The David Sedaris Masterclass: Will It Help Aspiring Writers?

You guys. I am so excited for this one. I am SUCH a huge David Sedaris fan. I’ve seen him live at a book reading, I own all of his books, and I’ve read every article I can get my hands on. It’s pretty safe to say I’ll be very biased when taking this course, however, I do want to see if it can actually help me.
As you may know, I have a passion for writing. Not just songwriting, but essay-style writing, very similar to Sedaris (although I would never dare to put myself in his league).
If you’re not familiar with David Sedaris, he is a “New York Times Bestselling Author and Humorist,” which is a fancy way of saying he’s a hilarious writer. He has the ability to take any boring story (picking up trash, riding a bus, etc) and making it a side-splitting tale.
I’ve written a couple of essay-style stories on this blog before: My middle school talent show here and my work playlist mishap here. These will serve as the “before” essays so we can compare and see if the class works.
Important Notes on the David Sedaris MasterClass:
I just need to point out a few things here:
- This is my 5th MasterClass. I’ve taken Christina Aguilera‘s, Reba McEntire‘s, Deadmau5‘s and Danny Elfman‘s so far.
- Although I’m a huge David Sedaris fan and MasterClass is an affiliate, I promise to make this an honest and thorough review. I’ve been very open about what parts of MasterClasses I don’t like in previous posts.
- This review series will be based on assignments, not segments. There are only 14 segments in this MasterClass, but there are multiple assignments. In order to determine if they are successful, I will break each segment into its assignment.
*This post contains affiliate links

David Sedaris MasterClass for Writers
If you’re taking (or have taken) the David Sedaris Masterclass, please let me know!
I'm taking the David Sedaris MasterClass! Click To TweetI’d love to discuss your thoughts and takeaways on it. If you prefer to watch rather than read, here is my video on the class:
Keeping a Journal for the Class

The first “assignment” we get is to keep a journal throughout this course. I kind of do that already with every MasterClass I take, but I think this one is geared more toward just journaling your whole day.
Right away, the workbook is LOADED with great info. It’s a little overwhelming, to be honest. There are so many things to remember (let go of perfection, exaggerate, quote funny people, etc etc) that it’s hard to know where to begin. However, there is a ton of genuinely useful, actionable advice here. I highly recommend taking some time and going over each piece of advice slowly because although it’s a lot, it’s useful.
Each tip also comes with an example from a David Sedaris piece.
Ask Better Questions

This seems like the first actionable item in the class and is far less overwhelming than the task list we got before.
Being highly observant is a key to being funny. However, being observant in a funny way is a different skill and something you have to develop on your own. My “brand” of humor has always been to observe and point out the absurd. I can pick apart any movie scene and tell you what’s dumb about it (I do that in my post where I rank every Whitney Houston music video from worst to best here). Whether it’s funny or not is subjective, of course.
David Sedaris hates questions like “How are you?” He says they don’t go anywhere and are meaningless. I agree, but his alternative question is “Do you know many people in wheelchairs?” I….I mean, I guess my millennial upbringing would just steer me away from a potentially problematic question like that, but I’m not a NYT bestseller so, maybe that’s why.
“Do you know many doctors?” is another question he asks that usually gets people to discuss their own diseases. I would just say “No, I only hang out with stupid people” and that would be the end of it. I do love the idea of replacing “how are you?” with off-the-wall questions though.
Here are some suggestions for unique questions for my fellow musicians:
- “Who is your least favorite pop star?”
- “Which of Taylor Swift’s songs do you most relate to?”
- “What is your most embarrassing song on your playlist?”
- “What’s your most memorable on-stage moment?”
- “What’s the best (or worst) concert you’ve seen?”
- “Why is Whitney Houston the best singer of all time?”
- “Who is your dream collaborator? Do you think they would be easy to work with?”
Fill in the blanks for your audience, but I really do think this is great advice and I plan on using it if I ever leave my house again.

Obviously, in order to be an interesting writer, you have to lead an interesting life. This means you have to have experiences, take chances, and go outside of your comfort zone.
Sedaris has had some absolutely wild experiences: Getting a tumor removed by a fan, feeding a bird raw duck meat, visiting a monkey farm. I’d like to think I say “yes” to most experiences, but I will keep it in mind to say “yes” to more. As a hermit introvert, I think the first step is just leaving my house.
Simply having an interesting story to tell is 50% of writing interesting stories. The other 50% is writing them well. I have 0% of what it takes so far.
Creating a Practice for Writing

David Sedaris writes every single day and strongly recommends that we do the same. I think this is true if you’re a songwriter also. He cancels events to stay home and write. This kind of contradicts what he just said about saying “yes” to experiences, but I guess you can say “no” to ones you know will be boring.
We end this segment with two assignments: Retell a story you’ve written from a new perspective. There are three options to rewrite the story, but I’m going to write about what I *wish* had happened. I’m using my elementary school horror story. This is a throwback to my Danny Elfman MasterClass assignment.
The other assignment is to give yourself a time and place to write every single day. I am going to do this, but it will be just a boring diary so I don’t plan on posting it. I do a lot of writing on my other blog if anyone cares.
What do you think of the David Sedaris MasterClass thus far? Do you plan on asking anyone unique questions? Let me know in the comments!
Time for my Shameless Affiliate Plugs!
Click Here for the David Sedaris Masterclass
MasterClass is now doing exclusively All-Access Passes where you can take any class at any time, which is how I do it and recommend it anyway. So even if you’re not sure about the David Sedaris one, you can take any of them through here.
If you’re not sure what other classes there are, I’ve reviewed a few of them but here is the home page so you can browse.
You can give MasterClass as a gift! It’s a great idea if you know someone who’s a huge fan of any of the teachers.
mla
Your questions:
“Who is your least favorite pop star?”
Pentatonix (if they count. I really appreciate acapella, and I originally really liked them, but somehow *and I’m not sure how* they’ve really gotten on my nerves).
“Which of Taylor Swift’s songs do you most relate to?”
Honestly, I do know who Taylor Swift is, but I can’t think of a single song, so probably, given that fact, none of them.
“What is your most embarrassing song on your playlist?”
I haven’t had a playlist in a long long time, but I’ll go with Thriller. I had that on a mix-tape when I was in middle school and it’s an important part of culture, but not so great.
“What’s your most memorable on-stage moment?”
5th grade, I wasn’t exactly on stage, but I had to read a fictional story I had written about Pilgrims…in front of the class. I had to pee, really really bad, and was dancing around when I finally asked the teacher. I had to leave class in the middle of reading a terrible story. I was mortified.
“What’s the best (or worst) concert you’ve seen?”
BEST: much to my surprise, this is a tie, between:
– Zakir Hussain in the late 90s in Oakland, CA
– Chick Corea in 2018 in Santa Fe, NM
Both concerts were magical, incredible. The musicianship was otherworldly!
“Why is Whitney Houston the best singer of all time?”
Because she’s dead…I’m not going to argue against a dead person, and she was, indeed, an incredible singer!
“Who is your dream collaborator? Do you think they would be easy to work with?”
Esperanza Spalding! She is beautiful, incredibly talented, smart, and she comes across as incredibly cool, which makes me think she’d be easy to work with and to be around.
My questions for musicians:
1) If you could be as accomplished a musician as Miles Davis, but never achieve fame (you’d make a decent living, but never be famous), or you could be as famous as Miley Cyrus, but you’d never be a great musician, what would you choose, and why?
2) If you had to have a lap-dance from either Seal or Lenny Kravitz, who would you choose and why?
3) If you could get six months of free bass lessons from either Christian McBride, or Les Claypool, whom would you pick? Do you think your teacher for the next six months would agree with your choice?
4) Uptown Funk or Carwash? Why?
MellaMusic
mlaAhahaha I loved this, thank you! My answers to your questions:
1) The first one for sure. Fame scares me, I’m very introverted and wouldn’t want everyone knowing everything I do!
2) LOL I honestly don’t know – I feel like Lenny Kravitz is more eccentric so I’d get a better show? So I guess him haha
3) Definitely Christian McBride (no offense to Claypool at all, he’s great also) and no I don’t think he’d agree with my choice because he’d get annoyed with me and my lack of bass talent about a month in, haha.
4) I think Carwash only because Uptown Funk was overplayed to the extent that I need a few more years before I can enjoy it again, lol
Thank you so much for answering and I’d love to know your answers to your own questions as well!
Paper writer
Outstanding article!