Management Tips And Inspiring Stories

Looking for some inspiration as you make small business plans for 2022? There are plenty of wonderful books for entrepreneurs out there — from tips on how to work more efficiently to detailed research on what makes certain companies more successful than others.

But some of the most meaningful and inspiring reads for entrepreneurs come from outside the standard business book recommendation. To help mix up your reading list, here are eight nontraditional books with strong insights, lessons, and anecdotes that can resonate as you think about your own journey.

Business Partnerships and Teams

Black, White, and The Grey: The Story of an Unexpected Friendship and a Beloved Restaurant | Mashama Bailey and John O. Morisano

  • From the reviews: “It’s one of the best and most honest books about business, partnership, race, class, culture, and gender I’ve encountered.” – Hunter Lewis, Food & Wine
  • How it appeals to entrepreneurs: This story of one of America’s most celebrated restaurants features simultaneous narratives by The Grey’s head chef (Bailey) and her business partner (Morisano). It’s a lesson in perspective and building meaningful relationships that translates to all kinds of ventures — not just restaurants.

Big Friendship | Aminatou Sow and Ann Friedman

  • From the reviews: “A hybrid of memoir, cultural criticism and advice, ‘Big Friendship’ describes experiences that are common in deep friendships but rarely acknowledged.” – The Washington Post
  • How it appeals to entrepreneurs: This is an excellent book for managers and business partners, as Sow and Friedman portray moving ways in which the work behind building connections is important. It’s easy to get lost in a focus on products and growth. Look here for a new approach to building meaningful relationships with your staff and your team.

Crafting Your Message

Nicely Said | Nicole Fenton and Kate Kiefer Lee

A Swim in a Pond in the Rain: In Which Four Russians Give a Master Class on Writing, Reading, and Life | George Saunders

  • From the reviews: “While the genesis of A Swim in a Pond in the Rain can be found in the creative writing classroom — and writers at any level of their careers will glean priceless pearls from nearly every page — the genius of Saunders’s book, and his clear intention in offering it up, is to elucidate literature for the engaged reader, deepening the reading experience. It is also a blueprint for a greater engagement with humanity.” – BookPage
  • How it appeals to entrepreneurs: Another book about writing, A Swim In A Pond is a welcome companion to Nicely Said. Business owners will take away lessons about building their message and their story, as Saunders dive into the craft of classic works of literature. But more importantly, Saunders explores questions about emotion, compassion, and empathy. Given the staffing challenges all kinds of businesses are facing, diving into a work like this to gain a better understanding of how to connect and what drives those connections can offer a new perspective for the hiring and team management process.

Asking For A Friend: Three Centuries of Advice on Life, Love, Money and Other Burning Questions From a Nation Obsessed | Jessica Weisberg

  • From the reviews: “Jessica Weisberg’s hilarious, enlightening odyssey through the history of advice columns chronicles the evolution of our anxieties over how to act. However weird or offensive some of our questions have been, it’s heartening to know that at least we’ve always been trying. A surprising and delightful read.” Mac McClelland, author of Irritable Hearts: A PTSD Love Story
  • How it appeals to entrepreneurs: Business owners can find advice anywhere. The volume can be overwhelming at times. This book flips the idea on its head, diving into what drives successful advice-givers and why they resonate with large audiences. It gives you an opportunity to reflect on where and how you receive your advice, how it influences you, and how you might better be able to influence clients and customers.

Inspiring Stories

Notes From A Young Black Chef | Kwame Onwuachi

  • From the reviews: “You couldn’t ask the universe for a more colorful creative culinary adventurer than chef Kwame, who blends the stories and history of his African and African American heritage into a literary pot of brilliant cultural flavors. An amazing recipe of a life lived to the fullest, Notes from a Young Black Chef is seasoned with herbs of pain, hardship, abuse, and confusion but also infused with the flavors of joy, triumph, excitement, challenge, and winning.” Alexander Smalls, coauthor of Between Harlem and Heaven
  • How it appeals to entrepreneurs: Onwuachi’s inspiring tale is essential reading for any aspiring trailblazer in their field. His honest reflections on bouncing back from failure and learning from mistakes will help keep business owners motivated, whether they’re just getting started, looking to grow, or testing out something new.

Open: An Autobiography | Andre Agassi

  • From the reviews: “An honest, substantive, insightful autobiography. . . . The bulk of this extraordinary book vividly recounts a lost childhood, a Dickensian adolescence, and a chaotic struggle in adulthood to establish an identity. . . . While not without excitement, Agassi’s comeback to No. 1 is less uplifting than his sheer survival, his emotional resilience, and his good humor in the face of the luckless cards he was often dealt.” The Washington Post
  • How it appeals to entrepreneurs: The entrepreneurial journey can be a lonely one at times, leading to doubt and uncertainty. Agassi’s memoir holds up to its title — it avoids cliche and shows an athlete at the top of his game working through challenges to find himself on and off the court. It’s a refreshing read for any business owner during challenging moments.

Barbarian Days: A Surfing Life | William Finnegan

  • From the reviews: “Finnegan’s treatment of surfing never feels like performance. Through the sheer intensity of his descriptive powers and the undeniable ways in which surfing has shaped his life, Barbarian Days is an utterly convincing study in the joy of treating seriously an unserious thing . . . As Finnegan demonstrates, surfing, like good writing, is an act of vigilant noticing.” The New York Review of Books 
  • How it appeals to entrepreneurs: Barbarian Days is all about the hypnotic effects of fully pursuing your passion — something business owners can easily relate to. Even for entrepreneurs with no connection to surfing at all, this book will hit home with anyone who has committed much of their time to something they love.

Square has the tools to run your business — on your own terms. To help celebrate businesses paving their way forward, we partnered with Forbes on the Next 1000 initiative to spotlight bold entrepreneurs and share their most valuable lessons. By sharing firsthand experiences, we’re helping businesses celebrate resilience, build skills, and explore what’s next. See how Square works, and get more expert guidance for the next era of small business.

Maria Flores

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