Have you ever had a freelance gig go straight into the toilet?

Happens to all of us eventually.

In comedy, we call them “Hell Gigs”

And they’re kinda funny. Eventually.

I mean, it’s painful, believe me, to stand before a roomful of strangers, your voice amplified twelve times the natural volume, saying things everyone knows are supposed to be funny… 

… and feel pure disdain coming back at you. 

But “dying up there” is almost worth the stories you get to tell for years with other comics. 

We’ve all got ‘em. And nothing gets a group of comedians howling at the bar like a good “sliding down the steely pole of death” hell gig story.

In freelancing, hell gigs are not quite as funny.

First, because you typically suffer through them alone. 

Unlike comedy, there’s no group of other comics in the back of the room finding your misery hilarious, which is actually a strange bit of salvation in those moments. 

Just you, and the client (or their entire team), and a lot of passive-aggressive email messages with questioning tones and strained voices on unfortunate Zoom calls.

Nope. Nothing funny happening there. 

It can feel like the most serious thing that’s ever happened to you. As if your entire career is crashing down around you.

My last freelancing hell gig as a direct response copywriter was so bizarre and painful that I couldn’t talk about it for months without my left eye twitching. 

Things had started out well enough. 

I’d met the client at a small group mastermind. He was smart and seemed pretty dialed in. I found his product and market interesting and he’d written books on the subject, so a lot of the requirement boxes were checked.

Outside the coziness of the mastermind though, things changed pretty quickly.

I knew I was in trouble when halfway through the project my client screen shared to show me the current value of his country’s currency and said, in his thick Eastern European accent… 

“I need this to sell really big so I can afford to leave this country. Do you understand? This must be the best copy you’ve ever written, or I am in big trouble.”

Oh boy.

Things had gotten a little weird before then, but this moment confirmed my biggest fear… 

I was dealing with a desperate person
who had irrational goals for his campaign. 

Worse, early into the research, I realized he was selling an unvetted product in a niche where, although he had written books to a very different market… he was about the worst person you could need to sell as a trusted authority to his new chosen market.

He’d basically made up the product, could offer no proof or credibility of results, simply guessed this was a valuable niche for his made-up product, and believed that “killer copy” would be the salve for all of these fatal wounds. 

So many RED FLAGS!

How did I not see them sooner? 

I’d love to tell you this happened in the first years of my career. 

These are the kinds of scars we tend to earn in the first years of our freelancing careers. Torture to go through, but just like in comedy, fun to show off at the bar during conferences and compare with other copywriters…

“Oh yeah, lookattis one right here on my left cheek… MLM client, 2007. Brutal.”

“I have one just like that from a ClickBank client. Still flares up every time I sweat.”

“That’s nuthin’ (lifting eye patch)… got mauled by a rabid bizop client at JVZoo.”

(Collective gasp!)

However, THIS particular hell gig happened almost a decade into my career. 

And I have no valid excuse for getting into a crazy-ass situation like this. 

I saw all those giant red flags and still moved forward, HOPING for the best. 

So dumb.

My eye is twitching right now just remembering it. 

How did it end, you ask?

That’s the part that gets me. Because in the handful of other freelancing hell gigs I’ve endured, there’s usually a way to end it amicably. 

Like with a “healthy divorce” you both see the writing on the wall, both accept a level of responsibility, and agree on a way to end it without the other feeling angry or wronged. 

BTW, for that to happen, sometimes you’ll need to return the client’s money. If you see the Hell Gig warning signs very early on, the greatest feeling is to be able to say, “I’m sorry. I’ve come to realize we’re just not a good fit. I’m returning your deposit.”

And be done with it. 

The pride and relief you feel at that moment are incredible. 

It’s why you always want to keep a “f*ck you” fund equivalent to the price of a typical gig in the bank. 

Of course, you could sit and play the blame game, split hairs about who’s at fault, and spend a week bitching about it on Facebook… 

(which your peers love because it makes you look weak and they’re happy to point you out as an example of the kind of freelancer their prospect does NOT want to encounter)…

OR, you could take back control over your sanity, your reputation, and your career, by quietly and confidently ending the nightmare right there. 

In this bizarre Hell Gig though, things were beyond repair. We muscled through a first draft with what we’d been given, and he kept pushing for us to “sell harder”. 

After I voiced my concerns and asked over and over again for more proof, any kind of testimonial or case study, or some personal story that at least made it clear he had every reason to believe this product would produce results, he grew more and more irritated. 

It ended with him refusing to talk to me threatening to “expose” me as a fraud, and all kinds of other insane things that bordered on legit criminal stalking. 

It sucked. And it hurt. I’ve yet to find the funny in that one. 

There is always value in even the worst scenarios, however, because when we’re in this for the long haul, we know that one bad gig cannot ruin our careers. 

If we’re doing this right, following the Pro Code, and putting integrity above all else, our reputations will deflect the spears of the occasional bad decision. 

Best of all, because I now coach freelancers, I’ve been able to turn all my scars not just into warnings… but into tangible lessons for how to avoid Hell Gigs altogether.

I’ve created dozens of frameworks and even fill-in-the-blank-simple phone scripts for attracting the best kind of clients and repelling the worst kind. 

They’ve saved other freelancers in my Freelancer’s Journey Accelerator coaching from entering into nightmare scenarios, and ending them quickly when they do happen. 

The big lesson here is that you don’t have to go through life alone as a freelancer. 

And when seeking a mentor, ask to see their scars. 

The nastier the better. 

Click here to see where you are on the Freelancer’s Journey and how to avoid clients from hell.


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