Have you ever been recounting some event from your life to someone and suddenly noticed that they have obvious boredom or even irritation flash across their face?

Or do you regularly see your conversation partner’s eyes flit around the room while you try to get through all the details of “how your weekend went”?

When someone says the word “storytelling,” it often makes one think of authors, scriptwriters, and poets. Some kind of difficult creative endeavor.

Storytelling is a common and necessary part of daily life and conversation. Most people do it every single day of their lives, but a frightening number of them don’t know the first thing about telling a story well.

They make their listeners tune in and out of focus, and make them wonder when it’s going to be over or what the actual point is. And sadly, a lot of these people are also completely oblivious that they have this negative effect on people. It might sound trivial but I know from experience that the way you converse is super important. It contributes serious weight to the way people feel when they consider spending time with you (or even when they hear your name).

Telling stories is a specific part of conversational skill that I want to talk with you about.


I’m not going to try to discuss all the intricacies of storytelling in this post. I could write for pages and pages about what makes a good story, and how to construct it and blah blah blah. That fine detail actually IS better reserved for lasting creative works, and not for your chat over coffee.

The point right now is to get you thinking about the way you tell YOUR stories. Have you ever stopped to consider whether you’re good at it? Or how your listener actually feels while you’re telling it?

You probably fall into one of three groups:

1. Unskilled at stories and unaware of it.

2. Unskilled at stories but very aware of it (which is super uncomfortable).

3. Already reasonably skilled or very skilled. It counts if you’ve been working on it.

Learn from the masters

After a certain point learning this skill hits something of a plateau. But I believe that moving up the smaller increments into master-storyteller territory is equally as rewarding.

There are lots of master storytellers you can watch for serious inspiration. Try TED talks and other recorded stories online, such as the MOTH podcast or their events near you in-person.

Consider a great, successful standup comedian. A person like that is literally guaranteed to have spent thousands of hours learning to tell stories in the funniest, most engaging way they can.

You don’t have to do that, though. Most people get by just fine with a couple of dozen hours of casual practice. You don’t expect to meet a friend for lunch and be completely riveted by his tale about something embarrassing that happened that week and then applaud afterward, do you?

Still, comedians are a wonderful source of inspiration. I look to them for the ultimate picture of what a polished story sounds like. The best of them use pauses and timing, gestures, intonation, and of course the content to keep the interest of an entire audience.

Now, most of the time their goal is not to tell a story exactly how it happened, but they are constantly focused on holding attention and getting laughs.

That’s where we can find common ground that’s useful to us normal people (because getting onstage every week to talk at a room full of strangers is NOT normal). The point of answering questions like, “How was your vacation?” or “What did you do this weekend?” is not to give an accurate, chronological account of the events of said time period.

Seriously, that might sound ridiculous right now but are you guilty of that yourself sometimes? Do you end up giving way too many details in a strict order and losing the point of the story?

I used to do that exact thing. For instance, in describing my weekend I’d make sure I lined up the events in my head in order of occurrence, and verbally go through them like a list to my friend. After a while I noticed that people would sort of cut me off after a minute, or I’d lose my train of thought (very literally in this case!).

It took me a long time to see what was happening and start retelling things in a more interesting way.

How you can get better

There are simple things you can do to drastically improve.

Here’s where I can start giving some concrete advice, now that we’re on the same page:

No one cares what you did on Saturday at 1:00, and 2:00, and 5:00, and “oh we went to three different bars and here are all the things I ordered to drink…”


They want to hear about one interesting thing that happened, and for you to use just enough descriptors to paint a picture and get to the point. You can bring other things up later, but conversations are a give-and-take, a back-and-forth. Use your “turn” to speak wisely.

If you’re talking about your vacation, commit to memory just a couple of the best details or stories to tell when someone asks you about it. You can always talk about other events from that trip later.

For example, let’s say you just came back from Spain. You could sum up the whole feeling of one spontaneous weekend there by describing a market you happened upon and found some fruit you’d never seen before, and it was delicious.

Another problem I see too often is that a guy will derail his whole narrative by naming every person who was there at the party or wherever. He’ll then describe what they were all doing at each point in the timeline. It’s especially painful if I, as the listener, do not personally know any of these other extra folks.

I might be rambling a little bit myself here. Oops! Let me give a few bullet points to remember when it comes to stories:

  • Stick to the essentials: where, what, why/how, and with whom
  • Only mention people who are directly relevant to the outcome of the story
  • Decide at the beginning what the point of the story is. Is it funny? Making a unique observation? Expressing how you felt about something? Don’t deviate too far from that.
  • Don’t get too hung up on chronology and specificity. General is often better for keeping your word count low.
  • PAY ATTENTION to your listener(s)! If they’re getting bored or restless, cut some stuff out and get to the end. You’ll usually have another chance to talk in 30 seconds.
  • Give the listener a chance to participate and ask questions. Most people have short attention spans. So welcome their interruptions if they’re asking good questions. It’ll add to the fun of the conversation!

Don’t wait to use this in your life

I wrote this in the hope that you can have some more fun in telling people all about the things that happen in your life. I want you to be able to feel exciting moments with them rather than boring ones.

It’s really something when you start noticing more people hanging on your every word. Or when you get a big laugh because you expertly timed the “punchline.”

The best part is that you can go and try out these ideas immediately! Next time you’re catching up with a friend over coffee, maybe you’ll surprise yourself. And don’t forget that it’s just conversation, and you always get a new chance tomorrow.