50 Short Lessons From 50 Books In 2019

On comedy, writing, personal development, and life.


Here’s my 2019 reading list. This year I read a lot about comedy, writing, personal development, and pursuit. I also managed to read 8 fiction books, which is a step up from last year.

Below you’ll find one takeaway, quote or lesson from notes I took throughout the year. I do this so I can remember where (or from whom) I learned things down the road.

Scroll all the way to the bottom to see my top 5 books and honorable mentions.

(*Links are affiliate links, meaning if you buy a book I receive a small commission at no additional cost to you.)

Enjoy and happy reading!


The Bedwetter by Sarah Silverman: MIAT — make it a treat. “…similar in spirit to “everything in moderation”, but still very distinct. Moderation suggests a regular, low-intake of something. MIAT asks for more austerity; it encourages you to keep the special things in your life special.”

Stay Hungry by Sebastian Maniscalco: “Maybe the only difference between me and [a guy that quit comedy] is that I didn’t give up, no matter how frustrated and full of doubt I felt at the time.”

Robin by Dave Itzkoff: “Robin was a genius, and genius doesn’t produce normal men next door who are good family men and look after their wives and children. Genius requires its own way of looking at the world and living in the world, and it isn’t always compatible with conventional ways of living.”

Free Roll by Brandt Tobler: The idea of a “free roll”, or putting yourself in situations where you have everything to gain and nothing to lose, was probably the biggest takeaway for me. Also learned a fair bit about gambling.

Born Standing Up by Steve Martin: “I continued to pursue my studies and half believed I might try for a doctorate in philosophy and become a teacher, as teaching is, after all, a form of show business.”

Born A Crime by Trevor Noah: “The first thing I learned about having money was that it gives you choices. People don’t want to be rich. They want to be able to choose.”

Braindroppings by George Carlin: “..the language of comedy is fairly grim and violent…after all, what does a comic worry about most? Dying. Bombing…They want to go out with a bang, be a real smash. And if it goes well, they say, “I killed ’em. I slaughtered these people.”

Sick In The Head by Judd Apatow: I think this should be required reading for comedians and comedy fans.

Zen and the Art of Standup Comedy by Jay Sankey: They say you can’t learn standup from a book, which I agree with, but this was the best book I read in terms of practical standup advice. Here’s an example: “The difference between getting belly laughs and silence isn’t just the wit or style of your delivery, but the degree to which the audience cares about the subject you’re talking about.”

The Comedy Bible by Judy Carter: I bought this book the week I moved to Boston and started doing standup. There were a lot of good nuggets that helped me get started, like “The biggest lesson about comedy: truth is funny and shows up even when your luggage doesn’t.”

Me Talk Pretty One Day by David Sedaris: This book helped me see what kind of writer I could be. I never thought a book could be a collection of short humor essays. I’ll work my way through DS’ whole collection in the next year or two.

Running With Scissors by Augusten Burroughs: Bought this because it was listed as a humor book. Didn’t think it was that funny, mostly sick and depressing. Well-written, though.


The Creative Habit by Twyla Tharp: Resourcefulness spurns creativity. “Whom the gods wish to destroy, they give unlimited resources.”

Write Tight by William Brohaugh: One of the few books I read on Kindle. Read in January, and it opened my eyes up to concise writing. This, The Elements of Style and Stephen King’s book had the biggest impact on my writing skills in 2019.

On Writing by Stephen King: “It starts with this: put your desk in the corner, and every time you sit down to write, remind yourself why it isn’t in the middle of the room. Life isn’t a support system for art. It’s the other way around.”

On Writing Well by William Zinsser: “Take special care with the last sentence of each paragraph — it’s the crucial springboard to the next paragraph. Try to give that sentence an extra twist of humor or surprise, like the periodic “snapper” of a stand-up comic.”

On Writing by Charles Bukowski: “A man’s soul or lack of it will be evident with what we can carve up on a white sheet of paper.”

Writing Tools by Roy Peter Clark: Rewrite, rewrite, rewrite. “If it sounds like writing, I rewrite it.”

Daily Rituals by Mason Currey: “The great thing in education is making our nervous system our ally instead of our enemy.” This quote is a nice way of saying routines and automation free you up to be more creative.

The Elements of Style by William Strunk: “Vigorous writing is concise. A sentence should contain no unnecessary words, a paragraph no unnecessary sentences, for the same reason a drawing should have no unnecessary lines and a machine no unnecessary parts.”

View From The Cheap Seats by Neil Gaiman: “You can fuck around with the rules as much as you want to — after you know what the rules are. You can be Picasso after you learn how to paint. Do it your way, but do it their way first.”

Personal Development

Meditations by Marcus Aurelius: So many things. The power of small one-percent improvements, for example: “Within ten days you will seem a god to those to whom you are now a beast and an ape, if you will return to your principles and the worship of reason.”

Outliers by Malcolm Gladwell: Success is, to a degree, predictable. There’s a story in this book detailing how the majority of kids who play pro hockey are born between September and December. They end up being the biggest kids, meaning they get the most positive reinforcement and wind up getting the best coaching. Really liked this book and have 2 more MG books waiting in the wings.

The Laws of Human Nature by Robert Greene: “Weak character will neutralize all of the other possible good qualities a person might possess. For example, a person of high intelligent and weak character may come up with good ideas, but they will crumble under pressure or not take well to criticism, or think first of their own agenda, or their arrogance and annoying qualities will cause people around them to quit.”

The Big Leap by Gay Hendricks: When you aren’t living to your potential, or purposely doing stuff to self-sabotage, your body can actually create “illnesses”. This has definitely happened to me.

Chasing Excellence by Ben Bergeron: Passion beats drive. “Sticking with something you love is like biking downhill….with something you don’t love, it’s like biking uphill.”

Can’t Hurt Me by David Goggins: I read this book in a single sitting, about 6 straight hours. Didn’t take many notes but was very inspired by David’s story.

Everything Is F*cked by Mark Manson: The first few chapters, especially Feeling Brain vs Thinking Brain, were really good. I liked Subtle Art much better.

Misc Nonfiction

The World According To Tom Hanks by Gavin Edwards: “People, if they want to, should be able to throw all their belongings in the back of a car and drive somewhere else and start over. When you make that impossible, you rob them of their ability to adapt and change and grow.”

Lone Survivor by Marcus Luttrell: “..the real battle is won in the mind. It’s won by guys who understand their areas of weakness, who sit and think about it, plotting and planning to improve. Attending to the detail. Work on their weaknesses and overcome them. Because they can.”

I’m A Stranger Here Myself by Bill Bryson: Whenever I read Bill Bryson it’s as much about his stories as studying his style. I look up to him. Fun observations on America and great humor writing.

In Vino Duplicitas by Peter Hellman: This book tells the story of Rudy Kurniawan and the faux wine scandal the documentary Sour Grapes is based on. I liked it but probably enjoyed the documentary more.

Barbarian Days: A Surfing Life by William Finnegan: A masterclass on passion and the pursuit of a thing. Book felt longer than maybe it had to be. Good read if you like travel or surf books.

Kitchen Confidential by Anthony Bourdain: “…character is far more important than skills or employment history…a guy who shows up every day on time, never calls in sick and does what he said he was going to do is less likely to fuck you in the end than a guy who has an incredible resume but is less than reliable about arrival time. Skills can be taught. Character you either have or don’t have.

Dopesick by Beth Macy: “The average nonaddicted person’s perception of the future is 4.7 years. The average addicted user’s is 9 days.”

Without You, There Is No Us by Suki Kim: I thought about this book for days after I read it. Haunting in a good way. If you’re interested in North Korea, I recommend.

Educated by Tara Westover: “Vindication has no power over guilt. No amount of anger or rage directed at others can subdue it, because guilt is never about them. Guilt is the fear of one’s own wretchedness.”

Schadenfreude by Tiffany Watt Smith: “Where a friend’s disappointment might help us manage their comparative success, digging into a celebrity’s pain does more than anesthetize our own relative lack of beauty and talent. It has the quality of a punishment too.”

Sufferings In Africa by James Riley: This was one of the most popular books in the 1800’s. and I had a hard time with the 19th-century prose. Lots of re-reading paragraphs. Story was great, though, and gave me an interesting perspective on how books have evolved.

The Happiness of Pursuit by Chris Guillebeau: Read on a bus to Prague in January. “According to Seinfeld, the goal [of comedy] is “refining the tiny thing for the sake of it.”

The Shortest History of Germany by James Hawes: Meh. Learned a few things about German history, but the book seemed a bit propagandistic.

Vietnam by Max Hastings: I knew next to nothing about the Vietnam war until I read this book. It took 14 months to finish, but not because it was bad. It was just dense and I kept starting new books. Trying to read more history like this in 2020.

Misc Fiction

A Gentleman In Moscow by Amor Towles: Started slow, but I ended up really enjoying this one. Constant references to Montaigne inspired my recent purchase of How To Live, which I’ll read in 2020.

Pulp by Charles Bukowski: For better or worse, I’ll probably read all of Bukowski’s books at some point.

The True History of Lyndie B. Hawkins by Gail Shepherd: Excellent middle-grade book with a powerful message written by one of my relatives. Highly recommend. “The only thing new in the world is the history you don’t know.”

Camino Island by John Grisham: Needed a taste-breaker. It was decent.

Clash of Kings by George R.R. Martin: Loved this book and the entire Song of Fire and Ice series. Way better than the show, which I was late to the boat on and watched after I read all the books.

A Storm of Swords by George R.R. Martin: Favorite of the series.

A Feast For Crows by George R.R. Martin: Struggled to get through this one.

A Dance With Dragons by George R.R. Martin: Liked, and am excited for the rest of the books (like everyone else).

Top 5 Books Of 2019

1. Robin by Dave Itzkoff

2. Kitchen Confidential by Anthony Bourdain

3. A Storm of Swords by George R.R. Martin

4. Educated by Tara Westover

5. On Writing by Stephen King

Honorable Mentions:

  • Can’t Hurt Me by David Goggins
  • Dopesick by Beth Macy
  • Sick In The Head by Judd Apatow
  • The Creative Habit by Twyla Tharp
Here’s the actual stack along with 3 notebooks full of notes, half-baked ideas, and jokes. My 2019 creative input/output, if you will.

Mostly humor essays.

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