WWN3: How Therefore Shall We Storytell?

We’re about to cover some sweet storytelling tips and how to get better at this crucial skill.

But first, a word from our sponsor.

Which is me again.

In one week, I will be launching a new offer with Wade Skalsky from the Understory Dispatch.

We’re still finalising the details but here is what we know:

The offer is live group coaching from me and Wade, on how to start a newsletter ghostwriting business.

I will teach you to write better and faster, Wade will teach you to package that skill into an attractive newsletter ghostwriting offer which can net you anything from a few hundred to a thousand bucks per client per month (writing one newsletter a week).

  • The cohort will start in April.

  • All of it will be recorded etc. for easy access.

  • Spaces will be capped so we can do it well.

And while we haven't finalised the price yet, I can say two things for sure.

The first thing is that this round is a beta run so it will be the cheapest it ever is, if it ever is offered again. (That depends how much fun we have.) And the second thing is that the price will reflect the fact that this can be a six-figure business if you do it right.

After all, the reason I’m running this with Wade is that he has built this into a six-figure business working 20H a week. So all that said and done…

To register for the waitlist (no commitment) and find out all the details early, tap the link for Wade’s newsletter below.

I’ll check the clicks on Saturday and send everyone who did so an email with the details.

I don’t know how to work the tagging right in beehiiv so if you click that and don’t get an email from me on Saturday, holler. I might have just missed you.

How Shall We Then Storytell

But how do we get better at telling stories?

How do we take entertainment, education and empathy storytelling to the next level?

Well the first thing is to realise that we all tell stories.

All the time.

A lot of people trip themselves up by thinking that this is a “special” skill that certain people have and others do not. And so they never try to get better.

But storytelling is not for the entertainment elite. It is for you, and it is for me. It’s for your granny spinning yarns around the fire, your kids telling about their new sticker books, your boss telling you about the meeting with their boss, your client telling you about their business problem, your least favourite politician telling you porkies, your favourite email marketer sending another offer.

Storytelling is for everyone, everywhere, at all times and forever.

And it is for you.

Use it. Don’t lose it.

With that in mind, how do we do it?

First, Choose Your Weapon

Before you even take a single step you need to answer this question:

What kind of story do you need?

One does not bring a morningstar to a spear fight. Not only is it a serious faux pas but it will also get you killed, or cut up pretty good.

With stories it’s the same. Metaphorically. Mostly.

I guess technically a bad story can get you killed, but I digress.

Choose your weapon wisely. Refresh your memory with last week’s issue if you missed it.

Do you want to persuade, empathise, sell, draw your reader alongside and influence them?

Write an empathy story.

Do you want to educate, shift their perspective, teach a moral lesson?

Write an educational story.

Do you want to make them laugh, cry, smile, enjoy themselves?

Write an entertainment story.

Use the right tool for the right job and the battle is all but won.

Second, Build Your Arsenal

Of course, it’s hard to pick a weapon when you don’t have any.

So build that arsenal. Now, not everyone needs a dozen entertainment stories on deck. I’ve got hundreds, but I’m a novelist, a storyteller and I need plenty.

Everyone needs a library of persuasion stories though.

So build one.

Sit down and think of things that happened to you. Childhood memories, stories from parents or grandparents, your wedding day, whatever. Funny, unexpected etc. Make a list. You can reuse them in different ways.

Take each and write a one sentence summary. Then circle back and flesh it out when you are using it (focusing on the point you want to support).

Maybe you’ll use that story as a hook for an email (entertainment story) or build it into a novel (again, entertainment) or boil it down to the essential ideas and use it in copy or marketing (empathy) or even illustrate a lesson with it (education).

But you gotta have it first…

Third, Study the Masters

As you assemble this arsenal, realise you don’t just have to use your own stories.

You should also be consuming stories.

Partly so you can save them to your arsenal, but mostly so you can learn from their skill.

Now. This is not first because you do need to know what kind of stories you’re trying to tell before you start studying.

The common advice will be to study great novels, films, stand-up comedians. I’ve given that before. But…

…not since I realised how fundamentally different the main forms of storytelling are.

You have to study the kind of story that you want to tell. You’ll never benefit from studying a novel if you’re trying to write copy.

Okay, damnit this is a nuanced place. Fine.

You will benefit from studying a novel if you’re trying to write copy. But only if you understand the difference and look for the things you can apply.

Spend time studying the kinds of stories you want to tell.

Fourth, Hone The Edge

It’s hard to talk of this in the abstract.

Because again, it depends on the kind of stories you want to tell.

And part of this will be better saved for next week or else this will get too long. But here are a few tips that will help you with whatever stories you are telling.

None of what follows is rocket writing. But you have to practice it, not just shrug and say, “yeah I know that” and continue sitting on your metaphorical ass eating metaphorical crisps (chips to the Americans).

Show, don’t tell.

Don’t tell me Bob was angry, show me Bob storming out the room. Better yet, make me hear the thud of the door that Bob slams it as he leaves.

Stories are all about the small sensory details, the little phrases that make us feel the scene.

I posted about this on X-Twitter yesterday.

And as the great David Deutsch added in the comments:

Don't tell them it's true, prove it.

Which is exceptionally powerful in copy and any persuasive work. Every time you make a claim (tell someone something is true) you create an objection. You increase the defensiveness of the reader, you get their backs up.

“Is this guy lying to me?”

So bypass that. Go straight to proof. Back it up, tell stories, get under their skin.

Prove it, don’t assert it.

Show it, don’t tell it.

Focus on one big idea.

Every great story has one big idea.

Yes, even a complex novel like Dostoevsky’s Crime and Punishment is wrapped around one single moral theme, which drives everything in the novel. For more on this, check out “The Moral Premise” by Stanley D. Williams.

If you’re writing a novel, every single line in that novel should be driven by the central moral imperative that frames the story.

(Read the book, I’m not going to rehash the whole argument here.)

If you’re writing an education story, you have one moral lesson.

The Tortoise and the Hare is all about not getting complacent and arrogant.

The Farmer’s Fire is all about not being lazy and putting off the work.

The King and the Dragon is all about Christ defeating the dragon.

One story, one lesson, one focus.

If you’re writing an empathy story it’s even more important. Each story needs to be honed down so it’s doing one thing. Don’t try and juggle or you’ll miss the mark.

Now, you can have secondary threads in a longer story, or you can have stories that happen to do more than one thing at once. Perhaps it’s an origin story that also breaks down one of the key objections to the product (See David’s book for more) but there’s always one focus.

Anything else is a bonus by-product of focusing on the main thing.

Keep it real

Keeping it real, well, we can and will do a whole issue on this next week.

Because it’s probably the most important rule of storytelling that applies across all stories.

And we’re going to circle back to David Garfinkel’s book, plus weave in some of my own experience there.

Because I could talk for hours on what makes a good story, how to tell better stories etc. but if I did that in here it would become a 5,000 word monstrosity and I think we’d be overdoing it for a Wednesday afternoon…

But next week we’re going to cover the four key things for keeping it real in storytelling, what I call the “Story SPECs” that help you see what is and is not working.

We’ll also drill down on exactly what makes a story feel believable and how you can use that to your advantage.

But meanwhile one last thing…

Fifth, Practice The Blade

No, not study the blade.

Practice the blade.

There is no substitute for getting into the dojo and practicing.

Practice telling stories.

You can use story everywhere. In tweets, copy, fiction (obviously), essay and in conversation. Share stories with friends, see what resonates and save it.

Create video, write, whatever. Share it online. Watch what succeeds and what doesn’t.

But a word of warning…

Make sure you measure the right metrics.

If you’re telling a story to sell, emails saying “that’s an amazing story, loved reading that” are a bad sign. That means you strayed too far into an entertainment story. Sales are a good sign. That’s a sign that the persuasion story did the work it was meant to do.

If you’re sending a story out on X-Twitter to build relationships? Then likes and clicks and reposts aren’t what you want to track - it’s DMs and comments. Those are what are telling you that you’re actually connecting.

Focus on the right metrics.

And I’ll see you next week for the fourth and probably final episode of storytelling with James.

Until next time, may you practice your storytelling and pipe-smoking with abandon and enjoyment,

James Carran, Craftsman Writer

P.s. Don’t forget to tap that link above so I know you’re interested in the newsletter ghostwriting cohort.

Join the conversation

or to participate.