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Anec-don’ts and Insta-fails: Storytelling, social media marketing, and Jenna Kutcher of Goal Digger

I love fewer things more than a really good story. But I loathe anecdotes. I know, I know. What possible bone could I have to pick with anecdotes? What, on earth, has she found to bitch about now? Those quick little examples, quirky little stories, that we tell to harmlessly and efficiently communicate, “oh, yeah, I get it, that happened to me.”

Wrong. Anecdotes are toxic. I hate them. I try never to use them when I am speaking, presenting, lecturing, or otherwise engaging another human being’s ear. You should do the same.

An anecdote is no more and no less than a “you had to be there” story. As in, you tell me a story, it is poorly constructed and therefore boring. 

You have made the classic mistake of assuming that because it happened it should be narrated. I’m disinterested, you get weird, and, realizing your story sucks, say the bullshit phrase: “well, I guess you had to be there.”

Sure, blame me because your story sucks. Forget that the entire reason we have stories in the first place is so that I don’t, in fact, “gotta be there.” If you tell a story, and I had to be there to get the story, then you haven’t told a story, you have told an anecdote and, also, wasted everybody’s time.

An anecdote is not a story. An anecdote is a quick, “this thing happened to me.” An anecdote is a one-dimensional series of facts that people call a story when they don’t know better. An anecdote may have had a point. It might even have some concrete detail. But the one thing it doesn’t have is the one thing that a good story can’t exist without:

Plot. Structure.

I’m going to teach you plot structure in the next episode–Episode 14–so that you never have to tell another you-had-to-be-there story for the rest of your life. Today’s episode, however, is all about hammering home the very important point that…


The object dujour to illustrate such hammering is another business and marketing entrepreneur guru. Because there is no group on earth worse than social media marketers at peddling you-had-to-be-there anecdotes, while acting as if those same anecdotes are the second coming of Jesus…not for any religious significance but because that man knew how to tell a story.

Anecdotes are good for capitalism. Why? Because they make your brain lazy, your thinking cliche, and your connections to others superficial. All good things for a profit margin because they keep you dissatisfied and uncritical so you consume, consume, consume to give your life some semblance of meaning.

You know what would really give your life meaning? Wading through the hellfire of plot construction to tell a good story that makes people feel things–sadness, mirth, anguish, relief—that shit is hard. And because it is hard, it is meaningful.

You know what’s neither hard nor meaningful? Anecdotes. 

The one thing that makes it possible for us to live together in a collective group called a society is the fact that we can tell one another stories–not anecdotes, stories. That’s it. 

Before there was Instagram, and writing, and, I don’t know, maybe the wheel, there was making words out of your mouth hole so that your little life lessons in your limited experience could help others around you in their limited experience. You didn’t have the ability to write things down and refer back to them, you just had the stories that created enough meaning to get circulated to other people. If you told a shit story, that story died. And rightfully so. 

RIP to your shitty story don’t let the door hit your ass on the way out.

Now, I love writing. I love documentation. I love that we can refer to things. I love podcasts. But I don’t love that in the process of gaining all of that, we’ve forgotten how to tell a decent story. Not just forgotten, but actually become downright fucking hostile to a well structured, carefully crafted story because, you know, that’s “inauthentic” or “fake.”

Right, because my carefully written story is so much more disingenuous than the trite stream-of-conscious ramblings you let roll fall of your mouth.

We have always used stories as a way to translate knowledge from one person to another, from one community to another, so that the knowledge sticks without everyone having to suffer physical and emotional distress anytime a lesson need be learned. People wouldn’t have survived very long if every time we needed to learn whether a berry was poisonous we had to go and eat the berry.

Oh, there’s another cliche: “you’ll just have to experience it for yourself.” Yup. Or you could, you know, LEARN HOW TO TELL A STORY SO I DON’T HAVE TO.

Fairy tales are a great example. Every society has used some version of fairy tales forever–call them fables, call them myths, call them the Bible, whatever. A fairy tale’s primary purpose, at least up until the modern era, was to so viscerally and profoundly scare the shit out of little children that they didn’t do stuff they weren’t supposed to do, stuff that would put the rest of the group in danger. 

The Boy Who Cried Wolf is about not screwing around with the trust of your people because if you take them for a ride, they’ll let you die. It’s not about being honest. No society on earth survives because of honesty. It’s about not betraying the social contract.

The Little Mermaid is about sticking to your own kind–because if you try to be something you’re not and abandon your people, you’re going to have to commit suicide and turn into sea foam. It’s not about love or being yourself or any other Disney nonsense. 

But here’s the thing: if you’re trying to teach an angsty, stubborn teenager who thinks they’re invincible not to run off and explore a whole new world, anecdotes are not gonna get it done.

What are you gonna say? “hey kid, I know the hormones are raging and you’re having a real case of FOMO, but don’t run away and chase the guy from the neighboring village. See, I knew this mermaid one time who tried to get legs from a sea witch to chase her man and, well, the witch stole her voice and the mermaid couldn’t tell the guy she loved him so, well, it gets complicated but eventually she killed herself and…well, I guess you had to be there.”

Wrong. Wrong wrong wrong wrong. You can’t just transfer shit into somebody else’s head by giving them a few facts put into chronological order and then piling on a bunch of life lessons. 

They’ve gotta feel Ariel’s desperation. Her dissatisfaction has to be that teenager’s dissatisfaction. That teenager’s longing has got to be Ariel’s longing. When Arial is tempted and tricked by the sea witch, that teenager has to feel that betrayal. Feel king triton’s “I told you so.”

That’s the only way this shit works.

Missing from the anecdote version is what we call in rhetoric “vicarious experience.” The whole reason stories exist is to trick my brain into believing that I have experienced something that I haven’t experienced. When I listen to a really good story, my brain processes the experience as it would if I had been doing the play by play of the story myself–not exactly, obviously, but approximately. 

Of course, that ONLY works if the story is made to create that vicarious experience. Just any stringing together of words along a timeline doesn’t get you that result.

There’s a lot of research out there about “how powerful storytelling is” because of the way our brain processes stories. That’s only true if the word “story” here also includes a stellar plot structure. If, however, that story is an anecdote, a “you had to be there,” story, that research is dead wrong. 

I’m not just irked because there’s a lot of bad advice about storytelling.  I’m irked because that same bad advice also promises us we’re going to get this “instant connection and impact” just from circulating some cliche anecdotes.


If you want someone to connect with you, to get with you, for your souls to entwine in harmony or whatever, you gotta do that work. Your shitty Instagram caption riddled with banality and artificial “aha” moments are NOT doing that work.

Lego my egacy 

Not understanding storytelling isn’t really your fault, though. You’re getting a ot of superficial, profit-driven advice. Like this platitude-fest called the Goal Digger podcast, created, not surprisingly by some social media influencer business guru person named Jenna Kutcher. Like Rachel Hollis, whom I discussed back in Episode 5, no doubt this Jenna Kutcher person is running circles around me in followers, fame, and fortune…

…but not fucking storytelling! 

Here’s Kutcher’s Instagram-filtered version of what storytelling does for the human race.

I count one, two three, four….five rhetoric red flags. For the sake of time, I will speak to two of them.

Red flag number one: anytime anyone, anywhere, uses the phrase “free to be who you are.” 

Sorry to be the bearer of bad news, my friends, but you are not free to be who you are. 

Actually that’s not quite right. 

You are welcome to just be who you are and then spend the rest of your life telling you had to be there stories because who you are is a swirling contradiction of nonsense in need of stories to make sense of your life.

Red flag number two: the use of the word “legacy.” 

Kutcher is using the word legacy here interchangeably with the word “archive” but they don’t mean the same thing.

Your social media MIGHT be your legacy. Might be. But if it doesn’t become your legacy then it simply becomes your archive. Your archive, your estate, those are the material things you owned, created, or managed while you were alive. You might die with hundreds of thousands of Instagram posts. Donald Trump will, hopefully soon, leave the U.S. presidency with I don’t even know how many Tweets. Those tweets are part of his archive. But are they his legacy?

Maybe. If they mean shit to anybody. Your legacy isn’t just the stuff you leave behind. Your legacy is the meaning that people make of your life, in large part based on whatever effort you made to funnel your life parts into a point while you were alive.

But all of those mundane moments of your life? Those don’t add up to a legacy. You’re not living your legacy day in and day out. Day in and day out, your life is a swirling ball of chaos held together with beliefs and habit. You don’t live stories, you TELL stories. 

Whether or not the stories you tell or the stories other people tell about you will amount to a legacy has everything to do with whether that story is any good. You tell stories when you take all of that chaos and put a structure to it to make sense of it for yourself and someone else. 

You LIVE in the chaos; you narrate the meaning.

By that logic, Kutcher is incorrect to say there is not a “one-sized-fits all plan”–maybe not for business, or marketing. But for telling a good story? There absolutely is. It’s called a plot structure. If you’re wondering what plot structure is, too bad, that’s not until episode 14. In the meantime, here’s an anecdote from Kutcher showing what plot structure definitely is NOT.

Now, credit where credit is due, Kutcher has the right impulse here. She’s trying to use this story of loss to convey to you a lesson she wants you to learn, namely, that social media is our legacy. Good instinct. Bad follow-through.

Several problems: 

Problem #1: there’s no vicarious experience. 

There’s about nothing less impactful than saying a loss was, “such a shock.” Then, when she heads over to the Facebook page and all she says is, “I felt reconnected.” No details, no illustrations, nothing to make me get what’s going on in her head in order to experience it for myself.

Problem #2: she says “I suddenly realized,” or some variation, not once, not twice, but THREE times. 

One sudden epiphany in a story is bad enough but THREE epiphanies? Life doesn’t work that way. Most people don’t go through life having epiphanies, let alone three epiphanies.

To make matters worse, this is the third issue, nobody has an “epiphany” that after someone dies you can go to their social media to reconnect. My mother died in 2013 with a bunch of voicemails sitting in my recently deleted. It wasn’t a stretch for me to at point think that I could listen to those voicemails. That’s not an epiphany, that is an incredibly obvious thought.

Also, my mother’s voicemails weren’t her legacy. They were just a bunch of voicemails saying hello and asking me to call her back. That uncanny unsettling feeling I feel when I hear my mother’s voice in those voicemails momentarily brings her back to life, but that’s not legacy. My mother’s legacy is something that I make for her through the way I tell the story of what I make her life mean to others. Nobody else is gonna feel anything just listening to some voicemail. 

Social media marketers like Kutcher have us all thinking that amassing an archive is the same as leaving a legacy–that somehow all of these little moments and pieces and behind-the-scenes looks into our kitchen renovation and the selfies without makeup are giving our lives and the world value simply because they are quote-unquote “authentic” or “real.”

Or, as Tyler Durden Brad Pitt puts it in Fight Club:

Your social media isn’t your legacy. It’s just documents. It’s just an archive. like pages and pages and pages of a diary by some head maid in the 18th century responsible for making sure that the silverware was accounted for. Now, those pages are just gathering dust sitting in some library somewhere. Sure, a good historian could probably make it mean something. But by itself? Meaningless. 

That’s why we need narratives—not anecdotes, not just some list of chronological events labeled a “story” but a NARRATIVE–so we can make meaning out of an endless list of household objects that in themselves are just future Goodwill donations.

Oh Caption, My Caption

Now, presumably, given all that ish she talks about the importance of stories, Kutcher will, eventually, get around to telling us how to tell a good story. Spoiler alert: she does not.

God isn’t it frustrating when some podcaster harps on and on about something like the importance of stories and then just, like, never gives up the goods? Just keeps telling you that you need to wait to the next episode? I hate that.

Here’s what Kutcher does, eventually, get around to saying:

Oh boy…is there a LOT here to hate. But first, let me acknowledge something that I like. 

One: a photo is not worth a thousand words. Some photos are. The self immolating monk image, for example, that is widely believed to have turned the tide of public opinion against Vietnam. Sure. 

Your Finsta photo looking halfway up your nose in the name of letting your true self shine against the oppressive standards of a society that doesn’t understand you? Not so much. 

I agree with Kutcher that stories–by which I mean narratives not whatever she calls a story–and images are best worked together. They are two modes of rhetorical action, one visual, one typographic, that need one another. If you can’t do both well then, frankly, you can’t do either all that well. 

That doesn’t mean, per se, that the self-immolating monk photographer needs to be able to compose an amazing written narrative. But it does mean that the principles of good narrative have to be already part of how that photographer composes photographs, like Susan Sontag.

That doesn’t mean, per se, that an amazing storyteller needs to be a world-renowned painter to write moving stories with tense rising action and earth-shaking resolution. But it does mean that the writer has to be able to envision the film playing in the audience’s mind as the story unfolds, like Martin Luther King Jr. 

I also agree with Kutcher that people are attracted to things that are appealing to the senses (remember that people who are non-sighted, and therefore non-visual are still people) and that give their lives meaning. I disagree that those are two different kinds of people–they’re all one person. 

I also disagree that, quote, “beautiful pictures” is the epitome of what grabs the senses. Language can be sensory. Ugliness can be stimulating. A well composed image of awfulness, with grainy texture and blurred edges, can shape hearts and mold minds.

Rhetoric has depth. It has breadth. Depth and breadth that exceed Instagram. I’m not hating on Instagram, just remember that, like all technologies, even writing, it cannot capture all of the range of human expression available to you. You have to diversify.

Now, let’s talk about what I don’t like about Kutcher’s advice on stories. Okay I guess I already kind of got there but whatever. 

First, did you happen to notice that she uses the word “story” interchangeably with the word “caption”? In fact, never in this entire episode, which is long, does this woman explain what she means by the word “story,” the difference between a story and a caption, and, ding ding ding….


I think the closest she comes is something like, “be raw and authentic.” Barf. Authenticity is a myth. DELETE. 

I believe she also says, “share your passions,” at some point. Double barf. Like I tell every mock interviewee and job cover letter writer: no one cares about your passions. Passion is a label people put on things to mean that they shouldn’t have to explain why something matters, cuz, it just like, does.

Am I passionate about rhetoric? Absolutely. So passionate, in fact, that in a decade, I have almost never begun a sentence with the phrase “I am passionate…”

Kutcher isn’t really giving storytelling advice. She’s giving content creation caption writing advice, which is transactional and ordinary and one-dimensional. She calls herself a storyteller but as there’s no actual story provided, let’s just call a spade a spade. 

She’s telling you how to write captions, not tell stories.

Caption is the social media word for anecdote, except add in twice the number of cliches. Also hashtags. At one point, she stops saying the word “story” altogether and just skips over to calling it “a meaningful caption.” `

A meaningful caption is not a story. It’s an anecdote with a lot of spaces added. It’s meaningful, maybe, in the sense that you, the creator of said caption, have tacked on a meaning. 

But captions are not meaningful in the very foundational, essential sense of creating vicarious experience. That’s not to say that your Instagram caption can’t be a story. It can. But don’t write an anecdote and call it a story. It’s still an anecdote.

Now, I said at the beginning of the show that I try never to use anecdotes when I’m speaking or engaging a listening ear. I do use anecdotes on Instagram. Why? Because not every fucking image needs a story. That’s why the people who invented Instagram gave you a caption with a word limit. It’s not a fucking blog! They’re different mediums.

Rod Stewart had an album called “Every Picture Tells a Story.” Well, he’s wrong. 99% of pictures capture a moment in time. Once in a blue moon, the picture of that moment does in fact tell a story. 

Your Instagram isn’t that. Your Instagram is snapshots of moments in time. By themselves, they say almost nothing. Or, at best, they say something totally obvious. You add the caption to try to provide a bit of context to help the viewer make just a little extra meaning out of the image. But that’s it–just a little extra meaning.

If you want to make maximum meaning, to push language to its limits, then you must, must, must learn to tell a good story. And you must learn the difference between a story meant to provide vicarious experience and a caption on Instagram meant to provide just a little context, maybe a little meaning. And must you become attuned to the subtle differences and similarities.

Again, if you want to! Or don’t. And just go be a good caption writing anecdote teller. But at least drop the cliches around it—the “you had to be there” and the “add a caption to an image and magic happens.” Instead just claim the ability to write a decent image caption. That is still a skill that has to be cultivated. 

It’s just not a story and pretending captions do what stories do contributes to our collective descent into the banality of evil. 
And with that, my little #rhetoricnerds, I will leave you to linger in what I hope is a pleasant mix of frustration and anticipation for Episode 14 when  I will teach you how to tell a story—a really good story— with the help of King Ezekiel from The Walking Dead.


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