#96 - Top 3 Challenges EVERY Storyteller Faces

Because storytelling ain't always easy



I’ll be the first to admit it: storytelling isn’t easy. While it is something we all do naturally as human beings and communicators, it is not something we do well naturally. That takes practice and effort. True effort and commitment to trying each day to get better.

I was listening to an episode of the Decoder Ring podcast recently that was critiquing the latest storytelling cultural boom—it looked at how the idea of storytelling has grown in popularity over the past couple of decades and what it means in our culture. I’ll write a whole post on it, but the host said something late in the podcast that I want to share here because while I’m not on board with everything she says, this one thing pinged all the parts of my brain. She said: “Stories are magical, but they’re not a magic trick. Just using the word story doesn’t cast a spell, the story has to cast a spell.”

She’s right. 100% this is not a parlour trick that will instantly make you a better communicator, it takes understanding stories and then identifying the ways they play a role in how you communicate as a person in your life, as a marketer, or as a business owner or employee.

We tell stories to connect, but only if those stories are interesting and relevant and well told. And that, my friend, takes skill. And even then, your story may not resonate because good storytelling also demands that you share your stories with the right people—people who will be interested. For example, the host of the show talks about a story a Microsoft marketer was proud of because it shows the impact of the company in remote villages around the world—she didn’t like it. And I didn’t blame her, it wasn’t a story meant to resonate with her. She wasn’t the audience. (Neither was I for the record—she and I share a scepticism about corporations that a single story no matter how magical can not overcome easily).

But I’m going off on a tangent.

Today I want to talk to you about the three challenges wannabe storytellers face in becoming great storytellers. The things that get in the way of that effort and commitment. We’ll get into the validity of storytelling as a tool for life and communications another day (I promise) though I’ve written about why storytelling matters in an early post of this newsletter

There are three things that get in the way of great storytelling especially if you’re just starting out using it as a communication tool. They’re maybe not what you would have guessed. These three things are the first obstacles to great storytelling. Starting with:

1. Focus.  

This is about you and about your story. If you can’t take the time to sit down, get clear about your story (what it’s about, who it’s for and why you need to share it), it’s going to be hard to create and share a story that is going to have impact. Or, like the Microsoft example above, you’ll share it with the wrong people and be crushed by their unimpressed response. That is a heartbreaking feeling that I don’t want for anyone and especially not you. That means getting focused in the act of crafting your story and making sure the story itself is focused on a single idea, hero, audience, and intended impact. A focused story and teller make for better storytelling.

2. Consistency.

I’ve written about this one before in the context of brand storytelling, but it is essential in all storytelling. It’s also another two-for. It is both about being consistent in your practice of story creation and sharing as it is about telling a consistent story. Whether the larger narrative you’re telling is about yourself or your company, or a product, it needs to remain consistent in voice, tone, approach. Your audience should experience your story and know it’s coming from you. The stories you share should be a smaller part of some whole. That’s where Purpose comes in—it’s an easy compass to ensure you’re showing up consistently (that’s post #3 of this newsletter I just linked there). Practicing consistency is a key part of becoming a better storyteller.

3. Getting started.

It’s the hardest one. You have an amazing idea, or you’ve launched a brilliant business, or you want to switch jobs, but you’re not sure about how to tell people about it. You’re not an expert, you’re not a writer, you’re not a marketer, you’re not whatever story you’re telling yourself that is getting in the way and stopping you from showing the world the brilliant being that you truly are. I’m going to call bullshit on that. You are enough. And with that enoughness, I want you to sit down this week, set aside as much time as you have (even if it’s just 15 minutes) and start putting together a plan for how you can share your story. Then do one thing, just one, that starts you doing just that. It can be a tweet or just a text to a friend. Start. Here are three steps to get you started today. You have a unique beautiful story to share, but if you don’t start the world misses out on that magic.

I hope this helps, let me know in the comments what you think about these challenges. How have they tripped you up as a storyteller? Did I miss anything? Are you struggling with other elements of sharing your story. Send me a note (by responding to this email) or comment below the post—I’ll try to help and I’ll definitely write about it in the future.


A Story Well Told

I spent the weekend watching movies and started it off with the 2018 film The Favourite starring (the indomitable) Olivia Cole, Rachel Weisz (who I have loved since her Mummy days) and Emma Stone. It. Is. Wacky. In the best most enjoyable way. The pacing, the ebb and flow of tension, the characters, the writing, and of course the acting. It stayed with me for days, it is STILL on my mind. It was one of those films I wanted to start again from the beginning when it ended to figure out how the director, Yorgos Lanthimos, did it—told a story so well. I was watching it with someone and it was late at night so no dice, but I plan to go back to it. It’s a period film, but there were moments that I laughed out loud at how wild it was. Then I googled the true story and was shocked at how true to real life the film was. Just a delight. I have some of Lanthimos’ other films on my watchlist now, I think I’ve found a new favourite (pun intended).



Chantaie Allick

Writer|Strategist|Storyteller

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