For John Bailey, life has been a journey of transformation. Born and raised in Mobile, Alabama, John lived in the close-knit community until he was 15. “Back in Mobile, kids did everything together — studying, going to football games, dreaming of college,” he recalls. But his trajectory changed abruptly when his family moved to St. Petersburg, Florida.
As the new kid on the block, John struggled to fit in. “I didn’t know anyone and didn’t want to tell my father what I was going through,” he says. Those struggles led him down the wrong path, and he lied about his age to gain acceptance, eventually landing in jail for the first time and being charged as an adult. That experience set off a cycle of incarceration that would define much of his life.
John’s Rearview Mirror
John’s life took the most dramatic turn when he was sentenced to eight life sentences for a non-violent drug offense. Spending nearly three decades behind bars, he saw the heartbreaking reality of the prison system. Men would leave, only to return a few months later. “It’s hard out there,” he says, recalling the fears shared by his fellow inmates. “You can’t get a job, there’s nowhere to stay. A lot of them were scared of going home.”
John didn’t necessarily have that problem in the outside world; He had a supportive family, money, and tools needed to be successful. Though he didn’t think he would ever leave prison, when his sentence was overturned after 28 and a half years, he was finally released.
“It felt like nothing. I was numb,” John admits. “A part of me was happy, but another part was sad because it felt like I left my friends behind.” He had made them a promise: “No matter how far I travel, those guys are in my rearview mirror. They’re sitting in the backseat of my car.” This promise drives John’s work today, reminding him that helping others also helps himself.
The Birth of Life from Inside Out
John’s nonprofit, Life From Inside Out, is proof of his resilience and commitment to supporting returning citizens as he promised. Inspired by the lessons he learned during his time in prison, John shares his vision with those who face the same challenges.
“I used to believe in a magic carpet,” he says. “During my time in prison, I’d get on that carpet, fly over my life, and then take off again to another point.” He felt his frequent dreaming helped him escape the dark reality of prison and made his time go by quicker.
Recently, Life From Inside Out secured another city grant, creating job opportunities for returning citizens. “Every day, something new happens, and it’s hard to believe,” he says. “But I know it’s because I’m doing the right thing.”
Looking Ahead with Life from Inside Out
John dreams of a brighter future for his nonprofit and the individuals it serves. “I see this going much further than it is right now,” he says. His goal is not only to provide support but also to inspire dreams. “I want them to dream like I did,” he adds.
For John, success isn’t just about measurable achievements. It’s about fulfilling the promise he made to those still incarcerated, letting them know that hope is alive and that their stories matter.“I can get them jobs,” John says, “but I ask, what is your DREAM job?” He wants them to aim high, reminding them that they’re capable of more than just getting by—they can build a future they’re passionate about.
“I did my time, but I didn’t let my time do me,” he says. And through his work, John Bailey ensures others have the chance to say the same.
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