Content that Entertains

Take a moment to reflect: when someone entertains you, what do they do?

Typically, when I think of being entertained, I imagine myself laughing.  But the scope of entertainment really goes well beyond that.

After reading several definitions and reflecting on my own experiences, I’ve realized that when someone or something entertains me, they’re enjoyably engrossing me in the subject.  In that moment, they have my full attention.

Note: Now, when I say enjoyably, that doesn’t mean that I can’t be entertained by something sad.  In fact, researchers have linked deriving pleasure from listening to sad music to the satisfaction of being able to feel as part of the human experience.  Deep stuff!

We know that content allows us to elicit emotion, prompt thought, discuss ideas, promote action, build relationships and so much more.  Entertaining content can do any and all of those things.  The twist is that it’s highly engaging.

Creating Content that Entertains

Some topics are drier than a martini, which makes the entertainment factor difficult to achieve.  However, it is possible to make fact finding expeditions more enjoyable.

As is the case with any content, it must be tailored to your audience to be effective.  The key to entertaining your readers?  Know what entertains them.  Easy, right?

How do you know what’s going to really leave your market wide-eyed, totally immersed, and wanting more?  You study them.  You poll them.

And you analyze the content that entertains you.  Is that a fool proof measuring stick?  Of course not.  But if it worked for you, it could work for others.

You may be worried that the internet already contains everything that you could possibly say.  You’re not wrong.  You may never have a totally original idea.

As a writer who essentially writes about writing, I sometimes got bogged down by this fear, too.

But our chance at uniqueness, at adding value, and at serving our market, is how we present the ideas that resonate with us.  Even if someone else thought of them first.

I like to think that my writing style is unique and that it evolves with continual practice and assimilation of new information.

What makes your content stand out?

Methods to Entertain with Content

There are a couple of main ways to entertain with your content:

  • Telling jokes
  • Telling stories

Let’s look at each in turn:

Telling Jokes

As we discussed at the beginning of this post, entertainment is typically correlated with amusement since people often laugh when they’re entertained.

And when we think about what makes us laugh, the number one thing our brain jumps to is jokes.  To take it a step further, our minds usually associate jokes with one-liners and punchlines.

But that’s truly an oversimplification.

Jokes can be subtle, interwoven into seemingly non-funny content.  Sometimes just the context, just the juxtaposition is hilarious in itself.

We see this a lot as we’re consuming content that seems pretty vanilla and then suddenly we’re randomly struck by some serious snark.  The phrase itself is funny, but the humor is amplified because it’s unexpected.

I sometimes fall into this category.  I tend to give off the reserved librarian vibe (unless I’m with my inner circle — then all bets are off!).  So in the rare event that I swear or say something slightly off color in my content, people notice.

Jokes can also take the form of narratives, with some of the best comics becoming legends just for telling their stories on stage.

Telling Stories

Stories are another prime way to entertain.  If you think about it, there’s a story behind every piece of content whether it’s written material, an audio recording, or a video.

It’s just a matter of the creator letting the story shine through.

Whenever possible, try to include anecdotes in your content.  It’s a powerful way to both engage and connect with others.

As you try to decide what elements about yourself to share, it’s important to remember that your perspective can be entertaining in itself.  You don’t need to be fancy.  You don’t need to put the most extreme moments of your life in public view (although it’s certainly an option).

People will relate to you just for being yourself.  When your content meets someone’s mind or heart at precisely the right moment, it’s pretty much magic.  It’s as if you were speaking only to them (and in some ways, you were).

People internalize what resonates with them.  The key for us as business owners and content creators is to create regularly, increasing our chances of making this impact.

Tips for Creating Content that Entertains

Here are some things to keep in mind as you’re trying to entertain your audience:

  • Grip your audience from the start.  You can ask a question, make a startling statement, or feature a joke.  Building suspense is also an option — and one that I may experiment with in a future post.
  • Create to be social, not to lecture.  Content should be easy to digest and come across as friendly.
  • Create as you would normally speak.  Doing so makes you seem more familiar and relatable.  Just don’t ramble!
  • Utilize pop culture references — but be careful with the timeliness.  I recently tried to mention Mimi from the Drew Carey Show as someone who wears too much makeup.  Then, I realized that the show aired 20 years ago and the Millennial audience of my client wouldn’t get it.  Had to go back to the drawing board on that one!
  • Show some personality.  We’ve all got one — so use it to broaden and enrich your community.
  • Emote, be vulnerable, and have passion. Your audience will be drawn closer.
  • Be interested to be interesting.  If you show genuine concern for and a desire to learn more about your audience, you’ll have their attention.
  • Expand your vocabulary.  The thesaurus is our friend!  Finding new ways to express our main ideas keeps our content fresh.  We just need to be sure that the language we use is appropriate for our audience.
  • Make it reader-friendly.  Use headings, white space, bolded text, and bulleted lists to make your written content easy on the eye.

Final Thoughts

As we’ve discussed over the past several weeks, we can create content with the primary intention of informing, inspiring, or entertaining.  However, while each piece of content has a main job to do (this piece is mostly informative, for example), highly effective content seamlessly, yet intentionally, blends information, inspiration, and entertainment into the same piece.

The most memorable content that I’ve seen provided me with an emotionally charged what (inspiration), a clear and relatable how (information) and a sense of satisfied contentment for having consumed it (entertainment).  Of course, content can still be good without perfectly nailing this trifecta.  It’s just something to strive for.

Tell me: What content creator really entertains you?  What makes their work so fascinating?

Finally, if I can help your content journey in any way, please don’t hesitate to reach out.


  • You write about content…& entertainment….I’ve come to consider myself a sort of solitary individual…I don’t always need others to be “entertained”, I can be thoroughly entertained siting in the shade on a warm evening watching the sunset,…..or in the winter watching the snow fall on the grassy surfaces….or the gentle rains of spring
    I guess I just mean that we don’t always need others to provide what may be right in front of us…

    • That’s a really beautiful point! I think we can do a lot for ourselves with our own minds and hearts if we take the time to listen.


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