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building second chances

Welcome to Life From Inside Out

Life From Inside Out is a community-based organization in St. Petersburg, Florida dedicated to supporting returning citizens, individuals impacted by incarceration, and families in transition. We provide resources, guidance, and compassionate support to help people successfully rebuild their lives after incarceration and reenter society with dignity, stability, and purpose.

Participant Spotlight

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Dale Estevez

Life From Inside Out mourns the loss of a dear friend, advocate, and member of our family. Dale wasn’t just someone who supported our mission—he lived it. As a participant himself, he understood firsthand the trials, barriers, and challenges that come with returning home after incarceration and trying to rebuild a life in a world that doesn’t always make that journey easy.

Dale became John Bailey’s right-hand man, a trusted friend who stood beside him and believed deeply in what Life From Inside Out represents. Their friendship went far beyond the work. Whether they were shooting a game of pool, laughing together, or going story for story about their experiences both inside and outside of incarceration, there was a bond between them that only people who have walked some of the same roads can truly understand.

His experiences gave him a heart for others coming home behind him. He knew the struggle, but he also knew the importance of having someone in your corner—and he became that person for others.

We are grateful for every conversation, every laugh, every game of pool, every story, and every moment he gave to this organization and to the people around him. His chair may be empty, but his presence, his friendship, and the impact he made will remain a part of Life From Inside Out forever.

Rest peacefully, our friend. 🕊️

From breaking bread to breaking barriers—your story will always be part of ours.

2335 22nd Ave So. 

#1 Unit 10

St. Petersburg, Fl.

33712

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