Why Success Creates More Work
(Comedy Mindhacks #1)
Before I jump into this post, a little note is worthwhile: I have spent 25 years of my life in academic circles both, as a student and as a professor. I don’t need to run through all my credentials here but I bring this up because, deep in my bones, I love researching and learning. I really enjoy exploring “theories,” too, and seeing how they help us understand and explain life and behavior. So, while I’ve mentioned this before on this site and while I’ve already written several posts on it,1 I’ve decided I’m going to launch a new series here called “Comedy Mindhacks.” This series will run alongside several other series on the site: a) The “Messed-Up to Set-Ups” podcast; b) Messed-Up But Managing; c) Fake News Weekly; and, d) Things That Matter. In the “Comedy Mindhacks” series I will focus on introducing theories that shed some light on comedy and may also give some tips for writing and/or performing. These “Mindhacks,” however, will be useful for ANYONE doing ANY type of public speaking, whether it’s teaching, lecturing, podcasting, preaching, etc. I also plan to do video spinoffs of these, like one I did HERE and HERE. So, if you want to see those in due course, follow me on Instagram and subscribe over on YouTube. Having said that, let me get to it.
Success has a funny way of creating more work. Depending on how you look at it, that can either be a good or bad thing. As is the case with pretty much any life skill, in stand-up comedy getting better at one thing naturally exposes you to the next challenge. You tighten your five-minute set, eventually you’re asked to do ten. You start getting booked at new venues, now you have to figure out how to adjust to different crowds. You get comfortable with familiar jokes, then you realize it’s time to write new ones.
There’s a name for this: the Success Expansion Principle. The idea behind it is simple: every win expands the game. But every level of success doesn’t just bring more opportunities, it also brings new responsibilities, new adjustments, and new things to master. What kind of makes my mind bend a little bit with this principle is the fact that success isn’t the end of the process like we so often think it is. Nope! Success just moves the goalposts. (Reread that last sentence.)
Author Robin Sharma puts it like this: “Your life will expand or contract in direct relationship to your willingness to walk directly toward the things that you fear.” That hits! And I think it’s very true when it comes to doing stand-up comedy. Because everything in stand-up gets easier once you stop avoiding what makes you uncomfortable. Pretty much every time I’ve hesitated in comedy, it’s because I was afraid of something. Afraid of bombing in front of a bigger crowd. Afraid of trying a joke that might not land. Afraid of talking to a booker and getting rejected. And every time I’ve walked toward those things, my world has expanded.
For years, I sat dormant telling myself, “Ah, doing stand-up is a bucket list item.” I had done public speaking for decades at this point. I’d sung, preached, lectured, taught, and so on thousands of times. But stand-up was terrifying. Eventually, I worked up the nerve to do it. Early on, I avoided crowd work. I didn’t trust myself enough to engage the audience without pre-planned material. But when I finally forced myself to do it, I realized I was missing out on an entire skill set that could make my sets feel more natural. Now I enjoy when I get to try it. That’s what expansion looks like: moving toward the fear and realizing it wasn’t as scary as you thought.
The same thing happened with longer sets. The idea of doing 7 minutes felt impossible at first. But when I did it, I realized the challenge wasn’t filling time, it was structuring it. Back in November of 2024, I did 30 minutes. Then in January of 2025 I did an hour. And I know that moving forward, whatever the next big, intimidating step is, I just have to keep walking toward it.
The challenge here is that expansion can feel like a struggle. In fact, it almost always feels like it. When you reach a new level, you don’t always feel like you’re progressing. You might actually feel less comfortable because suddenly you’re dealing with things you’ve never had to think about before. The first time I performed in a venue where I couldn’t see the audience because of the stage lights, I felt completely disconnected. That wasn’t a sign I didn’t belong there; rather, it was a sign I had stepped into something different, and I needed to adjust.
A lot of folks talk about “leveling up,” but leveling up, at least in stand-up, isn’t just about getting funnier, it’s also about handling more responsibility. In time, you get bigger opportunities and with them bigger expectations. The laughs may come easier, but so does the pressure. And that’s not a sign that something is wrong. That’s exactly how it should be.
If success isn’t expanding your workload, you may not be pushing hard enough. Growth in comedy, like in anything, isn’t linear though. It’s a constant process of solving new problems that only exist because you’ve already solved, at least partially, the old ones. So, if it feels like you’re always chasing something new to figure out, that’s a good thing. That’s how this works. That’s success expanding right in front of you. The only question is whether you’re willing to walk toward it.