How to Tell Better Stories in Daily Life

I want to become a better storyteller.

Of what, you ask? Of the kinds of stories we tell everyday. We constantly answer questions ranging from “What did you do last weekend?” to “What have you been up to since we last met?” 

I’ve been thinking about this topic for a while but decided to write this post after reading Penelope Trunk’s piece on managing your image by telling good stories. My hypothesis is that by being more aware of the stories we tell on a daily basis, we can look forward to and maximize storytelling opportunities without panicking or rambling.

How do you start improving your storytelling ability?

1. Know when stakes are low versus high. Sometimes when I’m telling my friends a story, in the middle of it, even I wonder where I’m going and what the point is. Most of the time it’s fine, because we’re catching up in a relaxed, casual environment. We listen to each other intently because we’ve all told stories that were a little more drawn out than they could have been. And as friends, we offer our time and attention to show that the person is worth it, and they reciprocate by listening too.

In these situations, the stakes aren’t nearly as high as they would be for an interview. This is why casual environments are exactly the right place to start practicing storytelling – so you can be polished and confident when you have to tell stories in higher stake situations.

2. Your audience should care about the outcome of your story enough to be slightly disappointed if you don’t finish it. I read that if you are telling a story, and in the middle you stop to say you need to use the bathroom and will be right back, your audience should beg you to stay to tell them what happened before you go. This is an ambitious goal, but I think it’s doable although maybe in ways that are less extreme.

3. For casual, personal stories: start the story right when the conflict and action is happening. Most of the time, we don’t have time to rehearse or think about stories before telling them to a friend. We just tell the story. So a good rule of thumb in this case is to avoid losing your audience by being overly-detailed in describing the setting, context, and background. If you know your audience well, you can elaborate on parts that they find exciting. They will likely give you visual and verbal cues that they want to know more about a certain part.

4. Don’t get bogged down by technical details that don’t matter in the overall scheme of the story. Say “last weekend” instead of: “Last Saturday…no wait, I mean Sunday, because I met up with a friend on Saturday so it couldn’t have been then, and I remember on Sunday, we….”

I have a tendency to do this sometimes and make a concerted effort to catch myself. If I talk to you, feel free to (nicely) remind me of this by tugging on your ear or something.

5. Practice. The more times you tell a story, the more you’ll understand which parts are exciting, boring, or confusing. The idea of practicing a story is applicable to founders pitching startup ideas. The more times you pitch, the better you’ll be – and a pitch is essentially a type of story.

The first few times you will suck regardless, so start telling the story and iterate as you go along. By seeing real people’s reactions, you will be able to figure out how to adjust the content or style. That’s how I’ve come to master some of the stories that I am really comfortable telling, that I know will help me connect and express what I mean.

Storytelling is an area that most people don’t spend a lot of time on, so a bit of investment and improvement could go a long way in making an impact both personally and professionally.

What are some insights about effective storytelling that have worked for you?

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