The Five Outcomes Waiting for You After Prison

There are five outcomes waiting for anyone leaving federal prison. Michael Santos names all five directly, and explains why the leaderboard on Prison Professors, and the willingness to advocate for yourself, shapes which one you get.

Why does a leaderboard matter for someone building a record in prison?

Justin asked Michael about changes to the Prison Professors platform, specifically encouraging people to write a certain number of words, 300, to earn more points, and about the leaderboard itself.

"We are trying to convince very cynical people to create more pathways for people to earn freedom," Michael said. "We want to incentivize the pursuit of excellence." The platform currently has 8,389 people, down from 9,000 after a staff member named Steve identified and removed duplicate profiles to keep the data valid. Combined, those profiles contain 14,700,000 words.

Michael described how the leaderboard functions as proof, not decoration: "If you go to profiles and go to the leaderboard, you can click on somebody and see his work. You can see how many points he has. You can see his bio. You can see the information he's uploaded." Case managers, unit managers, and regional directors can see the same thing. "That's how you build advocacy. That's how you build a campaign."

Justin pointed to a specific profile on the leaderboard: someone serving a 30-year sentence at Mendota in California, contributing consistently. "Totally self-directed," Michael said. "If he wants to pursue executive clemency, this would be a great asset for him because he will be able to show the parties how hard he's worked. He's not going to have to just talk about it. You can't fake that. All those entries are time stamped."

Does marketing yourself actually change your outcome?

Justin asked about people who delay taking action because they believe they still have time, especially when they hear the phrase "time stamped."

Michael answered with a comparison. "Ask somebody if the best cheeseburger they ever had was at McDonald's. I don't think anybody's going to say that. But nobody's going to doubt that McDonald's cheeseburgers are among the best-selling cheeseburgers in the world. Why? Because they market themselves really well."

He pointed to a specific, real example: Alice Walker received a commutation, then a pardon, and now serves as the pardon czar. "Is she the hardest-working person who ever lived in the Bureau of Prisons? I don't know. Maybe. But I guarantee there are a lot of people who worked very hard in prison who didn't get her outcome." Michael traced the chain of advocacy that led to her outcome: support from Kim Kardashian, which led to Kanye West's support, which led to an audience with the president, and Ivanka's support, and eventually the president's support. "Now she's home instead of serving a life sentence."

Michael was careful about what conclusion to draw from that. "I'm not going to tell you that advocacy is going to get you clemency. I'm not going to tell you it's going to get you a lower sentence. I'm going to say: are you the CEO of your life? Are you doing everything within your power to advance yourself as a candidate? Are you persuading somebody who is very cynical that you're deserving of relief? That's up to you."

How do you prepare for the halfway house transition?

Justin raised the transition many people face: shorter prison terms under the First Step Act and Second Chance Act mean some people serving four years are home in 14 or 15 months, often unprepared for the halfway house and the new complexities waiting there. He referenced Michael's own return home in 2013, when Michael has said he felt unemployable.

"Be the CEO of your life," Michael said. "If you don't know how to do that, download our full playbook." The framework starts with defining success, then building a plan to close the distance between where someone is and what they want. That plan requires goals, priorities, tools, and tactics. "Your profile is a tool," Michael said. Getting people to see that profile is a tactic. Building a coalition of support, seven advocates applying pressure where it matters, is a resource.

Michael illustrated the point with a specific story from his own life after release. Invited to give a keynote to federal judges in the Southern District of California, he told the coordinating lawyer he had a difficult case manager who likely wouldn't approve the trip. The lawyer replied that she couldn't say no to a federal judge. She said no anyway, and the judge overrode her. "She was so livid that a judge could override this case manager in a halfway house," Michael said. "That's the God complex that exists for a lot of people who work for the system. You overcome it."

He closed the point without softening it: "You can't say, 'I worked with Justin, so I hope it's going to work for me.' Justin did a lot of work in prison. I hope it's going to work for you. All I can tell you is you're the CEO. If you fail, you failed. Did you work hard enough?"

What are the five outcomes waiting for you after prison?

Justin asked Michael to walk through the five outcomes described in the Prison Professors playbook, so people watching could assess which path they're currently on.

"If you're brought into the criminal justice system and you're fortunate enough that you're going to go back to society after you're done, there's one of five outcomes waiting for you," Michael said.

The first is unemployment, meaning unemployment of a meaningful nature. "If you want to build a life that is successful and provides for your retirement, your children and your family, you can't really take a job at Starbucks and think that's what's going to deliver that." The second is underemployment, working, but below the level someone is qualified for. The third is homelessness. "I cannot tell you how many people I've interacted with who had master's degrees or professional degrees, and yet they couldn't get back on track." The fourth is returning to prison. The fifth is success.

"To be successful, you've got to be self-directed. You've got to be the CEO of your life," Michael said. "Recognize nobody's coming to save you. You've got to start building. Build and build. Expect trouble. Never stop building. There's more opportunity in the future than in the past. You've got to plan for it. Never stop building."

Justin closed the conversation with a phrase Michael repeats often: "I can't change the past, and I can't predict the future." And when people ask when to begin preparing, Michael's answer doesn't change: "The best day to plant an oak tree was 20 years ago. The next best day is right now."

Justin added a final instruction for anyone watching: leave this webinar with a clear next step. If there's a difficult conversation to have, have it. If there's someone to reach out to, reach out. If it's creating a profile, create it. If it's holding a loved one accountable in prison, don't just ask if they read something. Ask what they read, why they read it, and how it will help them.

Michael closed simply: "It's part of our journey, part of our ministry. I'm 100% committed to the mission, and I hope members of your community are doing everything in their power to get the outcomes they want."

Frequently Asked Questions

What are the five outcomes waiting for someone after prison?

Unemployment, underemployment, homelessness, a return to prison, or success. Michael Santos names all five directly and says the fifth requires being self-directed.

How many people are on the Prison Professors leaderboard, and how many words have they written?

8,389 people, after duplicate profiles were removed, with 14,700,000 words written combined.

Does advocating for yourself actually change your outcome?

Michael Santos points to Alice Walker's commutation as an example of advocacy working, but is direct that he won't promise it will produce clemency or a lower sentence for anyone else.

What does "be the CEO of your life" mean?

Taking full responsibility for defining success, building a plan, and working that plan without waiting for the system to reward you on its own.

What's the biggest mistake people make preparing for the halfway house?

Assuming the transition will go smoothly without the same planning that built their record in prison, and expecting the system to recognize good conduct automatically.