A tale of two copywriters

Nov 7, 2023

Those of you who are familiar with the famous “A Tale of Two Young Men” letter written decades ago to sell a record-breaking number of Wall Street Journal subscriptions will recognize today’s subject line.

(I left out the “young” and “men” because I wanted to cast a wider net and include everyone who’s a copywriter.)

The inspiration for that subject line–and today’s issue–comes from some of the answers I got to my recent Business Development Survey I sent out a few weeks ago.

Side note: I’m writing this issue in the early morning hours before our electric power is supposed to be switched off for the day. So I’m going fast to get as much finished as possible. Please excuse any more than the usual number of typos!

In any case, looking back at the responses again last night, I was struck by something.

It’s like anything in business–or in life. If you want to succeed at something, look to see what those who are succeeding at it are doing.

Let’s take a look at the differences in approaches, using that Wall Street Journal letter I referenced as a model…

A Tale of Two Copywriters

On a beautiful fall afternoon twenty-five years ago, two aspiring copywriters hung up their shingle and decided to go freelance. They were very much alike, these two copywriters.

Both of them felt confident about their writing skills. They had read all the classic books on copywriting and direct marketing. They had studied the most successful promos ever written and gleaned as many insights as they could from them.

What’s more, both were highly motivated to succeed as copywriters. They desired the high earning potential that could be achieved, and craved the freedom and flexibility that would come with it.

Recently, these two copywriters met at a 25th reunion of the Copy Chief Live event where they had first met.

They were still very much alike.

Both were still freelance copywriters. Both had been able to avoid working full-time for someone else… take time off when they wanted to… and use their copywriting skills to earn a living for themselves and their families.

But there was a difference. One of them was still experiencing the dreaded “feast or famine” cycle when it came to landing clients and keeping income coming in.

The other consistently bringing in more work than they could possibly handle–all high-quality clients who were happy to pay their fees and even royalties. This copywriter was typically booked several months ahead of time, and each year had seen their earnings increase.

Okay, let’s break away from the Wall Street Journal letter model (somewhat) and take a look at…

What Made the Difference

For most–not all–of my freelance copywriting career, the latter copywriter could have been me. But I’m not talking about myself.

I’m talking about one of the respondents to my recent Business Development survey.

Here’s what this copywriter wrote as their answer to the question about where they were struggling the most in finding clients:

“Honestly, finding new clients has come almost embarrassingly easy for me. I started my copywriting career as a [name withheld] copy cub, which has opened endless doors of opportunity. And I’ve never burned a bridge. When I work for a client, I reach out to other copywriters on the team. I get to know them and even help them where I can. And over the years, I’ve developed a network of connections throughout the alternative health and financial publishing industries. I’ve been blessed to never lack for work.”

Meanwhile, I received many responses to the same question from other copywriters similar to the ones below:

“I’ve been struggling with consistently getting better projects that allow me to practice my skills and get the best possible feedback.”

“No clue where to find them.”

“I’ve been struggling the most in finding potential companies and brands, especially those heavily focused on direct response marketing, to reach out to.”

“Getting a response. Was doing cold outreach, but gave up. Been told to f$@k off enough times that I decided to go after hot, or at the very least, warm leads on job boards.”

Seriously–the behavior referenced in that last sentence is over the line. Obviously you don’t want to harass potential clients. But if someone is that unprofessional, you don’t want to work with them anyway, even if you need the $.

So let’s look at the lessons we can learn from that first copywriter’s answer. Many of them are ones I cover in my new book, Client Badassery Secrets, which you get at the Amazon U.S. link here, or can now find on other booksellers’ websites.

#1: Mentor or learn from a top copywriter. When you are ready–meaning, you’ve gained at least some experience writing sales copy, have gone through all the books and courses, and have already studied many successful promos–learning from a top copywriter first-hand can be a game-changer.

Whether it’s investing in a mentor, gaining a mentor by working at a top direct response company or fast-growing business, or becoming a “copy cub” in exchange for ongoing work can be a HUGE needle-mover in your copywriting career. Hands down.

Obviously though, these opportunities are few and far between. And many can be outside your reach if you don’t have the money to invest or face other barriers. So let’s look at what else you can do based on that first copywriter’s answer…

#2: Never burn a bridge. Sometimes things won’t go well with a client (trust me, it happens to all of us). Sometimes the promo or email series you wrote won’t work. Sometimes you’re so fed up with the company you’re working for you quit without giving notice or otherwise leave on a bad note before going freelance.

One of the most universal lessons in business is to never burn bridges. Always deal with clients (and employers) in a professional manner. Don’t shoot off that angry email response because it makes you feel better in the moment. Meet your project deadlines. Do the best possible work you can.

And if a project goes awry or a promo bombs, reach out to the client to figure out what went wrong and try to fix it. Some of my most successful control promos with top clients came after the initial effort didn’t work.

I was able to come back the second time around with a huge winner, because they gave me a second chance. And the reason they gave me that second chance is I didn’t burn any bridges.

I also left my previous employer during a difficult time in my career (I had been “mommy-tracked” after coming back to work after having my first child). But I never went around bad-mouthing my employer, and when I left to go freelance I gave ample notice and thanked my past bosses for the opportunity to work there.

Once I left, I got nearly 90% of my initial clients the first few years as a result of referrals from my former co-workers, some of whom had also left to work for other companies.

#3: Get to know the people you work with on the client side, and build your network in other ways as well. When you’re working with a client, many times you’ll dealing with multiple people on their team.

Build a relationship with these people, just as you would your client. Even if they have a seemingly-lowly job title, treat them with the same respect as you would their boss.

Because they’ll eventually climb the company ladder, or leave to work for someone else. And they could be a great referral source for you. Plus, it’s just what decent people do. (Don’t be an a-hole even if you think you’re hot sh*t!)

The same is true for continuing to build your network outside of clients you work for. Networking with other copywriters can be just as valuable if not more valuable than constantly trolling for clients.

That’s because other copywriters may have potential clients come to them when they’re too busy to take them on, or it’s not an area of expertise they have. But if they know you’re taking on overflow work, or have that area of expertise, they’ll likely send those clients your way.

Hopefully looking at the differences between a copywriter with an “embarrassing” number of potential clients coming their way, and those who are struggling, has been eye-opening.

I’m going to wrap this up now since my power could be going off any minute. But I’ll be back at you with more client-finding insights in the weeks ahead.

In the meantime,  go to the Amazon link here and get my Client Badassery Secrets book into your hot little hands… or the new e-book on your Kindle… for dozens more tips and tactics.

Yours for smarter marketing,


P.S. One quick tip I want to share here because it’s super-timely. If you’re looking to raise your rates, but aren’t sure how to do it without potentially losing clients…

…or you’re looking for a way to bring in more cash right now by reactivating past clients…

It’s the perfect time of year to have what we used to call in the publishing business a “price rise campaign”.

Let your current and past clients know that due to rising inflation, you’ll be forced to raise your fees in 2024.

But give them a chance to “beat the coming price rise” by booking you now for a project.

And obviously, make sure part of your booking process involves getting that 50% advance in your pocket in order to book a slot in your schedule.

You can also use “rising inflation” to re-negotiate an ongoing retainer arrangement you have with a client.

Or to negotiate a salary increase if you work for a company.

And if you haven’t raised your rates in way too long, this gives you the perfect excuse.

You’ll find other hard-won secrets and insights about everything from starting out as a freelancer, negotiating royalties and better-paying deals, and dealing with nightmare clients… to being the “hot girl (or guy) at the bar”, making the move to in-house or full-time 1099 employee, and much more.

Plus you’ll get access to my free Client Screening Questionnaire and Sales Call Script, plus my Client Badassery Manifesto… all included in the “Client Badassery Secrets Tool Kit” you’ll find details on how to get at the beginning of my book.

Go here to get my Client Badassery Secrets book on Amazon now for a fraction of the value it can bring you if you implement just one of the hundreds of tips and tactics you’ll discover.