📚 Books with Plucky, Swashbuckling & Wry Protagonists

Seven books with wild adventures and a dose of humor

With the launch of ChatGPT and the era of AI upon us, it feels like the clock speed of the entire tech industry is increasing rapidly. Combine that with the pain of an economic downturn and it’s been an exhausting 2023 so far.

Fiction reading is one way I recharge myself and reflect on my work life. So, I’ve been giving some thought as to what type of books are appropriate for the moment tech finds itself in. And I think it mostly comes down to the main character that the book features.

The times call for a plucky, can-do protagonist that defeats the odds by forging paths less taken. You need a main character that thrives in chaos. (Just like an AI startup founder!)

You need a book that explores how systems are broken and reforged. How about a ragtag group of heroes that simultaneously work the system but aren’t afraid to burn it down either? (What better way to prepare for a generational change in computing paradigms?)

But that’s not enough. You also need a protagonist who will make you laugh. And let’s be honest, there’s a bit of hype going on, so you need a cup of wry sarcasm from the narrator as a reminder to not take anything too seriously.

Should there be unbelievable capers? Swashbuckling? Oh, you bet your chatbot there should be!

Here are seven character-driven books filled with can-do protagonists that get into wild adventures because of their oversized ambitions & sense of duty. And all of the books have genuine humor to keep the flow lighthearted. Read any of them and you’ll be inspired to take that next giant leap.

The Lies of Locke Lamora by Scott Lynch

Locke Lamora is a headstrong orphan turned con man. Needless to say, he doesn’t find it easy to trust others - he sees the system from the outside and can figure out how to use it for his own gain.

High-stakes capers ensue with Locke taking a series of more - if you’ll permit me to use our industry jargon - non-consensus bets.

In short, he would have been a crypto startup bro if he lived in 2023. But you’ll fall in love with him anyway.

Lamb by Christopher Moore

Lamb is the story of Jesus Christ’s teenage years according to “Biff,” Christ’s Childhood pal. The Gospel is indeed a bit silent on the part of the story between birth and the climax. Moore fills in the details with lots of dramatic ironies: Scene one opens with Jesus smashing a lizard with a rock and then bringing it back to life, just for show. (He’s a bored teenager, after all). Tongue and cheek aside, the story winds its way through a coming-of-age tale that, while it pokes fun at the rules and rituals of religion, maintains a poignant respect for spirituality and its ability to overcome adversity.

Biff himself teaches us that perhaps it takes a lot of grace, patience, and wisdom to exist in close orbit to someone destined for greatness.

Vorkosigan Saga by Lois McMaster

Meet Miles Vorkosigan, a prince with serious growth deformities growing up in a warrior society. The novel where he is introduced chronicles his journey to accidentally become a space pirate admiral through a mix of moxie, luck, and charm. “That escalated quickly” is the theme of Mile’s life. We learn about someone who never gives up, no matter what the odds.

I have a soft spot in my heart for a protagonist who needs to use intelligence and charm in a society where physical strength often wins. Very Horatio Hornblower.

Another amazing thing about the Hugo-winning series is that, despite being published in the 1980s, it includes a diverse cast of characters - strong female leads, a person with a physical disability, a gay man, and a transgender character. Groundbreaking for its time.

Microserfs by Douglas Coupland

Daniel and his ragtag group of friends work for Microsoft in the 1990s. Here’s an example of the too-close-to-truth humor Coupland works into the plot: After his ideas are torn apart in a Bill Gates review, a friend of Daniel refuses to leave his office and Daniel has to slip food under his door. To this day, the friend only eats flat foods.

As the story progresses, the group leaves Microsoft to try their hand at a Silicon Valley startup. Exploring themes of triumph and disaster, work and life balance, coming of age, and purpose in our vocational endeavors, it’s a surprisingly funny and poignant look at life.

Perhaps a good reminder for us: All that has happened before will happen again. Our industry is a repeating cycle.

Project Hail Mary by Andy Weir

Ryland Grace is a junior high school science teacher turned world-saving space explorer sent on a one-way suicide mission. Needless to say, geeky wry humor pervades this science-back puzzle-solving adventure.

Murderbot Diaries by Martha Wells

What if a soldier-robot with a terrifying amount of violence potential became self-aware?  Join them on their journey as they explore their relationship to morality and taming of their own inner demons.  Also, the robot is the most sarcastic introvert you will ever meet.

It’s a great way of exploring how ChatGPT probably really feels about us meatbags when it doesn’t need to be polite.

The Scholomance Trilogy by Naomi Novik

This book is generally described as “Harry Potter, but with monsters.” Turns out that puberty in magical children attracts demons and monsters, so they’ve created a special school separated from the rest of the world to deal with it.

However, it’s the main character El that I loved the most about this series. She’s fearless, is an outcast with incredible powers, and just Gets Stuff Done. As the narrator of the book, she’s not afraid to count up all the BS she needs to deal with.

Redshirts by John Scalzi

Ensign Andrew Dahl is not special. Indeed, one might say he tends to fade into the background like an extra in a TV show. Yet when many of his friends and fellow low-ranking noncoms end up dying on special missions or are involved in the rather all-too-common emergencies on board their star cruiser, he realizes he IS living the life of an extra in a poorly written TV show and his friends are an expendable group to create high drama. Undeterred, Andrew travels back in time to 1970s Earth to confront the producers and writers of the show and save his friends.

Much of John Scalzi’s writings fit the “clever premise + witty humor + page-turning story” trope - so there are lots more books to explore by this author.

Happy Reading

These are all breezy novels and easy reads - yet all of them make you think about life and work in some new way as the plot creates a paradigm change. Enjoy!