Seven Notions to “Let Go of” to Be a CEO in Today’s World

Challenge these common conceptions to excel in your leadership position.

After working for 26 years in the for-profit capital sector of our economy and nine years with the poor, forgotten, and demonized people of our society, I see life much differently than before. I feel as if I’ve awakened to a new understanding of the rules of how we interact for the betterment of society. 

Homeboy Industries is the largest and most successful reentry program in the world. It was founded and is led by Father Greg Boyle, a Jesuit priest, who dedicates his life to helping men and women get out of the gang lifestyle. As they transform their lives, these men and women show us why people should not be defined by the worst thing they’ve done. Homeboy has helped thousands of people heal from complex trauma and become contributing members of our society—even when it seems like everyone has given up on them. In many ways, this effort can be viewed as a fight against racial and economic inequities, for the population we serve are poor people of color who have never been given a fair chance. 

For over 30 years, Homeboy Industries has provided hope, training, and support to formerly incarcerated and gang-involved people allowing them to redirect their lives and become contributing members of their community.

In my time at Homeboy, I’ve made friendships and built relationships that are remarkable. I’ve experienced more sorrow and more joy in these past few years than in my whole life before that. Along the way, almost by providence, I was able to see how business can be done with a different set of priorities so that everyone benefits: owners, management, and those who have never been able to sustain a job but now do. I learned how to help the “unemployable” become employable. I’ve participated in the development of business models that provide not just economic impact but social impact. 

I’ve lived my whole life in the mode of “don’t break the rules.” What my time at Homeboy has taught me is that people need to go out of their way to help people and that we need to do business differently. To do well in the marketplace while providing social value, we must break the rules. In order to truly help individuals and ourselves, we must not be so rule bound. We need to bust up the system, swim upstream, and avoid the herd mentality. We need to take a step back and truly understand our own roles in society—and let go of outdated notions.

Every year, Homeboy Industries builds work readiness skills for thousands of program participants through employment opportunities across the nine social enterprises it owns and operates.

Here are just 7 of the 55 rules to break, as fully explained in my book, The Homeboy Way: A Radical Approach to Business and Life. 

    1. Rule to Break:  The world is all about “us” and “them.” It’s harder to demonize someone you know—relationships counteract tribalism and judgmentalism. Get to know your co-workers. Seek to understand the lived experiences and histories of those who come from a culture different from your own. Don’t demonize anyone.


    1. Rule to Break: I’m at the top of my profession, so I know what to do. Being well trained for the business world doesn’t mean all that much when leading the way forward in other arenas—we need to know our limits. Be open to knowing that you need to learn new things.


    1. Rule to Break: A business is an entity unto itself. A business is not insulated from its surroundings. All businesses are local businesses. Being a stakeholder in the betterment of the community not only helps local businesses but also, by extension, lifts up everyone in the community.


    1. Rule to Break: The boss is always right and deserves your respect. Step back when you find yourself needing to be right or requiring absolute respect. There is always something else behind “insubordination.” The stresses of life catch up to many people and happen to us all. To change one’s life is hard work, and there’s dignity in this hard work. It is in this hard work where, paradoxically, profound healing begins. So let us all not be angry and judgmental when we feel threatened by a minor workplace slight. Let us view it as a chance to be humble and acknowledge someone else’s pain.


    1. Rule to Break: In this world, there are winners and losers. Let’s dare to think always in terms of win-win. One person having success does not mean that success is taken from someone else. Generosity and gratitude need to be cultivated and put into action so that everyone is able to succeed. This can happen for all, not just for those who work in an organization like Homeboy. You can shift your mindset even in large bureaucratic organizations. It’s about an individual mindset that spreads into a collective mindset.


    1. Rule to Break: We should always strive for certainty. I broke my rule of certainty and instead used the rule of faith to decide to join a nonprofit serving people I had no connection with. Certainty will blind you to your own biases and conclusions. We need to be comfortable managing in times of uncertainty, particularly in human-services organizations.


  1. Rule to Break: Responsibility is a burden. In loving yourself and others, burdens turn into joys. Everyone should pursue joy. In that pursuit, I found my path forward. The stressors of the responsibility I once felt are now secondary to the times where I found joy. Joy is a powerful state. Finding joy takes time, contemplation, and openness. Once there, everything else in life just falls into place.

The Homeboy Way is the “how” of mutuality, compassion, and kinship for a better society.  As leaders, we must lead in a different style and be on the forefront of change.

Thomas Vozzo is CEO of Homeboy Industries and author of  The Homeboy Way: A Radical Approach to Business and Life.