My Storytelling Secrets That Connect and Convert

Jenna Kutcher 

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June 2, 2021


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Do you ever scroll through Instagram and read captions wondering how people come up with such beautiful or inspiring or funny stories to share? I’m right there with you—sometimes it can be a challenge to recognize and uncover our own stories that feel worth sharing or even knowing how to share them given all the mediums we use online. 

The good news? Storytelling is a skill that can be honed. You need not be a natural at it to do it well, you can learn and grow in this arena which is awesome. 

I want to share with you how to dig up meaningful stories and share them in a way that feels natural and cohesive and not cringey, so that you can use them as tools in crafting your own legacy but also a means to communicate through your marketing and messaging in order to connect with the RIGHT people.

Because our stories matter and sharing them with others is the quickest way for your community to understand who you are and what you do in a memorable way and it provides a way for them to connect with you on a deeper level and visualize themselves in their own unique stories. 

Determine your core brand stories

So how do you know WHAT stories to tell? We all have that Facebook friend that goes a little *too* deep a little *too* often and we feel a vulnerability hangover for them… heck, I am allllll for vulnerability and rawness, but we also want to make sure our stories are being presented with the goal of connection, not just plain old shock value or complaining for the sake of complaining or venting about our circumstances, your stories have power, wield that power wisely and thoughtfully. 

Now, before we get into the types of stories you can be sharing online, let’s talk about what each one should incorporate—because there’s a simple formula you can actually stick to that will ensure the stories you share are effective and leave readers with a better understanding or insight into who you are. First, keep it simple. I know it sounds rather obvious, but when you’re writing a caption or an email to your community, you still want to keep in mind that we live in a fast-paced world with not the longest of attention spans. Your story should have a beginning, middle, and end and will resonate best if that order follows an obstacle-success-solution story arc. 

Start with a challenge or dilemma: why did you start, was there a challenge? And then in the middle: how did you move through it, what actions did you take, and when did this take place? And the end is less of a true end with most personal stories that we’ll share—but instead think of it as a progression and close with a way that ties up the story and offers a little finality which creates relatability, optimism, or connection for readers.

Second tip: show your personality. Just like we like seeing the humans behind brands and not just their logos and products, we also like to hear the personalities behind a brand voice. THIS is what makes your brand completely unique and “YOU,” so let who you are, quirks and all, shine through. Authenticity means aligning your brand values with your personal values, and one quick way to show that is by letting people into who you are as a person and using language that fits you and the way you communicate! The goal is to have your spoken voice match your online voice and it can take time to hone that but the more you practice, the easier it gets! 

And finally, leave ‘em with the higher purpose. Like I said, we’re not just sharing our stories for our own personal reasons, to vent or to brag about ourselves. There needs to be a deeper connection involved that leaves the reader feeling more understood or less alone or inspired to take action. This is where our “why” stories come into play so strongly… your “why” story or origin story likely began with facing some sort of challenge, deciding to make a change, and then launching on the current path you’re on… right? 

These kinds of stories have the opportunity to leave a piece of your legacy behind, so always be sure they connect back to a deeper purpose than just solely sharing something interesting about you. You always want to help the reader connect with the story in a way that helps them move forward. 

Creating the Story Content

I recommend starting by having a functional story, an emotional or transformational story, and a moral story that you can rework in fresh ways and that make up the core messaging of your brand. 

The functional story is something that makes someone say, “This person or service could make my life easier or better because of this experience.” It’s a story for how you can relate to your clients on a, you guessed it, functional level. 

Then, your emotional or transformational brand story is something that helps your ideal client connect with you and think, “Oh my gosh, I’ve been there too.” This story is something that enables your clients to understand you on a deeper level because you’ve walked through something challenging and made it to the other side, and they can see themselves in that same position. 

Lastly, your moral story is sort of like your big “aha!” or your “why,” and it’s something that connects your ideal client to your broader mission or goal and empowers and invites them to step into who THEY are meant to be.

See how each of those story examples begins with you and your experiences but ends with how it impacts your audience? THAT is the key to exceptional brand storytelling and it’s the main thing I want you to walk away from this episode with if you don’t take anything else.

Press play on this episode for helpful storytelling prompts that will guide you to look at your past and experiences and be able to share them in a way that impacts your clients and readers to further connect them with your deeper purpose and mission.

How to Seamlessly Share

For starters, take time away from the moment instead of trying to capture new stories in real time… A lot of times people post quickly while they are IN a moment, like while it’s happening. It’s the “insta” part of our culture but instead, I invite you to give a moment space. 

I like to keep a note in my phone where I scribble down certain experiences, stories, lines, takeaways, and encounters so that I never forget special experiences AND so that I don’t feel pressured to share them right away. It’s a great way to stay present and yet remember details you want to later share, and it helps you to build up a vault of ideas for the days when you’re stuck on what to share or how to share it.

Another thing I always consider when writing a story-based piece of content is thinking in terms of the end result: What do you want someone to know or understand by sharing this story? What is your goal in sharing it? Is it to connect? Is it to encourage? Is it to inspire action? Or is the goal simply to entertain or make someone smile? That’s valid in and of itself… the end goal doesn’t always need to be some major transformation or emotional shift. Just make sure you include your reader in the storytelling process. Make them feel a participant in the experience. This is how you tell effective stories that inspire people into action. 

As you introduce new stories to your audience or in your content, I also recommend telling a story a few times and paying attention to how people receive it each and every time. That doesn’t mean you share the same verbatim caption 5 times on Instagram, but try to retell that same stories or pieces of the same stories in fresh ways in all kinds of different mediums from blog content to emails to social posts to IG stories.

And remember, not everyone is going to see ALL of your content every single time, so even though it might feel like you’ve said the same thing over and over again, to a new follower or someone who’s just been introduced to your brand, it could be the touchpoint they need to more significantly understand you and your journey.

The Big Picture

Whenever I have something I want to be a memory, I think of how I can share a little piece of it with someone else to imprint it in my brain and theirs.

I look at social media as a piece of our legacy and so I want my stories to live there. Does this mean I share everything? Definitely not… in fact, most people are surprised that I’m actually a pretty private person and don’t share probably 95% of our personal and family lives. But the things that I know will resonate with and touch my audience… those stories are worth sharing. And they’re important.

THAT is what stories are—they’re starting points for conversation and they open the door to connection, which is imperative for building trust and, yes, ultimately making conversions in your business.

Your business and brand needs stories to survive and to thrive. We have the opportunity to use the experiences we’ve learned and grown from to help our own audiences learn and grow, too… And that’s powerful. 

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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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