I'm 6'1… or 6'2. (It's pretty close.) I weigh 165lbs. And my eyes are green… or hazel, depending on who you ask.

I know this sounds a bit like a Personals ad, but I promise it’s not.

The "green eyes" part isn't actually relevant. The weight is the important part to pay attention to, and here's why:

In college, my friend Tyler and I entered a boxing competition. At the time, each of us weighed somewhere around 165 lbs.

But we had a problem:

There was a guy named Kyle who was going to fight in that weight class.

Kyle wasn't like us. He was an actual boxer.

Tyler and I knew how to box. But we were not "boxers."

We knew that if either of us had to fight Kyle, he would completely and utterly destroy us. So we got creative.

We decided to lose as much weight as we possibly could.

That way, there was no way we would be in Kyle's weight class.

I spent the next few weeks eating 1,500 calories per day. The majority of my diet was meat, beans, and vegetables.

The only reason I survived was because I had "cheat days" on Sundays, where I ate disgusting amounts of the food I had been craving Monday through Saturday.

In the 24 hours before weigh-ins, I lost all the water weight I could by chewing gum and spitting out my saliva (gross, I know) and taking a hot bath at a friend's house in hopes that it would make me sweat… which would ideally lead to me losing even more water weight.

At weigh-ins, I stepped on the scale at 148lbs.

I was hungry and thirsty and exhausted.

Tyler and I went to Fazoli's and stuffed ourselves.

The day after weigh-ins, the weight classes were revealed and thankfully, neither of us had to fight Kyle.

Tyler fought that night.

He lost.

The next night, I fought the same guy Tyler had fought the night before.

I also lost.

I wish I could tell you I took away a lesson from this. But the weekend of the boxing competition was also the weekend of my 21st birthday.

So I had other things on my mind.

But in this week’s Email Marketing Motivation — we’re going to review a piece from a writer who endured the pain of competition AND learned a lesson from it.

His name is Chris Orzechowski and he’s the founder of Orzy Media — an email marketing agency that helps ecommerce brands scale their businesses with email.

Let's dive in.

The Piece

Subject: a painful lesson I learned back in college...

Lessons We Can Learn From This Piece

1. Tease the reader

Pay attention to the opening of this email.

Notice how Chris zooms in and hints at one particularly painful lesson…

Then zooms out again to give you the context of the story…

Then starts to zoom back in again.

This is smart for a few reasons:

First, because it teases the reader.

It shows that there is a valuable lesson he's going to reveal in this email… but he's not going to do it just yet.

And because you know that he's going to share something valuable — you keep reading.

In copywriting, this is called an open loop. Normally, open loops are direct. They'll read like:

"In tomorrow's email, I'll tell you all about XYZ."

Or…

"I'll tell you more about that later."

But the open loop Chris uses here is much more subtle. It's implied, rather than stated.

Because he tells you that one of the lessons in particular was painful, you trust that he will eventually come back to that lesson.

Second, opening the email like this is smart because it gives a reader context.

Context is one of the things that makes you care about a story. When you understand the "bigger picture" in which a story is occurring, it’s easier to make sense of what’s happening in the story itself.

It lays the foundation for the rest of the story. It gives you the basic information you need to know before Chris can get into the details.

And third, because it shows that Chris will deliver on his “implied” promise.

By the end of this section, you can tell he’s starting to get back to the “particularly painful lesson” he mentions at the beginning of the email. The transition is super smooth.

2. Pull from "old" material

If you want to write storytelling emails, two of the most valuable skills you can have are:

Learning how to identify stories in your daily life
Understanding which life experiences from the past will make good stories

While I'm a big fan of learning how to tell stories from your daily life in emails (because there's something incredibly powerful about giving your readers insight into what's happening in your life right now)...

I also recognize that some days, you'll want to tell a story from the past instead of one from the present.

Maybe it's because you had a boring day.

Or because whatever happened today was too personal to share with your list.

Or just because you have a good story that you've never told in an email before.

Whatever the case — remember that, by simply being alive for this long, you've accumulated a long list of stories you can tell in your emails. So don't be afraid to pull from old material.

That's exactly what Chris did in this email. And it works very well.

If you want help transforming that old material into compelling stories, this can help.

3. Remember what makes a good story

So… what makes a good story?

Chris's email is a great example:

Conflict. Tension. Action.

Check out this section:

If you're drawing a blank on what to write an email about — just write about a time you got into some sort of conflict.

The good news is that this doesn't have to mean physical conflict with another person. It can be a conflict with yourself.

A conflict with an inanimate object (like a can opener that doesn't work like it's supposed to).

Or even a conflict with a bug.

So if you don't have a backlog of arguments or wrestling matches to draw from — that's okay. Just think about times when you've struggled against something, whether it's a person, an object, a bug, whatever.

4. Draw the parallel

Chris's story is a perfect analogy. He shows you exactly how a bad wrestling match is related to bad writing.

That's one of the major keys to writing good storytelling emails:

You should be able to connect your story with something your audience wants or struggles with.

In this case, the audience cares about writing well. So Chris draws a parallel between his past experience (a bad wrestling match) and the thing his audience struggles with (writing badly), as well as the thing they want (to write well).

Think through this before you sit down to write your email. Ask yourself:

"How does my story relate to what my audience wants or struggles with?"

If you can answer that question, you're much more likely to end up with a good storytelling email.

5. Inform, but don't teach

Your inbox is kind of like a donation box at Goodwill.

People can throw whatever they want in there. You don't really have control of it. As the person responsible for sorting through its contents — you're generally not looking to spend a lot of time doing it.

You just want to get the job done.

So it takes something really interesting to get you to stop and pay attention.

(This is why storytelling emails are so powerful. And why email copywriting is so important. It's designed to get readers to stop and pay attention.)

That being the case, people generally aren’t looking for full-on tutorials within their emails.

Because even though they might recognize those emails as "valuable," here's what happens with them:

They tell themselves they will read the email later, when they have time.

They're busy. They don't have time — ever. They forget about the email altogether.

They never read it.

All that work you put into a super "valuable" email becomes kind of pointless.

In fact, this is actually a lesson I learned directly from Chris — no "hard-teaching" in emails.

Don't give someone a step-by-step tutorial.

Instead, entertain them. Tell them a good story. Give them a quick tip. Tell them to click a link. That's it.

The email inbox is not designed for "deep reading." Play to the strength of the medium.

How To Apply These Lessons To Your Email Marketing ASAP

Here's a quick summary of the lessons from this piece.

Tease the reader
Pull from "old" material
Remember what makes a good story
Draw the parallel
Inform, but don't teach

And here's how you can apply them to your email marketing:

Write an email about a lesson you learned the hard way.

Tie the lesson you learned to something your audience wants or struggles with. Draw the parallel.

Here's the easy way to do this:

Tell a professional story.

Talk about a project that went haywire, a time you missed the mark, or the worst client you've ever had.

If you go with a professional story, a word of caution:

You have to be able to clearly demonstrate that you've learned your lesson and corrected the problem. Otherwise, you risk making yourself look incompetent… which, I don't need to tell you, is not good.

For example:

If you tell a story about the time you totally bombed while giving a presentation…

You should be able to follow that story with something like:

"At the next presentation, I [did XYZ to fix the problem], and the audience loved it. My boss came up to me afterwards and said it was one of the best presentations he's ever seen."

That's a simplistic example, but it should give you an idea.

So there it is.

Tell a story about a lesson you learned the hard way. Tie that lesson back to a lesson your audience needs to hear.

And if you want bonus points — segue from that lesson into a product pitch. (See Chris's P.S. for an example of how to do that.)

Here's What You Should Do Next

Thanks for reading Email Marketing Motivation. Here's what you should do next:

Click here and join my email list. I'll give you a heads up when I publish the next episode of Email Marketing Motivation, AND you'll get free access to my subject line copywriting handbook, Subject Line Shortcuts.
Click here to join Chris's email list and get his book, Make It Rain: The Secret To Generating Massive Paydays From Your Email List, for FREE.
Share this article with someone — or a group of people — who would like it. They'll be impressed by how smart and thoughtful you are.
Check out my course, Stories That Sell, if you want my comprehensive guide on how to write storytelling emails that earn more money for your business and help you connect with your audience in a genuine way.

EMM09: "a painful lesson I learned back in college…" by Chris Orzechowski