The 5 Books I Recommend Most Often to People Seeking Career Advice

The three reasons to publish a book recommendation article on the internet:
- To show everyone how smart you are.
- To fill space when you can’t think of anything else to write about.
- To share books you think people would actually enjoy or benefit from.
My reasons for writing this article span all of the above.
Kidding!
I am sharing this because I genuinely think these will help you if you are searching for meaningful work. (And okay fine, maybe a little bit of reason number one. Also two. Let’s keep moving.)
Almost all of the people that come to me for career advice ask me for book recommendations. I think they are craving something tangible-something to grasp onto as they struggle to process the thoughts and feelings that come with a job search. Or maybe it’s just that they value my advice, but they really value the advice of someone that has taken the time to write an entire book.
Whatever their reasoning, I get it.
I know that I could more rapidly digest 90% of the information in any book through an article or by watching a YouTube video, but there is something about the tactile nature of a book that seems to make the knowledge transfer much less ephemeral for me. It is as if the commitment required to procure a book, read it, mark it up, go back to it again to make sure I really understand, and then (finally) proudly display it on my shelf, makes it more tangible than reading or watching online.
I am particularly fond of books about work (it’s cooler than it sounds), but I love discovering any book that can teach me something, so my library is always growing. But when people ask me for a book recommendation to help them with their career-or when I think a book might help-I continually return to the same handful of favorites.
These are the five that I recommend most often:
(Note — I have included links for ease of exploring further, but these are NOT affiliate links. I am not compensated in any way should you end up purchasing.)
The Adventures of Johnny Bunko by Dan Pink
“You can make career decisions for two different types of reasons.
You can do something for instrumental reasons — because you think it’s going to lead to something else, regardless of whether you enjoy it or it’s worthwhile…or you can do something for fundamental reasons — because you think it’s inherently valuable, regardless of what it may or may not lead to.”
I was initially dismissive of this book, even though I’m a Dan Pink fan. I just wasn’t sure I needed “America’s first business book written in manga style” in my life. That’s right, this is actually a graphic novel, written by Pink and illustrated by Rob Ten Pas.
Don’t let the shiny pictures mislead you though, the approachable format belies the uncompromisingly direct and honest advice within.
The titular Johnny Bunko is bored and miserable, toiling away in a cubicle for the fictional Boggs Corporation. He finds himself in this plight despite the fact that he followed all of the advice his parents and teachers gave him about picking a career. Eventually a pixie named Diana appears and proceeds to act as his career coach (I never said I recommend it for the story arc), giving him 6 pieces of advice throughout the book.
I think I was hooked when I read the first piece of advice: “There is no plan.”
An excellent read for those just starting their career as well as those of us that found ourselves pretty far along a career path we didn’t like.
Designing Your Life by Bill Burnett and Dave Evans
“For most people, passion comes after they try something, discover they like it, and develop mastery — not before. To put it more succinctly: passion is the result of a good life design, not the cause.”
I avoided this book for a long time because I hated the title.
To me, Designing Your Life sounded like a self-help book steeped in mysticism a la The Secret. Or perhaps a CBS sitcom about a “a plucky young fashion designer trying to survive a demanding boss, a crazy roommate and the New York dating scene!”.
And can you really “design” something like life?
I still don’t love the title, but I do love this book. In fact, I probably recommend Designing Your Life more than anything else these days, thanks to its practical, yet oddly counterintuitive advice.
Just as they do in their coveted Life Design class at Stanford, Burnett and Evans use this book to explain how to take design principles and apply them to your life (well, really just your career. The title is as misleading as it is cheesy). Everything around us was designed by someone they argue, and every design started with someone trying to solve a problem. It makes sense then, to use these same principles to make sure your career ends up more like an Aeron chair than the Ford Edsel.
Most of us jump right to problem solving when working on our career (if we “work” on it at all). A key component of design thinking though, is to first go through problem finding, since a great solution to the wrong problem is just as worthless as no solution at all. This works for a career plan because so often the problem we are trying to solve is “find a dream job”, when in reality such a thing might not exist.
When I discovered this book during a period of career soul-searching, I found the idea that there was no single “correct” solution to my search to be incredibly freeing. Once I knew that there were multiple paths out there that would bring me fulfillment, it was much easier to just pick one and give it a shot. I reframed my career as an iterative, experimental project that I was free to change up whenever it wasn’t working.
I love recommending this book to anyone that is unhappy with their career, but struggling with how to take the first step.
The Dip by Seth Godin
“Quit or be exceptional. Average is for losers.”
I have to be careful when giving this one out.
It makes for a great recommendation because it can easily be read in one sitting, but most of the people I give this book to end up quitting their job. Sometimes without a backup plan. Sometimes the day I give them the book.
When we start almost anything-a job, a hobby, a marriage-it’s fun. We are excited. It doesn’t feel like work at all.
Then, as time goes by, it gets harder and harder and all of the sudden it isn’t fun anymore. We want to quit. The trick, according to this book, is to figure out if you are in a Dip, “the long slog between starting and mastery” or a Cul de Sac, a situation “where you work and work and work and nothing much changes.”
You push through Dips, you quit Cul de Sacs.
Pushing through a Dip reaps extraordinary benefits because so few people can actually do it. It’s what makes you the best in your office, your field, or even the world. Staying in a Cul de Sac just makes you miserable.
Now, the book purports to help you figure out whether you are in a Dip or a Cul de Sac, but I find this less helpful than the parts about what to actually do once you know. In other words, I don’t return to this book over and over again to help me figure out what to do, I return to it to help motivate me to do the thing I already know I should do. (Seth Godin probably planned it this way because he is a wizard).
So while The Dip doesn’t do one of the main things it claims to do (at least for me), I still love this book.
The message is succinct and powerful and can provide a much needed nudge.
Do Over by Jon Acuff
“Ever feel like you don’t know exactly what you want to do with your life? Know who else feels that way? Everyone.”
With Do Over, Acuff pulls off the impossible feat of sharing practical and useful information while simultaneously being really funny (if you consider cheesy dad humor funny, which I very much do).
Acuff also avoids my biggest pet peeve with most of the “career” books written by successful entrepreneurs: telling readers to just quit their miserable job and “chase their dream” like the author did. Instead, the advice he shares is realistic and applicable to someone that wants a new job, someone starting a new job, and even someone that has suddenly lost a job.
I think this book resonates with me (and so many others) in part because of how well it is organized. I know that might sound odd, but think about it-when in the throes of a job search, clarity on next steps is paramount.
Structurally, the book is organized into the 4 core skills that should be developed to survive all of the different career bumps one might encounter. And while I appreciate the layout and the direct advice, it also happens to read like a collection of stories. In other words, it doesn’t feel like homework.
Do Over is one of those books that you read because you are really enjoying it and it is not until you are done that you’ve realized you learned so much.
When Breath Becomes Air by Paul Kalanithi
The fact of death is unsettling. Yet there is no other way to live.
I saved the outlier for last.
When Breath Becomes Air is a memoir written by a neurosurgeon diagnosed with stage IV lung cancer. Released posthumously, it offers little in the way of explicit career advice, but the lessons within about what makes a life worth living are some of the most crucial I have learned anywhere.
I hesitate to use any of my own words to describe this book, because they seem unfit next to the beautiful language Kalanithi used to portray his journey. Also, I just don’t want to spoil the experience for anyone.
I recommend When Breath Becomes Air to everyone, no matter where they are in their career-or their life. We have largely trivialized the idea of something being “life changing”, but this book truly did change my life.
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