Like many others, my life from March 2020 through the end of the year was spent predominantly in one place. This break from vagabonding meant I was able to read a lot more than years past - but my nomadic break also allowed me time and space to reflect on my perspective shift toward reading.
Prior to 2020, picking my next book to read was a pressure-filled undertaking. I felt I needed to pick the right book so that my time was being spent productively and on something that mattered. I became adamant that I should read certain books, either because they would help me advance in a certain area of my life (e.g., personal finance, career) or because they were "classics" and I was ashamed for not reading them yet (e.g., Anna Karenina).
In addition to this selection anxiety, I was hampered by the realization that each book would cost me $15-$25, and if I did not read the entire book I was leaving value on the table. This self-imposed pressure to extract value from each book left me with a sense of obligation as I read new books rather than a curiosity to discover each new ideas.
I was putting pressure on selecting the right book, extracting value from each book (relative to the cost), and finishing each book I picked up. There had to be a better way - but what was it?
When I thought back to times when I was fully engrossed in a book, none of the things I worried about - like selecting the right book or extracting value - were the reasons I enjoyed reading. Rather, reading captured my attention and through the activity I was able to make new connections or be transported to a new world.
I realized that I could make some subtle changes to my perspective and environment to architect a situation to enjoy reading once again.
I shifted my mindset and perspective in 3 important ways:
First, I needed to remove the need to find the perfect book from the selection process. I realized all I needed to do was find what my interests were gravitating towards in the current moment and select books based on that.
I found that this was a "hack" to help me be excited about the next book. When I began traveling full-time in July 2018, this was quite easy to do. I would naturally select a book that was about my next destination, providing easy inspiration to be excited about it, because I was interested in the next destination.
This led me to books like House in Bali, Complete Notes from Singapore, and A Geek in Japan - prior to visiting Bali, Singapore, and Japan respectively.
Other times, I led my natural curiosities - personal or professional - drive me to certain books. For example, when I was interested in learning Sales (Sales Acceleration Formula, Fanatical Prospecting, and New Sales. Simplified.) Or when I was on a Chef-kick (Heat, Dirt, and Kitchen Confidential)
I removed the pressure for finding the right book, which led to more enjoyable reading experiences and a more curiosity-driven selection process.
I’ve always had a compulsory need to keep track of every dollar in and out of my bank accounts. This can be a double-edged sword.
On the one hand, I feel generally in control of my spending decisions - whether my spending aligns with my general life goals (e.g., gym membership) or is potentially in contrast with those same life aspirations (e.g., a night out drinking with friends). On the other hand, I tend to over-analyze where my money goes and will often need to assign value to what I purchase.
For many years, I saw the purchase of books (physical or digital) as a cost. Meaning that I was spending money with a transactional mindset - e.g., "I am spending these $20 to extract value from a book and put that knowledge into my brain for future use." Unsurprisingly, a transactional mindset did not contribute to an enjoyable reading experience.
Recently (over the past 3 years), I shifted my thinking from any money spent on books from a cost to an investment.
This shift may seem like mere semantics, though it proved to be a large shift in my perspective - which translated to a much more enjoyable reading process.
When I shifted to the investment mindset, I removed the pressure of extracting value from each book. An investment (to me) was signaling that books are an important part of my life and money spent towards attaining them was just how I manifested that life priority. The intrinsic value of purchasing books was enough for me.
Another important shift was removing financials from the equation altogether.
I started with the old-fashioned, but often forgotten about, tactic of joining my public library (the New York Public Library) when I was living in NYC. Through the library, I started checking out physical books for weeks at a time, removing the financial constraint (cost or investment) of purchasing a book.
Although this helped me select books more readily (without the financial constraint), I was still hampered by only being able to have a few books being checked out at a time and a physical trip to the library branch necessary to exchange a book (life was rough).
Then, I learned about the ability to reserve e-books through the library’s Overdrive system. This meant I was able to loan 3 digital books at a time and check them in and out whenever I wanted via my Kindle.
Financial freedom attained - my financial constraint evaporated and there was no longer any pressure when selecting my next book.
While I was no longer bound by financial constraints nor a pressure-filled selection process, I still had one more hurdle to overcome: the need to finish a book I checked out.
Being a metrics-driven person, I felt that for a book to “count” towards my books read in a year, I needed to read every word and make it to the last page.
I felt that way until I was listening to a podcast by Naval Ravikant who supposed the “novel” idea of if you are not enjoying a book within the first few chapters, stop reading it and try something new.
While seemingly a small idea, this allowed me to read many more books and enjoy them. Simply by stopping to read anything that didn’t resonate with me at the moment.
This didn’t mean that I had selected a “bad” book, rather that it just wasn’t the opportune time for me to be reading it. By removing the metrics-driven approach to reading (finishing) a certain amount of books, I ended up reading more books than ever before.
I learned that by removing a singular focus on a goal sometimes helps you achieve it.
My mindset shifts allowed me to reconnect with my passion for reading in 2020. Aided by the pandemic-removal of other life passions (e.g., travel) I was able to read more in 2020 than ever before.
Below are my favorite reads of 2020 (in no particular order) - but feel free to stop reading them if they don't resonate.
Probably my favorite (albeit longest) read of 2020. The fact that he was able to lead two generation defining companies (Apple and Pixar) simultaneously, leaves you in awe of his drive and tenacity.
The personal insights into the man (yes, he was an asshole) are incredible and heartbreaking. The narrative style is engaging and I found myself not wanting the book to end. It captured the better part of my week, but well worth the time.
Another biography that captured my attention, not so much for the story (his rise throughout ABC/Disney almost seemed too perfect), but for Iger's perspective on being an organizational leader. In contrast to many popularized notions of what it means to be a CEO, I found that Iger’s approach to managing people refreshing. Balance and empathy as his constant refrains.
Yes, there remains the implicit bias of an autobiography, but my key takeaways were: a formula for how to deliver effective feedback, how to practice intentional empathy, and the process to remove ego from your decision-making. A must-read for anyone who manages people.
Red Notice reads almost more like a crime-thriller than a memoir. A truly incredible story of an American financier in Russia.
If you can read past Browder’s self-importance at times, you’re in store for a wild ride through almost inconceivable amounts of corruption and one man's journey in spotting opportunties before anyone else and exploiting them.
Can easily be read as a cautionary tale or a blueprint for making money at other’s ineptitude, depending on your perspective.
As an antidote to the modern fetishization of startup culture, Wiener presents the “realness” of what working at a startup is truly like.
Throughout the memoir, Wiener takes the lens of an outsider that’s mistakenly been let into the "startup-bro" culture - almost like a scientist observing her experiment's subjects. While she doesn't hide her contempt for "Big Tech" and the often ostentatious nature of Silicon Valley - Weiner presents a sobering reality check on startups that aim to "make the world a better place."
A no-nonsense guide to modern sales prospecting. Blount dutifully lays out the reason most salespeople fail to generate leads and dispels many of the myths that surround sales prospecting.
The biggest takeaways for me personally were: the reminder that nobody cares what you have to say (this could be applied outside the sales world), and by being an effective listener you can outperform 90% of people who are selling something similar to you. Finally, always make your sales conversation about the other person’s problems, goals, and desires.
Yes, I read (some) fiction! Roy’s beautifully crafted novel follows a multi-generational family in India and the loss of childhood innocence.
The juxtaposition of “small” and really “big” things is a constant push and pull, but overall the story is an illustrative reminder of how a single day can change the course of your life.
If you are looking for one book that tells you step by step how to validate a business idea you have (product or service) - stop looking, this is it.
A tactical guide on how carefully crafting questions can get you to the truth about how people feel (and whether or not to pursue an idea).
My key takeaway: if you just avoid mentioning your idea, you automatically start asking better questions. Similar to Fanatical Prospecting - talk about other people’s lives instead of your idea.
Fun, easy to read memoir from SNL’s “Weekend Update” host. Obviously funny but also surprisingly insightful. Jost provides a good reminder that no matter what credentials you may attain in life, the majority of people continually suffer from insecurity and imposter syndrome.
Key takeaways: where/how you grew up becomes a big part of who you are (whether you like it or not), and no one (in comedy or life) succeeds in a vacuum - go find your people.
An absolute must-read for anyone who is in consulting or client-services. Practicing vulnerability even when you are the “expert” does not detract from but instead adds to your credibility.
Key takeaways: From the first conversation (even before they are a client) focus all of your effort towards providing value - don’t worry about if you give them too much and they take it for free. Additionally, having a bad client is worse than having no clients.
A practical read on how to build and sell a business that can run without the owner's direct involvement. Warrilow provides useful frameworks on how to structure your business and specialize in what you do exceptionally well.
I feel like this book will be one I revisit often as the lessons are really time-sensitive based on what stage your business is in - though the foundational lessons are ever-prescient.
While the Covid-pandemic may subside (hopefully) in 2021, I look forward to using my 2020 reading tactics to expand the scope of my 2021 reading list. If you have any recommendations for my 2021 reads, be sure to let me know via Twitter.