Ode to sh*tty clients

Jan 20, 2023

Yesterday I had my first mentoring session with one of my new copy mentees, who’s fairly new to copywriting.

I also had a great interview with Troy Ericson for his “Secrets of Scale” podcast. (I’ll share it when it goes live.)

Even though both conversations were quite different, they had a lot of common themes.

In both cases, I shared how I got started with my freelance career… how I approach working with clients… and how that’s helped me achieve what I wanted.

And here’s what I realized…

Mindset is a HUGE part of “making it” as a freelance copywriter, or really anything you do.

You can KNOW all the right tactics… get all the right “templates” for running your business… and understand all the right “do’s” and “don’ts” for finding and closing clients, etc.

But being able to implement these tactics and apply them regularly and effectively to your business requires confidence and the right mindset.

Many of us find it hard to feel confident when we’re just starting out. Heck, I know people who’ve been reasonably successful copywriters for years who still struggle with it.

I had some advantages coming into this freelance game which gave me an edge in the “confidence” department, which I’ll share in a moment.

But a lot of my mindset “wins” that have allowed me to consistently charge higher fees, make profitable royalty and performance-based pay deals, and steer clear of clients when I see their “red flags” a-waving resulted from one thing:


Also known as “the school of hard knocks”. Hence the subject line for today’s issue.

I’ve learned so many valuable lessons from the sh*tty clients I’ve worked with… and the ones I’ve avoided…

They’ve given me the battle-tested confidence required to hold firm to my principles, set needed boundaries, and never compromise on expectations I set.

And they’ve helped me help thousands of Copy Insiders like you, Kim, as well as those who I’ve personally mentored.

Today’s topic reminds me of a conversation I had with a copywriter friend years ago. We thought it’d be great if there was a database of f*ckwad clients to avoid (this goes doubly true for those to avoid going exclusive with or working for).

Never got around to doing that… but I have achieved expert-level status on recognizing client “red flags”. (I get into some these and other hard-won wisdom in my Client Badassery Secrets e-book, which you can get for half-off here.)

So let’s talk about a few takeaways that my sh*tty clients and almost-clients have taught me over the years…

Sh*tty Client Lesson #1: Be short and specific in your proposals.

Let’s say you’re on a call with a prospective client. You talk about their business and various areas where they need help. You then end the call by saying you’ll forward them a proposal.

(Note: That part’s a smart move versus feeling like you need to give them a price quote right then and there… generally that’s not a good idea. You want time to think it over first, because once you say a price out loud they’ll hang onto it like a dog with a bone.)

Here’s a common mistake freelancers make: they want to demonstrate how knowledgeable they are. So they give away the store for free by outlining a complete strategy and then what they would charge for each component.

This not only gives away your valuable knowledge for free, it overwhelms the client. They don’t know where to begin. You want to make it super clear for them.

Narrow down your initial conversation at the end of your call to one or two specific deliverables that are the highest priority. Then tell them that’s what you’ll send them a proposal on.

And then your “proposal” can simply be a few sentences, perhaps in an email. Tell them “3 emails for $X,XXX” or whatever… don’t tell them exactly what approach you’d take with each email or load them up with other details.

Then, if they accept your pricing, you forward your agreement with all of your terms outlined. But keep it simple and straightforward. You want to close that specific starter project, do a good job for them, and go from there.

Remember: Walk before you run. (You can even use this phrase with your prospective client). This can save you from other issues, like going in too “deep” with a new client before you realize “Egads… I wish I hadn’t signed up for all this!”

Another reason not to outline an entire strategy in your proposal: the client may decide not to hire you and do it themselves instead. This happened to me once early in my freelance copywriting career.

I was eager to show off all I knew about back-end retention marketing for the Healthy Directions supplement business I launched and ran before going freelance. I got on a call with a publisher that had just launched a similar supplement business, then forwarded a proposal for a retention back-end.

I told them the proposed timing of each effort, offer, etc. I basically handed it to them on a silver platter for nothing. And what did I get in return? Screwed.

“We’ve decided to go ahead and do this ourselves.” I got burned and learned.

(I’m holding back on naming names here… it was a few decades ago after all! But it still happens ALL.THE.TIME. So beware.)

Sh*tty Client Lesson #2: YOU set the rules and boundaries for how you work… not the client!

You probably have heard me and others tell you the “rules” for running your business. For example, you likely know you should ask for a 50% advance and receive it before starting work.

But all too often, new-ish (and even old-ish) freelancers get coaxed into starting on a project before getting that advance. In some cases, it’s because it’s a tight deadline. Or it’s because you didn’t have the guts to ask for one in the first place!

Don’t kick yourself… I see this all the time.

But having been on both sides of the client equation, I know that a client’s priorities can shift… or there’s some kind of lengthy management approval process that can grind on forever… or their accounting department has some kind of archaic rule about using only 30-day payment terms (I find the bigger the company, the more common this is!)

I’ve always held firm that I will not start work (or hold time in my schedule) until that 50% advance is safely in my bank account. In some cases (like copy reviews and consulting), I require 100% upfront. Because I’ve seen too many times when a project is a “go”, and suddenly it’s not.

Think about it… would you expect that a contractor you hire to remodel your kitchen would go get all the supplies needed, start the demolition, and begin work without receiving an advance payment? I think not! (Though I do think once they start demolishing your existing kitchen, they have some leverage.)

See yourself as the professional you are and set the right rules and boundaries for your business. Your clients will respect you far more from the outset, leading to a better working relationship. And you’ll let the “trash take itself out” when it comes to avoiding problem clients.

The same is true for other rules and boundaries you create for your business, like using a contract. But let’s move on to the next lesson I want to share today…

Sh*tty Client Lesson #3: Just because you fail doesn’t make you a loser!

I mentioned earlier that I got into this freelance copywriting game with perhaps more confidence than others might.

It was because I’d already had a successful 13-year marketing career: running a supplement subsidiary and growing it to the equivalent of $40 million in sales in the first 3 years… working as a publisher with people like Jay Abraham and Denis Waitley… and growing a direct-to-consumer health insurance business into the most profitable division of a major insurance company.

So when I took the leap to freelancing and walked away voluntarily (after finding myself “mommy-tracked” after having my first child) from a six-figure base salary, I figured worst-case scenario I could always get another job.

But I wanted the freedom and flexibility–and the higher earnings–that freelancing would give me. So I used a six-month retainer arrangement that paid me 90% of what I’d been making in exchange for 50% of my time as a bridge… and then took on other clients from there, earning 50% more my first year as a freelancer!

My point here, though, is why I felt confident I could do this when I’d never worked as a copywriter before. I’d certainly written copy as part of my various marketing jobs or been the person overseeing it (I’m sure my former employees still have nightmares about my red ink-marked up pages landing on their desks).

But I also knew that even the best copywriters failed at times. My former employer worked with the creme de la creme copywriters–I’m talking people like Clayton Makepeace, Jim Rutz, Gary Bencivenga, and Gene Schwartz… and others who were more “up and coming” at the time like Doug D’Anna, Parris Lampropolus, and David Deutsch (yes, I was the client on some projects with those last three!)

And because no one knows exactly what copy will work best (yes, not even AI!), it’s always a judgement call when it comes to testing. You have to go outside the box at times to get a big winner. And sometimes, these out-of-the-box (or even inside-the-box) promo tests would fail miserably.

Did that mean these copywriters were failures? Hellz, no! In fact, the president of our consumer division, Bob King, used to say: “If you’re not failing enough, you’re not trying enough new things”.

I personally saw how that philosophy empowered the entire team to grow that company exponentially over the six years I was there. And later saw how a new management team that took over shrunk the company considerably and hamstrung its growth prospects by insisting on a different philosophy: “Let’s just keep doing what we know works.”

This is practically a whole other Copy Insiders issue, but some of my first initial “big breaks” writing long-form copy with royalty potential were either complete bombs or near misses.

But the clients I worked with were smart enough to give me a second try, either hiring me for a whole new project or testing a new headline/lead in the case of a near-miss.

The result? Here’s a small sampling from early in my copywriting career…

  • A 10-year control for a joint supplement that paid me hundreds of thousands in royalties (and made millions for my client).
  • A promo that beat Parris Lampropoulus’ “unbeatable” 7-year control that made me the first female copywriter to get a Boardroom control.
  • And a widely-imitated financial newsletter promo that beat the late Jim Rutz’s control not just once, but twice.

If you’re working with a small-minded or overly risk-averse client, they’re not going to be able to handle the fact that direct response copy is not a 100% guaranteed venture.

NEVER guarantee that your copy will work. There are way too many uncontrollable and unknown factors that have nothing to do with your copy.

Remember the “40/40/20” rule: the success of any promotion is based on 40% “list” (who it’s going to), 40% “offer” (the product or service itself and the pricing), and only 20% “creative” (which includes design and format as well as copy).

So your copy is just a tiny part of the equation–but a crucial needle-mover in today’s ultra-competitive niches!

And if your copy doesn’t work, figure out why it didn’t… and see if you can get a second try. Because often, that second try is what hits it out of the ballpark!

I’m going to be doing a whole series of emails next week about how developing the right mindset can help you attract better clients, negotiate better deals, and minimize client hassles.

Many of these mindset lessons you can also apply to running your own business, managing your boss if you have a J-O-B, or even to your personal relationships.

So keep an eye out… and please share the Copy Insider “love” with others you think would enjoy reading this. Send your fellow copywriter friends here: www.copyinsiders.com. They’ll get that fabulous copy checklist you got when you signed up, too!

There’s also some great conversations happening on social media regarding my recent posts on the “3 big lies clients tell you”. I invite you to join us and “like” my posts and/or better yet, share your thoughts and experiences in the comments.

Read my latest “client lies” posts and follow me on LinkedIn here… on my Facebook page here… (note: I don’t accept friend requests for my personal Facebook stuff unless I know you in real life… that’s my boundary there)… and on Instagram here.

And if you don’t already have my Client Badassery Secrets e-book, you can get it here for half off.

I’ll be taking a bit of a breather over the next few days…I’m  working on my sh*tty first draft of my first-ever screenplay, and hoping to make some good progress.

And I’ve got some other good things I’m cooking up that you can benefit from in the coming months.

So I’ll be back at you next week to give you some more mindset-shifting breakthroughs!

In the meantime, don’t forget to “share the love” so I can get even more Copy Insiders on board to benefit. And I hope to see you on social media, too.

Yours for smarter marketing,