100 Books Like How to Fail at Almost Everything and Still Win Big

By now, you might have noticed a theme: if I don’t enjoy reading a book, I don’t trudge through it for the deep insights or how-to information. The storytelling needs to be as strong as the concepts are useful.

Just like The Copy Workshop Workbook, I read an earlier edition of this book when I was just starting out – and it formed the basis for some of my thinking around how to influence – i.e., persuade – consumers and the role psychology and behavioral economics play in crafting effective marketing and brand development programs.

I also recommend this book if you are a consumer, too (who isn’t), because it will help keep you from falling into many of the traps that Cialdini identified.

I’ve never found a book that lays out the whole-life approach to success as well as this book.

I was particularly impressed by the emphasis on things like marriage and masterminds—the impact those have on our success in life is often overlooked. It gave me a solid framework to look at my own life and see what areas I needed to focus on more, and I consider this book a big part of my success in life.

Daniel Kahneman’s book is a must read for all who desire to understand their mind/brains and thereby maximize the use of the mind’s power over our lives.

In clear language, Daniel Kahneman illustrated the heuristic shortcuts that often limit our understanding and predispose our actions. We all hold onto outdated psychological mechanisms that create self-imposed limitations, and in doing so, we can find ourselves living out self-limiting lives.

Kahneman does an excellent job at showing us how we think we understand what we really don’t. His transparent and careful treatment of his subject has the potential to change how we think, not just about thinking, but about how we live our lives.

Once I understood the power of the subconscious mind, I needed a set of tools to leverage it to reach my goals. This book provided that framework and a deep understanding of how that part of our mind processes the world.

I don’t have to force things anymore—I can use these tools to get all parts of my mind on board with the plan, moving in the same direction as part of a unified team. This makes everything easier when pursuing my goals.

This was the first book that piqued my interest in human dynamics and relationships. Steven’s seven habits ask us to examine our patterns of interaction with others and consider how we can think and act differently in our work. Steven’s approach opened my eyes to some bad habits I had, while also inspiring me to learn more.

Along with a few business dilemmas and dramas, this book set me on a path of inquiry about humans, relationships, work ethics, and the power of words and conversations. 

I have always been self-motivated, but this book gave me the tools to turn up the dial from a 7 to a 10.

In this book, I learned to apply the SAVERS system every morning (Silence, affirmation, visualization, exercise, reading, and scribing), and I have been doing it for years now. I wrote my book by heeding this advice and waking up at 4 am for months in order to write before working out and heading to the office. Every morning, including today, I read excerpts from at least 20 books, review my annual goals, study a foreign language, exercise, and more. One of the things I have learned about this framework since building it into my life is that it is much easier to hang new habits you want to start onto this system.

Once you implement this, you never have to start from scratch again. I have been… show more.

I love this book and re-read it at least every couple of years. All of Dan Kennedy’s books are fantastic, but this one is special.

As a real estate agent, I didn’t realize how much my view of the world and the economy held me back. This book helped shift my perspective, and I now see the world from an abundance mindset instead of a scarcity mindset. I give this to anyone who is stuck in an "if I win, then someone loses" mindset, and it will shake them out of it. I also love his chapters on the magic of generosity and on learning to expect "the phenomenon" at least once every few years (you will have to read it to learn more).

I love how this book has freed me up to go after my goals without hesitation because, as an entrepreneur, it is my job to grow… show more.

One of the biggest reasons that I have been able to become a successful real estate agent is also one that surprises other people: I got lucky. Luck is one of the biggest reasons for my success. I am sure that you know "lucky people," those people for whom everything seems to go right. I know them too, and this book tells you their secrets.

It turns out that luck is not a fortuitous chance but rather a set of rules that you can implement to become more lucky yourself. I love this book and the four rules it gives on how to become more lucky in your life. My paraphrased short version of these rules are: maximize your chance opportunities, expect good things to happen, turn your bad luck into good luck, and listen to your gut.

I love this book, and if you want to have more good… show more.

Researching the early days of the comic book industry is hard. Extraordinarily, gut-punching hard. The records are scant, and everyone involved is long dead. This is why I was so blown away by this exhaustively complete record of the founding fathers of comicdom and their (often shady) exploits.

I found myself silently muttering, “How’d he find that??” on nearly every page. 

For those interested in a compelling work of fiction built loosely around Nazism and the occult, Michael Chabon’s The Amazing Adventures of Kavalier & Clay is the perfect novel.

Whether it’s one of the protagonists, a young Jewish magician, escaping Nazi-occupied Central Europe in the coffin of the “Golem of Prague” or the eponymous cousins finding success with their own comic book series infused by contemporary esoterica, Kavalier & Clay evokes the world in which young, first and second generation Jewish immigrants from Central and Eastern Europe created the Marvel and DC superheroes and super(natural) villains, often allied with the Third Reich, that have defined our popular culture for the past eighty years.