I did not expect to enjoy Originals by Adam Grant very much, but I was pleasantly surprised. The book was chosen for a book club at work, and the subtitle (“How Non-Corformists Move the World”) and cover art conspired to make me skeptical. I am glad I gave it a chance, though, because I came away from it with four valuable lessons.

The first lesson was about managing your personal risk portfolio as it relates to the projects you undertake. I have heard many entrepreneurs talking about quitting their day job specifically so that they would have no safety net. This mindset says that if you have a backup plan you might not give 100 percent. Grant himself mentions thinking this way when he decided not to invest in Warby Parker because all the founders were still in school at Wharton and had safe job prospects afterward. He gives several examples of successful founders who launched major projects as after-hours hobbies (Pierre Omidyar of eBay, Scott Adams of Dilbert fame). My favorite illustration was T.S. Eliot, who was a banker when he wrote The Waste Land. Eliot later worked in publishing and never counted on poetry to be his full-time occupatin.

A related idea in the book was to make lots of bets by trying many different projects. This is about managing risk, but also about giving yourself the freedom to generate new ideas. Once you have come up with a couple of dozen lousy ideas, Grant says, you begin to think outside the box and may hit on something truly original. Maya Angelou wrote six autobiographies and 166 poems but she is remembered for the quality of her best works, I Know Why the Caged Bird Sings and “Still I Rise.” Even if most of your projects are failures, if you keep them small people will evaluate you on the peaks of your success instead.

Having lots of failures can yield valuable information. Grant mentions the power of negative thinking for self-critique. He is careful to advise not over-indexing on failures, though: any undertaking with a stochastic component will result in some failures even when you do everything “right.” This is the converse to the failing of many business books, which select on success and work backward even when taking the same steps might have been a disaster nine times out of ten. The author spends a fair amount of the book exploring the reasons for one of his own failures, citing not investing in Warby Parker as a “false negative” for his prior mental models.

The fourth take-away is to get input from others with diverse perspectives. Although it is important that you trust the people whose input you solicit, it is even more important that they have different backgrounds, experiences, and outlooks from yours: CEOs whose companies are failing often withdraw into more narrow social circles, which only compounds the problem by putting them into an echo chamber. If you are getting perspectives outside your field, do not rely on the speaker’s enthusiasm as a substitute for expertise. Dean Kamen was an expert in health care technology who got very excited to revolutionize transportation. Jeff Bezos was a big backer, which may be why I remember reading so many breathless articles hailing Kamen’s invention as the next big thing long before it was released. (This Time magazine article, entitled “Reinventing the Wheel,” gives a sense of the excitement when the project was still known by its codename, Ginger.) You may know that this was the Segway, which was too expensive and too different from existing options (“where do I put the grocery bags?” one critic asked) to be more than a novelty. Kamen has since returned to health care where he originally made his mark; an area where his expertise and enthusiasm are complementary.

These four ideas — managing risk, making many small bets, thinking about how you may fail, and engaging experts outside your field — stand in contrast to much of contemporary advice to entrepreneurs, which advises going all-in and not looking back. I appreciated Grant’s measured approach. The biggest lesson from this book reminded me a bit of the debate between Malcolm Gladwell’s popularization of the “10,000 hour rule” and David Epstein’s work on genetic predisposition to certain sports (see this series of posts for a deeper look into the debate). Grant is closer to Gladwell’s point of view: originality is a trait that can be learned. That in itself is a valuable lesson.