Productive Flourishing
Productive Flourishing
Bobby Herrera: The Empowerment of the Struggle (Episode 208)

Bobby Herrera: The Empowerment of the Struggle (Episode 208)

Today’s guest is Bobby Herrera, co-founder and CEO of the Populus Group, an army veteran, and the author of The Gift of Struggle. He joins Charlie to talk about the power of sharing your stories of struggle with your team and those around you. Listen to hear how Bobby changed his stories of struggle, and how you can convert yours from something that keeps you from being successful to the gift that it is.

Key Takeaways:

[0:05] - Charlie’s new book, Start Finishing: How to Go From Idea to Done will be released on September 24th, 2019. The book shares tools, practices, and mindsets that will help you finish the stuff your soul is yearning to do. There are contributions from Charlie’s friends, colleagues, and teachers.

[4:20] - Bobby’s book, The Gift of Struggle, is a parable/story-style book, that seeks to understand the gift of struggle. He wrote this book to give others permission to lead the way they want to without fear or doubt of struggling along the way.

[8:25] - Writing the book wasn’t something Bobby necessarily planned to do. He’s a story-teller by nature, and as he started speaking to veterans and telling stories to kids, he was encouraged to write them out in a book. It has opened up opportunities to connect with others, and guide others in a way he wasn’t in his own leadership journey.

[10:10] - Being able to share the stories through live story-telling is a much different engagement than when it is written down. Bobby gets fulfillment from the way people are responding and sharing their own experiences of how they’re applying what they’ve learned in the book.

[11:50] - Bobby shares the story of Dr. Joe, and how he helped navigate his first macro-level leadership position. In a feedback session with Dr. Joe, he helped Bobby identify who he needed to learn from, and what it meant to be a real student.

[15:00] - In the book, Bobby also shares the story about his demotion. As a result of the demotion, he did some self-reflection on the choices he was making, who he was learning from, and how he was learning. He wasn’t taking advantage of the resources he had access to around him. This was one of the most important lessons he has learned in his leadership journey.

[17:10] - Asking for help, and asking the right people for help, is incredibly important to help you move forward. In our journeys of struggle, we often ask for the easy help, rather than asking for help from the people who will help us grow. We have to take ownership of our part, and realize the control we have over our situations.

[20:30] - You don’t have to have come from a certain background to be in a position of power. While that is a reality in some situations, it doesn’t have to be. The most important part of leadership is seeing and encouraging potential.

[22:25] - During a Q&A with some students in Seattle, a student asked Bobby how he was able to overcome the boundaries created by color. He shares the story of how he called the student up to race, and the moment he had a breakthrough. The race to the top (of our own stories) isn’t about who is beside us, it’s about running, and running a second faster each time. The things around us aren’t holding us down as much as we think they are.

[27:00] - We all struggle. Every struggle teaches us something, and that’s a gift. Leadership is sharing that gift, though it’s not a chronological journey. The book is structured so that each chapter asks questions that readers can apply to their journey, wherever they are at that time.

[30:25] - The essence of leadership is that you can’t start changing other people until you change yourself.

[31:335] - Telling your own stories can be very difficult. One of the hardest stories Bobby shares in the book is a story about his son. When writing the book, he wanted to use the power of story to provoke thought and reflection in the reader, so they could make connections to their own stories.

[35:40] - Leadership, creativity, and doing the work that matters is messy business. “The mud” is where the work happens. It doesn’t mean you’re doing something wrong. Too often, we smother the struggle, when there is actually so much empowerment in the struggle.

[38:50] - Bobby’s time in the military helped him frame some of the struggles he faced growing up in an economically disadvantaged family. It gave him a rigor and discipline that wasn’t always there. Resilience, discipline, and tenacity are all learnable traits. Anything worth being good at, is worth being bad at the beginning.

[42:15] - One of the biggest mistakes Bobby made starting his company was not sharing his story at the beginning. Once he was able to share his story, it transformed his company into a community. Sharing his story humanized him. Don’t make this same mistake! Let people know the invisible force that drives you.

[44:50] - There were several stories that didn’t make the final draft of his book. As with leadership, one of the most important parts of the editing process is choosing what you want to focus on. In this book, he wanted to focus on leadership.

[46:35] - Bobby’s invitation for listeners is to think about who you want your story to matter to when the time comes for it to settle. Reflect on this, because at the end of the day, that’s what really matters. Every choice that you make and how you choose to lead will have a direct impact on that.

Mentioned in This Episode:
Productive Flourishing

Start Finishing, by Charlie Gilkey

Bobby Herrera

The Gift of Struggle: Life-Changing Lessons About Leading, by Bobby Herrera

The Populus Group


Productive Flourishing
Productive Flourishing
Productive Flourishing (formerly the Creative Giant Show) explores how to do the work that matters to become your best self in the world. Host Charlie Gilkey and occasional co-host Angela Wheeler take listeners on a deep dive into the lives of leaders, changemakers, creatives, and entrepreneurs who are thriving in life and business by doing work that matters. Listen in to see how they cultivate meaning, success, and happiness as well as their approach to productivity, business, health, and the challenges (yes, even the deep, dark ones) that show up in their lives.