10 books to read if you want to quit your job and become your own boss, according to people who did it — and also wrote about it
Escaping the 9-to-5 and becoming your own boss is hard. Nearly 16 million Americans are self-employed, according to a 2019 study by Pew Research Center. Business Insider asked four professionals who quit their jobs to start new careers what their favorite books were and compiled a list of 10 essentials. From step-by-step guides to novels written in first person, here's what they recommend. Click here for more BI Prime stories.
Despite what pop culture has conveyed, quitting your job is a big decision. Walking out, theatrically telling off your boss, or deciding to leave on a whim generally doesn't happen. Instead, pivotal career changes can be stewed over for months — or even years. If becoming your own boss or starting your own business has been at the forefront of your mind for quite some time, it may be best to hunker down and study the wisdom of those who have done it themselves. Business Insider reached out to four professional entrepreneurs with books of their own to see what their top choices were for readers looking to leave their cubicle days behind. 1. "The Big Life: Embrace the Mess, Work Your Side Hustle, Find a Monumental Relationship, and Become the Badass Babe You Were Meant to Be" by Ann Shoket Nicole Lapin is a bestselling author and self-described "finance pro" — but before she was writing books and coaching the internet on what to do with their paychecks, she was a news anchor with nearly $20,000 in debt. Not wanting debt to control her life, Lapin left her job in broadcast news and decided to start a production company. She shared how she learned from her money mistakes with her millennial audience — Lapin's third, and latest, book, "Becoming Super Woman," tackles what to do when you feel burnt out and find yourself working hard but not moving forward.
Lapin finds that Ann Shoket's book speaks to millennial women with aspirations beyond climbing the corporate ladder. In "The Big Life," Shoket includes personal anecdotes about her decade-long post as editor-in-chief of Seventeen Magazine and expands on the idea that one should craft a passion, not a career, to achieve meaningful success. "It reminds you to stop and think if you're living a life you're proud of, and if you're not, to do something about it," Lapin said. 2. "Leave Your Mark: Land Your Dream Job. Kill It in Your Career. Rock Social Media" by Aliza Licht Lapin recommended Licht's first book, "Leave Your Mark," for those looking to start over in their careers the right way. Like Lapin, Licht left her "dream job" as a public relations professional after 17 years to build and market her own brand. Since then, Licht launched a career-focused podcast and became a digital consultant. In "Leave Your Mark," Licht talks about what it is like to make a momentous career change, what skills are needed to succeed as an entrepreneur, and how to harness social media to grow a new business. Licht's advice is also littered with "'The Devil Wears Prada'-like moments and insider secrets," Lapin said. 3. "168 Hours: You Have More Time Than You Think" by Laura Vanderkam For more than 15 years, Jon Acuff was a marketing executive, working to tell the stories of dozens of companies. Today, he is a full-time public speaker and author of six bestselling books, hosting events for companies like Walmart, Nissan, Microsoft, and Comedy Central. His own book, "Do Over: Make Today the First Day of Your New Career," talks about how to sharpen your skills, even when your career hits the ceiling.
But Acuff finds Vanderkam's "168 Hours" to be the perfect explainer of why "busy" doesn't mean what we think it does. "People are constantly telling me they are too busy to pursue new endeavors — but if that's true, why does the average American over 18 have time for 4.5 hours of TV a day?" said Acuff. "You have a lot more time than you think to work on the things you care about, and Vanderkam does a wonderful job explaining that." Vanderkam notes in her book that successful and happy people allocate their time differently than most. And for a more well-rounded life, people need to drown the daily grind and make room for their true priorities. 4. "The War of Art: Break Through the Blocks and Win Your Inner Creative Battles" by Steven Pressfield Acuff said that although Pressfield's book isn't necessarily about entrepreneurship, he recommends it to nearly anyone about to embark on a new adventure — fairly synonymous with starting a business. "Pressfield's unflinching look at resistance — that potpourri of fear, doubt, and anxiety that accompanies big decisions — has helped me dozens of times over the years," said Acuff. "The War of Art" is described as a practical guide for homing in on creative breakthroughs. Pressfield writes that recognizing your obstacles is the answer to beat "self-sabotage" and procrastination. 5. "This Is Marketing: You Can't Be Seen Until You Learn to See" by Seth Godin Cathy Heller, host of the podcast "Don't Keep Your Day Job" and author of the book with the same name, has made a career out of helping people become their own bosses. But before all that, she was a recording artist, licensing her music out to TV shows and movies. After a while, Heller found herself teaching other artists to license their work when the idea of becoming a career coach clicked.
Heller believes Godin's book "This is Marketing" to be "the only book people need to read on the subject." "Seth teaches us that marketing isn't sleazy, it's the opposite," said Heller. "Marketing is having radical empathy and making sure you are effectively communicating that you made the thing that people need." In "This is Marketing," Godin, a former dot-com business executive, argues that good marketing should never solely solve the problems of the company, but of consumers. The book touches on the idea of trust and how to implement new-age communication techniques through Godin's own intuitiveness and real-life examples, added Heller. 6. "The Big Leap: Conquer Your Hidden Fear and Take Life to the Next Level" by Gay Hendricks "'The Big Leap' is such a powerful book because everyone plays within the limits of what they decide is possible," said Heller. "We stay small and we suffer unnecessarily ... Hendricks helps us see how we confine ourselves and shows us a way to break through this upper limit." Hendricks' bestselling book was first released nearly a decade ago and includes anecdotes from his personal life as an executive career coach, as well as insights into the careers of other successful people, including Dell Computer founder Michael Dell. Heller said Hendricks encourages readers to tap into their "zone of excellence" to unleash "a whole other realm of genius" — a message "everyone needs," Heller added. 7. "Grit: The Power of Passion and Perseverance" by Angela Duckworth The New York Times calls Duckworth "a scholar you have to take seriously" — one that has coauthored bestselling books and was awarded the MacArthur "genius" fellowship for her analysis of the noun prominently displayed on her 2016 book. For Heller, however, Duckworth's "Grit" not only provides commentary on the character trait many strive for, but the need for optimism when searching for success. "This book highlights that what matters most isn't talent or your zip code," said Heller. "It's not about being dealt a lucky hand, it's about having persistence." Duckworth, a psychologist and researcher by trade, uses examples of success from history, follows cadets as they traverse through West Point, and interviews heavyweight executives like JPMorgan Chase CEO Jamie Dimon and Seattle Seahawks coach Pete Carroll. Though what may be the most compelling parts of "Grit" are Duckworth's analysis of her own success, confrontation with her lack of genius, and discovery that what's needed most to fuel grit is optimism, said Heller. 8. "Starting a Business All-in-One For Dummies" by Bob Nelson and Eric Tyson Sophia Amoruso first started out slinging vintage clothing on eBay in 2006 as a high-school dropout, harnessing social media to help her grow it into one of the fastest growing retail businesses, NastyGal. Her 2014 memoir "#Girlboss" regales her path to success. In 2015, she left the company she created to build another, Girlboss Media, a professional networking community for women.
Amoruso recommended "Starting a Business All-in-One for Dummies" because it was one of the first business books she ever picked up. "They're super comprehensive and cover all you need to know about establishing a business," said Amoruso, "from legal to finance to the nuts and bolts of getting set up." The number of people who've quit their jobs and started their own businesses is on the rise. Nearly 16 million Americans are self-employed, according to a 2019 study by Pew Research Center, and 30% of the US workforce works for self-employed individuals. 9. "The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers" by Ben Horowitz "Horowitz has had an ultra-influential blog for years, and this book is a culmination of his incredible experience both building, scaling, and investing in startups," said Amoruso. Horowitz is the other half of Andreessen Horowitz, the titan of Silicon Valley venture capitalist firms. An avid music fan, Horowitz does something fairly unconventional in his book: He dissects business lessons from his favorite rap lyrics. "The Hard Thing About Hard Things" is described as a mix of humor and hard lessons, lessons from Horowitz's own experience building a successful venture fund, as well as his own experiences gleaned from being an entrepreneur himself, Amoruso said. "An essential," she added. 10. "Essentialism: The Disciplined Pursuit of Less" by Greg McKeown Amoruso said that for any entrepreneur, "focus is key." "That's one thing I've learned the hard way," she said. "As an inspired entrepreneur, it's easy to pursue all of your ideas at once, but vetting them and phasing them strategically is incredibly important." That's why Amoruso recommended "Essentialism": A book that enthusiastically tells readers to review the requests made of them in their careers, reevaluate their priorities, and be okay with saying no. McKeown interviews entrepreneurs and executives across industries to see what their career turning points were — where they stopped answering every email, attending every conference, and committing to late nights in the office. He also provides helpful venn diagrams and graphs to make decision-making proactive for those who want to become an essentialist. This article was originally published on Business Insider February 12, 2020.SEE ALSO: The 14 best books to read to break into venture capital, according to successful investors, founders, and professors in the VC space READ MORE: Required reading: These are the books top professors at the best business schools in the country are having their MBA students read Join the conversation about this story » NOW WATCH: Taylor Swift is the world's highest-paid celebrity. Here's how she makes and spends her $360 million.
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