Copywriting Lessons from Legendary Books

Although digital copywriting is relatively new, copywriting has been used for hundreds of years to sell products. Some of the best books on copywriting I have ever read were written decades ago. Some are even older than that. It’s a shame that they don’t get the attention they deserve—mainly because we often equate new with better.

But a lot of the new marketing and copywriting lessons and techniques you read about on blogs aren’t new at all. In this article, I’m going to break down seven lessons from the following four books:

In my mind, these four books have all achieved legendary status. Every section of each book is gold, which is why I encourage you to read them.

That being said, I’ve picked out some of the most important lessons that I think will apply to your online marketing and business. I’ll bring any dated advice into the 21st century with some current examples of it in action.

Let’s get started… 

1. You Should Read the Rest of This Article Because it’ll Make You a Better Copywriter

Animals instinctively react to certain noises in a specific way because more often than not, that action pays off.

It turns out that even though humans might be a little higher on the sophistication scale, they too have these automatic reactions.

Dr. Ellen Langer, a renowned social scientist, conducted a study in 1978 to find out how everyday people react to certain words. She had actors approach a line of people waiting to use a Xerox (copy) machine. She instructed them to use one of the following three sentences to try to get in front of the line:

  1. Request only: “Excuse me, I have five pages. May I use the Xerox machine?”
  2. Real information: “Excuse me, I have five pages.  May I use the Xerox machine because I’m in a rush?”
  3. Nonsense information: “Excuse me, I have five pages.  May I use the Xerox machine because I have to make copies?”

What do you think happened?

When no reason was given, 60% of people still allowed the actor to go ahead of them and use the Xerox machine. I’m a little surprised that it was that high.

What about when the actors said they were in a rush? Ninety-four percent of people let them go ahead.


So, clearly you just need to come up with a great reason and you can get what you want, right?

Not quite. The final line that the actors used produced some surprising results. An incredible 93% of people still let them skip ahead.

Go back and read the line they used (#3). Their reason for jumping the line was because they needed to make copies. Well of course they needed to make copies! Why else would they want to use the copy machine?

So what can we conclude about this? It turns out that people—when not paying close attention—often follow simple scripts, just like animals.

In this case, since the favor was fairly small, the people followed this script:

favor asked > reason given > comply

But there’s one thing I left out: another part of the experiment was making a larger request. The actors used the same lines but asked to copy 20 instead of five pages.

When they did this, the actors had the following success rates:

  • Request only: 24%
  • Real information: 42%
  • Nonsense information: 24%

In this case, the request was large enough to get people to consciously pay attention and evaluate the request. Since the last explanation was silly, it made no difference in people’s response rate compared to the request-only scenario.

Here’s the conclusion: When making a small request of readers, give any reason why they should do it.

For example:

  • Could you share this article on Twitter because I would like more people to see it?
  • You should read the rest of this because…(Hint: look at the headline for this section)
  • Please leave a comment below because I’d like to hear what you think.

Does that make sense?

Let’s look at using “because” in action.

I’ve noticed that Pat Flynn has used this in his post introductions in the past. For the long posts (asking more), he comes up with detailed (good) reasons why the reader should read:

If it was a shorter post, he could give a briefer and less convincing reason.

The reason why “because” works is because people like to have a reason for what they’re doing. It just seems logical.

You can use this concept in blog posts, landing pages, widgets, social media, or even in emails.

I took a look at Brian Dean’s latest sales page for his course. He used the word “because” a whopping 17 times:

Does it have to be “because”? I know you’re thinking it, and it’s a great question. That original experiment only tested the word “because,” but the conclusion shows that the word doesn’t really matter.

It’s the principle that matters.

For small requests, as long as you provide a reason (any reason), readers will be more likely to comply.

2. Your Product Matters More Than Your Talent

Have you ever heard the phrase “He could sell ice to an Eskimo!”

It’s often used to describe the perfect salesman: the guy who could sell someone something that they don’t need.

If there was one lesson from Scientific Advertising that you should take to heart (there are many), it’s this:

The main reason for a lack of success from advertising is selling people what they do not want.

If your conversion isn’t good, chances are it’s not because you’re not an expert salesman.

Sure, being good at selling will help you maximize your conversion rate, but the main factor behind your conversion rate is the value you provide.

So why does this matter to you and your business?

The next time you see that your conversion rates aren’t great, take a hard look at your offer.

You don’t need to read more blog posts about the latest tips and techniques to make a great landing page. You need to learn more about your visitors. This goes for anything, not just a landing page. If you’re trying to get visitors to click something, watch something, sign up for something… anything that requires them to give up something valuable (email address, money, a lot of time), you need to provide value.

If people aren’t signing up for your email list, instead of trying a different color button, try a different lead magnet. The more your visitors want it, the higher your conversion rate will be.

Is learning about selling and CRO pointless? Don’t get me wrong, I’m not saying that CRO and sales techniques are useless, but they are a much smaller part of the puzzle than the value you provide.

You’ll be better off:

  1. knowing exactly whom you’re targeting (Hint: build a buyer persona)
  2. testing different offers (find out what they value)

After you’ve done that and achieved a solid conversion rate, then start split testing your headlines, copy, and buttons.

3. Successful Marketing is Not Guesswork

Another lesson from Scientific Advertising I wanted to include in this post is this:

Successful marketing does not involve guessing. Ever.

It sounds simple, but many “marketers” spout BS about their results without ever measuring the impact of their work.

Let me share a few stats with you…

Almost 80% of marketers do not directly track their email ROI. That’s shocking. Email marketing is one of the easier types of marketing to track.

A study found that only 44% of companies are able to measure paid search ROI effectively.

That just gives you an indication of how much low-quality work is out there. If traffic goes up over a few months, how do you know you had anything to do with it if you didn’t track it? You don’t.

If you don’t track your ROI, you could be throwing money down the drain by pursuing marketing methods that don’t produce tangible results while missing real opportunities.

Step 1: Start Tracking

If you’re a marketer, you should be tracking everything you do on a client’s or your company’s site. If you’re a site owner, this would be a good time to start.

Having too much data is better than not having enough.

What do you need to track?

At the very minimum, you need to track:

That’s it. You can do that with free software such as Google Analytics, or you can get a little more advanced with other providers like KISSmetrics.

But what about referral traffic, search engine traffic, click-through rate on ads, etc.?

The answer is that you sometimes need to track them, and it’s usually a good idea to track them all the time. It really depends on your focus. If 95% of your conversions come from PPC ads, then search engine traffic isn’t a big concern. The good news is that most of this data is collected automatically by your analytics software or ad platform.

Step 2: Determine Marketing ROI

Return on investment is a simple concept. You can calculate it with a simple formula:

ROI = ($ of profit)/($ of cost) * 100%

If you’re tracking your ad spend, content cost, or whatever your marketing campaign consists of, figuring out the cost is easy. Assuming you’re tracking your sales correctly through your analytics software, it’s also fairly easy to see which sales came from your campaign.

A marketing ROI of 5-10% is your goal, but if you’re able to exceed that, you’re doing great.

Step 3: Revise Marketing Strategy Based on ROI

The results of a marketing campaign will tell you if you need to adjust your marketing strategy. If you break even on your ROI, you can usually continue the campaign. Once you optimize it, you can typically achieve profitability.

If you get a negative ROI, your time and resources are probably better spent on other marketing tactics. Re-adjust your overall marketing strategy to reflect this.

4. Commit Your Prospect to Buying

Are you a hypocrite?

Ask anyone, and they will tell you: “Of course, not!”

Which is strange when you consider that hypocrites are everywhere. In fact, most people (including myself) can point out an instance when their behavior might have been hypocritical.

So, what does this all mean? It means that sometimes people behave like hypocrites without even realizing it. But if you brought their beliefs to their attention right before that potential hypocritical action, they wouldn’t take that action.

This is a principle called consistency, explained in Cialdini’s Influence.

People like to act consistently with their principles and beliefs.

And it makes sense. The reason why we believe in and value things is because we think we’re right—we think we know what’s logical and important. So, of course, we’re going to try to act consistently with those principles and beliefs whenever we get the chance.

Use consistency in your copy: Before you ask a reader to do anything (share, answer, purchase), mention a related principle or belief. Sometimes you don’t even need to mention it explicitly. All you need to do is frame your request in terms of that principle or belief.

This is a lesson that I’ve seen many bloggers pick up on fairly recently, particularly in pop-ups.

For example, if you go to ConversionXL, you get the following pop-up:

If you’re at the blog, it’s because you’re interested in learning about optimization from some of the best pros on the topic.

It’s easy to brush off most pop-ups, but when you actually have to choose: “No, I prefer to suck at optimization,” it changes things. To choose that option, you’d have to act against your primary motivation.

Of course, exiting the pop-up doesn’t mean you suck at optimization, but this phrase alone will help the site collect an extra percent or two of its visitors’ email addresses.

5. ALL People Care about These 8 Things

Humans are complicated, right?

Everyone’s their own special snowflake, right?

Not quite.

Although each of us is unique in some way, we share many of the same traits.

In Cashvertising, Whitman lists the “life force 8”, which are 8 motivations of all people. At our core, we’re driven by the same things, and you can use that to write better copy.

Here are the life force 8 motivations:

  1. Survival, enjoyment of life, life extension
  2. Enjoyment of food and beverages
  3. Freedom from fear, pain, and danger
  4. Sexual companionship
  5. Comfortable living conditions
  6. To be superior, winning, keeping up with the Jones
  7. Care and protection of loved ones
  8. Social approval

We’ve known for a long time that people buy based on emotion, not logic.

If you can relate your product to any of the life force 8 factors, you can stir up emotions in your reader that will help you improve your sales and conversion rates.

I’m going to break down each of the life force 8 motivations and give you examples of how you can use them in your marketing.

1. Survival comes first: Unless someone has a mental health issue, they will do almost anything to survive.

You might have heard of or seen the movie 127 Hours. It’s based on Aron Ralston’s real-life adventure. He was exploring a canyon in Utah when he slipped and his arm became trapped between a boulder and a wall.

After exhausting all possibilities and unable to free himself, Ralston thought he was going to die. But he didn’t. Ralston amputated his own arm with a dull blade.

People will go to great lengths to survive.

If you have a product that could potentially save someone’s life, show it. If you can get a visitor to see themselves in a dangerous situation, you’ll make your sale much easier.

In one article on the Home Security Superstore website, the author writes about how pepper spray can be used to protect oneself:

Our first example today is from San Diego where a man grabbed a female pedestrian from a local roadside and sexually assaulted her until she pepper sprayed him and broke free. The assailant jumped the woman as she was leaving her car. After she sprayed him he let her go and ran off.

If you’re a guy, you might not understand how much of a common fear this is. In big cities, particularly in certain areas, assault of any kind is a serious risk for (typically) smaller women.

Every time a woman reads the above passage, it brings her very real fear to life.

They soon get to the end of the article, which has multiple links to products and reviews on the site:

Guess what most readers will do now?

If you guessed go to the store and check out pepper sprays, you’re right.

I think a short video illustration would be even more effective. The more “real” you can make it seem, the more emotional your reader will be.

2. Food is an easy sell: We are wired to like food. It’s not surprising that as food has become easier to get and more reliable to produce, people have gotten more obese.

If you have a delicious food product, you should have a pretty easy time selling it.

Describe the flavor and experience of eating your product, and people will be ready to buy it in an instant. Pictures or video will make it easy for people to imagine the taste.

Even though pizza commercials haven’t changed much in decades, they still work. All they need to do is show a few different types of pizzas, and the goal is accomplished.

For example:

Are you hungry now?

However, you can easily apply this offline as well. If you do marketing for a bakery, offer free samples to people walking by. After one bite, most people won’t be able to resist walking inside and buying something. This is a big part of many big bakery chains’ marketing plans.

Finally, don’t be afraid to associate your product with food. Food will get your visitors’ attention, and if you can convince them that your product will make their meal better, they’ll buy. You can sell, for example, cookware, dishware, furniture, TVs (to watch while eating), etc.

3. No one likes fear or pain: People go to great lengths to avoid pain, and fear is just an extension of pain. Being afraid is natural when you think something bad is about to happen.

Don’t make the mistake of thinking that fears and pains are based on physical problems—just as many are mental.

Again, anything you can do to clarify fears and pains and then show how your product can relieve them will help sales.

Take Logitech for example. They know most parents fear leaving their children with babysitters, even those they trust. That’s why they market their home security cameras by speaking directly to this fear.

4. No one wants to be alone: If you’ve ever stepped foot into an Internet marketing forum, you know how popular the dating niche is. Online dating is a $2.1 billion industry.

Although most products don’t directly help people find a partner, many help indirectly. Think about products and services such as:

  • clothes
  • gyms/fitness classes
  • personal trainers
  • cosmetics
  • flower shops

Basically, any product that can be framed as a tool to help you appear more appealing to the opposite sex will awaken an emotional response.

When you see an advertisement for a gym, do you see overweight, unfit people in it? No, you see attractive models, and you feel the desire to look like them.

5. Comfort is underrated: “Comfortable living conditions” is what Whitman calls it, but I like to think of it more as a lack of stress.

Think about a time where you weren’t sure how you were going to pay rent or worried that you were going to be laid off. These are extremely stressful and worrying times. And during those times, you would have given anything to know that your bills were taken care of and that you had a steady income.

If your product helps solve a problem for people in uncomfortable situations, show it.

This is really what the insurance industry is all about. They portray their products to make you feel anxious if you don’t have them.

6. People like to win: Even though we might try not to, we constantly compare ourselves to others. We look at others to see:

  • how much money they make
  • how big their house is
  • how happy they are
  • and so on…

This is one of the biggest factors behind word-of-mouth marketing.

It’s one of the hardest emotional drivers to market to, but it can be done if you have a “high status” product.

Essentially, you need to create a product or brand that, when seen, will make others envious and cause them to want to purchase it.

Apple has done this extremely well by making electronics that are slightly more expensive than those of competitors’ but with a great look.

Everyone knows that Apple products are stylish, which is why people stand in massive lines for each product release. People want the latest product that puts them ahead of the curve.

7. We protect one another: Just as we don’t want to be alone, we also don’t want those close to us to be taken away from us or hurt.

One way of marketing your product is to tie it to the happiness of others.

In the weeks leading up to all major consumer holidays, including Valentine’s Day, companies frame their products as a way for you to show the people in your life you care about them.

8. People just want to be accepted: Yes, people want to be loved and to find a mate, but they also just want to be accepted and liked by others.

You can tap into this by marketing your product as a way for your site visitors to fit in with others or become part of a tight-knit group.

One great example of this is Tough Mudder. It’s a company that puts on insane obstacle courses. People run through water and mud, and over massive obstacles. But the real appeal is the comradery.

The event requires you to sign up and complete the challenge as a team.

In essence, the company is offering an experience that makes you think along the lines of:

“Yes, I’m paying for something that’s grueling, painful, and unpleasant. But we’re doing it together, so it’ll be fun. We’ll help each other, suffer together, and celebrate in the end together.”

6. Simplicity Always Wins

The hardest thing for most marketers to understand is that your visitors don’t have the same level of knowledge as you do.

You’ve likely spent years reading about marketing and learning about your product or service. This makes it really easy to talk over the head of your visitors.

The problem is that if a visitor can’t understand what you’re offering, they won’t buy.

Whitman summarizes the 4 concepts of successful simple writing in Cashvertising. Here’s my take on them:

  1. Use short, simple words. There’s no need for fancy, rarely used words. Whitman recommends writing at a 5th-grade reading level. I actually write at just below a 4th-grade level. You can test your writing level by pasting some of your writing into this online calculator.
  2. The shorter your sentences, the better. I rarely write long sentences because that’s when they get confusing. Try to limit sentences to 10-15 words.
  3. The short, short paragraph trick. Whitman correctly advises limiting regular paragraphs to 4-5 short sentences. Having even fewer is better. Most of my paragraphs consist of 1-2 sentences, which makes skimming easier.
  4. Pile on personal pronouns (e.g., I, you, me, he, she, him, they, them, etc.). Writing in a conversational tone helps you connect with your readers. It helps your writing feel personal instead of it sounding like another corporate message.

While all these rules apply to print copy, they apply even more to web writing. I’ve addressed similar points in the past.

7. How to Stand Out From (Any) Competition

The final lesson is from Breakthrough Advertising, and it’s about 4 states of sophistication.

In plain terms, that means that there are 4 stages that a market can develop into. They go from stage 1 to 4:

1. You are first in your market: When you’re the absolute first to cover a topic or create a product, your copy can be simple and direct.

Put the need your product fulfills, or a claim of what it does, in the headline. That’s all you need to do to attract attention.

For example, when SEO was first starting to get popular, a simple 400-word article with “What is SEO?” in the headline was all that was needed to get traffic:

2. Second in your market: If you’re not quite the first, but you’ve caught a topic early, just take the direct claim a bit further.

For example, KISSmetrics’s guide to beginner SEO talks about how search engines work at a basic level. It’s a good explanation of why SEO is important and how it essentially works.

3. Prospects have heard all the claims, all the extremes: Once most visitors know the basics, you need to include more practical information to sell them your product or service.

In other words: show, don’t tell.

A guide to SEO on Search Engine Land goes through all the basics of how SEO works using videos, text, and pictures. But the creators go one step further and include links to SEO tactics and techniques.

4. Elaboration and enlargement: Once everyone meets those minimum standards, you need to go all out. You need to expand on all aspects of the content or product and make it better.

You could make it easier, quicker, more reliable, simpler, or add extra useful features to it.

To continue with our example, the SEO niche is pretty advanced now. When I created the “Advanced Guide to SEO,” I included everything about the topic. There were tons of current tactics that worked, accompanied by step-by-step instructions.

These four stages are essentially the Skyscraper Technique in action, except they were written about many years ago.

Each stage of maturity for a topic or product raises the bar. Make things substantially better, and you will get attention from customers.

Either create something before it gets popular, or take it to the next level.


I’d like to finish this article by giving you one additional lesson: You can learn a lot from the past.

Whenever you’re learning about a new subject, whether it’s copywriting, marketing, design, or something completely different, don’t head to the most popular blogs right away.

Instead, read through some of the highest rated books of the past, no matter how old they are. You’ll learn about how some of the fundamental concepts of the field came to be. It’s those lessons that you can build upon so that you can become more adept in a particular field.

I’ve given you seven lessons that are jam-packed with useful copywriting and marketing knowledge, but I haven’t even scraped the surface of these four legendary books. If you learned a few new things from this article, I strongly encourage you to read or re-read any or all of those books.

What other copywriting and marketing books have you read and loved? Let me know in a comment below because I’m really curious.


This post originally appeared on Quick Sprout, and is re-published with permission.

Image Credits

Featured Image: P. Kanchana/
Screenshots by Neil Patel. Taken August 2015.