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Michael Santos

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Jay-Z is one of the most influential artists of the modern era. He spoke about writing music with emotion, integrity, and authenticity. When something is authentic, he said you can feel when it’s authentic and when it’s not. By living authentically, we build trust. People know when we’re being authentic, and they know when we’re not.

In 2005, staff members locked me in segregation. An officer charged me with violating the prison’s disciplinary code for “running a business” from prison. 

I authored many books while incarcerated. When those books elicited media attention, I frequently had to take a trip to the Special Housing Unit. 

In the SHU, the captain questioned me about my writing in prison. 

I understood the potential risks and rewards of writing and publishing books while incarcerated. The work could bring unwanted attention from staff members. They preferred that people served time without doing anything that was out of the ordinary—like writing books. 

A model inmate would have a job, avoid disciplinary problems, serve a sentence, and get out. 

Yet statistics show the challenges that people face after prison. Rather than being a model inmate, I aspired to emerge from prison successfully. That goal required a different adjustment strategy.

After concluding my sentence, in 2013, I began building business opportunities—some of those opportunities related to the work I completed while serving my sentence. I wrote books and courses and created other projects with the hopes of teaching and inspiring people in jail and prison. Those activities led to speaking engagements. 

In 2016, I spoke at a judicial conference with more than 1,000 people in attendance. Besides state and federal judges, many leaders from state and federal prison systems attended. 

One of those people was then a warden in a federal prison; previously, he led the security team at Lompoc, where I had once served time.

My keynote speech focused on the importance of providing people in prison with positive role models. By offering resources to build hope for imprisoned people, I felt confident that more people would use their time inside to prepare for lives of meaning, relevance, and contribution. 

After the presentation, the warden approached me, asking if I remembered him. I remembered. We had many conversations while I was locked in the SHU at Lompoc. 

He told me that my keynote made a favorable impression on him and invited me to visit the federal prison in Atwater to make a presentation. I agreed but suggested that we could do so much more. 

Rather than merely giving a motivating speech, I asked for an opportunity to create a program to teach and inspire people inside. He agreed to let me pitch the idea to his executive staff. 

Following that meeting with the warden, I wrote a new softcover book, Success After Prison, and created the course “Preparing for Success after Prison.” That course included ten lessons, self-directed, open-ended questions, and accompanying videos. 

With the course, I hoped to create a resource for people in jail and prison. Together, we could improve outcomes for all justice-impacted people and therefore positively impact society as a whole.

People in prison responded to the course because they could see the authenticity. As a result, I’ve built a business around the product, generating millions in revenues and opening income opportunities for formerly incarcerated people.

When we’re authentic, we create opportunities for lasting value because people can see the truth in the messaging.

  • What do your current activities show about your commitment to authenticity?
  • If a potential mentor saw your actions over the past week, what would they think about your commitment to success?
  • In what ways are you documenting your pursuit of success?
  • How will the documentation you’re preparing relate to the career you want to build in your future?
  • What kind of project could you create that would serve your community while simultaneously allowing you to earn a living?

Word of the day: elicit / Define elicit:

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