The best business books for every stage of your career

Whether you’re a Gen Z newbie or a seasoned boomer eyeing the exits, here are the books that can guide your career.

The best business books for every stage of your career

These are the best books to guide your career.

No question about it, you need different insights and strategies at each phase of your working life. After all, the workplace and your perspective on it are bound to change as you go along, these days more than ever. And consider: With life expectancies getting longer, your career could easily span half a century. With that in mind, we combed through hundreds of business books (some new, some timeless) to find the ones we think can help you make the most of each stage of your career.

For the first time in recent history we have five generations working side by side. To reflect this historic moment, we collected our picks for the best career books for each generation—plus one bonus book for everyone.

Gen Z

  • What Color Is Your Parachute? 2020: A Practical Manual for Job-Hunters and Career-Changers by Richard Bolles. It’s not for nothing that Parachute has sold more than 10 million copies in 28 countries. Although it’s been around since your parents were kids, the latest edition is an up-to-the-minute guide to conquering the current job market—and invaluable for figuring out what you really want to do with your life.
  • You Look Like a Thing and I Love You: How Artificial Intelligence Works and Why It’s Making the World a Weirder Place by Janelle Shane. This hilarious book, by a Ph.D., in electrical engineering, is a master class in what A.I. can do—and what it can’t. (The title is a quote from an algorithm.) A.I. is taking over more and more of what humans used to do, and that trend is going to get bigger. So, no matter what career you choose, think of learning all you can about A.I. as a kind of career insurance for the future. You Look Like a Thing is a great place to start.


  • Expect to Win: 10 Proven Strategies for Thriving in the Workplace by Carla A. Harris. Once you’ve picked up enough experience to start moving up at work, it’s time for a savvy guide to getting your ideas heard and standing out from your peers. The author is a Harvard MBA and Wall Street veteran who is now vice chairman at Morgan Stanley. Drawn from her own experience, this is a candid, step-by-step analysis of her own career (from the perspective of a black woman)—including her mistakes, and how to avoid repeating them. It’s a lively read packed with wisdom for anyone intent on becoming a leader.
  • The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change by Stephen R. Covey. This is one of those books you see executives pull out of their briefcases on airplanes for a quick refresher, and there’s a good reason for that. Its famous list of rules—for instance, “Begin with the end in mind” and “Seek first to understand, then to be understood”—have served as guideposts for successful people in business since 7 Habits was first published in 1994. The ideas are deceptively simple, but the book is a must-read, if only because its impact on corporate America has been enormous.

Gen X

  • Working with Emotional Intelligence by Daniel Goleman. Almost 90% of the traits and behavior that set great leaders apart from also-rans, according to detailed research into more than 500 companies, have little to do with I.Q.—and everything to do with E.Q., a set of interpersonal skills that Goleman maintains anyone can learn. At this point in your career, when you may be poised to rise into senior management, the author’s colorful case studies and in-depth commentary could help make you a shrewder negotiator, a more persuasive influencer of higher-ups, or a boss who gets big things done.
  • Disrupt Yourself: Master Relentless Change and Speed Up Your Learning Curve by Whitney Johnson. This generation started working at just about the moment when the pace of change in business (and life) started speeding up like crazy. Yet, over the decades ahead, just keeping up—let alone thriving—is likely to demand even more agility. Enter Disrupt Yourself, a down-to-earth new handbook for dealing with constant change, and coming out ahead of it. Johnson, whose consulting clients include Oracle and Gartner, has also taught this 7-step method in Harvard Business School’s Executive Education Program.


  • Second-Act Careers: 50+ Ways to Profit from Your Passions During Semi-Retirement by Nancy Collamer. The traditional notion of retirement —what the author calls “a trifecta of golf, gardening, and grandkids”—is all but obsolete. If you’d like to keep active after “retirement age,” but don’t know exactly what your options are, this book’s for you. Collamer, a longtime career coach, tells how to envision the life you want, and then find a practical path to get there. The book describes 50 possible pursuits, from part-time jobs, to passion projects, to starting an online venture, along with the pros and cons of each.  
  • Purpose and a Paycheck: Finding Meaning, Money and Happiness in the Second Half of Life by Chris Farrell. An economist who hosts a Minnesota Public Radio show called “Conversations on the Creative Economy,” Farrell spent a few years digging into research on aging, and found that most of the stereotypes about older people are wrong. His fascinating book covers a range of topics, including why companies need multi-generational teams (whether they realize it or not), and how to get a job despite recruiters and interviewers who call you the dreaded “O” word, for “overqualified.”

Of course, at any age and no matter what you do for a living, sooner or later you’re bound to run into a co-worker (or a boss) who seems determined to jump on your last nerve.

So here’s one last recommendation: Working With You Is Killing Me: Freeing Yourself from Emotional Traps at Work by Katherine Crowley and Kathi Elster, who are partners in career coaching firm K Squared Enterprises. Got a backstabbing colleague, a micromanaging manager, or an uncooperative employee? The authors make a persuasive case for learning how to keep other people from affecting your own productivity—or just plain driving you crazy.

Stay in the know

Regardless of which stage you're at in your career, knowing the ins and outs of managing career development skills, settling in at a new job, or finding the right part-time gig, you need to have the right tools. Join Monster today and get weekly emails filled with career advice and job search tips. Additionally, as a member you can upload up to five versions of your resume so recruiters can find you when the right position opens up.

Anne Fisher has been writing about workplace trends and topics since 1994. She is a columnist for and the author of If My Career’s On the Fast Track, Where Do I Get a Road Map?