Once a month or so, I get a call from a friend looking for career advice. They’re tired of their job/industry/routine/life, their kids have flown the coop, and they’re finally ready for a big change. And because they know I’m a veteran of several career changes, they ask me for advice.
I usually begin by asking them to describe their ideal day, followed by a series of questions. Then I recommend that before they do anything else, they read a few carefully selected self-help books to stimulate their thinking.
If you’re contemplating a career change, here are five books at the top of my list:
1. What Color is Your Parachute? I’m a huge fan of the most well-known guide to career change: What Color Is Your Parachute? by Richard N. Bolles. This book is so famous, its title has almost become a cliché. But that doesn’t mean it isn’t useful. When I left academia to go into journalism 20 years ago, I locked myself in a café for several months and did nothing but follow this book’s script. The basic premise is that in order to make a meaningful career change, you need to zero in on two key variables: what you like and what you’re good at, and where these overlap. (BTW? Much harder than it sounds.) Six months later, after doing the many and varied exercises contained within, I had a great job as a producer with Chicago Public Radio. Tip: You only need to read the core chapters on What? Where? How?
2. The Crossroads of Should and Must. I’ve been shouting to anyone who will listen for years about Elle Luna’s The Crossroads of Should and Must: Find and Follow Your Passion. Like “Parachute,” this book is also partly about how to finding meaningful work and/or embark upon a career change. But it’s also about going to the very core of who you are and figuring out how to be authentic to that self—what Luna calls your “must.” That isn’t an easy or comfortable journey. (Try the “write your own obituary” exercise and you may well end up in tears.) But the book is utterly inspiring because Luna believes so firmly that each of us does have an amazing gift inside. We just need to figure out how to unlock that creativity and release it into the world. A friend of mine refers to this book as “The Bible.”
3. Reinventing You. Dorie Clark is an absolute rock-star when it comes to professional reinvention. I’ve read all three of her books. But her first one—Reinventing You: Define Your Brand, Imagine Your Future—is probably the best place to start if you’re in the early stages of a career change. Clark offers very practical about how to move your career change forward. For example, she talks about the importance of having what she calls a personal “Board of Directors.” Rather than seeking out one mentor as you change careers, Clark suggests that you set up a group of people who can offer advice. This diversity enables you to draw on a range of viewpoints—and skill sets—that complement your own. I followed this advice on my most recent career change, and I continue to reap benefits from the network I set up.
4. One Person/Multiple Careers. Marci Alboher’s One Person/Multiple Careers: A New Model for Work/Life Success narrates the rise of so-called “slash careers,” in which people mix and match different career paths (what’s now known as a portfolio career.) This is a good book for people who already have a good handle on their skills and interests, but feel that these cannot be realized within the same profession. Reading about others who are running that bed-and-breakfast while still keeping a foot in advertising is empowering. Alboher also provides some useful advice on how to manage things like business cards and websites so as to feature multiple aspects of your portfolio.
5. The Subtle Art of Not giving a F*ck. Mark Manson’s The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life is all about getting in touch with your personal values. Like Luna, but with a somewhat more vulger lexicon, Manson exhorts us to live our lives so as to be consistent with those core values. So it’s about letting go of that panel of elders some of us carry around in our heads and who judge our every move. In some ways, I would recommend reading this book before any of the others. There aren’t any exercises to do; it just forces you to think hard about who you are…and who you would like to be.