5 Books To Read When You’re Considering Making A Big Change

Changing careers is scary. Whether you’re finally taking the step to pursue your lifelong dream, or looking to leave a profession that’s making you miserable, it’s not always easy to leave what you know to go after something that seems uncertain.

I changed careers when it became clear to me (and everyone else) that I wasn’t suited to be a lawyer. Looking back, it’s easy to see that I faced little risks. I was young, childless, and had a college degree. But at the time, it seemed like a daunting prospect with a very real risk of failure.

Reading books helped me push past that fear, and also gave me some much needed perspective. If you’re thinking about changing careers, here are a few books you might want to read to help you figure out what to do next.

When You’re Scared Of How Things Will Turn Out

Getting There: A Book Of Mentors, by Gillian Zoe Segal 

When you’re deciding whether to make a big decision, it’s easy to feel like you’re all alone. But chances are, someone has probably experienced whatever struggles you went through, and made it through the other side just fine. Writer Gillian Zoe Segal compiled 26 stories from such contributors as former New York mayor and entrepreneur Michael Bloomberg to Teach For America’s Wendy Kopp. Whether you want reassurance that even experts struggle sometimes, or you’re scared about not having a backup plan, this book reminds you that you’re not the only one going through this journey

When You’re Not  Unhappy But Want To Do Something Else

When To Jump: If the Job You Have Isn’t the Life You Want, by Mike Lewis 

Mike Lewis was a high-flying venture capitalist. Although he wasn’t unhappy with his job, what he really wanted to do was to become a professional squash player. His friend told him that he was “crazy,” but later added that “there’s a difference between clear and stupid.” Lewis did end up fulfilling that crazy but not stupid dream, and became the 112th best squash player in the world. However, it didn’t come overnight–he spent 18 months preparing for it. Successful career change rarely comes from spontaneous decisions; it’s usually a result of deliberate planning and calculation. If you have a crazy dream but don’t know how to start, this book can help you identify your next steps and the level of risk that’s appropriate for you based on your personal circumstances.

When You Feel Like You Don’t Have Enough Information

Thinking In Bets: Making Smarter Decisions When You Don’t Have All the Facts by Annie Duke 

Making a career change involves making decisions when we don’t know what’s going to happen. In a sense, we’re placing a bet on our future success, and the uncertainty makes it hard for us to take strategic actions. Former poker player Annie Duke outlines the psychology of how we make choices when there are a lot of uncertain factors, including the traps we fall into that can hurt us later. While Lewis’s book can help you outline and execute your next steps, Duke’s book can help you decide whether that next step is the right one to take in the first place.

When You’re Worried About Failing In Your New Career

Permission to Screw Up: How I Learned to Lead By Doing (Almost) Everything Wrong by Kristen Hadeed  

Many people who are scared of changing careers are afraid of failing–particularly when they’ve been successful in their current job. When I made my career change, I remembered talking to many others who wished they could do the same, but they didn’t want to risk a bad outcome. Hadeed, who founded cleaning service Student Maid when she was in college, outlined how her series of mishaps led to lessons that eventually turned to success. It’s a lighthearted and easy read, with plenty of lessons and practical anecdotes about the ups and downs of starting a business with no experience. Even if you’re not interested in being an entrepreneur, this book offers plenty of lessons on taking on “risky” endeavors. If nothing else, this book reinforces that the cliché, “Everything has a silver lining,” really does apply in life.

Drive: The Surprising Truth About What Motivates Us by Daniel H. Pink 

When you’re young, you were probably told what you should strive for by your teachers and parents. You might have gone through college following this path without questioning what intrinsically excites you. However, extrinsic motivation can only last so long–it might lead you to a series of awards and accolades, but if your work doesn’t drive you internally, you won’t be satisfied. What if you don’t know what that work should be? This book is a great place to start. You probably won’t get the answers right away, but you can start by asking yourself a series of important questions.