What I Learned from Stand-Up Comedy

Daniel Guan
4 min readMay 14, 2020
Credits: Sarah Larson Photography

In early 2019, I needed a new hobby.

I moved to Chicago to start my first job after graduating college. By day, I worked as an account manager at a tech company and kept partners informed of product updates. By night, I loaded up Netflix in my tiny studio, and queued the numerous standup specials that they released.

I looked up to stand up comedians for their ability to command the stage. Their ability to have a monologue with the audience and tell stories was always inspiring. If you think about it, it’s no different than giving a presentation at a company all hands meeting (you just have to make people laugh!). With all this, I decided to plunge into the trade head first.

I enrolled into two stand up courses at the legendary Second City theater. This is the same place where the likes of Steve Carrel, Tina Fey, and Stephen Colbert have graduated. Within the 10-week class, students would come together in to dissect famous sets, brainstorm material, and workshop it in a mock show. We were encouraged to attend one of many open mics across the city to test out what we drafted in class. The class would end in a public showcase at Second City, a culmination of all the edits, rewrites, and work you had put into the class.

The opportunity for embarrassment was high.

By the end of the two semesters, I had a blast: I made new friends from all walks of life and got back into analyzing writing like I was back in college. If anything, I came out of those two classes more confident than ever in my ability to ramble about anything on stage and make people care about it. Reflecting on my experience, there were five key takeaways I was able to draw:

1. Your life and your perspective is your greatest source material

What makes each comedian unique is the perspective they were able to draw from their own life experiences. It’s part of the reason why everyone can talk about the same topics (dating, work life, family) and write unique material: it’s all from their own perspective. This was enlightening to me as I always thought you had to be born funny to be a comedian. Telling a joke on stage was no more different than complaining about your life to your best friends.

2. Be genuine or no one will laugh

As much as your life is your greatest source material, it’s why you should not write jokes about something you don’t know anything about. Could I tell a joke about what it means to be a rich millionaire living off a remote island? Of course not — (yet.)

There’s a credibility that comes with delivering a stand up set and putting a front will not allow you connect with the audience. So until that day I become millionaire, I can at least share my thoughts of what I would do if I was one.

3. How you tell it is just as important as what you tell

One comic I look up to is Hasan Minhaj. If not for his thought provoking commentary on current events, his energy and animation on stage exemplifies why performing is important. How you deliver a punchline is just as important as the joke you tell.

This is not to say that everyone must perform a solo act that waves their hands everywhere. However, if you are going on stage and delivering a monotone speech, it’ll be difficult for your audience to stay awake for the show.

4. Feedback is a gift

One of the best resource when writing jokes was the support of my classmates. At the end of each workshop, we would breakdown each punchline and brainstorm ways it can be funnier. It’s one thing to retell a story as you know it, but it can be elevated that much more if you could fill in gaps people identify that make the joke that much better.

5. Roll with the punches

Jumping into standup, you quickly learn to embrace being uncomfortable all the time.

I bombed my first open-mic. I had only three minutes, the setting was a barely filled pizza bar, and I forgot half of my set. No one laughed in the entire bar and I quickly wanted to sneak behind the back door.

Eventually I started to set small goals with each open mic. If I can get at least one person to laugh at my jokes, it leaves me with a sense of confidence that there’s potential in it. If I am able to navigate through a forgotten detail in retelling a story, it leaves me with a sense of relief that I am able to be flexible under pressure.

Stand Up Comedy and Your Professional Career

It’s no surprise that these takeaways can be applied to just about anywhere. In my daily job, every presentation almost feels like a stand up set. I’m there to present on an idea from my perspective. I rely on feedback from my peers to improve my storytelling and roll with the punches when things don’t go as planned. Having your partners laugh too doesn’t hurt either.

I’ll definitely want to return to performing open mics and write more material in the coming months. Everyone can take away a lot from standup comedy. I’ll amend a quote from one of my favorite movies, Ratatouille.

Your only limit is your soul. What I say is true — anyone can [be a comic]… but only the fearless can be great. —

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Daniel Guan

Bostonian transplant living life in the Windy City. Currently @Facebook. Formerly @Converse & @BuzzFeed. Find me on Twitter @DanielJGuan.