How Comedians Teach You to Write Good Transition Sentences

Think back to the last time you saw a really great stand-up comedy show. The jokes were funny. The comedian was a good story teller, transitioning effortlessly between segments, and everyone seemed to be having a good time.


Now think about a time when you saw a really terrible comedian. It may have been the same night; he may have been the opener for the headlining comedian. This experience was probably quite different. The jokes had potential, but fell flat. There were awkward pauses, and the entire bit seemed to be a mishmash of random anecdotes.

This is a pretty typical experience, but most people don’t actually analyze why they loved one comedian, but didn’t care for the other.

The last time I was at Cobb’s Comedy Club, I sat through a very average comedian, but was later blown away by the headliner.

As my friend and I left, we discussed why these two comedians had such different effects on us. It wasn’t the quality of the jokes; we agreed that they both had good material. However, the delivery was completely different.

The headlining comedian masterfully transitioned from one topic to the next. The segments were often seemingly unrelated, but we hardly noticed. What resulted was a fluid show from start to finish that captured our attention the entire time.

And that’s the power of good transition sentences and phrases. They are capable of taking your audience or reader from one idea to the next without sounding disjointed or jerky. Transitions thread together several different ideas to create one cohesive story. But it’s done in a subtle way, and that’s why good transitions are so difficult to master in our everyday writing whether that be an essay, email, or cover letter.

So what are transition sentences exactly?

A transition sentence is any sentence that is designed to move your audience from one idea to another without causing confusion or losing fluidity. You may have been taught that the words “however,” “therefore,” and “furthermore,” among others, are transitional words that, in turn, compose transitional sentences. However, this is the most basic form of transitional sentences. In this blog post, I’ll be talking about more subtle and complex forms of transitional sentences and how they take your essays and writing to the next level.

Unfortunately, many people believe that transitions only happen at the beginning of paragraphs in order to connect their different ideas. That is not true. Transitions should actually happen within paragraphs to move slowly from topics and segments before introducing new ones.

That sounds really vague, how about some examples?

Sure, but before we get into any written examples, let’s look at what world-class comedians teach us about transitions.

Stand-up comedy is much like an oral essay. The comedian tells jokes, usually in the form of a story, and moves from one segment of material to the next by connecting them with good transition sentences.

Take a look at this short clip of Jim Gaffigan.

Throughout this four and a half minute segment, Jim pokes fun at holiday traditions that we all recognize. But he doesn’t focus on just one holiday; he covers Christmas, Easter, Thanksgiving, the 4th of July, Halloween, and Valentine’s Day.

While all of these holidays are related to Jim’s overarching theme of holiday traditions, he still has to connect each holiday with good transition sentences. Some of these transitions are very apparent and easy to spot, but let’s take a look at one that is particularly great.

At 1:46 in the clip, Jim starts talking about Thanksgiving. He pokes fun at the fact that our tradition is to eat a ton of food. At the 2:10 mark, Jim continues this theme of food and eating to bring his audience to the next holiday via the following the transition sentence:

“Most people use holidays so we can eat more. I normally don’t have a burger, a brat, and a steak. But, it is 4th of July.”

This is an awesome transitional sentence. In the sentence immediately before this, Jim was talking about overeating during Thanksgiving, and he’s able to move his comedy seamlessly to the 4th of July by staying on this same topic. His audience doesn’t even realize they’ve just broached an entirely new topic and an entirely new set of jokes for Jim to tell.

This is just one small clip of Jim Gaffigan’s full stand-up routine. But if this were an essay, we see how we’d use each holiday as a paragraph. On the other hand, we might decide to write an essay about “The Oddities of Our Everyday Life” and use this entire clip as just one paragraph.

In that case, we would have to transition from different ideas that aren’t as closely related as holidays, just as Jim would do throughout his entire routine. As you can imagine, a full one-hour show about holiday traditions is bound to get boring!

So how do I transition between ideas that are not at all related?

Look no further than this blog post!

It isn’t immediately apparent how writing essays, blog posts, and cover letters are related to stand-up comedy. But when I thought about what makes a great stand-up comedy show and what makes great writing, the answer became clearer.

The truth is, just about any two things are somehow related. In fact, you may be familiar with the six degrees of separation. The theory is that anyone or anything is related to another within six introductions or connections. Let’s take a look at this visually:

This is a relatively simple example as comedians and writers are only separated by one degree. But you can imagine how it has the potential to get quite complicated!

The six degrees of separation theory was introduced in the 1960s but was never actually tested until much later. However, it turns out that the theory actually holds true. As a result, no two things are actually completely unrelated; rather, they are seemingly unrelated, and it is up to you to discover that relation.

But relating two seemingly unrelated subjects is only half the battle. The true challenge is doing it in a way that flows naturally with your writing. That’s exactly what I’ve done in this blog post.

I want you to go back to the first six paragraphs of this post. Notice how I was able to transition you, as the reader, slowly from talking about comedians and then moving to my main topic: writing good transition sentences.

Let’s break down how I did this step by step, so you have a reference for trying it in your own writing.

In the first paragraph, my goal was to first introduce stand-up comedy as my stepping stone. However, I also wanted to wean you slowly into my main subject: good transition sentences. The trick here is to do this in a non-abrupt manner. Notice my careful word choices:

I intentionally used the word “storyteller” to solidify the fact that, like a writer, a comedian tells a story to his audience. This way, when I push writing and stand-up comedy closer together, the idea won’t seem completely foreign.

I also dropped in the word “transition” to get you familiar with this word being used in the context of a comedian and stand-up comedy rather than just in the realm of writing.

Lastly, the word “segments” helps me lightly relate a stand-up comedy routine to an essay. After all, an essay is simply a collection of segments, or paragraphs.

The goal of this first paragraph was not a hard sell, trying to say that stand-up comedy is directly related to writing. My plan was to simply begin relating the two, even if only subconsciously.

The second paragraph is quite different. Rather than focusing on particular words, I chose to connect an idea instead: without good transitions, a stand-up comedy routine isn’t all that great.

My goal here, obviously, was to compare good and average stand-up comedy. But remember, I’ve already started relating stand-up comedy to writing. My ultimate goal is to provide you a relatable example to “sell” you on the importance of good transition sentences and their power to make average writing great.

Notice the key sentences I use in paragraphs three and four to solidify further the power of transitions in stand-up comedy:

All I’m doing with these paragraphs is providing further anecdotal support that great stand-up comedy is highly dependent on great transitions.

Once I’ve adequately supported my stance, it’s time to start really bringing it home. The fifth paragraph doesn’t beat around the bush; it comes right out and says what you, as the reader, have already been toying with in your head. Also notice how I reiterate some of the same words I used in the opening paragraph: “segments” and “transitioned”:

At this point, I’ve got you hooked. You’re most likely nodding your head in agreement, and I’m now completely free to move my writing to the main argument:

The first sentence in this sixth paragraph is the clincher. I finally come out and say, “Hey, good transitions take something average and make it truly great.” Also, this is the very first time I ever use the words “transition sentences and phrases” as these terms are largely related to writing, not stand-up comedy.

As soon as I do that, I slyly drop in the word “reader” to begin completing my transition from stand-up comedy to writing. With the phrase in green, I’m finally able to move the conversation completely to a point where I broach the subject of transitions and writing.

I’m now off to the races, free to compare stand-up comedy, writing, and transitions interchangeably. As the reader, by this point, you are completely comfortable making these connections, and it doesn’t seem odd or awkward. The beauty of this is that had I not walked you through this entire process, you may have never realized how I managed to do it. And that is the power and beauty of transitions; they occur without you realizing it.

In your next essay or blog post, try to keep transitions in mind. The way I’ve managed to do it here is quite complex and takes much thought and practice. But start small, and you’ll quickly realize the benefits great transition sentences and phrases have on the power of your writing.

I’d love to hear your thoughts and feedback in the comments!

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