This year, I read 150 books, a personal record. A friend once scoffed at my dedication, saying all the advice he wanted he could get from his Stanford connections. Why consume public ideas when you can tap into private minds?
At the time, I didn’t have a good comeback. Nothing beats surrounding yourself with people who lift you up. But not everybody has that luxury, and books are an affordable passport into the greatest minds of history. They’re the great equalizer.
And even if you have a dazzling rolodex, reading books is still irreplaceable. Books take us beyond the bullet-point answer or witty one-liner, to reason and think for ourselves rather than imitate some charismatic person. It’s one of the rare mediums divorced from a social feed.
So if you love books like me, here are five of my favorites. And if you don’t, well, this can be your Sparknotes!
Switch: how to change when change is hard
If aliens watched us work, they would notice that we spend all our energies trying to make numbers go up, and then feverishly checking that they do. Often, this involves convincing other people to visit, convert, come back, support us; in short, changing their behaviors.
Switch covers three surprises about making people change:
- What looks like a people problem is often a situation problem
- What looks like laziness is often (emotional) exhaustion
- What looks like resistance is often a lack of clarity
A few examples:
- People eat 35% less popcorn from a medium-sized bucket than a large one (changing appetites is hard, changing context is easy and effective)
- People are more motivated when partly finished with a long journey than starting a shorter one (progress keeps us emotionally engaged)
- People are more successful when told something specific like “don’t spend cash unless it makes cash” vs. just “save money”
Eye-opening read, especially from the lens of persuasion and design.
The best books are the ones that whisper what you need to hear in your greatest moment of need. This year, I struggled a lot with what ifs (what if I joined Instagram? What if I stayed at a hyper-growth startup? What if I joined another startup?)
The Midnight Library is a novel whose main character is able to explore every what if. She winds up at a fantastical library where each book is a different version of her life. She travels to these parallel lives and experiences being insanely rich and famous and everything in between.
Some memorable lessons:
- Nearly every version was her living out someone else’s dream — unsettling and probably applies to 99% of us
- Even the most picture-perfect life involved unforeseen sacrifices
- What we look at matters less than what we see; life is but a creation of the mind
Constant what ifs often come from cherry-picking the best thing about one possibility vs. the worst thing about our current outcome. For example, it’d be cool to have Elon Musk’s clout but it would suck to be heavily scrutinized, be 3-times divorced, age multiple decades, etc.
Perhaps the best antidote is asking whether you’d want to trade everything you have for that one good thing. And if the answer is yes, you have a decent shot assuming you put it all on the line.
Story of a happy marriage
This one is a collection of essays by Ann Patchett. When I read her work, I can’t help but think: ah, this is art. Her voice is exquisite.
In one story, she shares an encounter with a reader who claims that everyone can write one good book. After all, they can tell the story of their life. This feels so applicable to building products. People who’ve never built a product believe that the hardest thing is coming up with a brilliant idea.
Yet there’s an under-appreciated chasm between a brilliant idea and a real product. Making things is the real trick.
It’s always harder than expected, and it requires trading in the living beauty of imagination for the stark disappointment of the first version. It requires trading in the hopeful option of “I can do X” with the sobering reality of “I guess I’m not that good at X (yet)”.
Most people want to be the noun without doing the verb; the few that actually do, make it.
Art of the good life
This book gave me the words to understand why some of my friends could never leave the comfort of a 9-5 where they nurture various hobbies, while others seem to only chase all-consuming paths like starting a VC-backed startup.
It boils down to one question: who’s in the driver’s seat — your experiencing self, or your remembering self?
Your experiencing self wants a fulfilled moment-to-moment life. Your remembering self wants a full and vibrant photo album. Example: climbing Mount Everest (literally or metaphorically) is a wonderful memory, but rather torturous in the moment; it’s a trophy for the remembering self.
I grew up believing there’s a mandatory trade-off: I’m either making sacrifices now for a better future, or I’m coasting now and wasting my future.
But the photo album metaphor made me wonder: do I really want to wait X years to look back on trophies that were torturous to win? Is a full album really the best goal if there was no enjoyment along the way?
Could we find things that we enjoy doing that also compound favorably over time? Or invest in a healthy portfolio of activities, some to build our photo album and others to feel fulfilled now?
No easy answers, but this book is a great starter especially going into 2022.
Ready player one
Watching Zuckerberg’s demo of the ~Metaverse~ gave off major throwback vibes to the Ready Player One movie. So I went back to read the original novel and had a blast.
Set in a post-apocalyptic future, Earth is so grim that people spend all their time in a virtual simulation aptly named the OASIS. School is like the Magic School Bus where teachers can take you on a virtual field trip anytime; chat rooms are virtual spaces you can customize; leveling up your avatar is the new popularity contest.
Is OASIS the greatest video game ever created or a self-imposed prison for humanity?
If you’re interested in building the virtual world, this one is a must-read. A video demo can skate by on fancy theatrics, but a novel is like a product: it has to sweat the micro-details to deliver something unforgettable.
- Hatching Twitter: spills the juicy details of Twitter’s founding story; think Chaos Monkeys and Bad Blood, but far more gripping
- Chatter: the most crucial conversation is the one you have in your head; read this if you want tools for better self-talk
- Building a StoryBrand: how to turn your customer into a hero with your product as the guide
Finally, thank YOU for giving me a reason to write! This newsletter continues to be the highlight of all my days. See you in the new year! 🎆
👋 P.S. If you want to join a top startup, check out who's newly funded and hiring or benchmark your startup salary & equity