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Cutting a piece of paper seems like a simple enough task.

But for much of my childhood, I got anxiety every time I had to do it.

From the time I was in kindergarten, any piece of paper I cut looked a hot mess.

The problem? I’m left-handed. And most scissors are made for people to use their right hands to cut. So if you use “traditional” scissors with your left hand, your paper ends up looking like this:

As a kindergartener with perfectionist tendencies, I thought something was wrong with me. I avoided cutting whenever possible. And when that wasn’t an option, I learned how to cut with my right hand, so I wouldn’t feel so inadequate when working with scissors.

It wasn’t until I got to fifth grade that I discovered left-handed scissors existed. It was like a miracle. Finally, I could cut with the hand that felt most natural to me, without feeling like I belonged in a remedial class. I realized that I wasn’t the problem. I just hadn’t had the equipment needed to help me perform at my best.

Who do I blame for the years of scissors-induced trauma?

Sure, the marketers of these companies are an easy target. I could hurl accusations to them about their discriminatory practices, lack of empathy and insensitivity toward the 10% of the population who are left-handed. Hmph.

But the marketers are only a scapegoat of a bigger problem. The probable source of their disregard for left-handers was their buyer personas.

The personas that so many smart marketers live by caused them to make many qualified customers feel like they didn’t belong.

Inclusive Buyer Personas: The Foundation That Gives You the Keys to the Kingdom

Have you ever tried to buy a gift for someone you don’t know?

Over the holidays I went to a party where we did a white elephant gift exchange. A few hours before, I found myself aimlessly roaming around trying to find a cool gift a stranger would enjoy.

It’s hard buying gifts for people you don’t know very well. You end up finding something that is boring or generic enough so as not to offend anyone. But in trying to find a basic item, most of the time you end up forfeiting the opportunity to deliver a gift that the recipient will love.

Your business is like that. The products, services and experiences you deliver are like a gift you are giving the customers you serve. The better you know your customers, the better equipped you’ll be to give them gifts they’ll be excited about.

That’s why savvy marketers treat their customers like their good friends.

Gwyneth Paltrow’s lifestyle company Goop tripled their year-on-year revenue in 2017. Elise Loehnen, their Chief Content Officer, told me they attributed a large part of that growth to producing content and products for their readers who they view as their “friends”:

“So, that’s really what we focused on is talking to our readers the way that we would talk to our smartest friends and giving them all the context, all the information that they would need to feel like they’re making a great decision or a great purchase.”

Grammy-Award winning singer, actress and entrepreneur Rihanna thinks of her fans and customers the same way:

“I have this perception that my friends are the consumer.”

In real life, you don’t need a document that details everything you know about your friends to help you be a good friend to them. But in business, a document like this – also known as buyer personas – is essential. It provides a guidebook for you and everyone on your team for how to interact with your customers to keep them coming back to you.

Good buyer personas are detailed enough that they demonstrate that you know your customers as well as you know your best friend, especially as it relates to the problem you help them solve.

When your personas are done right, they help you attract the customers you want like a magnet.

They provide a roadmap that enables you to know exactly what to do throughout your customer journey, to draw your customers closer to you. In particular, buyer personas help you with the following:

One: Personas Drive Products

There’s no need to guess about what kinds of products your customers want to buy from you.

When you know them well and pay attention to what they say and do, over time what they need most will become obvious, much the way it does with you and your friends.

Sprinkles Bakery knows that their ideal customer has a dog. So they’ve introduced a product line of “pup packs” designed to delight both dog-owner customers and their beloved best friends.

The products you produce for your customers should be such a perfect match for them that they say, “Here, take my money!”

Two: Personas Drive Copy

Many of us use a different kind of lingo when we talk to our friends. It’s less formal. It’s rife with inside jokes that make it difficult for those who aren’t in our inner circle to follow along. The words we use with our friends deepen our bond.

A few years ago, I read Joanna’s post here on CopyHackers about time management. Every time I read it, I laugh out loud when I get to this part:

My mom wouldn’t get the joke. Many of my friends wouldn’t get the joke. But I get the joke. And that’s all that matters.

Joanna knew I would get this joke reference from 1998 because she knows me, her ideal reader and customer.

The way you talk to your customers is part of what makes them feel like they belong with you as well.

Thus your buyer personas should reflect the intimacy you have with them, that informs the way in which you communicate with each other, particularly in the copy you use along your customer journey.

Three: Personas Drive Photography

Business is about belonging. Effective marketing will signal to your ideal customers that they belong with you. They will feel like you see them, get them and designed your products, services and experiences to fit them perfectly.

When your buyer personas reflect your customer friends, it makes it easier for you to produce imagery that either is a reflection of who they are or who they aspire to be.

Nike’s mission is to bring inspiration and innovation to every athlete in the world. They define an athlete as “anyone with a body.” When you consider it that way, the imagery associated with who their ideal customers are could take on many forms and multiple personas.

Nike has embraced that diversity of various personas with the photography on their Instagram page.

Your photography should communicate “you belong here” to your ideal customers.

Buyer Personas: The magnet that simultaneously attracts and repels

By their very nature, buyer personas help you exclude certain groups of customers. Not everyone can and should be your customer. The same way that everyone can’t be your friend.

But the excluding that you’re doing should be intentional. The challenge is this:

Far too many brands have personas that exclude large groups of customers, without their marketers even realizing it. It isn’t too difficult to understand why so much exclusion marketing happens.

It comes down to a scientific term known as homophily, which essentially goes like so:

“You’re just like me. You’ll fit in just fine here.”

The homophily principle says that “contact between similar people occurs at a higher rate than among dissimilar people.”

A group of researchers from the University of Arizona and Duke analyzed various studies of homophily over many decades. They published their findings in the paper, Birds of a Feather: Homophily In Social Networks. Here’s how they summarized their observations:

Similarity breeds connection. This principle—the homophily principle—structures network ties of every type, including marriage, friendship, work, advice, support, information transfer, exchange, co-membership, and other types of relationship. The result is that people’s personal networks are homogeneous with regard to many sociodemographic, behavioral, and intrapersonal characteristics. Homophily limits people’s social worlds in a way that has powerful implications for the information they receive, the attitudes they form, and the interactions they experience. Homophily in race and ethnicity creates the strongest divides in our personal environments, with age, religion, education, occupation, and gender following in roughly that order.

The authors went on to add:

“By interacting only with others who are like ourselves, anything that we experience as a result of our position gets reinforced. It comes to typify ‘people like us.’”

In other words, when marketers go through the process of doing their ideal customer research and creating their buyer personas, they are more likely to profile prospects that are more similar to them, rather than dissimilar.

While that similarity helps you to focus your efforts on a group of customers whom you have an inherent degree of familiarity with, it also causes you to leave out those groups of customers who have backgrounds and experiences that deviate from your own.

Thus, it isn’t a far leap to hypothesize that many of the marketers who worked on scissors when I was a kid didn’t have a ton of left-handed people in their world. As a result, their frame of reference for considering how to serve left-handed people was limited or non-existent.

If a restaurant owner, chef, or meeting organizer doesn’t have people with dietary restrictions in their inner circle, they are less likely to fully consider those who do have them when they’re creating their menu.

EDITOR’S INTERJECTION: How long did it take for restaurants and pubs to add hooks for handbags under their tables?

While many brands have gotten away with marketing to “people like us,” trends show that approach won’t be so effective in the future.

The makeup of the people we serve is changing in multiple ways. Here are some noteworthy demographic trends you should be aware of:

While demographics shouldn’t be the only consideration when constructing your buyer personas, it is important to note the impact these demographic characteristics have on the psychographics and behaviors of the people you are serving.

And if your marketing is targeted effectively to your ideal customer, but it excludes one of their friends, then you run the risk of losing out on multiple groups of customers.

For health reasons, I follow a gluten-free diet. Thankfully, when I go out to eat with my friends, they are very good about making sure we go to a restaurant that has plenty of options for me to eat. My friends go through this effort because they want to include me. They want me around and aren’t going to let my dietary restrictions get in the way of our quality time together. And if a restaurant works for them, but doesn’t work for me, we don’t go.

With all the various types of differences that exist, buyer personas that only focus on what has historically been considered “mainstream” could be signaling to a large number of potentially loyal customers that “this isn’t for you.”

Ade Hassan is the founder of Nubian Skin, a company that specializes in lingerie and hosiery for women of color. Here she is explaining to me how being told “this isn’t for you” one too many times compelled her to start her company.

For the visual learners like me, here’s what comes up on Amazon when you type in nude hosiery:

Here’s what those “nude” stockings look like on a woman of color like me (just to be sure we’re all on the same page – this ain’t cute!):

And here is the hosiery that Nubian Skin sells, with a range of nudes for women of color:

When your buyer personas exclude customers you didn’t intend to, those very customers go off in search of other companies who acknowledge their needs and serve them.

“You get a car! You get a car! And you get a car!”

Buyer personas are a powerful marketing tool. But like with any tool, their ability to help or hinder your business is only as good as 1) the inputs that go into it and 2) how you use it.

Even though far too many personas unintentionally exclude, there are plenty of smart marketers who’ve done an excellent job of using personas to include more of their ideal customers.Even though the homophily principle implies that many people are limited in their consideration of others because their circles are largely similar, there is other research that showcases the ways in which the homophily phenomenon can be overcome – ways that can help you be more inclusive in your marketing: openness and empathy.

A 2017 study of more than 12,000 British households found that the personality trait of openness caused respondents to be more likely to have friends who lived farther away, were of the opposite sex and were of another ethnicity.

Professors at the Universities of Iowa and Toronto authored a New York Times article where they argued that empathy is a choice:

“While we concede that the exercise of empathy is, in practice, often far too limited in scope, we dispute the idea that this shortcoming is inherent, a permanent flaw in the emotion itself. Inspired by a competing body of recent research, we believe that empathy is a choice that we make whether to extend ourselves to others. The “limits” to our empathy are merely apparent, and can change, sometimes drastically, depending on what we want to feel.”

In it, they cited various research studies that show that empathy is lessened for people who are different from us, particularly those who are of different races, nationalities and creeds.

When you treat your customers as your friends, it becomes easier to make sure your friends are taken care of. Openness and empathy are woven into how you treat each other.

When you think of your customers and the relationship you have with them, the focus isn’t on how they are different and how that might inconvenience you. It’s on making sure that you do what you need to do to include them in whatever it is you’re doing.

It is important to note that inclusivity isn’t always about accommodating differences that may require a different approach to your products and services.

At times it’s just about refocusing your targeting efforts to welcome customers who could be loyalists to your brand, if introduced to your product and consistently engaged in a relevant manner.

The craft beer market is starting to embrace this concept. According to a New York Times report, the industry is looking beyond “young white dudes with beards” as a means to bolster slowing sales growth. As a result of their openness in recent years, the Brewers Association hired a diversity ambassador and has established a set of guidelines and resources to assist brewers in making their brands more inclusive. They are making progress as consumption of craft beer among women, African-American, Native American, and Hispanics are on the rise.

3 ways to know if your personas are a repellant for loyal customers

Your customers leave you clues that help you figure out whether or not they like what you’re doing. And because the topics of diversity, inclusion and belonging can still be touchy for folks, the good news is you can use cold hard data as your guide when it comes to assessing your brand.

Here are three sources to turn to for insight.

One: Evaluate if your customers are representative of the population

Ideally, your customers should be reflective of the population that fits within the demographic of your buyer persona. If 85% of your customers are women and 50% of the people who check all the boxes for the characteristics you describe in your persona are men, that’s a signal that something about your marketing doesn’t make men feel like they belong.

Basecamp co-founder Jason Fried used this approach to identify that the company needed to diversify their team. He penned an article that declared his company’s

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Famous American investor Jim Rogers took a trip to Ethiopia.

It was during one of the worst famines in recorded history.

Foreign assistance to Ethiopia was, according to Rogers, commendable… but destined to fail.

See, 3 million Ethiopians were starving. But the country produced enough food to feed 60 million people.

They didn’t necessarily need more food.

They needed an infrastructure to carry the food they had from the rainforest to the desert.

So what’s that got to do with Facebook ads?

FB advertisers find themselves in similar situations when trying to troubleshoot ad campaigns that aren’t working.

They focus on bidding, on audiences and on ad structure – forgetting far too often about the importance of the most fundamental stuff in marketing and advertising:

Content and copywriting.

“But People Don’t Read Long Ads on Facebook”

Popular belief is that with Facebook ads, only the images matter; the copy does not. (This was particularly devastating for the Copy Hackers team to learn.)

Most marketers also believe that the copy should be short.

But are they right?

AdEspresso recently ran a Facebook Ad Copy Length experiment that challenges this belief. In it, they tested seven different ads for the same offer, where everything was the same for each ad except for the copy. Here’s a summary of their copy tests:

  • Variation A: One Sentence, Version A (claim with data)
  • Variation B: One Sentence, Version B (question)
  • Variation C: Bullet Points
  • Variation D: Bullet Points + Emojis
  • Variation E: One Paragraph
  • Variation F: Three Paragraphs
  • Variation G: Six Paragraphs

AdEspresso then polled marketers to see which variation they thought would win.

Nearly half of the marketers polled guessed Variation A: One Sentence would win.

But not only did Variation A NOT win. It also had a much higher CPA.

Turns out Variation E: One Paragraph was the ultimate winner, followed closely by Variation F: Two Paragraphs and then Variation G: Six Paragraphs.

Even better? Not only did the longer copy in these ads bring in the most leads… but long copy also had the lowest CPAs across the board.

That experiment showed a big increase in Facebook ad performance… based solely on changing the copy. (More about it here)

CAVEAT: When you write longer copy, you effectively change the message, too. So an easy argument here is, “Well didn’t the message also change?” Of course it did. Longer copy gives you room to explore more facets of a message, increasing your messaging surface area – or effectively increasing the size of the net you cast, allowing more message to pull in more people.

These results are not just for AdEspresso.

I once took a course from Perry Marshall, a business consultant endorsed by FORBES and INC Magazine. He also wrote the world’s best-selling book on Facebook advertising, and he teaches clients how to successfully write long-form FB ads. One of his clients, Revelation Pets, had a sales increase of 300 percent in the month after taking his course. And another student dropped her cost per lead from $7 to $1.76.

I’ve written about long ad copy and how it helped BetterBack – a company that appeared on Shark Tank – run a profitable campaign.

I’ve shared how long ad copy helped Strategyzer sell $2,199 event tickets at 1866 percent ROI.

But maybe you’re still not sure long copy actually works in Facebook ads???

Okay, lemme give you another example. But before we dive into it, think about the size of YOUR email list today. How many subscribers do you have? How many did you acquire last month alone? And how about last week?

With those numbers in mind, take a look at this case study:

Case Study: “I Will Teach You a Language”
uses long Facebook ad copy to get 3000+ subscribers in 1 week

I’ve been running campaigns for I Will Teach You a Language since September 2015.

Founder Olly Richards speaks eight languages and helps others learn new languages quickly through storytelling. For the past three years, FB ads have been consistently building Olly’s email list.

In a seven-day period recently, we received 3,118 opt-ins at £0.54/lead.

The secret is no secret at all: I consistently write lots of ads in which I engage in storytelling, which allows us to get leads at a good cost. I use long copy.

Here’s the ad that brought in all those leads in one week:

And now take a look at the comments! That ad got 2.2k likes, 545 shares, and 443 comments (708 total comments, if we count nested ones).

SIDE NOTE: Also in this example, someone wrote a comment that got 18 replies related to the ad topic. Nested comments are more proof that they’re reading!

Long-form copy has been given a bad rap in the marketing world.

People love to tell you that nobody reads online.

And here’s the thing: that can be very, very true.

But any great conversion copywriter will tell you this: 

Don’t write for the people who don’t read online. Write for the people who do.

K, so how?

I’m about to walk you through 10 techniques for using long-form content and storytelling in Facebook ads. These are the exact techniques I follow to get results for my clients. And in case skepticism starts to creep in as you read – or in case you go put a pot of tea on and return to read the rest of this post having forgotten everything you just read – I’m also going to share a few more case studies as we go….

But first, let’s agree on this.

Engagement with your Facebook ads MATTERS.

Long ad copy can be incredibly engaging, and that’s a big part of what makes it a powerful weapon to fight off Facebook ad fatigue. And this is important for two reasons:

1) High engagement helps you get a higher relevancy score, which Facebook rewards with more impressions and lower CPM. Facebook itself recommends working on the ad text when it comes to improving the ad’s relevancy score.

2) Facebook ad delivery does not depend only on bids but also on the user experience. An official FB video says it is also about the user value, which combines both relevance and user engagement with the ad.

Agreed? Aligned? Got that tea made, and ready to hunker down? Let’s do this….

10 Techniques for Writing Effective Long-Form Facebook Ad Copy

Writing high-converting Facebook ads can feel intimidating, but you really don’t need to be an experienced copywriting expert to knock it out of the park.

Good ad copy comes 90 percent from reading and listening, and only 10 percent from the writing itself. Joanna wrote a whole book on listening for your message and teaches it all the time here, here and here.

Ready to test out long-form copy for yourself? These 10 tips can help you see results.

1. Understand and Reflect Your Customer’s Struggle… Specifically

If you were reading a page from your ideal customer’s diary, what would their struggle look like?

Understanding specific pain points and how your product or service can relieve them is key. Below is an example of an ad we ran that opens with a very visceral struggle:

This long copy uses Joanna Wiebe’s favorite framework: PAS. Problem -> Agitation -> Solution.

Here are a few key things to note with this Facebook ad copy:

  • We built desire before pitching. We didn’t go for the hard sell. We captured attention, provided value… and then appealed to a need. At the end, we finally offered the solution: a downloadable training kit.
  • We were specific. We used a singular, detailed story that many people can relate to in order to evoke an emotional connection. We didn’t just say, “She felt like she wasn’t part of society.” We SHOWED how she didn’t belong. If you can apply specific storytelling to a pain point, you’ll see great results.
  • We didn’t cut out the stuff most marketers cut out. The parts of the ad copy that most engage your reader are the details. We didn’t lose sight of the need for details, and we didn’t prioritize some random idea of “always be short” over the power of storytelling.

Specificity increases the likelihood that people will take action on your campaign. Two professors at Duke and Stanford University, Dan and Chip Heath, proved this over a 20-year research period. In their book “Made to Stick,” they described how concreteness and specificity make it easier for people to understand and respond to a message, which is what you want to happen in your Facebook ad copy.

In one of the book’s examples, researchers Shedler and Melvin Manis of the University of Michigan ran an experiment (in 1986). Subjects pretended to be jurors for a fictional trial about whether “Mrs. Johnson” should retain custody of her 7-year-old son. Jurors were presented with an equal number of arguments for and against. Experiment groups broke down like this:

  • Arguments for custody, featuring no specific details
  • Arguments against custody, featuring no specific details
  • Arguments for custody, featuring specific but unrelated details (e.g., a description of the boy’s toothbrush)
  • Arguments against custody, featuring specific but unrelated details (e.g., a description of the boy’s toothbrush)

How did jurors side?

Jurors tended to side with the argument that included vivid details. Even if the details were unrelated to whether or not Mrs Johnson was or was not fit to keep custody of her son.

This experiment demonstrates the impact storytelling has on an audience. Dan and Chip Heath note, “By making a claim tangible and concrete, details make it seem more real, more believable.” (Bookmark this tutorial on how to be specific in your copy)

2. Frame Your Message with Something Timely

Facebook is for new things. New announcements. New life changes. News. And new forms of news.

So little wonder stories that seem immediately relevant perform well as Facebook ad copy.

A while ago, I saw a story about a missing parrot who turned up speaking Spanish and without its previous British accent. I had a lightbulb moment and knew it would be the subject of my next Facebook ad. Here’s what I wrote:

When you see something newsworthy, why not make it the basis of your new long-form Facebook ad?

Many stories that get covered by the media COULD relate to your niche. Spin the story into an ad.

3. Mine the Comments for Facebook Ad Copy Inspiration

The comments section on an ad will be filled with everything from the hilarious to the outrageous.

Sometimes you can mine those comments and turn them into ad copy. For example, someone left this comment on one of our ads:

Of course I couldn’t use the same language left in the comment, but there was a seed of an idea there.

I wondered if, when trying to learn a language, it would actually help to date a native speaker.

So I searched Google for people’s experiences, both positive and negative. What I found became the ad copy below, where we used a different spin on storytelling – and some humour – to make a point.

Let the comments on your ad guide you toward the next ad you’ll write…

That Facebook ad copy follows the old copywriting rule: the job of a line of copy is to get your reader to read the next line.

Short copy doesn’t build up to the next line. Long copy does.

4. Use the Power of Analogy in Your Facebook Ad Copy

“Like Jaws in Space.”

That’s how the people behind the movie Alien pitched it. They took something their audience knew and wanted more of… and they connected it to their new product. And it worked – they sold the script and got funding. Because analogies and similes are powerful in sales. They help people understand more quickly – they’re a shortcut for actual knowledge.

For example, if you asked me “What does a Pomelo taste like?” and I answered “Like a grapefruit but without the bitterness,” you’d get it.

Analogies make it easier to understand something new by invoking concepts you already know. I try to use analogies frequently in my Facebook ad copy. They’re an essential part of good storytelling. Here’s an example:

We compared learning a language to running a marathon.

Note that I always try to address what an ad will be about in the first sentence; doing so keeps people engaged. You don’t want someone to read three paragraphs about running before they realize that it’s really about learning Spanish.

Make the analogy clear up front.

Analogies can work for any type of copy. If you saw a headline that read, “A typical bag of popcorn has 37 grams of saturated fat – 17 grams more than the USDA recommends in one day,” would you know just how much this was?

The Center for Science in the Public Interest (CSPI) made this quantity applicable to consumers’ everyday lives. In a 1992 press conference, they announced:

“A medium-sized ‘butter’ popcorn at a typical neighborhood movie theater contains more artery-clogging fat than a bacon-and-eggs breakfast, a Big Mac and fries for lunch, and a steak dinner with all the trimmings—combined!”

That made the front pages of The Los Angeles Times and USA Today. The Washington Post wrote about it. And it was featured on CBS, NBC, ABC and CNN.

The public response was so strong, in fact, that movie theaters were forced to stop using coconut oil in order to keep up popcorn sales.

5. Write Facebook Ads Based on Common Mistakes or Rookie Mistakes

Let’s say you help people learn to cook Italian food.

You might want to run an ad addressing the common beginner’s mistake of adding pineapple to pizza or ketchup to pasta. (Yes, I got myself banned from Italy.)

Fixing common mistakes for your readers builds trust and demonstrates credibility while offering value. Here’s a Facebook ad that uses this strategy, highlighting simple mistakes and showing the fix.

6. Try Opening Your FB Ad with, “It’s a common misconception that…”

All industries are plagued by misconceptions that affect their image. It’s the reality of life.

If you’re able to address a misconception in your Facebook ad copy, you may clear up a customer’s conscious or subconscious objection. When addressing misconceptions, make sure to explain your stance and back it up with evidence and stories whenever possible. Here’s what this might look like:

What is an objection you know your audience has? Write a long copy ad around that, neutralizing the objection. 7. Turn Your AMAs into Facebook Ad Copy!
Answer Questions You’re Always Asked

What’s one question you’re asked over and over? There’s got to be at least one.

Answering questions that your audience frequently asks will strike a chord with many members of your target audience, who almost certainly have the same Qs. It’s also another great chance to offer value to your audience and build a relationship with them early on. After all, for every person who dared ask a question, there are at least a thousand others who have wondered the same but never voiced it.

This is a high-converting ad we wrote to address a question we were asked regularly:

Write long-form Facebook ads that answer the questions you get asked the most.

To start keeping a collection of these questions – so you can write endless ads that follow this technique – try:

  • Emailing your list to ask them to submit their questions to you in a Typeform
  • Updating your welcome / nurturing / onboarding sequence with an email that invites subscribers to send you their most burning question
  • Adding a Typeform to your new subscriber or new customer thank-you page, asking people what they most want to learn from you
  • Embedding a form in the bottom of your blog posts, inviting people to submit questions
  • Hosting a Facebook ask-me-anything
8. Interview Your Clients and Use What They Tell You to Write FB Ads

When trying to come up with interesting copy, which would you rather do:

  • Sit at a cat cafe, staring at a blank page, looking confused, eating a big hunk of cake, getting frustrated and eventually leaving to sob in your car as you cradle your foodbaby.

Or:

  • Call up a client and ask..
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Back in 1949, a psychologist from the University of Wisconsin set out to study primate behavior.

Harry Harlow and a couple of his colleagues set up an experiment.

Source: Drive by Daniel H. Pink

They got some monkeys together, prepared a simple puzzle, put the puzzle in front of the monkeys and watched the scene unfold.

The scientists expected the monkeys to show disinterest.

But when the monkeys saw the puzzle, they began solving it. Immediately. With zero treats or incentives.

Over the next 14 days, Harlow and his team watched the monkeys problem-solve away their days.

Instead of losing interest and wandering off, the monkeys kept getting better and faster.

That’s when Harlow proposed a theory:

What if monkeys – and their distant relatives – actually found problem-solving intrinsically rewarding? And what if people found challenging, engaging tasks fulfilling and would happily do them not because they had to, but because they wanted to.

The scientific community thought both Harlow and his theory were ridiculous.

Humans? Motivated by work? Please.

Everyone knows you’ve gotta dangle the fear of punishment and the desire for payment over their heads. Otherwise they turn into good-for-nothing slobs.

So Harlow didn’t bring his observations up again. He wanted a career and going against the scientific consensus meant its certain death.

But a theory of this magnitude wasn’t destined to die.

Over the next decades it would be picked up by others, tested in companies like Intel, and go on to drive the structure of tech darlings like HubSpot, Basecamp and Google.

But we’ll get back to Harry Harlow (and how his ideas affect your business) in a moment.

First, let’s have a quick chat about the question every adult in your social circle felt obligated to ask when you were five:

What do you want to be when you grow up?

Mom, when I grow up,
I want to be a business owner

I didn’t.

I wanted to be a fighter pilot. Then for about five solid years, a vet. Eventually, I became an archaeologist.

And because archaeological fieldwork (the fun stuff) destroys your body by the time you hit thirty, I opted for the less-deadly option of freelance writing instead.

I hated it.

Not the work itself. I loved that.

I hated being a freelancer. I didn’t want to drink mimosas, work from anywhere or give up and go in-house.

I wanted to be more…

To be a business owner.

Like Harlow’s monkeys, I wanted something that challenged and excited me.

Can I be a business owner please?

Technically I owned a business.

I’d registered an LLC with the state of Texas at the start of 2016.

But I was acting like an employee, spending my days on client work alone and not investing time or resources into growing that business.

According to a survey by Clockify, a time tracking tool, I wasn’t alone: 38% of freelancers spend less than 2 hours a week promoting their business.

I was sick of simply freelancing and yet I was reluctant to join the business owner camp. Because growing my business would mean shifting my priorities and making painful changes.

It would mean investing in myself.

And this idea terrified me.

So if you’ve ever found yourself thinking:

“I want to do more than just freelance. I want to own a successful copywriting business that’s demanding and exciting and scary.”

Then this post is for you.

I’ve been consciously transitioning from freelancer to business owner since July 2018. Even in these short four months, there have been plenty of struggles.

Surprisingly, the majority of them were self-inflicted.

The crippling fear when I got in touch with three of my best retainer clients and told them that, from January 2019, I won’t be taking any paid content writing work on because I was focusing entirely on conversion copy and strategy.

The gut-wrenching panic of freeing up two full days a week to focus on growing my own business by investing time in writing long-form blog posts, planning webinar and podcast pitches, creating new products, building relationships and setting up funnels.

The myriad of tiny deaths my ego suffered every time I decided to ask other smart people for feedback on my ideas and offer feedback in return…

None of this felt good.

But it helped me get on the road I want to follow.

I didn’t do it alone.

My transition from freelancer to business owner is largely thanks to the books, studies, and individuals that helped me develop my own personalized framework- the same one I’d like to share with you in this post.

1. All the treats in the world ain’t enough

It all started the day I met Daniel Pink. 

Well… “met” probably isn’t the right word. He introduced himself to me through the pages of his book “Drive”.

You know when you read something that confirms your deepest suspicions about the way you work? The ones that you’ve half voiced over a pint at the pub but otherwise safely tucked away.

Pink pulled these right to the surface by bringing me face to face with Harry Harlow, the monkey man from earlier, and the psychologists who picked up and built on his theories: Edward Deci, Daniel Kahneman, Amos Tversky, Mihaly Csikszentmihalyi.

Because the theory that human beings are motivated to do work for work’s sake – if that work is interesting, engaging and meaningful –  refused to die.

Why use monkeys when you’ve got students?

Twenty years after Harlow’s experiments, recent graduate Edward Deci decided to follow in his footsteps, sidestepping traditional thinking once again.

Deci ran a series of experiments using college students and a Soma cube.

A modern Soma cube on Amazon

He split the students into groups and ran the experiment over three days. On day one, students were given the puzzle and a few shapes printed on a piece of paper. Then they were asked to solve it.

Halfway through the experiment, Deci went out of the room under the pretext of entering some figures into his computer. He told the students they can do whatever they wanted while they waited.

On day two, Deci paid one of the groups for every solved puzzle. Again, halfway through, he left just like last time. Then on day three, everyone was back to solving puzzles for free.

The results were intriguing.

The unpaid groups spent most of their “free” time playing with the puzzle throughout the experiment. But on day three, the paid group lost interest. They played with the puzzle for considerably less time than the unpaid groups. 

Deci noticed this:

It [the money] encouraged them to try to solve the puzzles, but it robbed them of the desire to engage in this playful activity for its own sake. 

How monkeys and puzzles relate to growing a business

The Soma puzzle led Deci to start researching two types of human motivation: extrinsic and intrinsic.

Extrinsic motivation taps into your immediate wants and needs. More money. More food. A place to sleep. The admiration of others. It’s an external driver that nudges behavior.

Pink sums up the way we did (and still do) things perfectly:

For as long as any of us can remember, we’ve configured our organizations and constructed our lives around its [external motivation] bedrock assumption: The way to improve performance, increase productivity, and encourage excellence is to reward the good and punish the bad. 

Intrinsic motivation, on the other hand, taps into your internal desires. It’s not trying to lead you with a carrot or hit you with a stick. It’s there to draw on the things you (not someone else) find meaningful.

HubSpot‘s famous 2013 Culture SlideShare is an example of a company using intrinsic motivation to hire their team.

Source

Instead of saying:

You should do this because we offer you a great pension, a salary and a stable career.

They said:

Here’s a decent amount of money so you don’t have to worry about the bills. A good leave policy so you can see your family. A contribution towards your future because you’re worth it.

But we know that’s not enough for you- you want to build things that matter. So here’s access to other smart people who’ll challenge you and a chance to build something you’ll love. And if you want in, we’ll trust you to be all in. We’ve got your back and you’ll have ours. 

They tapped into people’s intrinsic motivation- the desire for meaningful work- and reaped the benefits.

Elementary, my dear copywriter

Sherlock Holmes is the original intrinsically motivated entrepreneur.

If we ignore the opium use (it was the 1800s…) Holmes is an accurate representation of the driven conversion copywriter, eager to carve out a space for themselves.

He created his own job title: consulting detective. Found his own clients by building authority. Always went above and beyond. Chose work that challenged his mind and created meaning.

Deci theorizes that it’s intrinsic motivation that drives the entrepreneurial behavior we need to build a successful, satisfying business.

In his book “Why We Do What We Do“, he sums up why extrinsic motivators aren’t all that:

[Rewards turn] play into work and the player into a pawn. 

Extrinsic motivation introduces an external driver. Something to rebel against.

Because no matter how appealing the reward, it’s got a hidden cost. One that says: If you want this, you gotta give up some freedom. You’ve got to play the game my way. 

Intrinsic motivation, on the other hand, can walk hand in hand with the same rewards that extrinsic motivation gives you without the negative impact.

HubSpot’s culture may be driven intrinsically, but the company is still profitable and growing. It’s a business, so it’s optimized for making money. As it should be. It’s just optimized to do more than that too.

This got me thinking:

As a freelancer, my motivation was mostly extrinsic: money in exchange for a job well done. And it left me feeling empty.

As a business owner, however, I could leverage my intrinsic motivation and be more than just another writer.

But first, I’d need to get past some arbitrary constraints.

Some limitations increase creativity, but this one kills it

Too many arbitrary rules can stifle intrinsic motivation.

Sam Glucksberg from Princeton demonstrated just how much in the 1960s.

Source

Glucksberg ran a variation of the candle test.

In the candle test, you’re given a tall candle, a box full of tacks and a box of matches. To complete the test successfully you need to attach the candle to the wall. Glucksberg tested whether offering people money for solving the problem will improve the time it took.

Here’s what he found:

Offering a monetary reward increased the average time it took to complete the candle test by 3 and a half minutes.

I’m going to let that sink in for a moment.

People who were offered money to solve this problem sat in a room, staring at a candle, a box full of tacks and a box of matches for three and a half minutes longer than other participants before tipping the tacks out of the box, placing the candle in the box and using the tacks to secure the box to the wall.

Glucksberg discovered that offering an external reward increased linear thinking and decreased out of the box thinking. Yet creative problem solving is essential for most common business challenges you’ll encounter.

Take a common challenge like lead generation.

Imagine you joined a competition. To win, you had to get 20 high-quality ready-to-buy leads in 10 days.

What kind of thinking will help you get there: linear or out of the box?

Let’s follow these two diverging paths a bit further.

Linear thinking is likely to send you down the well-trodden path with your blinkers on. You’ll follow all the pre-established rules, scour the internet for best practices, and try to get there using the traditional way.

But what could happen if you stepped off the road and thought around the problem?

That’s how Garrett Moon, co-founder of CoSchedule, started building up his first piece of software in the middle of the night. Or how Laura Lopuch used cold emails to grow her freelance business 14 times over. And it’s also why Chanti Zak uses quizzes for lead generation when everyone else is too busy creating guides.

They didn’t look at the problem as a linear equation. Instead, they looked at the assets on hand and leveraged them.

As business owners, we are solving problems almost constantly. If extrinsic motivation increased the time it took to stick a candle to a wall, what kind of damage is it doing to our day-to-day?

Here’s what happened when I tied myself to my desk

When I first started freelancing, I had no idea how to set up my day. So naturally I asked Google.

The articles I found came in two flavors:

  1. I work in a serious copywriting office with strict boundaries and a door. I make serious copywriting money. And I wear pants every day.
  2. I sit on a beach drinking fruity concoctions with umbrellas in them. I make some money and I’m all free and bohemian. Pants are for losers.

Clearly, I wasn’t the second kind. So I made myself sit in my office, 9 to 5 Monday to Friday.

This did not go well.

My self-imposed schedule made me hate my work, my office, and even weekends (because why have fun when you can feel guilty about not working!?)

As I kept reading more and more of Edward Deci’s books and papers, my hatred for set hours finally came to a head.

That, and something Joanna Wiebe said. Something that Todd Herman said to her at a moment she needed it.

It’s ok to work weekends. 

Loud bangs started going off in my head. If it’s ok to work weekends, then why wouldn’t it be ok to work at random hours?

I work better in sprints. I’ve tested this.

I’m at my best between about 8:30-1:00 then again between 6:00 and 11:00pm. The mid-afternoon is a dead zone for me. My brain stops working and I transform into a zombie.

Turns out, I’m not alone.

Where productivity goes to die

You know who’s really dedicated to their work? Doctors and nurses.

Yet here’s what happens at hospitals around the country between 2 and 4pm:

Patients are three times more likely… to receive a potentially fatal dosage of anesthesia and considerably more likely to die within forty-eight hours of surgery.

Gastroenterologists… find fewer polyps during colonoscopies… so cancerous growths go undetected.

Internists are 26 percent more likely to prescribe unnecessary antibiotics for viral infections, thereby fueling the rise of drug-resistant superbugs.

Daniel Pink refers to this period as the trough. It starts about 7 to 8 hours after you wake up and lasts for a few hours before you perk up again in the evening.

And this seems to happen for most humans in most countries regardless of gender, race or nationality.

Source

We feel awful during the mid-afternoon. As a result, our decision-making abilities and attention spans are severely impaired.

So what do you do when your best asset turns into something out of The Walking Dead for a set period of time every day?

What would a CRO do with data like this?

If your daily schedule was an underperforming piece of copy, you’d optimize it. You’d consult the copywriting formulas, check your swipe files and adapt a strategy to suit the client’s goals.

So that’s exactly what I did. I took a look at my freelance business’s best asset (me) and created a schedule around my peak performance times. And here’s what that resulted in:

  1. I gave myself permission to take a break mid-afternoon and work again in the evening. Plus, I now work weekends when I want to. (It’s weirdly fun.)
  2. I split my work into chunks ranging from 15 minutes to two hours. Instead of imposing a sit-down time, I check in with my energy levels and decide. If at the end of a 20 min session I feel like working more, I keep going. And if I need a break, I take it, then get right back to work.

When do you produce your best work?

And conversely, what are your least productive times?

Do you work better in marathons or in sprints?

And if you could design your own ideal work schedule, what would it look like?

If you are not sure, Pink suggests a simple exercise in his book “

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Right now is a fantastic time to create an online course and teach others.

Case in point:

Chances are, you’ve heard that making an online course is your path towards an impressively profitable business:

You can transform lives with an online course: your students lives, and yours. Perhaps you’ve already created a course and launched it. Or you’re thinking of putting a course together but you keep letting things get in the way. Like the whole Time Factor: you’re too busy to do what you’ve already got on your plate. How do you squeeze more hours from your already-swamped day to allow for another project? How can you still teach others, provide value and get compensated well for it – but avoid the time-intensive requirement of launching and running live courses?

Answer: by removing yourself from the equation and switching your live course to an evergreen one.

Switching to evergreen is super easy… right?

Wrong.

See, it’s not as straightforward as creating an email funnel and installing a scarcity plugin. With an evergreen course, your students are destined to fail. Approximately 15% of students in massive open online courses cross the finish line. So, they end up asking for a refund because they didn’t get value from your course. 

As Troy Dean of Rockstar Empires optimizes for high completion rates because:

“The benefit of such high completion rates is that our students get better outcomes, a deeper understanding of the subject and a new skill set to apply. As a business, this has helped us keep our cost per acquisition relatively low because the positive word-of-mouth about our courses brings in new students.

With an online course, you want sky-high completion rates.

Engagement is a strong indicator of a student’s engagement in a course. Meaning they find your course informative and – just as importantly from a business perspective – are positioned to be a repeat buyer.

Let’s back up a sec: What about customers already paying $500 or more for your online course? Won’t they complete it because they spent so much on it?

You’d think the stats would be better – as what we pay more for, we value higher – and you’re right. Teachable’s 2017 study found that completion rates were 61% higher for courses priced above $200 vs those below $50.

But raising your online course’s price won’t increase your completion rate. That problem’s root lies deeper than a quick surface fix. I found that out the hard way when I switched my $750 live course into an evergreen course.

I remember it like it was yesterday. {insert nostalgic music}

Ten years ago, long before I started AmbitionAlly, I launched “Cure Cravings Forever,” my very first online course. It was – what I call – my “training business” in the health space. After a failed launch attempt, I decided that I would create all of the course materials live after I sold the program. Each week’s lesson would be a live presentation, allowing time for me to answer questions at the end.

See, I was hedging my bets, just in case no one bought which didn’t happen as 30 students enrolled.

This approach ended up being a blessing. Refunds were non-existent. I got to know each of my students, and the results they got were mind-blowing. All the needed ingredients for a killer online course.

A few years later, I used everything that I had learned to create my first signature digital marketing course, called “Launch It and Profit.”

A little bit after launch, I turned this course into an evergreen one with ongoing open enrollment. Suddenly, my refund rates went from 0.3% to a sickening 7.73%, and my once-stellar completion rate of approximately 60% plummeted.

My business was bleeding money.

Why? Because I didn’t have the same level of involvement with each student. Sure, I could have changed my guarantee to stop offering refunds. Or I could’ve added physical products which, according to Clickbank’s data, reduce refund rates down to 1.5% because no one bothers to ship stuff back. But I wanted to offer refunds. And I didn’t have a physical product that made sense to add. So I asked myself:

How could I offer high-touch evergreen training – without burning myself out – and slash my refund rate in half?

Ten years ago, if you wanted to personalize your students’ experience, you needed custom coding and prayers to the plugin gods that nothing would break on your next WordPress update.

That approach didn’t cut it for me. So I decided to dust off my Software Engineering degree and enlist my developer husband’s help to make a solution for my students to succeed. We created the AccessAlly course marketing automation companion for WordPress, which now hosts thousands of happy clients’ courses.

To guide this “evergreen but it feels like a live course” solution, I put myself in my students’ shoes. I thought about the elements that squeezed the most from my own $20,000+ investment in courses, like:

  • Being able to test the waters before I purchase
  • Knowing exactly which part of a course applies to my situation (so I can skip the rest)
  • Gaining momentum and making progress through a course quickly
  • Having 1-on-1 access to the course creator when I really need it
  • Meeting other course participants to go deeper into the work together
  • Earning perks, bonuses and rewards along the way
  • Getting reminders when the course I signed up for falls off my radar

This list served as my starting point to work seven strategies into my courses and ongoing membership program. The goal: to increase engagement and cut my once-super-high 7.73% refund rate down to 3.6%.

Here’s exactly how I tackled all seven of those points. You should grab at least two ideas from this list and use them in your evergreen course strategy.

Gamification Hack #1: Use the Login Optin Strategy as a “gateway” course

Did you know the people who buy courses are more likely to sign up for a free course first?

That’s what I learned when I created a free course about email list building, called The 30 Day List Building Challenge.

In the past 4 years, there have been 56,938 sign-ups to this course.

56,938 sign-ups for our free course

The course starts on the day you enroll and runs for 30 days.

Side note: If I could do it again, I would have shortened 30 days down to maybe 10 days. Shorter would have been better for results and conversions! Many people lose steam around Day 12, but plenty have seen results by that point. Or they decide to do the challenge again later.

If your free course is 30 days, it’s too long says @NathLussier on @copyhackers
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Your conversions range from 1% to 10% of free members becoming paid customers, based on data across the SaaS space for freemium conversions. Our average course conversion rate of 4.5% from free to paid members bears this out.

So, how can you increase that 4.5% conversion rate? By using The Login Optin Strategy.

When a participant logs into the membership site to access the free course, they see all of the paid courses available for purchase, too. This view acts as a cross-selling dashboard. Think of it as a non-smarmy way of selling paid courses to people who enjoy courses!

I apply this strategy with my own courses.

When I moved to the following member dashboard design, I saw an increase in sales of our paid courses. From our paid 30 Day List Building Challenge, we saw a direct 4.5% conversion to a low-cost paid program. Overall, 5.6% of people who signed up for our free course purchased a paid program of some type, including our software tools.

Check out this course dashboard, where both purchased courses and the ones a student hasn’t purchased yet (like in the bottom right-hand corner) are available:

Free and paid courses are shown on the same dashboard Gamification Hack #2: An assessment quiz can increase your probability of selling from 5% to 60% 

As I created new courses that my audience wanted, it was harder for students to decide which course was right for them.

So I created a quick assessment quiz that guides students towards a specific course or module based on their business’s needs.

Like this assessment which leads them to our Simple SEO course:

This quick assessment quiz guides students towards a specific course or module

Using this approach has another benefit: Selling to logged-in or paying members. According to Marketing Metrics, the probability of selling to a new prospect is 5-20%. The probability of selling to an existing customer is 60-70%. You do the math!

One key thing to note: I made this free quiz so anyone could take it, regardless if they were a student of our free or paid courses. After the assessment gave their results (AKA next steps), the applicable course was available for purchase.

Gamification Hack #3: Highlight your evergreen course student’s “footprints” to engage them more

Peter Drucker famously said, “What gets measured gets managed.”

For courses, measuring improves at least these two things: 1) the course itself, and 2) the ability of your student to complete the course. Show your student how far they’ve come and lead them to the next step to continue their journey.

Here’s an example from my 30 Day List Building Challenge:

See, you’re almost 3/4th of the way through this course. Well done, you!

With a live course, you see how participants are doing… whether they’re engaged and asking questions on live Q&A sessions… or not.

But once you switch a course to an evergreen model, it becomes really difficult to see where students are getting stuck or dropping off… and how to keep them engaged. The reality is that you don’t get help when you’re not being engaged with directly. You just give up and throw the towel in.

When my course went evergreen, I had more refunds and dissatisfied customers. So, I set up a series of progress tracking via checklists and videos to see at a glance how each participant was doing.

There are obvious trends as the first few modules tend to get the most views and completions. Certain metrics lead to cancellations and refunds, as Travis from Member Up has identified, like:

  • How recently a member last logged in
  • How active they are once they login (i.e. pages visited or videos watched)
  • If they completed lessons or modules
  • Whether they participate in forums or click on links in an email

Using this data, you’ll spot super active members (and identify trends in what pages are getting the most views!). Plus, you’ll also pinpoint students who never logged in. Check out this member’s “footprint” as they traverse the members’ area.

You see the dates that they were last active:

See the specific date (and time) when a member was last active in your course

And you even see the frequency of logins and engagement levels for a student’s login history:

Oooh, look – there’s a big gap between the last two dates. Wonder if they got stuck at a specific point.

The biggest thing for me – beyond the visibility I got about my students’ progress – was the added motivation that came for participants themselves.

It turns out that when you feel like you’ve already made strides, you’re more likely to keep going. This motivational technique taps into completion bias: we like to finish what we start. When we feel like we’re making progress, we get motivated.

Take Natalie MacNeil‘s media training program. She applies this strategy on two levels:

  1. See your progress in her course, and
  2. See your progress within each module.

In the left screenshot (below), see the progress bars in the module dashboard, showing you how much of the course you’ve completed. In the right screenshot, you feel awesome as you check off completed tasks for each module.

Feelin’ good about my progress!

In fact, finishing small tasks (or clicking on a checkbox!) releases dopamine, making it easier to tackle bigger tasks. According to a study shared in Harvard Business Review, people who completed small tasks and checked them off also had a higher degree of satisfaction.

Higher satisfaction is definitely what we’re going for in our evergreen courses! So we have lower refund rates and better results to attract future students.

Thanks to this data, I built in more follow-up in the early stages of my evergreen courses, which leads us right into strategy #4.

Gamification Hack #4: “Fully engaged students represent an extra 23% in revenue.” So keep ’em coming back… 

When you automatically follow-up with participants who aren’t as engaged, you reduce refunds and help your students accomplish your course’s promised outcome.

Because let’s face it: if a student never logs in or drops off after the first lesson, they’re not getting their money’s worth. Maybe that doesn’t feel like a problem. After all, they bought – they supported your business, and now you can make payroll and buy more Facebook ads. But here’s why low completion rates are a problem: Students who don’t take your course are less likely to buy more courses or refer you to their friends. According to Gallup’s research, customers who are fully engaged represent a 23% premium in terms of share of wallet, profitability, revenue and relationship growth over the average customer.

Engagement is an important business metric.

You’re in business for the long run. Meaning you’ll be releasing new courses and programs. You want to tap into that extra 23% revenue that engaged participants represent. If you did nothing for a year but optimize engagement, you could, theoretically, grow your business by 23%.

One way to engage is by reminding students via email.

I wanted a trigger to email the students who haven’t logged in recently, so they can come back. But, when I turned my live course evergreen, you couldn’t connect your email marketing platform with your students’ course activities. So I built that auto-remind feature into AccessAlly:

Automation is so beautiful

Next, I put together an “automation loop” to check if a student has logged in within the last week or two. If the answer is no, then an email is sent to remind them about the course.

Below is a screenshot of my Infusionsoft automation “course engagement” campaign:

I give ’em a few days to log back in and continue the course. And if they don’t, I follow up again. Here’s what that follow-up sequence looks like:

3 days gives them breathing room to clear deadline-projects… and get back to their coursework.

With this type of email automation tied to your course progress tracking, you provide the personal touch that you had with a live offering. From an automation marketing perspective, you can use any email marketing platform (and here are top ones that work well for this).

Here’s the email I use to prompt an inactive student to log back in:

Sweet, to the point and motivating – a perfect blend.

Obviously, your email won’t be hyper-personalized to your student – like mention the name of their dog or how much you liked the questions they asked – as it would be in a live course. But your email might still kick-start a personal interaction, as you’ll see in strategy #6 coming up.

>>I made this re-engagement email into a template, so you can send it today

Software companies do a great job of this, like this example from Typeform:

And Duolingo checks in to see if you’re still focused on your goal:

Technically speaking, your follow-up email can get as granular as you want to:

  • Mention the last module they completed
  • Use the assessment information to remind them why this particular course or module is going to help them succeed
Gamification Hack #5: Use the “Points-Based Reward System” (or how our 65% cancellation rate dropped to 38%) 

Point systems! This reward is often what people think of when they see the word gamification. Frequent flyer miles, hotel points and even Expedia have used points in their loyalty programs for decades.

Looks familiar, eh?

Think of it as a “credit system” that acts like a bank account, where you deposit points and withdraw points based on the actions you take. For our members’ area, we decided to call our points “hearts” and tie them to a few different perks, which we’ll get into more under strategy #7.

My biggest lesson on setting up and running a credit system is this:

You need to have a very clearly laid-out and transparent process for how points are earned and what they can be used for.

You might even need to come up with a monetary value for your points. For example, we made each point worth an actual dollar, so students could purchase points and also see them as more than just a vanity gamification “trick.”

Also, we wanted to give points early and often. If you feel like you’re gaining momentum, you’re more likely to want to keep going. This behavior ties into the idea of early wins, a motivation method discovered by the employee onboarding realmMichael D. Watkins distilled hundreds of interviews with..

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As humans, we suck at listening.

And that’s bad for marketing and copywriting.

One study found that 50% of adults couldn’t describe the content of a 10-minute oral presentation just moments after hearing it. Results from 48 hours after hearing the talk were even worse: 75% of the listeners couldn’t even recall the subject matter.

But it’s not our fault.

We can safely blame science. The science of listening actually prevents you from being a better listener. Turns out our brains have the capacity to digest up to 400 words per minute of information. Even a rapid-fire speaker from New York City can only say around 125 words per minute.

If we do the math, that means your brain is idle for roughly 75% of the time someone is speaking to you.

Brains don’t like to be idle.

Brains like motion, activity, movement – DOING.

Our oddly wired brains aren’t the only problem; we can also blame social media for our half-assed listening behaviors. Consider the rules of social media marketing, which focus on making and rewarding noise:

  • You should share several times a day (source)
  • You should engage frequently by publishing content people want and participating in forums (source)
  • The more shares you’ve got, the more shares you’ll get
  • The more followers you’ve got, the more followers you’ll get

Success metrics for YouTube are all about counting views, subscribers, likes and comments. Google / YouTube naturally rewards views with cold hard cash. When you make enough noise frequently enough that people hear said noise, you get rewarded. Even trolls get rewarded (with tons of attention) for adding to the noise.

As marketers, we’re so used to pushing noise that it’s hard to stop and listen.

Listening is an act you won’t be rewarded for. Not like you will for making noise.

Think about it: does anyone receive rewards from others, like upvotes or ad revenue, for listening?

I’m not talking about rewards for being quiet – not at all. I’m talking about social, financial and other rewards for showing that you’ve listened. Commenters don’t get rewarded. There is no mechanism in place to easily reward people who actually took in and processed what you said in your YouTube video, blog post or Facebook Live. The reward goes to the noisemaker. There is no social reward – and no subsequent dopamine release – for the listener. 

We’re trained to talk not listen.

When we think of great leaders, we recognize the great talkers, such as Bill Clinton or Barack Obama, rather than the quiet ones who listen. I challenge you to name three leaders who preferred an open ear to filling the void with words. How many of your past employers have quietly taken in what you’ve said, processed it and – only after truly listening to you – responded to you? How many boardroom conversations go like that?

We’re trained to talk not listen – and that’s a huge problem for marketers, says @copyhackers
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In his book The 7 Habits of Highly Effective People, Steven Covey explains our desire to speak – not to listen – as our desire to be understood:

“If you’re like most people, you probably seek first to be understood. You want to get your point across. And in doing so, you may ignore the other person completely, pretend that you’re listening, selectively hear only certain parts of the conversation, or attentively focus on only the words being said, but miss the meaning entirely.”

Now as I’m writing this, I’m conscious of the fact that a few of y’all may be thinking this:

“Oh, but I AM a great listener. I hear and could repeat back to you every word you said to me.”

Hearing is using your ears to listen to noises; listening is making meaning from sound. So, to be a great listener, we must make meaning from – aka understand – what other people say.

To do that, we use different ways of listening like these:

  • Pattern recognition: You can pick out your name when it’s spoken in a crowded room.
  • Selective muting: You’ll ignore a sound that’s repeated excessively.
  • Unconscious filters: You’ll mute or amplify what you’re hearing based on a range of unconscious filters – culture, language, values, beliefs, expectations, intentions – that create your reality.

We’re gonna get into how to be a great listener soon. But here’s a simple starting point: To be a good listener, your job is to be an engaged, active participant in the conversation. Jack Zenger and Joseph Folkman of Zenger/Folkman, a leadership development consultancy, put it in clear terms:

“[Good listeners are people] you can bounce ideas off of – and rather than absorbing your ideas and energy, they amplify, energize and clarify your thinking. They make you feel better – not merely passively absorbing – but by actively supporting.”

Being active and engaged is a huge part of listening.

And here’s why listening is so important to marketers:

When we listen to our customers, non-customers and readers, we can fix business problems using what they tell us. And then cool things happen. Like suddenly you see a 52% uplift in conversions (like Moz did after hosting live customer interviews). Or you establish a stronger value prop, like Jen Havice did. Or you know what product to build – Jobs to Be Done consultants at The Rewired Group famously use voice-of-customer data to recommend new products to some of the world’s most innovative companies.

As marketers, our whole job is to listen. All of your best copy comes from what customers say – not what’s inside your head – as Jo has talked about:

But you have to be able to listen well in order to get great marketing and copy wins. Your customers don’t need to hear you. You need to hear them. And then you need to process what they told you. And mirror back what you heard. With the empathy that comes only after you’ve really listened.

So here’s a masterclass in the art and science of listening, starting with the basics:
  • Put your smartphone on airplane mode when you’re talking with someone. Yes, actually do this.
  • Shut the door to the room when you’re talking with someone in it. Yes, actually do this.
  • Focus on the conversation that’s happening right where you are. Yes, actually do this.

Now here are 8 better ways to listen better to your customers, your teammates, your boss – everyone.

#1 – Ask better, more intentional questions

When you try to understand your customers by listening to them, you create a safe environment. Sometimes this is as simple as engaging with the right questions.

One of the easiest questions to ask for best results: “Why?”

In Steven Telio’s article on conducting customer interviews, he explains why “Why?” is so powerful for marketers:

“If you need more detail, keep asking why. The process is a variant of cause-and-effect thinking, and through a series of ‘whys’ the questioner can drill down to a specific level.”

The question “Why?” gets you into the nitty-gritty. To be clear, you don’t have to ask it as a monosyllabic “Why?” each time. You can rephrase it into a partial summary that really shows you’re listening, like “I heard you say you love Basecamp software. Why is that?”

That said, your entire conversation should be more than just asking why (although you can get super-far with that question alone). Also try asking questions that both force you to listen and show your speaker you a) heard what she said, b) understood it and c) desire more insight from her.

To do this requires you ask better questions.

So, when the convo stalls – or you sense the speaker is holding back on you – ask one of these questions:

  • How did you feel when _______ happened?
  • Tell me a little more.
  • Why do you think that is?
  • What you said about _______ is really interesting. Can you elaborate?

By now, you may be starting to notice that asking good questions and listening better will not only improve your skills as a marketer… but will also make you a better contributor to work discussions, a more trustworthy freelancer, a more available partner and/or member of your family… even a better world citizen. Yeah, even that. Listening is kinduvabigdeal.

#2 – Be empathetic and curious

You build empathy like you build super-fast typing skills: with time and practice. And you should build empathy. Because it plays a huge part in business. That’s because business is about meeting human needs, explains Thai Nguyen. If you don’t understand another human’s needs, you will find it impossible to meet them as a business. And that’s gonna make doing business painful and not profitable (AKA not what you want).

So be empathetic and try to understand your customer’s life, struggles and desires. Not through your eyes. But through theirs.

While you’re digging into empathy, you may find yourself increasingly curious about what your customers are going through. Curiosity in conversation is part of a skill that Krista Tippett, author of Becoming Wise, calls “generous listening.”

“It involves a kind of vulnerability – a willingness to be surprised, to let go of assumptions and take in ambiguity. The listener wants to understand the humanity behind the words of the other…”

Both empathy and curiosity are at the heart of great copywriting, great UX – all the most important stuff in product marketing today. 

#3 – Take GOOD notes

Maybe you’re already taking notes during a convo. I know I do. Because I’ve gotta see the words written down in order to retain them.

But unless your notes help you understand others – and plan your response – they’re practically useless.

So try this…

Sabina Nawaz, global CEO coach, has the ultimate effective listening hack for you: the Margin Notes technique:

“Margin Notes allows you to think, process information, make connections between points of discussion and ask effective questions instead of blurting out the first thing that comes to mind.”

During your next interview with a user or a customer, divide your page into two sections: body and margin. Now here’s what you put in each:

  1. Body: capture only what the other person is saying. Aim for key points vs verbatim.
  2. Margin: write down your ideas, judgments, rebuttals and questions for each point.

Your page will ultimately look like this:

(Source)

When you speak in the interview, only talk about notes from your side of the Margin Notes that haven’t been addressed. Cross them off as you go down the list.

You’ll listen better by using your Margin Notes to:

  • Write down themes from your main notes
  • Capture your questions and flag them to ask at the appropriate time
  • Test your assumptions
  • Pay attention to what’s not said but communicated via body language

When it’s your turn to talk, remember: you don’t have to share everything in your Margin Notes. Just the relevant stuff.

#4 – Throughout the conversation, recap what you hear

To quiet your restless mind, Genevieve Conti suggests that you review and summarize the main points of the user or customer you’re listening to.

When they’re finished talking, you restate the points.

Double-check that you’ve understood their message by saying things like, “What I hear you saying is…” or “When you say that, do you mean ____?”

When you practice this technique, you:

  1. Process information better,
  2. Pay more attention to your speaker’s message and meaning, and
  3. Make people feel heard (AKA the biggest benefit as when someone feels heard, they feel understood).

Also – big important side note – the word “So” is your best friend when summarizing, according to Julian Treasure.

#5 – Listen to the non-verbal conversation, too

In a world of texting and Slack chatting, it’s more than a little possible that our ability to read body language needs improvement. The screens we stare at impact our basic ability to read another’s emotional state – like an eyebrow’s twitch, small smile, scratch behind an ear and the other the small hints of body language shown in this TEDx talk:

Reading minds through body language | Lynne Franklin | TEDxNaperville - YouTube

With our advance towards smartphones, we’ve crippled our ability to connect. This isn’t a surprise to you, but it needs to be said. Because it’s a ginormous problem. Sherry Turkle, MIT sociologist and author of Reclaiming Conversation, has studied how our devices are killing the art of conversation:

“Because conversation is the most human and humanizing thing that we do. It’s where empathy is born, where intimacy is born—because of eye contact, because we can hear the tones of another person’s voice, sense their body movements, sense their presence. It’s where we learn about other people.”

Reclaim the lost art of conversation by learning about micro-expressions (i.e. small quick facial expressions) and eye reading.

Good actors – think Meryl Streep, Gary Oldman – intuitively use these gestures. Practically speaking, start watching TV or movies with the volume down so you can read what each character is feeling and saying. (BTW, this is best done with subtle dramas, not action movies where plot lines are formulaic.)

Try it yourself. Watch this clip from Doubt on MUTE and guess what the characters in the scene are thinking.

Doubt - Meryl Streep and Viola Davis - YouTube

#6 – “Listen around the edges”

Brendan Salter, owner of Salter Mediation, thought he had good listening skills from when he was senior management in a national company. When he became a mediator – a skilled negotiator between two suing parties – he found out that he had the wrong idea of listening:

“I realise listening is not only paying attention to the words being spoken but how they are being spoken, the use of language and of voice and how the speaker uses their body… and perceiving and understanding these messages.”

Humans are wired for a need to belong, as psychologists Roy F. Baumeister of Case Western Reserve University and Mark R. Leary of Wake Forest University found. Your speaker – or interviewee, customer, non-customer, email reader – wants to connect with you. They want you to understand them. 

Good listening is that connection’s bridge.

Kathleen Milligan, business coach, has been called one of the world’s best listeners by NLP Canada. I emailed her to find out how understanding manifests in a conversation. She wrote:

“Once given the space to share, relief and connection quickly develop. The information will come as time passes. Know your experience in the moment. And, when listening to the speaker, let it be their experience.”

Milligan suggests that, in your next conversation, give your speaker the space to share. Your role is to practice the generous listening that Tippett notes, where you:

  • Listen to your speaker’s voice
  • Hear how it rises and falls
  • Note the pauses in between words
  • Listen for the spots where your speaker needs a prompting question to keep the momentum going
  • Keep the focus – or experience – on your speaker

“I listen around the edges,” says Milligan, who conducts her out-of-town client sessions via phone. “I follow patterns and – especially without having a visual – I am extra-tuned into the places where changes occur: like voice tone, breathing patterns and tension eases or tightens. There are many unconscious similarities in everyone’s story.”

Now it’s your turn. Hit play on this video, close your eyes and practice your listening skills.

#7 – Quiet your mind (so it doesn’t try to interrupt your listening)

Be silent.

A lot.

Now I know that practicing silence in a world buzzing with noise is hard. But it’s oh-so necessary. And I’m not talking about “escaping from the chaos by plugging in headphones.” Instead, to be a better listener, you need to key into the everyday silence in your world.

One of the easiest ways is to practice meditation.

Now here’s a heads-up: When you meditate – and follow in the footsteps of greats like Jeff Weiner, Jerry Seinfield, Oprah Winfrey – you often start with a quick taste of failure. Am I doing this right? Why isn’t it working? Just like you can’t expect to make a hole-in-one the first time you step onto the golf green, you can’t expect to reach new spiritual levels on your first try with meditation. Instead, you practice. Every day, you show up with the goal of improving yesterday’s success.

Soon your mind settles down into the silence.

I promise you: quieting your mind will happen. For the past two years, I’ve been practicing meditation. On stressful days when deadlines loom, the blank page sneers, my toddler won’t nap and I’m up shit creek without a paddle… mediation keeps me sane.

“The picture we have is that mindfulness practice increases one’s ability to recruit higher order, pre-frontal cortex regions in order to down-regulate lower-order brain activity,” says Adrienne Taren, a University of Pittsburgh researcher studying mindfulness. That higher order cortex region is associated with awareness, concentration and decision-making… AKA your must-needed ingredients to listen well

So meditate. (Block 5 mins to try Headspace or Calm on your phone.)

And then: bring that practice into your next conversation when you need focused concentration.

#8 – Don’t just listen to the words – listen to “the layers” of noise

The cluttered noise at a coffee shop is only noise if you think of it that way.

Instead, try thinking of the sounds around you as layered sounds… and treat those as mini-opportunities to fine-hone your listening skills. How? By picking out each sound layer.

Julian Treasure suggests you listen in a sort of “mixer” mode. How many channels of sound do you hear? Sit where you are right now and identify the layers of sound around you. It might be a jet cutting through the sky 20,000 feet above you, a garbage truck breaking, your cat stretching over your keyboard, your chair squealing as you adjust, the blinds of your open window lightly tapping the window frame, a breeze rustling the tree leaves in your backyard. These are all..

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“Yeah, I love you too,” I said. My boyfriend and I were boating on the lake I grew up on. In Texas. In the blistering summer heat.

“But it’s SO HOT. Why did you stop the boat? Can we please go?”

Then I realized why he was saying so many sweet things to me – he was proposing. To marry me.

And I got excited.

Not about the usual stuff: a gorgeous white dress, table full of presents, wedding cake, the 200+ peeps who I wanted to celebrate that day with me, the honeymoon and, y’know, my future husband.

But also about something else.

Something only a marketing geek would think about in that moment.

Emails.

More specifically, I started to wonder how I would use email to get my 213 ideal guests to:

  • RSVP on time,
  • Understand the logistical details and
  • Not ask me a million questions at inopportune times, like in the 2 or 3 manic days leading up to the wedding.

It was a challenge I was totally game for. You get it. You’re reading this, so you get it – the interest in optimizing emails of any kind, even and especially for a wedding.

Fast-forward through the tough negotiations with my parents and in-laws – I loaded up my guest list into MailChimp. I was going to write one helluva show-up sequence for my wedding. I was going to email the sh*t out of my wedding. I was going to make Joanna Wiebe proud.

…Turns out only a little proud since I failed at automation.

BUT! I did get:

  • An average 77% open rate,
  • Only one unsubscriber and
  • Just ONE truly epic failure that cost us a fair amount of money in the end.

Here are the marketing lessons I learned from treating my wedding invitations as an email marketing case study.

If my wedding email copy was going to convert, I needed to focus on one specific segment. Or the copy was going to be crap.

You sit down to write. And seconds, minutes, hours later, you’re still staring at that blinking cursor.

You’re not struggling because you’re a bad writer.

You’re struggling because you don’t know whom you’re writing to.

This was exactly the problem I had with our wedding email list.

My wedding invitation list was made up of people with almost nothing in common: single people, coupled people, heavy drinkers, non-drinkers, conservative friends, #imwithher friends… and people we honestly didn’t know.

(You had them at your wedding too. They gift well, so it’s cool.)

There was no way I was going to please everyone. Plus, trying to would dilute the quality of the content.

The bigger reason was I wanted to make sure they saw my emails. Lyris Annual Email Optimizer Report found that 39% of marketers who segmented their email lists experienced higher open rates.

I decided to focus on the people who I really wanted at the wedding but who were still on the fence about whether or not they were coming. The obligatory invites were gonna show up no matter what; I needed to convert the on-the-fence people.

In sales funnel parlance, I was gunning for the qualified leads. The people who had expressed interest but weren’t committed. My challenge was how to turn these qualified leads into buyers (aka attendees at my wedding).

How do you convince people with a half-dozen wedding invitations each summer to choose to go to YOURS?

Our wedding was going to be the 31st wedding we’d attended in five years. No, not a typo. Everyone we knew was being invited to a bajillion weddings every year.

My job was to identify the message my on-the-fence would-be guests needed to read to choose us.

I needed market research.

Luckily, my fiance and I – with 30+ invitations received in the last years – were fully immersed in the market. We were the market. And we knew this:

Emailing out professional photos of us lovingly gazing at each other wasn’t going to cut it.

In fact, it would have the opposite intended effect. If you’re on the wedding circuit, getting yet another invitation doesn’t get you excited for the wedding. Instead, you think twice about the several thousand dollars you have to commit to flushing down the toilet spending on people you love.

Not to mention, our emails had to stand out in our guests’ inboxes. In 2016, an average of 33 emails was sent per day. Plus, our invitation had to stand out from all the OTHER wedding invitations they were getting.

We needed to emphasize the reason on-the-fence people go to weddings: FOMO.

So, we had to make it seem like we were a blast and that the event was going to be awesome. So awesome that you’d want to tell everyone you know about it. So awesome you wouldn’t dare miss it.

That was the strategy behind sending our save-the-date email:

Subject: Don’t make plans June 18th, 2016

It worked.

Our “Don’t make plans June 18th, 2016” email had a 90% open rate.

Yay for a high open rate!

Next up: I needed to get people to RSVP.

The dead-simple, direct marketing tricks I used to snag a wedding unicorn: on-time RSVPs

Once people opened our emails, we needed them to actually read them and take action. On time.

This was tough.

I needed to make it as easy as possible for people to do what I wanted them to do.

I’d been in marketing long enough to know that no one does anything that requires effort. If it’s not stupid easy, they won’t do it.

No one does anything that requires effort. Like RSVP for a wedding. @copyhackers @margoaaron
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For a successful email marketing case study, I needed people to take two specific actions:

  1. RSVP
  2. Book their hotel room

And I needed #1 and #2 both done before the deadline. So we wouldn’t incur any fees.

But here was the problem. (It’s one you’re sure to recognize from your own marketing.)

We had a LOT of information to convey. Information that could be distracting. Information that could be overwhelming – so overwhelming that people would stop reading our emails and go do something else BEFORE taking action. Information like:

  • Date
  • Time
  • Attire
  • Location
  • Weather
  • Parking
  • Hotel info
  • Things to do in Houston
  • How to RSVP

Knowing overwhelmed people stop reading, I broke out my direct response toolkit. And I started thinking through how to [ethically] manipulate their behavior.

I used my DR copywriting background to write our save-the-date email.

Here’s what I wrote to make sure people took action (below the fold):

And here’s why this email worked:

  • There were no giant blocks of text
  • I strategically placed jokes to break up the dry, monotonous info
  • We weren’t trying to sound overly formal or “professional”
  • I used buttons – not hyperlinks – to ensure our CTAs were unmissable
  • We used plain English

Most importantly: If we wanted you to believe you were going to have fun at our wedding, well, the emails HAD to be fun, too. So that was a focus for me when I was writing ’em.

And it worked. People began to RSVP immediately.

…But not enough people.

So I used 3 more direct marketing tricks to increase engagement rates and get people to RSVP sooner (because a yes now is better than a yes tomorrow). These are the 3 tricks.

Trick #1. Make strategic use of the P.S.

People ignore large blocks of texts and for whatever weird quirk of psychology always read the P.S. (and photo captions). So, I reinforced the important information in the P.S. in every email I sent out.

Subject: We support small businesses

Here’s another example where the P.S. had 19.5% CTR:

Trick #2. Break the left margin at the right places

When you think about getting people to pay attention to things, you need to think about how to interrupt patterns. The clean left margin is a pattern that needs interrupting to grab attention.

In this bad example, your eye is naturally drawn to the solitary line of text under the picture:

Source

So we broke the left margin purposefully to attract our readers’ eye and highlight the important stuff.

Take a look at this email body – even if you skim it, you’ll know that you need to book your room.

Subject: Where to stay for our wedding (hotel details inside)

Trick #3. Set a deadline and remind people about it

We set a deadline and reinforced it over and over and over again. Like this great email from leadership mentor, Michael Hyatt, that uses BOTH the P.S. trick and deadline reminder:

No one wants to go back into their email and dig up important information. So we kept repeating it in critical places, like this:

Subject: It’s the Final Countdown

In the end, we only had to stalk a few people to get everyone RSVP’d on time and that was because they were legitimately not on email. Ironically, it was not my 87-year-old grandma – she is on email.

When you do things differently, you get more attention. From people who love what you do. And from haters.

This brings us to the actual wedding invitation, which was pretty epic, IMHO.

For our email wedding invitation, we sent our a well-edited professional video. We maintained the same quality direct response standards as our previous emails and even preempted the blowback we anticipated we’d get. This is what we sent…

Subject: Important message from Margo and Brian

Remember: we were focused on the on-the-fence people.

We knew the obligatory people were going to show up… and the judgy people were going to show up… we needed to win the undecided.

That, however, didn’t stop the judgy people from saying mean things behind our backs, like:

  • “That’s not the actual invite… is it?”
  • “Did you really let them do that?”
  • “You’re going to send out a paper invite, right?”

TBH, that stuff says more about the judger than the judged, but it still sucks.

Instead of letting it derail us, we used it as a positive indicator we were on the right track.

If your copy is off-putting to some, it’s perfection to others.

If your copy is off-putting to some, it’s perfection to others – @margoaaron on @copyhackers
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Because those strong emotions are part of storytelling.

As James Chartrand writes:

Good stories can move people to action. They can encourage sympathy and instigate donations. They can cause an uprising or a revolution. They can provoke a response or influence readers.

Our target market LOVED our invite. For proof, look at the analytics:

Of the 172 people who opened, they opened it 1,068 times!!! The people who loved it LOVED IT.

And they were showing all their friends. Of course, we were also tracking the YouTube video views, which were over 350. You’re never going to please everyone. Stay focused on your target market and ignore everyone else.

Which brings us to…

The always-ignored, uncomfortable truth about email marketing (because it has nothing to do with email)

The subject line is the most crucial part of any email marketing strategy.

If you can’t get someone to open the email, you’re dead in the water.

So our priority was to find compelling subject lines people would actually open.

Here were our subject lines:

Clear. Straightforward. Plain English.

And it worked. Our list average open rate was 77% with some campaigns at 100%.

I’d love to take credit for my awesome headline skillz, but the reason for that open rate was not just the headline – it was the relationship.

Your relationship with your list is more important than your copy

The people on our list knew my husband, our parents or me personally.

When you have a relationship with the person emailing, you look forward to their emails. It’s less about the copy and more about the relationship. It’s like someone seeing you speak at an event and then getting on your email list.

Humans are wired to want relationships. Psychologists Roy F. Baumeister of Case Western Reserve University and Mark R. Leary of Wake Forest University found:

At present, it seems fair to conclude that human beings are fundamentally and pervasively motivated by a need to belong, that is, by a strong desire to form and maintain enduring interpersonal attachments. People seek frequent, affectively positive interactions within the context of long-term, caring relationships.

In other words, if you’ve been reading and liking someone’s stuff, you’re more likely to WANT to hear from them – no matter what their copy says.

It’s why you don’t have to hear from Tim Urban or Mark Manson for like a month and they can write a subject line that says “poop on a stick” and you’re like, “Hmm, wonder what that’s about? CLICK.”

Because you already know you like them and you want more.

why a “poop on a stick” subject line makes you open an email, by @margoaaron on @copyhackers
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Building a strong relationship that makes people WANT to open your email is an exceptionally difficult thing to do. But it is the goal of strong content marketing and branding. And it was an advantage we had with our wedding list.

We were de facto in good standing because people liked us IRL or liked our parents (and we benefited from the Halo Effect).

That’s why we made a lot of jokes about our parents in the copy, like this:

And this:

But just because we got the relationship right and the majority of the copy right didn’t mean we got EVERYTHING right.

Let my confession begin…

At last, here is the HUGE mistake we made

When you use old-school print mail, you think about 1) reducing print and post costs and 2) households. As in, you send one print invitation to one household.

When you use email, you don’t have to think about print and post costs. And an address is not for a household but for an individual.

We didn’t think about that.

So we send email invitations to email addresses – sometimes multiple emails for a single household – and, as a result, people weren’t entirely sure who was invited and who was not.

Our assumption was that by sending one email to each individual person invited instead of to “couples,” people would understand that this was a specific invitation for them. As in, for ONE person.

Yeah… no. No one thought that.

Here’s why: people are accustomed to RSVPing as a couple or a family. We hadn’t considered that we were changing a social ethos. So, when people got to the RSVP page, they saw the prompt, “How many people are you RSVPing for?” and filled in whatever they wanted.

We had parents RSVPing for children who weren’t invited.

Single people bringing plus one’s just because they could.

One person even RSVP’d for their dog.

…No bueno.

The strangest part: Not a single person asked us for clarification.

Because of that, we had to have some extremely uncomfortable conversations. So uncomfortable that we decided about 15 extra people could just come to the wedding because we really didn’t want to keep dis-inviting people. At an average of $100 per guest, that mistake cost us about $1500. It was money well spent, of course – but something that..

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Cue: instant anxiety attack.

In a Facebook group, I had just announced my experiment for the next 100 days:

Write 100 headlines for 100 companies in 100 days.

To which a certain someone posted this comment:

Joel is a Copy Hackers veteran. I have tremendous respect for him.

So I naturally felt nauseous when I read his words of… what’s another word for “dyspepsia”?

His follow-up comment didn’t help:

The room started spinning.

My breath was shallow. My stomach made tiger noises, and I might have peed a little. What the hell had I just committed to?

For some unimaginable reason, I soldiered on, convinced I could prove Mr. Joel Klettke and all the [super-sane] naysayers wrong. So I began….

The terrifying climb to 10,000 headlines:
What I did every day for 100 days (even when it hurt)

Each day, I’d pick a topic to write 100 headlines about.

Oh, that’s another thing: every day, I’d write about a different topic. Because 100 headlines in 100 days wasn’t crazy enough – I needed to add that extra edge of insanity.

So each day I’d dive into a site for The Topic of the Day. Things like:

And I’d see what the players in that world were doing. (For consumer products, I’d check Amazon reviews just like Jo taught me.)

Then I’d write my headlines – more about that very soon – and share them with my growing list of 53 interested-in-watching-me-fall subscribers. My first few posts to those fine folks – which you can check out here – were ROUGH. See, I had no process. I was doing what we all do when we start writing copy but don’t really think about it as more than words on a page. My hacked process went like so:

  1. I’d write as many headlines as I could (without a template or starting point),
  2. Identify themes in those headlines,
  3. Highlight a few words,
  4. Hit a wall and
  5. Glance at my list of ~400 headline formulas.

Each time I glanced at those formulas, I generated anywhere from 3 to 8 new headlines. Some stuck too close to the template. Some were the product of what was clearly the wrong mindset. Some went off the rails entirely. If you want to see how disparate a group of headlines written fast can be, check out my Tutorial Tuesday replay here, where I live-write a bunch of headlines in this reusable Airstory headlines template:


Sometimes I’d catch a hot streak and 100 headlines seemed to write themselves. Those days were magic.

It won’t surprise you to find that, as the days wore on and as 100 headlines turned into 2500 headlines, I learned a bunch of stuff. Like, I learned I’d need to adjust my voice rather than fit each topic into my voice – something I had completely overlooked during concept and something that was, alone, worth learning over the 100-day experiment.

That was a small lesson.

Five much larger lessons cropped up, which I’d love to share with you now (before we get into the pain of 10,211 headlines)…

The 5 big content lessons @prettyflycopy learned during his “100 headlines a day” experiment, on…
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Lesson 1: What headlines actually are.

Turns out each day was not an exercise in finding “100 ways for Justin to phrase things.”

It was an exercise in finding “100 value propositions for the company.”

Headlines are – very often – variations on a value proposition.

When I realized that, I found myself in a tricky spot. This was no longer a side experiment. This was a job. I was doing the work of copywriting. I instantly knew what Joel had hinted at:

The project might not be so fun.

BTW, I should mention I’m an in-house writer with a day job. So these posts were in addition to my full-time gig. And client work. And family time.

Lord help me if I had a lunch meeting – I had to tack on extra time in the evening. On weekends, replace “work” with “client work.” …Have I mentioned my wife is a saint?

Within 10 days, I could whip up 25 headlines in minutes – no template needed. Common formulas ingrained themselves in my brain and I started each day with lines like:

  • For ___ who want to ___
  • Get ___ without the ___
  • Helping ____ do ____
  • The only ____ that doesn’t ____
  • The (good news) inside (bad news)

These first headlines would never be the best of the bunch, but they eased me into the post. Writing them gave me a rhythm. I’d often find the germ of a better headline in the first attempts. It was the crappy first draft every copywriter needs.

As I mentioned, I started with about 400 headline formulas. As the first 10 days went by, I eliminated 110 formulas from my template. Some were duplicates, some were lazy… and others felt manipulative (more on that later). But a handful rose to the top.

By Day 20, I was rolling. I adapted recurring themes, discovered how to really empathize with the customer and found myself digging deeper. I even used a few lines in my client work and day job. And when I missed a single day? I felt so bad that, the following afternoon, I wrote 200 lines.

By now I was writing headlines like:

On Day 30, I felt like a whiz. Whipping 50-60 lines off the top of my head, no problemo. My subscriber list was growing. I started tinkering with themes from the 7 deadly sins, and I was sailing smooth. Sometimes a bad list of headlines cropped up, but no worries. I felt good. I felt alive.

I felt smart.

I should have expected what followed…

Day 40 brought complete and total burnout.

I was tired. I wasn’t sleeping. And my brain was drained.

Actual video of me at work

Also, my wife was over it. My kids had stopped asking me to play with them because they knew I’d say no. It was a dark time for the rebellion. If it weren’t for Joel’s quote on my screen – yes, I made it my screensaver – I might have given up.

On Day 50, I gave myself a day off. I still posted for my readers, but I didn’t write my 100 headlines. I broke the streak.

It felt GREAT, to be honest.

One day off wasn’t enough to make me a good family man again, but, hey, it was a start. Which brings me to…

Lesson 2: Take breaks.

Recharge your soul. Your sanity (and your family) will appreciate it.

By Day 50, I also changed the way I approached topics. I picked fun brands. There were a lot of Shark Tank products, weird Kickstarter campaigns and ridiculous items like mailable potatoes, light-up toilets, and wine for cats. Strange as it was, I loved these. I wrote headlines like:

Maybe this was my niche??

Just like that, two more big lessons smacked me in the brain…

Lesson 3: If you’re not enjoying the process, change the process.

This feeling might mean that you’re doing it wrong.

Keep tweaking until you find your fit.

And:

Lesson 4: The way you’re thinking about a “niche” may be entirely wrong.

I was looking for a category when I should have been looking for a voice.

The WHO mattered more than the WHAT.

Days 50-70 were light. I collaborated with other writers, like Lianna Patch, Alaura Weaver and Hillary Weiss, who let me write headlines for their existing content. Working with them made me step up my game. Because not only would I have to emulate their voice, but I’d also have their feedback. They’d be the judge of the lines.

Those posts made me feel so much less alone.

And I gained some street cred. People were reaching out to me, and I landed 3 podcast interviews. Recognizable names – like Joanna Wiebe! – subscribed to my recap or followed me on social.

I had become “The Headline Guy.”

I was getting faster, too. I could hit 80+ lines without referring to the list of formulas and often knocked out full lists of 100 headlines during lunch. This meant more free time at home with my family—something I did not take for granted.

By the time @prettyflycopy had written 7000 headlines, he started to get, well, kinda good at it
Click To Tweet

On Day 71, I went full masochist.

I threw out the list of formulas.

I took 37 classic direct response headlines, printed them out… and that’s all I used for the last 29 posts. From that point forward, it was Eugene Schwartz, John Caples, Jay Abraham… and me.

Things got veeeery interesting.

I revisited previous topics, chose a few I was afraid to tackle earlier, and homed in on brands I thought would be fun. By focusing on the direct response examples, the lists became more emotional. I was hitting on fears and wishes. The lines had more story. More empathy.

But there was a dark side.

I teetered on clickbait. (BTW, I *hate* clickbait. In fact, an underlying theme of this project was to prove clickbait shouldn’t exist. I was tired of clicking ads that used the work of copywriting geniuses only to be taken to disappointing articles. Eyes on you, BuzzFeed-style-headlines.)

I wanted only to use the power of these direct response classics for good. Because I knew, with a little extra effort, writers could properly manage expectations. So I dove into the curiosity behind the lines and phrased them to be more positive.

The new style took longer to write – some posts clocked in at 2 hours – but that was OK. It meant I wasn’t coasting. I was challenging myself.

I also cashed in a few mental health days. I still posted but didn’t write a list of headlines. This helped me regulate my sanity, remember my kids and spend time with my wife. Plus, it eliminated the soul-crushing anxiety that paralyzed my brain when I blanked on ideas for topics. I needed those small breaks.

By this point, I was getting fast, I was getting good and I was finding my groove not with 100s of headline formulas but with a small list of awesome ones. Next up, I found myself diving deeper into emotions I hadn’t really explored in my copywriting before – emotions like:

  • Fear
  • Frustration
  • Powerlessness
  • Anger
  • Betrayal
  • Revenge

The lines were good.

Probably some of the strongest I’d written.

But I didn’t like going to The Dark Side.

It felt manipulative. I realized that writing aggressive-style copy just isn’t me. More validation that – to me – voice is more important than topic.

On Day 90, I struck a balance between bolder emotions and the formulas I had memorized. I went back to The Light Side. Security, happiness, relaxation, hope. Ah, now this was me. And my headlines were – objectively – far better than where they’d been back at Day 20 or when I went to the Dark Side. Here’s a snapshot of Day 95:

At Day 100, I was ecstatic. I had written 10,211 lines. 100 days of posting. 106 days of writing headlines. Yes, it took a few extra days, but nobody seemed to care.

Lesson 5: Family first. Always.

I had learned a ton.

Mostly, that The Headline Project wasn’t fair to my family. I was a shitty husband and father for 3 months. I know that’s not the lesson you want to read, but I cannot overstate the importance of family first. I’m lucky the damage I caused was only temporary. Now my wife smiles and my kids rush me for hugs again when I come home. Because it’s playtime.

As for what I learned during the whole process, well, that’s the whole reason you’re reading this, isn’t it?

So, here we go…

16 hard-earned headline takeaways 1. There are no shortcuts.

Do the work.

No hacks, article, or template can match putting on the gloves and getting dirty. There comes a time to stop reading and start doing. Practice makes permanent. It’s the only way to make things stick.

2. Clear beats clever. But sometimes you can do both.

Some of my favorite lines were direct and infused with personality.

Like these ones:

  • Once you learn to think on your feet, it doesn’t matter where you’re standing (Dumore Improv)
  • Sorry. We don’t believe in wedgies (Pair of Thieves Underwear)
  • Send a potato. It’ll still be funny when you’re sober (Potato Parcel)
  • Just because dating can be awkward doesn’t mean you need to be (Nuphero Pheromone Spray)
  • Where we write like Ogilvy & drink like Hemingway (The Copywriter Club)

They’re fun, but and they make sense. Those headlines all came late in the day’s post – often in the last half – so you need to dig.

Dig to find the best copy, via @copyhackers @prettyflycopy
Click To Tweet

3. Don’t force your personality.

Sometimes I made light of sensitive topics. The biohazard cleaning post comes to mind.

But if you need these guys, it’s not a time to joke. Don’t put funny where funny doesn’t belong.

(Yes, this may sound contradictory to the whole voicey-nichey thing, but it’s not. This is something that wouldn’t be in my niche. See, I struggle to keep myself out of my writing. I need to find brands where that’s a fit.)

4. Boring topics don’t need to be boring.

Some of the tech sites were super nerdy. Bland copy for good software. And it’s a shame because they’re products that everyone can use.

However, the average consumer couldn’t understand what they do.

Surprisingly, these posts were fun to write once I swapped features for benefits:

  • Make your data sexy (Plotly graphing software)
  • Helping families make it through long weekends without WiFi (Duracell batteries)
  • Park your domains in a friendly lot (Domahub)
  • Speed reading isn’t a skill. It’s a Chrome extension (Spritz speed reading app)
  • How to animate your presentations like Pixar (Whiteboard animation agency)

I mean, I’m still not the guy to pitch a tech company. But if they asked me to explore the mainstream, I could give it a go.

5. Learn what you suck at.

Brands targeting women ain’t my thang. And that’s OK. Knowing this helped me turn down a project I now know I never could’ve done right.

6. Great things happen when you become your audience.

Remember Freaky Friday, The Change-Up or The Hot Chick? Or any of the other bazillion movies where characters change bodies?

After the initial flow of lines ended, I’d close my eyes and imagine myself as the consumer.

I’d mentally put myself in their body and ask myself:

  • Who would I be?
  • What would I want?
  • How would I feel?
  • Which pains hurt most?
  • What’s missing in my life?

Suddenly, the headlines were easier to write.

7. Writing headlines for a company you *think* you want to work with may result in a very different outcome.

I wrote 100 lines for a brand I had unsuccessfully cold-pitched.

Turns out, I struggled to find their voice.

I’m glad they didn’t get back to me. I wouldn’t have been a good fit. Now, before I reach out to a company, I practice.

Y’know, just in case they say yes.

8. Consumer products can be surprisingly fun to write about *if* they provide real value.

I never wrote much about physical goods before this.

But 7 of my top 11 posts were for products. And they were fun! I didn’t love writing about things you buy just to have (e.g., shirts, toys, grilling accessories), but if it adds value to your life – even if just a laugh – I’m all about it.

9. Google Images is a gold mine.

The day I accidentally clicked “image results” was a game changer.

I was writing about owl rescue, and I was stumped. When I saw the pictures, memes, movie stills and gifs, it was an awakening. The Harry Potter theme alone provided enough inspiration to finish the post. I never would’ve made that connection.

Now, whenever I get stuck, I go straight to images.

10. Write like Dr. Seuss.

Let your mind get silly. Funny rhymes, alliteration and a little wackiness are great for getting into a flow.

No, you’re not going to use them on your final product. But the path they lead you down might take you to your goal.

Here’s what I mean:

  • Rain, rain, go away. I’ll stay dry & watch them play (Under The Weather Sports Pods)
  • Would you, could you, on a boat? (Florida Sailing Club)
  • Sticks and stones may break your bones, but my words will make you money (Pretty Fly Copy)  (ß actually, I did use this one on my final product)
11. Bold the important words.

Identify the keywords in your sentence.

Delete the rest.

Now go make new sentences with what remains. Tinker enough and you’ll find your line.

12. Templates have a place in this world.

I’ve never been one to rely on templates. It always felt like color-by-numbers. But now I see, when you add your own spin, they have tremendous value.

That being said, here’s an Airstory template with the headline formulas I used during my 100 days. To help you kick-start your own headline writing.

Use the formulas in Airstory 13. Clickbait is never OK and I will punch you in the face..
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