There comes a time in your life when, no matter how well things are going, the monotony of everyday life begins to wear you down. Feelings of frustration, boredom, and, potentially, ambivalence to your work, loved ones, and even yourself begin to ferment.
When this happens, you must turn to books.
Books have the power to challenge, inspire, and motivate us to change our circumstances when they no longer serve us. They allow us to learn from the most brilliant minds on this planet, as well the mistakes from regular folks like me and you. Books are here to remind us that, despite what we might think, there is another way. A life lived with intention. A career led by purpose. A mindset that encourages you to become the best version of yourself.
There are a handful of books that do this for me. I consider them timeless and revisit them regularly throughout the year. Below, I’ve listed the top nine that have helped me overcome tough situations, increase my capacity to produce high-quality work, and have reminded me that money does not equal success. While these authors are unique in their own right, they have reminded me that living a successful life involves overcoming tragedies, solving difficult challenges, and making deliberate decisions every step of the way.
Do you feel pressure to buy the latest smartphone, level up your wardrobe, or lease a fancier car? This book is for you. Thomas shows you that most millionaires in the US aren’t driving fancy cars, living in mansions, or even working glamorous jobs. This book demonstrates, through several interviews with actual millionaires, that it’s entirely possible for average-wage earners to become millionaires as long as they exhibit patience and discipline. There’s no secret sauce to these millionaires’ accumulation of wealth — just plain ol’ hard work and frugal living. As Thomas writes in his book, “After twenty years of studying millionaires across a wide spectrum of industries, we have concluded that the character of the business owner is more important in predicting his level of wealth than the classification of his business.”
Former Marketing Director of American Apparel, Ryan Holiday, has made stoicism fresh and relevant again. In this book, Ryan applies the timeless principles of stoicism through using historic examples of the most successful people in history confronting the biggest challenges of their lives. From John D. Rockefeller to Winston Churchill, Ryan discusses how these courageous leaders turned their obstacles into opportunities. This book is perfect for anyone stuck in a rut or facing a difficult situation.
Part and parcel of living a successful life is dealing with tragedy. In reading this memoir, you can actively see Joan analyzing her grief and attempting to explain away her pain. It’s a simultaneously easy and difficult read — easy in terms of readability and difficult in terms of the impact it leaves with you. If/when you experience the loss of a loved one and are looking to hear from someone who has gone through the same, pick up this book. She has the ability to put into words what you cannot.
The premise of this book is simple: Non-conformists aren’t risk-tasking superheroes — they are people who pumped out a lot of average-quality work and actually made risk-adverse decisions before producing superior work that really moved the needle. Early on in the book, Grant uses the example of Warby Parker: He mentions that he had the opportunity to become an early investor in the company but declined because the founders seemed reluctant to drop-out of school and commit to growing Warby Parker full-time. Grant assumed that they would never be successful, so long as Warby Parker wasn’t the entire priority of the founders. Well, he ended up being wrong. The company is now valued at over $1 billion. What was the secret? Working smarter, not necessarily harder and being deliberate every step of the way. This book is great for anyone who wants to pursue entrepreneurship but feels like that they must risk everything in order to be successful.
This book is full of concrete tactics to remove the distractions that are preventing you from accomplishing the cognitive-demanding tasks that are required of us. I won’t ruin the entire book, because I think it’s worth a complete read, but one tactic he suggests is to, ‘work deeply.’ There are four strategies that we can use to accomplish this: monastic (isolate yourself for long periods of time), bimodal (set aside a few consecutive days where you’ll be working like a monastic), rhythmic (work three to four hours each day on a single task), and journalistic (alternate your day between deep and shallow work). This is just the tip of the iceberg, but you can see how practical Cal’s suggestions truly are. I encourage anyone who considers themself an information worker to pick this up.
In this book, Angela Duckworth, a critically-acclaimed professor of psychology at the University of Pennsylvania, details how talent is hardly a guarantor of success. What really moves the needle is grit — the magical combination of passion and perseverance. It’s not necessarily how smart you are, but rather the willingness to finish what you started. Angela drives home the point that it doesn’t matter so much with what skills you’re born with, rather it’s the act of rising from setbacks and the undertaking of sustained action that is often difficult and pleasant that will enable you to achieve your goals. At its core, this book is about taking matters into your own hands and the significance of realizing your own agency.
“The conventional mind is passive — it consumes information and regurgitates it in familiar forms. The dimensional mind is active, transforming everything it digests into something new and original, creating instead of consuming.” This is just one of the many pieces of advice that is hidden in this book. Robert, a master in his own right of writing timeless books on strategy, is an inspiring yet intimidating writer. His words are blunt yet profound. His thoughts are straightforward but filled with wisdom. I would suggest Mastery to anyone who is serious about perfecting their craft. As Robert explains in his book, “In order to master a field, you must love the subject and feel a profound connection to it. Your interest must transcend the field itself and border on the religious.”
This is the newest book on the list. For those of you who are unfamiliar with the author, Annie is a former professional poker player and now teaches poker to professionals, provides consulting services to C-suite executives and Fortune 500 companies, as well as writes about effective decision-making. As a lawyer, I find her knowledge directly applicable to my work. Among the topics that she covers, my favourites include dealing with uncertainty, understanding probabilities, and divorcing our decision-making from the outcome itself.
What I love about Chuck is that he never ceases to surprise me. For those that have been following his career over the decades (decades!), he’s evolved a lot as both a writer and critical thinker since Fargo Rock City. Although he’s primarily a pop culture critic, he’s always willing to dip his toe outside of rock music and collegiate sports and share his unconventional views on conventional topics (i.e. gravity). This book lends us some perspective that in a hundred years from now people are probably going to look at us and laugh at how truly wrong our assumptions about the world are. I don’t try to hide my affinity for Chuck. I encourage you to read his writing for no other reason than he is a colourful writer that somehow challenges you to think twice about things.