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Jacob Hill, a young entrepreneur who found himself behind bars, discovered an unexpected truth during his time in prison: many of the people he encountered were talented and entrepreneurial but lacked the self-belief to translate their ideas and skills into reality. Jacob shares how his own journey of self-belief evolved and how he’s now committed to fostering that same mindset in others through his work at Offploy, a social enterprise he founded dedicated to helping people with a conviction history find meaningful employment.
Entering prison, Jacob’s initial shock wasn’t just emotional; it was sensory. The huge difference between his former life and prison were overwhelming. "The environment – the noises, the smells, the other people, the life... I was now one of them." This was made worse by the fact that both his parents were police officers – one of whom was a retired drug investigator. Jacob describes the separation from society, not just physically but in every aspect of identity. Prison strips you of your former status, and in Jacob’s case, this separation felt even more pronounced given his family background and prior success.
Before prison, Jacob was named Young Entrepreneur of the Year, earned awards from royalty, and even gained investment from Sir Richard Branson. Yet, despite this, he would find himself constantly comparing himself to others and feeling as though he hadn’t truly achieved anything of worth.
Jacob began to see prison as time he could use to grow, to prepare for life outside, and to work on his ideas of self-worth and for self-improvement. "We might be prisoners of our minds, geography, finances, or actual prisoners but there's so much within our control."
"The biggest thing I realised in prison was just how much privilege I had. I had a university degree, a strong support system, and a mindset that allowed me to believe that even in the worst-case scenario, I would be okay," Jacob says.
Whilst in prison Jacob noticed that many of the people around him didn’t have the basic support systems he had, whether it was family, education, or the belief that they could do better.
“There were guys who didn’t think they deserved a second chance or just assumed they wouldn’t get one. They didn’t have the confidence or assurance that things could be different when they got out.”
This experience became the driving force behind the creation of Offploy. "Self-belief is the cornerstone of what we do at Offploy. We help people set goals, and we celebrate with them when they achieve those goals."
Jacob sees setting and achieving goals – whether it’s securing housing, managing mental health, or maintaining a steady job – as key steps toward rebuilding confidence. "Once people see that they can achieve things on their own, they become empowered to keep pushing forward.”
Jacob believes that having self-belief is one of the most critical aspects of reducing reoffending. “When someone believes in themselves, they’re more likely to take that first step towards change,” he says.
Jacob Hill, a young entrepreneur who found himself behind bars, discovered an unexpected truth during his time in prison: many of the people he encountered were talented and entrepreneurial but lacked the self-belief to translate their ideas and skills into reality. Jacob shares how his own journey of self-belief evolved and how he’s now committed to fostering that same mindset in others through his work at Offploy, a social enterprise he founded dedicated to helping people with a conviction history find meaningful employment.
Entering prison, Jacob’s initial shock wasn’t just emotional; it was sensory. The huge difference between his former life and prison were overwhelming. "The environment – the noises, the smells, the other people, the life... I was now one of them." This was made worse by the fact that both his parents were police officers – one of whom was a retired drug investigator. Jacob describes the separation from society, not just physically but in every aspect of identity. Prison strips you of your former status, and in Jacob’s case, this separation felt even more pronounced given his family background and prior success.
Before prison, Jacob was named Young Entrepreneur of the Year, earned awards from royalty, and even gained investment from Sir Richard Branson. Yet, despite this, he would find himself constantly comparing himself to others and feeling as though he hadn’t truly achieved anything of worth.
Jacob began to see prison as time he could use to grow, to prepare for life outside, and to work on his ideas of self-worth and for self-improvement. "We might be prisoners of our minds, geography, finances, or actual prisoners but there's so much within our control."
"The biggest thing I realised in prison was just how much privilege I had. I had a university degree, a strong support system, and a mindset that allowed me to believe that even in the worst-case scenario, I would be okay," Jacob says.
Whilst in prison Jacob noticed that many of the people around him didn’t have the basic support systems he had, whether it was family, education, or the belief that they could do better.
“There were guys who didn’t think they deserved a second chance or just assumed they wouldn’t get one. They didn’t have the confidence or assurance that things could be different when they got out.”
This experience became the driving force behind the creation of Offploy. "Self-belief is the cornerstone of what we do at Offploy. We help people set goals, and we celebrate with them when they achieve those goals."
Jacob sees setting and achieving goals – whether it’s securing housing, managing mental health, or maintaining a steady job – as key steps toward rebuilding confidence. "Once people see that they can achieve things on their own, they become empowered to keep pushing forward.”
Jacob believes that having self-belief is one of the most critical aspects of reducing reoffending. “When someone believes in themselves, they’re more likely to take that first step towards change,” he says.
Jacob knew that re-entering the business world with a criminal record was going to be hard. However, rather than hide his past, he leaned into it, using self-employment as a way to bypass the barriers many people with conviction histories face in traditional employment. Self-employment allowed him to regain his sense of freedom and work toward building something meaningful. “I’d always been entrepreneurial, and I knew I’d never be happy working for someone else”
He admits that finding traditional employment after prison can be extremely difficult, especially when offenses are public or notorious.
One of the most important pieces of advice Jacob shares with me is simple: don’t over-disclose. He recounts his own experience, where he unnecessarily shared details about his conviction in his CV, which ultimately hurt his chances of getting hired. "Do not over-disclose, like I did. If you're not asked about your conviction, you don’t need to disclose it. You’re not being dishonest, if the employer doesn't ask, you're under no obligation to share." It’s not only unnecessary but can also hinder their chances of being judged on their merits rather than their past.
"Stop shooting yourself in the foot. Get the job based on your character and skills, not just your conviction."
Jacob also suggests for those with conviction histories to carefully consider the type of job you want to get. Some jobs, particularly in regulated sectors like finance, education, or childcare, may require you to disclose your conviction. Other jobs may not. Understanding which sectors require background checks and which ones don’t can help narrow down your search and make the process smoother. Prioritising jobs where conviction disclosure isn't mandatory and looking for employers who don’t ask about convictions at the application stage. "Employers could do better when it comes to being upfront about their disclosure policies, but if a company doesn’t ask about convictions on their application form, that’s a good sign."
Jacob also suggests being realistic about the employment journey post-release. While everyone hopes to land their dream job, he suggests that sometimes starting with “any job” is a good first step to getting to where you want to be. "It might not be your dream job, but you need to start somewhere. Getting a job – any job – can be the first step toward securing a better job or even eventually working toward your dream career," he says.
Jacob breaks it down into stages:
A stands for "Any job,"
B for "Better job,"
C for "Career," and
D for "Dream job."
Take the first opportunity that comes your way and build from there.
One of the most common fears for many people upon release is the fear of the unknown including will I be able to find a job? These questions lingered in my mind, causing anxiety about how I would reintegrate into society. Even mundane tasks like going to the job centre or attending a parole appointment became anxiety-inducing events. The pressure to prove that I was making progress, while also managing the fear of being sent back to prison, was overwhelming at times. But these experiences taught me that anxiety is a natural part of the process, and the key is learning to manage it, rather than let it control you.
For many, the transition from prison to the outside world is daunting. Prison can become a place of routine, where survival becomes second nature, and release feels like stepping into the unknown. But life is infinitely better outside the walls. There is an entire world of possibilities waiting for those who are ready to embrace it. Whether it’s starting a business, finding a job, or rebuilding relationships, the potential is there for everyone.
Jacob knew that re-entering the business world with a criminal record was going to be hard. However, rather than hide his past, he leaned into it, using self-employment as a way to bypass the barriers many people with conviction histories face in traditional employment. Self-employment allowed him to regain his sense of freedom and work toward building something meaningful. “I’d always been entrepreneurial, and I knew I’d never be happy working for someone else”
He admits that finding traditional employment after prison can be extremely difficult, especially when offenses are public or notorious.
One of the most important pieces of advice Jacob shares with me is simple: don’t over-disclose. He recounts his own experience, where he unnecessarily shared details about his conviction in his CV, which ultimately hurt his chances of getting hired. "Do not over-disclose, like I did. If you're not asked about your conviction, you don’t need to disclose it. You’re not being dishonest, if the employer doesn't ask, you're under no obligation to share." It’s not only unnecessary but can also hinder their chances of being judged on their merits rather than their past.
"Stop shooting yourself in the foot. Get the job based on your character and skills, not just your conviction."
Jacob also suggests for those with conviction histories to carefully consider the type of job you want to get. Some jobs, particularly in regulated sectors like finance, education, or childcare, may require you to disclose your conviction. Other jobs may not. Understanding which sectors require background checks and which ones don’t can help narrow down your search and make the process smoother. Prioritising jobs where conviction disclosure isn't mandatory and looking for employers who don’t ask about convictions at the application stage. "Employers could do better when it comes to being upfront about their disclosure policies, but if a company doesn’t ask about convictions on their application form, that’s a good sign."
Jacob also suggests being realistic about the employment journey post-release. While everyone hopes to land their dream job, he suggests that sometimes starting with “any job” is a good first step to getting to where you want to be. "It might not be your dream job, but you need to start somewhere. Getting a job – any job – can be the first step toward securing a better job or even eventually working toward your dream career," he says.
Jacob breaks it down into stages:
A stands for "Any job,"
B for "Better job,"
C for "Career," and
D for "Dream job."
Take the first opportunity that comes your way and build from there.
One of the most common fears for many people upon release is the fear of the unknown including will I be able to find a job? These questions lingered in my mind, causing anxiety about how I would reintegrate into society. Even mundane tasks like going to the job centre or attending a parole appointment became anxiety-inducing events. The pressure to prove that I was making progress, while also managing the fear of being sent back to prison, was overwhelming at times. But these experiences taught me that anxiety is a natural part of the process, and the key is learning to manage it, rather than let it control you.
For many, the transition from prison to the outside world is daunting. Prison can become a place of routine, where survival becomes second nature, and release feels like stepping into the unknown. But life is infinitely better outside the walls. There is an entire world of possibilities waiting for those who are ready to embrace it. Whether it’s starting a business, finding a job, or rebuilding relationships, the potential is there for everyone.
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Help us get About Time off the ground. All donations are tax deductible and will be vital in providing an essential resource for people in prison and their loved ones.
Help us get About Time off the ground. All donations are tax deductible and will be vital in providing an essential resource for people in prison and their loved ones.
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