
The Other Side Academy is a two and a half year residential program for men and women coming out of incarceration, homelessness, or addiction. It is completely free of charge. My family found out about it through the Faith Matters Foundation and we have been donating ever since. Jackie and Jeff are both graduates who now work there full time, and this conversation blew me away.
✨Listen to the full episode or read for the breakdown.
What the Other Side Actually Is
The program focuses on whole person behavioral change. Not sobriety labels, not traditional addiction recovery. Accountability. Honesty. Integrity. Communication. Showing up on time. Learning to live in community.
The Other Side Village was created to serve people with dual diagnoses and mental health needs, offering the same program model with a path to permanent cottage-style housing at the end. Both programs are largely self-sustaining through social enterprises including the Other Side Movers, number one in the state, and the Other Side Donuts, number one last year.
Free of charge. No insurance needed. No family member footing the bill. No getting kicked out when your time is up if you are not ready.
What Real Community Looks Like
Jackie said something early in our conversation that I really loved. Once people experience real community, they often choose to stay.
Real community is not just people being kind to each other.
It is people who hold you up and also hold you accountable.
It is having someone in your corner who expects something of you instead of writing you off. Hard conversations. High standards. The belief that you are capable of more. Jackie described coming in with almost no eye contact, no self-trust, and no sense of her own worth. What changed that was not a program or a curriculum.
It was people who saw her and refused to settle for less than her best.
Their Stories
Jeff spent years in and out of homelessness. After years of this cycle, one day he was stabbed and eventually called the police on himself to get arrested because he could not see another way out. He saw a pamphlet for the Other Side Academy in jail and wrote them a letter.
Jackie was introduced to drugs young, lost her footing trying to cope with her daughter's major surgery, and spent years cycling in and out of toxic relationships and survival mode. She became exactly the person she had always told herself she would never be. When she heard about the Academy she committed to seeing it through no matter what.
She says if she had gone back out one more time she would not be alive.
Both of them now coach others coming through the program. Both say there is no greater feeling in the world than watching someone find their own worth.
The Biggest Misconceptions
Jackie was direct about what she calls the bigotry of low expectations. The idea that people experiencing homelessness do not want to change, that they are dangerous, that they are beyond help.
None of it is true.
Not everyone on the streets has a criminal history. Not everyone is a drug user. Many are people who lost a job, went through a catastrophic loss, or simply could not navigate the circular nightmare of needing an ID to get a social security card to get a job to get a mailing address. Homelessness is not a character flaw.
And the people who seem scary? Jackie said it simply. They are just people. Lost and broken like all of us in our own ways.
What They Have Learned About People and Love
When I asked what they had learned about people through this work, Jeff did not hesitate.
People are inherently good. Nobody is beyond help.
Jackie added that she has watched people from completely different backgrounds, people who would have been enemies on the street, become the closest of friends inside the community. The common thread was not shared interests or shared history.
It was the shared desire to change.
That is what love looks like at the Other Side. Not agreement. Not similarity. Just the belief that every single person deserves a chance.
Who in your life could use another chance today?
You got this.
🤟🏼Brynne
How to Support the Other Side: Visit othersideacademy.com or othersidevillage.com to donate, volunteer, or learn more. You can also support them by using the Other Side Movers, shopping at the Other Side Thrift, or stopping by the Other Side Donuts. Every dollar and every visit goes directly back into keeping the program free for the next person who needs it.

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Hi, I’m Brynne. I share my journey of becoming through stories and reflection - guided by a higher power as I explore identity, faith, and everyday life, inviting you to grow alongside me.

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