Collin’s 2018 Reading List

Collin Stewart, CEO

22 April 2019

A few people asked me for a list of my favourite books, while it’s hard to pick favourites, I was able to come up with my top 3 for each category. On any given day, I am usually reading three or four different books, one from each of the following categories:

  • Making myself a better human
  • Being less terrible at my job
  • Something on stoicism
  • Fiction (usually science fiction or fantasy)

I read something on stoicism first thing in the morning (no checking email/slack), I listen to something about making myself a better human or being less terrible at my job on my walk into the office, and I read fiction for 15 – 30 minutes in bed before falling asleep.

Making myself a better human

Why We Sleep

I used to hear stories of super successful people that only needed 3-4 hours of sleep a day and wished that I could have been one of them, now I realize the damage they’re doing to themselves and am happy with my goal of 8 hours sleep each night.

Did you know that lack of sleep was a known carcinogen? I didn’t until I read this book. The author does a great job of making the science accessible to someone without background neuroscience. In the end, he also leaves some very helpful tips for those that might struggle to fall asleep at night.

This is the one book I read last year that had the biggest impact on my life. I will read it again and again and again… I also bought it as a Christmas gift for 3 of my family members.

Factfulness: Ten Reasons We’re Wrong About the World–and Why Things Are Better Than You Think

This book delivered exactly what the title says. tl;dr – much of our worldview is comprised of what we read in the news and is overly pessimistic, Factfulness showed me the hard facts to support the argument that life on this planet is much better than I thought it was AND it’s getting better every year. This was a real eye-opener, educational, and

This was one of the books that Bill Gates recommended (not to me personally, obviously, I read his blog).

Seeking Wisdom

Wow, I finally finished this dense mofo. Have you ever been interested in Warren Buffett or Charlie Munger? There are four major parts to this book:

Part One: What influences our thinking

Part Two: The psychology of misjudgments

Part Three: The physics and mathematics of misjudgments

Part Four: Guidelines to better thinking

It’s only available in hardcover and isn’t cheap. I tend to loan out or straight up give away books from my collection but this one will never leave my collection.

Being less terrible at my job

Never Split The Difference

This book has saved our company tens of thousands of dollars, got me out of multiple tricky situations, helped me close customers, and helped me negotiate a $200 rent increase down to $4. You cannot afford not to read this book.

The author is an FBI negotiator and tells his story of getting into the field while mixing in what he learned along the way. It was a great listen with super valuable content. I’ve already listened to this book twice. There’s also a great Github summary here.

Lean In

This book opened my eyes to a perspective that I hadn’t given enough consideration to. I used to assume everyone’s brain worked just like mine… I was wrong. This book provided a really interesting perspective into what women in the workforce are subjected to, if you’re a male with female coworkers, this is a must-read. I’ve heard it’s a good read for females as well.

Measure What Matters

Our company has made a few runs at implementing OKRs, this book provided a clear roadmap to how and why we needed to do it sooner than later.

My journey into stoicism

Man’s search for meaning

“We who lived in concentration camps can remember the men who walked through the huts comforting others, giving away their last piece of bread. They may have been few in number, but they offer sufficient proof that everything can be taken from a man but one thing: the last of the human freedoms — to choose one’s attitude in any given set of circumstances, to choose one’s own way.” — Viktor E Frankl

Man’s Search for Meaning came highly recommended to me by a few people and had also been referenced in a few books that I had read so I figured it was time. Being an entrepreneur can be emotionally challenging at times and I had been looking for something to mentally toughen myself. I had read about mindfulness, Buddhism, Zen philosophy, and the ancient yogis but stoicism was the first that really resonated with me. This is not a book about stoicism but many of the authors’ ideas appear to be influenced by philosophy. I think of it as my gateway drug to stoicism because it opened my eyes to the idea that we can choose how we respond to any situation. The following quote, in particular, stuck with me:

“Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.” – Viktor E. Frankl

The author, Viktor E Frankl, was a psychiatrist and documents his experience throughout the Holocaust, including being admitted to and surviving a concentration camp. It provides a view into what life was like and uses that as his backdrop to share his teachings. I found it powerful and eye-opening.

The Obstacle Is The Way

Ryan Holiday studied under Robert Green (author of The 48 Laws of Power) which means his books tend to be thought provoking and exceptionally well researched. The Obstacle is the Way is probably the easiest entry point if you’re interested in stoicism. It’s written more like a business book than anything academic and weaves in great examples from the ancient philosophers and modern leaders.

A Guide to the Good Life: The Ancient Art of Stoic Joy

This book is a slightly more academic version of The Obstacle is the Way. The author covers the major stoic thinkers, their ideas, and where they differ. For me, it provided a map of the original thinkers so I could dive in further. I will definitely be rereading this one again. Being deep into the original texts at the time of writing, this book made them significantly more accessible.


This somewhat original text is a recreation of Marcus Aurelius’ writings as a source for his own guidance and self-improvement. It is super dense, a little scattered, and tends to repeat itself a little. In spite of it’s challenging format, it was one of my favourites because you can almost feel what Marcus was going through while writing. The semi-random format made for excellent daily morning reading. I would not recommend jumping in here until you’ve read the above books. Up next for me is Epictetus’ Discourses.


I used to read books from the above categories before I went to sleep but I found, like my old Star Wars sheets, that they were too stimulating. Since then, I’ve switched to reading fiction and found that it’s a great way to disengage my brain from reality and start my journey to sleepy time land. Here are a few of my favourites:

The Expanse Series – I got halfway through the first book and almost put it down… now I’m 7 books into the series and totally hooked. Set in space, creepy aliens invading, cool technology.

The Red Rising Trilogy – I’ve never read three books faster in my entire life. They were impossible to put down and the 4th book in the trilogy just came out last year with more to come in the future. Set in space with a super interesting division of social classes.

The Mistborn Trilogy – the second fastest trilogy I’ve ever read, I loved these books and am now reading the authors other series the Stormlight Archive and it’s exceptional as well (currently on book 4 of a 10 book series). Both books are set in fantasy universes that are exceptional, the author does the best world building of any author I’ve read.

This was a big year for learning for me and I only covered a small portion of the books I actually consumed. If you have a book that you think I’d like, I’d love to hear from you.