adore having everything in its proper place and it’s saved my butt numerous times, especially where work is concerned.

This hat, though simple to look at from the outside, can sometimes be the toughest hat to don. It’s a hat that takes practice.

But, when worn right, it can be the most comfortable hat of all.

So what do you think?

Can you stack 11 hats on your head without snapping your neck?

You just might be a freelancer! Share your tips for keeping them all straight in the comments.

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