Day One Reads – The Gift of Struggle

I love a book you can devour on a flight that lasts less than three hours. This little tome had me nodding and smiling the whole trip (with a couple of tears thrown in), and even had me stay in my seat as the plane emptied to make sure I finished it off!

The Gift of Struggle: Life-Changing Lessons About Leading

Category*: Reflective

Author: Bobby Herrera

About the author: Codi Shewan spent two decades working in the death-care profession, until in 2014 he leapt from an executive position in corporate funeral services to the entrepreneurial world. As a consultant and speaker, he’s on a mission to redefine “legacy” as something that you personify each day of your life: you can realize the power of your own positive influence while you’re still here. He is also the founder of From Strangers to Family, an experience which helps people feel connected in an often disconnected world.

About the author: Bobby Herrera is the co-founder and president of Populus Group. With a passion for building strong culture and communities through trust and storytelling, his leadership style is about empowerment, connections, and ensuring everyone has the opportunity to succeed.

Bobby grew up in a big family with parents who immigrated to America without much. While this is not an uncommon story, the leadership style and company culture that it inspired is. The belief that everyone deserves the opportunity to succeed is at the core of Bobby’s philosophy in business and in life.

Everyone has struggles and business leaders are no exception. Bobby’s passion is helping others understand how their individual struggles can help them connect with their communities and inspire other is what will ultimately transform their leadership style.

Bobby is a proud Army veteran and currently lives in Portland, Oregon with his wife and three children.

How I found it: This is another “grab it as I head to a flight” book. I picked it up at the same time I grabbed last week’s book The Jackass Whisperer. I love Patrick Lencioni’s work, so when I saw he offered a testimonial on the back, I grabbed it.

Book Jacket description:

Every leader has stories about the challenges they have faced and struggles they have overcome. In the moment, those situations require strength, patience, perseverance and courage. With time, those struggles provide us lessons for how to be better leaders. Bobby Herrera learned to see those struggles as gifts.

As the co-founder and CEO of Populus Group, Bobby never imagined the challenges of building a $500 million organization that serves tens of thousands of people. Throughout his life, he experienced the divergence between the intentional leader he wanted to be, and the less engaged version of him that showed up at the office every day. One day at a company meeting, he decided to share a story about one of his first struggles as a young adult. That story, a pivotal experience that had transformed Bobby’s life, inspired his employees with its radical transparency, humility and the idealism of Bobby’s dreams for the company.

In The Gift of Struggle, Bobby shares twelve of those stories from his leadership journey. Each chapter shares the details of the story, the broader lesson any leader can apply, a set of questions to reflect on, and an afterword for how the story later unfolded in Bobby’s life. Building on Bobby’s efforts, this book inspires readers to find their own stories, share their gifts of struggle with others, and become the leader they imagine they can be.

How well I feel it delivered on what the jacket promised (scale out of 10 with 10 being completely delivered): 10. Yes, I know I’ve been overwhelmingly positive on my ratings thus far, but I haven’t yet read one that I didn’t really enjoy.  

Amazon Rating: 4.7 (34 ratings – Canada)/4.7 (70 ratings – US)

Goodreads Rating: 4.17 (111 Ratings)

Who I think should pick it up: Anyone running an organization, no matter how large, should give The Gift of Struggle a read.

Anything someone might quibble with: While non-business examples are used to demonstrate some principles, most of the advice given is most applicable to those who would find themselves in positional leadership roles.

“Velcro quotes” (ideas that are going to stick with me moving forward):

  • “Incorporate a trust-building signal into your interactions. For example, the appointments I set for calls with my team members start at unusual times like 8:29 or 11:02, never the top or bottom of the hour. The psychological benefit of this practice is that by calling at precisely that minute, it sends the signal that I keep my word.”
  • “Leadership amounts to wanting more for our people than we want from them.”
  • “Brush your teeth with your weaker hand for thirty days. You need to learn what discomfort really feels like. The practice will teach you to think differently.”
  • “I believe the frustration we see in the eyes of those we are honored to lead is an invitation.”

Brush your teeth with your weaker hand for thirty days. You need to learn what discomfort really feels like. The practice will teach you to think differently.

How likely I think I am to make a positive reference to this book in the next 30 days: 100%. In fact, I wrote the author an email telling him how much certain sections of the book impacted me.

How likely I’ll put something I learned in this book to use in the next 30 days: 100%. The inside covers are absolutely filled with scribbles about how I can apply some of his concepts to my own company and my own relationships right away. Most notably, I’m trying to brush my teeth with my left hand for the next month.

Total Pages: 166

Total “pulled passages”: 32

Page to Pulled Passage Ratio**: 5.2:1

P2P Ranking within category for 2020: #2 of 4

Overall P2P Ranking for 2020: #4 of 6.

*I break books into one of three categories in order to better compare apples-to-apples.

  • Reflective: Relies on first-person stories or insights
  • Biographical: Tells the story of an individual or organization from a third-person perspective
  • Research-based: The author(s) collect third-party research to support their discussion of a particular topic.

**As I read, I highlight certain passages/insights that really connect with me. Things that make me think “buying this book was worth it for ideas/information like that.” At the end of the book, I go back and “pull” them from the book and copy them all into a single document. P2P Ratio indicates how many pages on average tend to go by between these particularly powerful insights. This book’s 5.2:1 ratio means I felt there was a passage worth pulling out and writing down every 5.2 pages.