Social Impact Heroes: Why & How Bill Payne of San Diego Second Chance Program Is Helping To Change…

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Social Impact Heroes: Why & How Bill Payne of San Diego Second Chance Program Is Helping To Change Our World

“Don’t rely on your title to define your role.” “President” is different than “CEO,” but everyone will call you an Executive Director anyway. The three roles overlap to some degree, depending on the size, structure, and specific needs of an organization. But what is important is that you identify where your organization needs your leadership and that you make the role your own. In my first few months in this role, I realized that the roles & responsibilities between myself and my Board of Directors needed to be defined, discussed, and agreed upon. It was something only I could do, so I did it, and it ended up paying dividends far into the future.

As part of my series about “individuals and organizations making an important social impact”, I had the pleasure of interviewing Bill Payne, President & CEO of San Diego Second Chance Program.

During his career, Bill has specialized in information technology, service strategy and management, as well as organizational change management. In 2020, Bill became the President & CEO of San Diego’s Second Chance Program. Bill holds a B.S. in Business Administration from Colorado Technical University and is an expert in the design and delivery of cost-effective solutions that deliver quantifiable results.

Thank you so much for joining us in this interview series! Can you tell us a story about what brought you to this specific career path?

I prefer to think of my professional journey as “building a career portfolio,” as opposed to having followed a specific career path. I was raised in an upwardly mobile middle-class family. That included instilling in me the common aspirational approach to identify a career field and follow a linear series of educational achievements and progressive series of jobs towards career goals and a vision for life. But early on and through my life, I ended up with a wide variety of interests. I attribute it to having a mother who was an educator by profession, and everything in life was a learning opportunity. And I also attribute it to having a polymathic father who was a technology professional, a civic leader, an athlete, and a youth sports coach.

My wide variety of interests and penchant for continuous learning led to a lot of experiences, including a stint as a child actor, an honorable discharge from our U.S. Air Force, and diverse professional roles in information technology, service strategy and management, and organizational change management consulting. A career path describes a linear pursuit, but this concept of a career portfolio is a journey featuring continuous discovery and fulfillment.

The steps along my journey that brought me to this role can be summarized in the word “impact.” At the most basic level, community-based organizations like Second Chance transform resources into impact. Our impact is on the people who are broken out of the cycle of incarceration and poverty, and our impact is on our communities that are safer and stronger because of our life-changing services.

Since moving to San Diego, I have had the opportunity to apply my professional skillset at Second Chance in many ways: as a donor, as a volunteer, and later as a consultant assisting with data system selection and implementation, project management, and management strategy. When I stepped into my current role as President & CEO, there was an alignment into a sweet spot where my skills, passions, and values aligned.

Can you share the most interesting story that happened to you since you began leading your company or organization?

I love that you asked for a story! Facts, figures, and statistics have their place in describing impact. But stories can provide so much more insight and color. And this is a story about an insight I gained into the “ripple effect” of the impact our organization has. Late last year, we were hosting a graduation ceremony for one of our collaborative court reentry programs.

This program serves adult offenders with histories of drug use and criminal justice contacts. Other treatment needs may include previous treatment failures, co-occurring mental illness, and high rates of health and social problems. The goals of these programs are to equip clients with the tools and resources necessary to overcome substance abuse issues, to successfully manage any behavioral health needs, while complying with the community supervision requirements and avoiding committing new criminal offenses.

Programs like these are not a walk in the park. They have a minimum enrollment of up to 24 months, and the average successful completion period is usually longer. A key feature of collaborative court programs is that there is a cross-functional Court Team that includes the presiding judge and our case managers behavioral health clinicians, an Assistant District Attorney and a Deputy Public Defender, and law enforcement representatives such as Probation Officers.

Late last year, at the graduation ceremony for a dozen program participants, there was the usual obvious evidence of impact on people’s lives. Program graduates were tearful, thankful, and joyous in their accomplishment. Their families and friends were proud and supportive. My staff was fulfilled by knowing and seeing the results of the hard work our team and our participants had done to reach this milestone.

But the feedback I got from a Probation Officer gave me insight into the ripple effect our organization has on so many lives. The Probation Officer told me that attending our collaborative court graduation, and seeing our participants and their families rejoicing, had a specific kind of impact on her. She seldom got to see such positive results from her professional efforts in a job that is demanding and can be draining, and the graduation ceremony reenergized her professionally. Probation Officers face large caseloads and they deal with potentially difficult and dangerous people. They do all this while managing staggering administrative tasks, working long hours, and trying to balance rehabilitation with public safety. I had never considered how the impact our organization has can motivate and strengthen the Public Safety professionals that our communities rely on.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Through the generosity of Joan and Irwin Jacobs, Second Chance is blessed with a beautiful and well-situated headquarters building in Southeast San Diego. When I was first starting, I worked in the same office space as my predecessor, which is the largest single office in the building. It was a little awkwardly furnished, with desk and table in decent shape but not necessarily the best fit for the room. But the previous CEO had been in that office for 10 years, so I assumed that the layout had been optimized, and since there was so much to learn and do, I didn’t put any thought at all into rearranging the furniture.

After a few months, and some turnover, I hired an Agency Coordinator whose role as my right-hand person has been critical to our continued operations. Since we would be working so closely, I decided to move into a different office that connected to a smaller office for the Agency Coordinator, so that we could more naturally communicate. I gave the big office to my Workforce Development Program Director, who had the biggest team and the most need for an office where he could meet with all his Program Managers.

The next Monday when I came in, I saw that he had rearranged the existing furniture into a much more comfortable, well thought out, effective arrangement in that office. My assumption that “it’s been like this forever; it must have been optimized” was obviously not true. I got a chuckle from that, and I got some meaningful insight about assuming that the long-standing “way we do things around here” have been optimized.

Can you describe how you or your organization is making a significant social impact?

Second Chance, which was founded in 1993 by Scott Silverman, is celebrating its 30th year of operations. Our mission to “disrupt the cycles of incarceration and poverty by helping people towards self-sufficiency” addresses the ongoing need for different and more effective approaches to public safety and criminal justice.

Starting in 2016, April has become Second Chance Month in the United States. In April 2022, the U.S. Department of Justice published their Dispatch newsletter, noting that “… at least half of citizens released from incarceration will recidivate (relapse into criminal behavior and return to incarceration) in some way following release. A major contribution to recidivism rates throughout the United States is lack of resources or connection to resources that aid prisoners’ prosocial integration into the community.”

The cost of incarcerating one individual in California has been increasing in recent years. According to the California Department of Corrections and Rehabilitation, the cost of incarcerating an individual in a state prison in California was approximately $71,000 per year in 2020, up from approximately $49,000 in 2010.

The trend for the cost of incarcerating one individual in San Diego County mirrors the trend in California as a whole. According to the San Diego County Sheriff’s Department, the cost of incarcerating an individual in a county jail in San Diego was approximately $142 per day in 2020, up from approximately $131 per day in 2010. In late 2022, our San Diego Public Safety Group provided a $246 per day cost for county jail to the San Diego Association of Governments (SANDAG), or close to $90,000 a year.

The systems that create cycles of incarceration and poverty are not only expensive, but they do not increase public safety or rehabilitate people who commit crimes. When a person who has committed a crime has served their sentence and is ready to lead a pro-social way of life, that person and their family need a community of support around them. To reenter and reintegrate into our society they need our society to see them as people, not problems. They need a second chance.

As we have for 30 years, Second Chance continues to demonstrate successful ways to implement a different and more effective approach to public safety and criminal justice. Our organization breaks the cycle of incarceration, helping individuals who are ready to change find true independence, learn healthier ways of living and become self-sufficient and contributing members of society. Through a series of integrated and mutually supportive programs and services, justice-involved individuals learn the tools they need to succeed for the long run. Our programs are the solution to the broken economics of the prison system, which is both expensive and ineffective.

Can you tell us a story about a particular individual who was impacted or helped by your cause?

One of the secrets to our success is that we have a significant number of people on our staff who are former participants in our programs. Our Director of Operations and Housing, Mr. Alex Macias, has been employed at Second Chance for 14 years, and he oversees our headquarters operations and manages our Transitional Housing program. Alex graduated from Class #128 of our Job Readiness Training program.

Alex is an authentic messenger, because of his lived experience. He uses that experience and his professional skillset to develop lasting supportive relationships with our participants through his compassion and his commitment. He expertly partners with other community-based organizations and with law enforcement leadership in a way that creates synergies throughout San Diego County. He also coaches and leads others to achieve the same results.

Alex embodies our impact as an organization on the lives of our participants and their families, and the behavioral health and criminal justice system in San Diego County. He recently shared with me the achievement of a life goal that is a great example of our impact. When Alex graduated our Job Readiness Training program, he set a life goal to have his then 3-year-old son, Alex Jr., be the first person in his family to be accepted into and attend college. Throughout his 14-year employment with Second Chance, he has taken steps to disrupt the all-too-common generational cycle of incarceration and demonstrate to his son that there is a different way of life from the criminal behaviors that characterized his previous life.

When his son was accepted into the University of California San Diego, Alex’s joy and sense of accomplishment could fill a stadium. He was smiling for at least a month. I still think of the impact that Second Chance had on Alex, who is now an accomplished professional who was giving back to our community by using his past as a lever to lift not just himself, but also his family. This calls back to the ripple effect our organization initiates that builds better and safer communities. I’m honored to be leading an organization that can deliver that kind of impact to Alex and to thousands of other people. We are currently enrolling Class #264 into Job Readiness Training.

Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?

Our society must demand change, politicians must enact rational changes, and our communities must support those rational changes.

The U.S. criminal justice system is designed to punish those who have been found guilty of crimes, with the goal of promoting public safety and deterring future criminal behavior. Our society must realize that the U.S. criminal justice system has not always achieved its goals of promoting public safety and justice for all, and that there is a need for reform to address systemic issues such as mass incarceration and police brutality. And then our society must demand change.

It is important to develop policies and practices that are grounded in evidence-based research and that balance public safety with the needs of marginalized and vulnerable communities. The relationship between the U.S. criminal justice system and social justice issues is complex and multifaceted. However, policymakers are recognizing that addressing social justice issues is critical to promoting public safety and achieving a fair and just criminal justice system for all. Addressing social justice issues requires that politicians enact rational changes to the criminal justice system.

There is overwhelming evidence that individuals who are reentering the community after incarceration have difficulty reintegrating into society due to social stigma, lack of support networks, and limited job opportunities. Providing rehabilitation services helps these individuals address underlying issues and avoid recidivism. Access to basic resources such as housing, education, and healthcare helps these individuals become self-sufficient and reduce the likelihood of recidivism.

The focus on recidivism as an-end goal of reentry into society from incarceration is being replaced by a focus on desistance and pro-social behaviors. This shift in approach is due to research that shows focusing solely on recidivism can reinforce stigma and discrimination faced by those with criminal records and may prioritize punishment over rehabilitation. A focus on desistance and pro-social behaviors recognizes the potential for positive change in all individuals and emphasizes the importance of providing resources and support to promote successful reintegration into society.

At Second Chance, our focus is on empowered self-sufficiency. Our communities must support a shift in focus towards reintegration into society to promote public safety and support rehabilitation for those who have been involved in the criminal justice system. That community support comes in the form of financially supporting the proven public-private partnership between our government and community-based organizations, and in the form of access to housing, education, and employment opportunities.

How do you define “Leadership”? Can you explain what you mean or give an example?

To me, leadership is the art and practice of adapting one’s styles to the situation at hand while collaborating, envisioning, directing, recommending, and contributing towards purposeful outcomes. Leadership is guiding a group of individuals with complimentary skills towards a shared purpose. Effective leadership also requires establishing mutual accountability and creating collective impact that reflects the efforts and contributions of the whole team.

To emphasize my definitions above, I’ll give a scenario that most of our readers will relate to: being assigned a group project when taking a class. I think we’ve all had the same experience: the group is formed, introductions are made, there is a general pause to see who will take the lead … and then someone does!

Everyone in the group has equal “status,” and everyone knows what the assignment is, but every time I’ve been in this situation, the same sequence plays out. A good way to understand leadership is to ask this question: What makes that person in the group step up?

I believe that the group project scenario demonstrates the following things about leadership: The leader has a willingness to lead, and the group accepts that leadership. The leader has confidence in their ability to lead, or, alternatively, is so frustrated by the lack of available leadership that they stepped up to lead. The leader is likely to be more successful if they have experience leading a group towards a similar objective in the past.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or each.

Here are the 5 things I wish someone told me, and in many cases wish I had immediately understood, when I first started in this position.

  1. “Don’t rely on your title to define your role.” “President” is different than “CEO,” but everyone will call you an Executive Director anyway. The three roles overlap to some degree, depending on the size, structure, and specific needs of an organization. But what is important is that you identify where your organization needs your leadership and that you make the role your own. In my first few months in this role, I realized that the roles & responsibilities between myself and my Board of Directors needed to be defined, discussed, and agreed upon. It was something only I could do, so I did it, and it ended up paying dividends far into the future.
  2. “Only do the things that only you can do.” This phrase is attributed to John C. Maxwell, who wrote the famous book The Five Dysfunctions of a Team. You may have gleaned from my short bio that this is my first time being in the CEO role. I’ve learned that there is a never-ending demand for my attention and efforts. As one small example, after years of providing technical support and training others on how to use Outlook I have a specific way I like to manage my calendar, but I’ve had to delegate scheduling and coordination to our Agency Coordinator.
  3. “Embrace the reality that you must be an expert at becoming an expert.” The first two things on this list about defining your own role and carefully selecting where you apply your limited time. I also needed to hear and understand that often, there are tasks that only you can do, and it’s clearly your responsibility to do them. However, you currently lack the necessary knowledge, skills, or abilities to complete them. Don’t just get used to this but embrace this. In my role I frequently must represent our organization to government officials and institutional donors. By applying myself to gain expertise in the criminal justice research related to reentry into our society, I can effectively align them with our mission and our way of accomplishing our mission.
  4. “You can operate at a deficit multiple times, but you can only run out of cash once.” I recommend treating your business like you are on an episode of Shark Tank, where you’ll never get what you want if you don’t know your numbers. Second Chance is a multi-program agency, so it is critical for me to understand the financial performance of each program like they were product lines. In the past, my lack of having a razor-sharp understanding of our financial performance caused an incredible amount of stress.
  5. “Use stories to find and share your joy.” At a very high level, non-profit organizations transform resources into positive impact on the people and communities they serve. If you find and share your personal joy in the impact your organization is having, you will be more effective in every stage — from attracting resources, to applying your leadership styles, to communicating your impact. The most effective way to share your personal joy is through stories.

Just yesterday, I was speaking to a community social league and I was asked a question about the typical journey our program participants go through after incarceration. Rather than describe our processes or share a set of metrics, I had a story about John C. John had been diverted from incarceration into one of our Collaborative Court programs. I described how John C. was transported to us from his residential substance abuse treatment facility, and was enrolled into our sober-living housing, our state-funded supportive services program, and our behavioral health program. I further explained how eventually, John C. would progress to go through our Job Readiness Training program, and then would get assistance finding employment through our network of employer-partners on his way to self-sufficiency.

The story, and my joy in telling it, was at least in part the reason I walked out of that speaking engagement with a $500 check as a donation from the lady who had asked the question.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Successful organizations like Second Chance have a track record of transforming resources into positive impact on the people and communities that we serve. More resources would result in more positive impact, but many resources such as public funding are “expensive” — it takes a lot of effort to remain compliant with the controls and the restrictions on using public funding. Or, resources that would result in more positive impact are scarce because it takes a lot of effort to attract private funding to your specific cause.

In contrast, our celebrities are often people of tremendous influence that have earned a wealth of financial resources, and celebrities often have homes in multiple communities. We discussed three things the community/society/politicians can do to help address the root of the problem we are trying to solve, so here is the movement I would like to inspire:

Andrew Carnegie is famously quoted as saying, “It is more difficult to give money away intelligently than to earn it in the first place,” and he believed that philanthropy should be focused on addressing the most pressing needs of local communities.

The root of the problem we are trying to solve, which is disrupting the cycles of incarceration and poverty, disproportionately affects people of color. I would find great joy in inspiring artists who are people of color, such as John Legend and Alicia Keys, to use their wealth and influence to bring resources to organizations like ours in every community in which they have a home.

John Legend has already started by releasing a documentary called “Home Free: A Conversation with John Legend on the Path to Reentry after Incarceration” (available on Amazon). I encourage everyone to invest 30 minutes to watch it. Also, I learned that in 2019 Alicia Keys bought a home in La Jolla, California, a coastal city within San Diego County.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

There is a well-known quote from business management author Peter Drucker, “you can only manage what you can measure.” My favorite life lesson quote is related to that, but I think it is more direct about a manager’s active role related to measuring results.

My life lesson quote is: “How you are measuring it is how you are managing it..” One of the crucial responsibilities of executive leaders is to develop the professional skills of the managers in their organizations. Measuring results is the focal point of each manager’s responsibilities to monitor and optimize their team’s services, and to continuously improve those services.

It has been my lifelong experience that choosing how any activity is measured influences the way that activity is performed. Measuring results in the wrong way can lead to “perverse incentives” that cause or promote negative or unintended outcomes. For example, if you only measure “calls answered” in a support center, then call agents might be incentivized to answer their phones and quickly get the person off of the phone without helping them, just to get to the next call. Experienced support center managers also measure things like “first time resolution” and “customer satisfaction” to balance their approach.

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂

That’s easy, given the movement to have artists who are people of color support reentry services in the communities where they have homes. Please tag Alicia Keys, the well known Grammy Award winning singer, songwriter, and pianist.

How can our readers further follow your work online?

Please visit, follow me on LinkedIn at ,and follow us on Facebook at .

This was very meaningful, thank you so much. We wish you only continued success on your great work!

Social Impact Heroes: Why & How Bill Payne of San Diego Second Chance Program Is Helping To Change… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.