12 Standup Comedy Techniques That Can Boost Your Mental Improv Skills

I used to think that dictation writing or dictablogging is just an extension of my usual writing processes.

But after sticking with this method of content production for several years, I realized that it’s just a more targeted form of verbal improvisation.

As you know, improvisation is usually associated with improv acting and stand-up comedy.

Make no mistake; it doesn’t matter if you’re just starting out with dictation writing or you’re a veteran. You better focus on the mental improvisation angle of the dictation process.

How come? Better improv improves your communication skills overall.

If dictation were a car, improvisation would either be the engine or the transmission system. That’s how crucial it is.

After several years of experience writing through dictation, my respect for stand-up comics and improvisational comedian have grown by leaps and bounds. I have nothing but the most profound admiration and respect for their skills.

It’s a fantastic craft that they practice.

The more I watch professional stand-up comics do their thing, the more inspired I get.

So what can we learn from these comedians?

Here are 12 secrets from improvisational stand-up comics that I have applied to dictation writing.

Believe me. These 12 secrets have made a world of difference in the quality and depth of my dictations and the volume of my output.

Tip #1: Expect Duds and Bounce Back Quickly

When a comedian tells a joke that either goes to everybody’s head or just flat out bombs, the comic on the stage doesn’t fall apart and feel emotionally devastated.

Instead, the veteran comic expects duds. These jokes simply did not resonate.

Maybe they will never be funny. Or they’re just not funny to this crowd.

Either way, it doesn’t matter. The comic quickly moves on to the next joke and the next one after that.

The same thing should happen with your dictation.

If your first version of a sentence, paragraph, or even a complete section isn’t correct, don’t feel that you have to be horrified. Don’t think for a second that you’re somehow chained to it.

It’s not productive for you to come back and pick at it again and again or tell the transcriptionist to just drop that section because it just feels like such an embarrassment.

You don’t need to be emotional. This stuff doesn’t have to own you.

Expect that from time to time, you will dictate gibberish. No one is perfect.

Just bounce back from it by either correcting it through self-editing or move on to your next point.

Make a mental note that there were some rough spots, and look forward to the transcript. Once you get the text, jump on it and look for the problematic portion and fix it.

No need to agonize over it. You definitely don’t need to think that this one setback means you are a lousy dictation blogger.

No need for that.

Tip #2: Read Yourself and Your Outline Like a Comic Reads a Crowd

You can tell apart a great stand-up comedian from somebody just starting out by the way they read the crowd.

Excellent stand-up comics deviate from the preset script they have in their minds depending on the crowd’s mood.

On the other hand, a newbie stand-up comedian feels that he or she has to stick to the script.

Who do you think tells the better jokes? Who is in the better position to “kill it” that night?

The answer should be obvious!

At the end of the night, the comic wants the crowd to get the experience that they paid for.

They’re not there to listen to canned jokes. They’re there for a shared experience.

You can apply the same practice to your dictation process.

While reading your dictation outline, allow yourself to step back from the process and “read yourself.”

Are there some parts that seem easy to you? How does it feel when you hit those sections?

I know that when I read an outline, there are certain sections that I feel like I can do blindfolded. I only need to read a few words from that section of the outline, and I already know what to say.

I can dictate several paragraphs’ worth of content just after reading those few words.

On some other sections, though, I feel stuck. The words roll off my tongue like frozen molasses.

Trust yourself enough to read yourself as you work with your outline. This way, you will get into the flow of the parts that make much sense.

The more comfortable you are with those sections, the smoother your improvisational speaking becomes, and your confidence grows.

By the time you hit the areas you’re struggling with, you have enough mental focus to power through. You have enough perspective to not insist that everything be “perfect.”

That’s what makes those slow and arduous parts so intimidating because you know you’d be struggling with those points at the back of your mind. After all, you want everything to be perfect.

But when you enter a state of flow with the parts of the outline you’re entirely comfortable with, you will make it through that emotional resistance and get to your outline’s next “easy” part.

Step #3. Pace Yourself to Enter Flow Momentum

What is flow momentum when dictating content?

It’s a state of mind and speaking where everything falls into place.

Even if you try to confuse yourself, you know where you left off. You never get lost. Everything is so clear and fast.

You can talk about so many different subpoints of your outline, and everything would make sense when you read the transcript.

You’re not just reading the main points and the subpoints that support them, but you’re telling stories.

You’re putting everything together. You’re connecting the dots, and it all makes sense.

That is the flow state because you have entered this unstoppable momentum and the words just roll out.

George Carlin went into these flow momentum passages, and they are wonders to behold.

My favorite was when he was talking about people who wanted to “Save the Planet.”

Then he got into this extended description of the many times the Earth went through catastrophic changes.

He let off a long list covering everything from earthquakes to magnetic reversals to solar storms and all sorts of other Earth-shattering developments.

And when he concluded, the crowd was cheering because they can tell that he got excited listing things off while painting a picture that everybody could agree with.

There was this sense of emotional connection where people just look at each other and realize that they see eye to eye.

This is only possible because he paced himself.

He started slow, making some logical points, and then he got into that ever-increasingly quick monologue within a monologue.

It would help if you did the same. You know where the rough spots in your outline are.

Pace yourself. No need to speed through your outline. You don’t have to play games with yourself.

Understand that those parts are going to be slow, and it’s perfectly ok.

But once you get through them and things start to fall into place, the point after the challenging parts are more manageable.

Allow yourself to enter the flow momentum. It turns out that the slow pace at the beginning was just your warm-up.

Think of it that way. Stop thinking of it as plowing through stone or trying to smash through concrete.

Instead, it’s a windup to get where you can pitch, and things go smooth and fast, leading to a fantastic ending.

Tip #4: Time Your Points for a Crescendo

In the George Carlin stand-up routine that I’ve just described, what made his final points so emotionally satisfying to the crowd was the fact that it set them up for an emotional crescendo.

The more items he listed, the more everybody realize that the idea that human beings are destroying their planet at this point in history is not just presumptuous but totally absurd because, during the billions of years that the Earth has been in existence, it’s gone through several mass extinctions, and several globe-shattering disasters, but the Earth is still here.

That’s when that sense of cosmic destiny kicks in.

While humanity may go the way of dinosaurs, when we focus on Earth and “what it’s been through, what it is going through, and what it will go through in the future”, we get a sense of calm and permanence.

That is the emotional crescendo that Carlin works towards. This is only possible because of how he timed his points.

You can do the same.

While you’re not trying to impress anybody when you’re speaking to a microphone, you trigger an emotional flow within you.

This crescendo translates into something convenient. The outline no longer feels like a trap or some sort of straightjacket.

Instead, you can quickly power through the points one right after the other, and before you know it, you’ve got another book, blog post, or article in the can.

This is how you can go from barely typing 3,000 words per day to 25,000 or even 80,000 words every day.

I ought to know. I’ve done it. I went from barely 2000 to 3000 words per day to so much more. I write 20,000 words per day consistently thanks to dictation writing.

Tip #5: Say “Yes…and” to Your Material

Improvisational speakers remember key points that they’re going to talk about, and they never seem to run out of stuff to say.

A lot of this has to do with the fact that they don’t “can what they’re going to say.”

Instead, they just remember the key parts of the outline and challenge their memory by saying “Yes…and.”

When you do the same with your outline items, you challenge your ability to remember what you’ve researched before.

You also challenge your logical skills in connecting whatever loose ends may be in your dictation up to that point.

This is a potent improvisational tool. Practice it. Keep at it.

If you feel like you’ve hit a wall, say “yes..and.”

You’re basically saying to yourself: “Ok, I’ve said that. What else is there?”

What does this mean? Where is it connected to in this outline? How can I make that connection?

This is a series of challenges that push you to tap your personal intuition and deepen your insight.

Tip #6: Add Depth and History Because if This Stuff Fits, Then What Else Fits?

When you’re talking about an outline point, you don’t have to just stick to the surface.

Although it seems that a lot is going on at a superficial level, you can actually add more depth to it by just asking key questions about what happened before.

As I dictate this article, when I discuss Tip #6, I realize that there’s always a back story for each claim you make. That is depth.

Also, if you’re able to fit Tip #6 with the last five secrets, you will see how it flows with the remaining six items.

Understand that the human brain operates in terms of connections.

So if you something that makes sense, the next logical thing to explore is what else makes sense? What other thing can I talk about that would fit what I just said?

I’m not talking about repetition, mind you. I’m talking about expanding or extending what was just said.

Comedians do this all the time. They say stuff that may not all be all that funny.

But when they add a backstory or deepen it with an emotional angle, it starts resonating.

This is a better approach than just realizing that you said a dud or you bomb, and then you kept picking at it. People get annoyed when they see that kind of stuff.

By adding depth and history, you’re not only adding more value to what you’re talking about, but you’re moving on.

Tip #7: Give Yourself Permission to Get Excited While Staying in Control

I know that sounds like a contradiction in terms: “get excited while staying in control.”

But it’s precisely the excitement that enables you to practice the discipline to stay focused.

Great comedians don’t make a point of constantly laughing at their own jokes.

Some use it as accent points. Others laugh at their own jokes to create transitions.

But for the most part, the mark of an excellent improvisational comedian is to stay in control while obviously being excited about what they’re saying and the setup that they’ve achieved.

Do the same.

When you realize that you are expressing the value in the outline items you are reading, you’ll get excited enough to move on to the next point and repeat the same thing.

Tip #8: Savor the Twists and Turns in Your Dictation

It’s too bad that I can’t include the audio of this dictation in this blog post.

But if you were listening to my voice, you would notice that I’m talking really quickly on some parts. On others, I am slowing down.

There are many twists and turns in my dictation, which adds a lot of much-needed diversity on an audio level.

Furthermore, it also has a different emotional impact on the listener and myself because I’m wearing headphones as I dictate.

I’m listening and reading myself as I go through the outline, much like a comic would pay attention to what they’re saying and reading the crowd at the same time.

In that process, there are many twists and turns in the comedian’s speech, which can make or break a particular joke.

One comedian who does this superbly is Dave Chappelle.

He would set you up by talking about something in a matter-of-fact way, and then he would throw you a curveball.

For example, he would say a very racist statement and tell the crowd that many people were saying that that’s the kind of thing white supremacists would say.

But then he would throw a curveball at the audience and say: “No. I know white people. That’s not how they talk. But that’s something I would say.”

And this unleashes a tsunami of laughter in the crowd.

Those twists and turns in improvisational and stand-up comedy can make a big difference.

The same applies to your dictation.

Although you’re not talking to a crowd, the twists and turns have an impact on your emotional state which impacts how you edit yourself as you speak.

As I’ve repeatedly said in this blog, what makes dictation blogging hard or easy depends on your emotional state.

When you savor the twists and turns in your dictation and allow yourself to be excited or look forward to different points in the outline, you make it through the rough spots.

You’re able to navigate the areas of your outline that you feel emotionally unsure of.

These usually are enough to stop you, but when you’re enjoying the journey of covering all these points on the outline, you make it through.

You don’t let these key points further down in the outline intimidate you.

Instead, you allow yourself to remain focused so you can say the things you need to say and move on.

Tip #9: Appreciate the Windup of Your Points

When you’re laying the foundation for a more significant point that you’re going to make, don’t go about it in a joyless manner.

Don’t think to yourself: “Well, I’m just laying the foundation, so it’s like I’m just stacking one heavy rock on top of another.”

If that’s your mindset, things are going to drag on far longer than you would like. This should not be a surprise because you’re looking at it as a chore.

When you appreciate that you’re laying down one point so another point can rest on it, which can then support another point, you would see where the big culmination is.

The comedian Bill Burr does this in a fantastic way.

He would go through the joke’s set up in an excited but somewhat emotionally objective way. Then he would give you the punch line.

And the way the windup is done makes the punch line even more powerful.

Do the same with how you wind up or build up your points.

Get excited about the crescendo or the payoff at the end.

Tip #10: Great Comics Let Go of Ego and Focus On Flow

The big difference between an amazing talent like Dave Chapelle, George Carlin, or Bill Burr and the typical rank-and-file comedian is one of ego.

A lot of up-and-coming comedians know timing. They know how to pace their speech to create comedic opportunities.

The technical proficiency is there, but unfortunately, when these comics feel that their bombs define them, they clam up or seem hesitant. Hence, the punch line just isn’t as good.

Dave Chapelle had bombed in the past. He’s a veteran to dud jokes. But he moved on.

And he learned from his mistakes, and he found his flow. You can do it too.

Let go of your fear of slowing down, speaking in circles, or just spouting out gibberish. Those things happen.

But you got to start somewhere, and the good news is, the more confident you are about the process, the more things will begin to fall into place.

Before soon, you will know what to do. You will remember them, and you will commit fewer errors.

But suppose you were just going to just obsess about things falling apart and audio being ruined because you just can’t get it straight. In that case, you’re not going to make as much progress as you would like.

You’d remain stuck.

You’re letting your fear hold you back.

Tip #11: Use Transitions as Opportunities for Inspiration

The great thing about dictation writing is that it opens many rooms for inspiration.

You’re not just reading an outline. As you move from one point to the next, you give yourself space and the time to be inspired.

As you probably already know, the whole point of speaking your content is only made possible by the power of inspiration.

For example, the outline that this dictated article is based on is less than a hundred words.

Where do the rest come from?

That’s right! Inspiration.

The good news is that when you’re transitioning from one point to the next, you can give yourself permission to be inspired not only by your excitement to talk about the next point but your confidence about the point that you just made.

And if you string this up throughout the rest of your outline, you go through it much faster and with less drama and stress.

Tip #12: Jump on Insights and Milk Them

There’s a reason that I’ve been watching a lot of Andrew Schulz.

The great thing about his comedy is that a lot of it is crowd work.

That’s a comedy term for the comic just randomly talking about a subject and then letting the crowd come up with specific things he will be talking about.

This interplay between the crowd and the comic makes such shows hilarious and memorable.

But operating in the background is the power of insight.

When somebody in the crowd says something borderline funny, it’s the amount of insight the comic comes up with that will seal the deal or lay the groundwork for a bomb.

Understand this and use it to your advantage.

When you are dictating a point, usually, an insight comes to you. Trust yourself enough to explore it and think ahead about how far you could go and its rough dimensions.

Cover that area and move on to the next point.

Milk those insights because they solidify your outline.

Then fill it out and make what would otherwise be just a clear point genuinely shine.

The Final Word on Learning From Improv and Standup Comics

Make no mistake. Sometimes it feels like you are jumping off a plane without a parachute.

But the good news is that dictation blogging gets better with time.

By using the 12 secrets above, you’re not only boosting your speed, but you’re also improving the quality of your dictations.