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From prison to a fresh start

28 Jul 2025
Two man sitting done chatting, looking happy. Both men are wearing black - one is wearing a black shirt with visible tattoos and the other has blonde long hair with a black football t-shirt.

For many individuals leaving prison, the road to employment can be daunting. But for Joe, a determined ex-offender in his 60s, the journey was made possible through the employability programme at HMP Holme House, guided by the unwavering support of Matty Flanagan.

Joe had served a two-year sentence and faced an uphill battle when it came to re-entering the workforce. Having never worked for an employer before, he had spent years assisting in his family’s fruit and vegetable produce company. However, after over two decades of unemployment and struggling with modern technology, he lacked the confidence and know-how to secure a job on his own.

In October 2024, Joe met Matty, a dedicated employability mentor who worked closely with him during a 16-week pilot programme (find out more about our Impact Pilots). Through one-to-one and group sessions, Joe gained invaluable life skills, confidence and self-belief. The programme covered everything from transferable skills and CV tailoring to effective job searching and disclosure guidance. 

During the pilot, Matty successfully secured interviews at a supermarket and access to a CSCS card course for candidates, offering real opportunities for a fresh start. Unfortunately, due to early release, Joe missed out on these opportunities. However, Matty refused to let that be the end of Joe’s journey. Before his release, Matty provided his contact details, encouraging Joe to reach out when he was ready to take the next step.

A few weeks later, Joe did just that. Matty invited him to Triage’s office in Middlesbrough, where they created an action plan and set achievable goals. Understanding Joe’s responsibilities, including caring for his ill father, Matty tailored job searches to match Joe’s skills and availability.

Through dedicated support and guidance, they identified a role that suited Joe’s needs—a delivery driver position for a well-known courier company. Matty assisted Joe with the online application and ensured all necessary documentation was submitted. Before long, Joe received an email with the good news: he had secured the job!

“I did not have a clue about how to get a job until I met Matty, who helped me get work and got me through my bad times. I am 66 years old and lost everything; I think I would have committed suicide by now without the help I have had up to now from Matty,” said Joe.

Initially, Joe was excited yet nervous, afraid he might struggle or fail. Matty reassured him that it was normal to feel this way and reminded him that success comes with time, effort, and perseverance. Drawing from his military background and transition to an office role, Matty shared his personal experiences, inspiring Joe to embrace the challenge ahead.

To ease Joe’s transition into employment, Matty went the extra mile. On Joe’s first day, Matty accompanied him, offering support and guidance as he delivered his first parcel. Understanding Joe’s difficulties with technology, Matty even created a simple step-by-step guide to help him navigate the courier app.

That first day, Joe successfully delivered 22 parcels. Today, he continues his morning deliveries, Monday to Saturday, and enjoys life outside HMP Holme House. Joe’s story is a testament to the power of tailored support, determination, and second chances. 

“I would like to say that without these people helping you in prison, so many people would be coming back to prison, so these people are a godsend for the system and worth every penny,” concluded Joe. 

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