A Copywriter’s Journey Through Dante’s Inferno

8 minute read

Most experiences between writers and clients are positive. But it only takes hearing one horror story to put a new writer on edge.

Let’s take a look at the most common areas these relationships can break down and how to spot the warning signs before anyone gets burned. With a little foresight, you’ll be able to avoid taking on difficult clients, while attracting and retaining good ones.

Avoiding the burning rings of fire

I’ve drawn inspiration from Dante’s Inferno, where he travels through the nine circles of Hell guided by the poet Virgil. For our purposes, I’ll be your Virgil as we explore these circles and how they relate to the world of copywriting.

You’ll see how to keep the writer/client roles on track and save yourself some angst, land clients you love and who love you… with time leftover to write an awe-inspiring opus. I promise.

I present to you the nine circles of copywriting Hell. Mind the cinders!

Based on Dante’s geography, the underworld is organized in circles according to their degree of wickedness.

Circle 1 – Limbo

Limbo is the giant waiting room in the afterlife, designed for pagans and the unbaptized. According to Dante’s lore, it’s annoying, but not all-out agony. You’d probably have a TV with one channel tuned to fake news. Magazines are doctors’ office rejects, and the floor is scuffed beige linoleum.

This is where we copywriters hang out, while our clients drag their feet getting back to us with feedback on a first draft. You would also park here when waiting for an editor at your dream publication to give you a yay or nay on your latest pitch.

Being stuck in limbo happens, and it inevitably causes imposter syndrome and writer’s block to creep. Worse, it can kill your concentration on other things… particularly an opus.

But, let me assure you… your client isn’t ignoring you on purpose. They get busy, and sometimes it takes them longer than we want to respond. That said, you cut back on your limbo time by making a simple change.

The answer here is communication.

Be organized during your discovery call to gather everything you need for a strong start. This is what makes any project a true collaboration.

Before you write word one, be open and honest, so you understand the direction and goals your client desires. Ask questions when you need to. Also share your ideas and thoughts on how you plan to get there; don’t just assume what they need.

Put a timeline in your proposal for draft reviews to keep everyone on schedule. You can avoid total re-writes and scope creep by checking in regularly. If your client is late responding to you, you cannot be expected to hit prior delivery deadlines, and it’s completely professional to send them a gentle reminder about how deadlines will shift if they can’t get you materials or answers you need.

Circle 2 Lust

Dante describes his second circle as the final destination for anyone controlled by their libido, a place battered by unceasing wind.

From a writer’s perspective, this is where a client or editor finally gets back to you about your work and says something like, “It’s okay… but we need something edgier and more exciting to appeal to Gen Zs and millennials.”

You can expect this place to be full of panicked marketing execs and digital magazine editors trying to communicate with hormone-fueled teenagers, social media influencers, and reality television stars.

So, how do you head this off?

Much the same way you stay out of limbo… good communication right from the start.

Keep in mind, sometimes a client may not grasp what they want until they actually see a draft of their ideas and realize it isn’t what they imagined. This is where the aforementioned project scope can grow into endless rewrites, if you aren’t careful. Remember to discuss and put into your agreement the number of rewrites you will do for one fee.

If you turn in a draft, and the client realizes it isn’t what they hoped for, have a frank conversation about how your draft lines up with the original ideas discussed, and what changes the client would like to see in the first revision. Often, you’ll find after a discussion, the changes aren’t as big as they seemed at first blush.

If you have doubts about your compatibility with a client, consider working on a trial assignment before entering into a long-term contract or retainer.

Circle 3 – Gluttony

This wintry circle is dedicated to those who want everything, even if they haven’t read the menu and don’t care whether or not it’s good for them. 

These lost souls possess a huge appetite, a fear of missing out (FOMO), and a big budget. They create a never-ending workload that rolls out like an opulent buffet, the likes of which are found only in the high-rollers’ dining rooms in the swankiest Vegas resorts.

To be fair, many copywriters attempt grabbing onto this brass ring. It’s tempting… that never-ending line-up of work and all manner of project types. Rather than admitting we aren’t experts at everything and referring out, we can end up over our heads and gasping for air.

We are often tempted to say yes to any job we are offered.

That’s good advice, if you can be mentored or learn the necessary skills quickly enough to do a good job for the client. If not, referring out to someone who will return the favor down the road is not a failure – it’s a smart business decision! Or, better yet, strike an agreement to work with a more experienced writer and gain the knowledge doing the actual work. Win win!

Circle 4 – Greed

This circle of Hell is reserved for the frugal yet materialistic. It’s similar to the gluttony circle – except the food’s not as good. 

These souls also want everything, but would rather not compensate you for it. If playing cops and robbers forever in the way of endless proposals, change orders, and bartering sounds like your idea of a good time, then the fourth circle would be Nirvana.

Go into every discovery call with a mindset of curiosity…

…not with a “this client is make or break” attitude. Accept only a fair rate for your work. And insist on 50% before you begin. This alleviates clients from getting off on the wrong foot or losing talented writers, and writers from feeling bitter before they even begin. The only exception is if you are offering your services to get a foot in the door while you learn, gain writing samples, references, or something else of value in the transaction.

Circle 5 – Wrath

After going through Gluttony and Greed, a writer can end up in the next circle, reserved for those filled with wrath. If you’ve been burned by a client – and again, this is rare – you may find yourself desperately trying not to become disillusioned and succumb to burnout. Sadly, by the time you arrive here, you can find yourself oddly triggered when a prospect asks how you came up with your pricing schedule.

This misplaced anger may surface at odd times and seriously derail a Zoom meeting, when attendees notice your hair standing on end, veins popping out of your forehead, and your eyeball twitching at any question of your fees.

Dante tells us wrathful souls spend eternity waging battle on the River Styx. For copywriters, it’s over weak coffee and leftover donuts in the conference room.

If a particular client or their work demands feels like torture, know when to call it quits.

You may be fond of the client, but can’t stomach something else about their business. Perhaps pollutants are involved in making their product. Maybe they hate puppies. Whatever the reason, this is your opportunity to create your ideal work/life balance, which is likely why you became a writer in the first place.

You should feel good about the work you’re doing, the product you’re supporting, and the way the client treats you. Writers and clients should go together like cookies and milk! Or, perhaps wine and cheese. They do exist, and once you find that pairing, your outlook and your output will soar.

Circle 6 – Heresy

Here, heretics spend eternity entombed in flaming crypts.

In the world of writing, this translates to pitching ideas that are bold, out of the box, creative, and non-trendy, then being told they’re too unorthodox. Until… a CEO loves one of them, and suddenly you’re a “god.” 

There are more play-it-safe companies out there than risk takers. If you have bold ideas, this can feel discouraging. But, it doesn’t have to be… you can go into every conversation with a big, bold idea and then a more conventional one as a back-up.

The key is, don’t be afraid to be creative and speak up.

Bringing fresh ideas to the table is what clients pay you for. Even if some of them get shot down, you only need one golden egg to find yourself working on an exciting project… and to make a name for yourself within your industry.

Circle 7 – Violence

This level is composed of three rings and is occupied by some very sketchy people. Suffice it to say, most have committed heinous crimes and landed here for punishment amidst burning sand, termites, blood and fire. Oh my!

Typically, the most violent a writer gets is when we have to kill off our perfect copy that was created in a labor of love. But this is part of the process, and better you do it than your client.

Learning how to “kill your darlings” is a necessary skill.

Doing away with that perfect sentence, paragraph or metaphor can be painful. On the bright side, being required to edit your own work to meet specific parameters will only make you stronger in the long run in working with other editors and clients.

Circle 8 – Fraud

person using laptop computers
Photo by Jefferson Santos

Apparently all sorts of con artists lounge around in ditches here. Picture a communal office where fraudsters make phone calls to the elderly and hackers try to break into your bank accounts. Fallen writers compose the scripts for these insidious calls and phishing emails.

Other copywriters can land here by failing to follow best practices, not doing proper research, source checking, or the worst sin of all, participating in downright plagiarism.

The solution here is obvious as just stated. Do your homework.

When writing, get your facts straight, and give credit where credit is due, and you won’t have any problems. Writers who cut corners and don’t follow an ethical path will not enjoy the longevity you will. When considering taking on a client, make sure they’re on the up and up. Do some looking to see what their customers have to say about them and their products. You don’t want to take on a project only to discover it’s part of a scam.

Circle 9 – Treachery

The final circle of Hell is an icy tundra where Satan is held in bondage and the world’s worst traitors mingle. Sort of like Washington, DC, depending on the time of year.

This is where you have a wonderful, lengthy discovery call, and expect to gain a new client and hefty retainer. Instead, you find your ideas have been written up and implemented by someone else – leaving you with no credit and no paycheck. (Again… not a common occurrence.)

This is where longevity comes in.

Writers and clients who work in this manner will eventually build a bad reputation. Vetting on both sides is important:  Do your research and get your referrals. It’s always a good idea to enter into any partnership with eyes wide open.

We have come to the end of our epic journey on how to avoid finding ourselves in copywriting Hell. Use these lessons to forge ahead without getting singed. Good luck, Godspeed, and remember to keep a fire extinguisher on hand.