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A Second Chance: Jack’s Goodwill Story

  • Sarah Wilson |
  • | Mission
Jack's Re-entry Story

Back in the warehouse at Goodwill of Central Iowa headquarters, you’ll find Jack working hard all day long. He bales items that go to recycling and to salvage buyers for donations that have cycled through the retail stores or that are unfit for resale. Jack is a dedicated employee that truly values his job and co-workers. Beginning with Goodwill in 2018 after his re-entry process as a donation and furniture handler at the outlet, he then transferred to the Johnston retail store, and eventually worked his way into operations.

If you met Jack today, you would never know what his background holds as he was grounded by the human connections in his life; his children, sister, niece, and colleague Eric. Jack continues to thank them saying he “couldn’t have made it without them.”

When Jack was released from prison, he was living in a halfway house. He was applying for jobs but getting rejections due to his past and his age. One day, a fellow resident heard of his struggle and mentioned Goodwill. The resident was currently part of a training program at Goodwill of Central Iowa and thought that Jack could get hired as well. The next day, Jack spoke with District Manager DeAnne and got hired. As Jack recalled, She gave me an opportunity that nobody else wanted to give me. And I was blessed by that.” 

However, the opportunity Goodwill provided Jack did not erase the struggles he would face re-entering society.

The Path of Re-Entry

Many people don’t realize that those re-entering society are just as nervous as their community is to welcome them back. Jack thought back and shared that throughout the two decades he was in and out of prison, phones had changed, cars had changed, and the rural town he grew up in became developed. 

Beyond the outside world evolving, the experiences he went through and the routine he had been accustomed to was completely different. For instance, while in prison his routine was void of making decisions and he was used to a strict schedule. When he was released and visited a McDonald’s, he struggled to make the smallest of decisions. In one specific instance, Jack recalled, “I didn’t know what to order. I hadn’t had to make a decision for so long so I asked the guy next to me what he thought sounded good. I said ‘Yeah, I think I’ll try that too’ since I was struggling making the right or wrong decision.” 

Throughout his re-entry process, Jack continued to work on decision making with the help of his Goodwill re-entry support team as well as colleagues that could guide him.

Unfortunately, Jack’s struggles did not stop there and would continue to impact how he would connect with those in and out of the workplace. “You just feel out of place. It feels like everywhere you go you feel out of place. When you walk in, it feels like everybody’s looking at you. Even if you’re just going to the store, you feel like they might think you’re shoplifting. I guess you’re just scared of going back. You don’t want anybody to get the wrong impression or the wrong feeling or think that you’re upset.” 

This caused Jack to feel the urge to explain his every move, whether to employers or his family members if he was late to work. Over the years, Jack would become better acclimated to venturing out in public and being comfortable.

Continuing on with the difficulty to connect with others, Jack shared that “It was hard on me just to open up because for so many years everything has failed inside you. You didn’t have many people that were your true friends [in prison]. You didn’t trust anybody. And you held so much back all the time and didn’t show your feelings because you couldn’t show emotion in there. But I’ve learned it’s okay to get in touch with your feelings and express yourself. When I first got out, I didn’t know how to really feel. In the past I was happy if I had money in my pocket and sad if I didn’t. I had nice cars and friends, but none of them were my true friends anyway, they were just there for whatever I had so I never really knew who I was. So [my time in prison] gave me an opportunity to find out who I really was and what I really wanted out of life. When I got out and things started clicking for me, it was pretty awesome. But I was scared at the same time because I wasn’t used to these kinds of feelings.” 

Despite the struggles that Jack faced in his new life, he continued to progress through making decisions, sharing his feelings, and asking for help. He was always guided by his sister and children, who he describes as his rocks. 

The Impact of a New Opportunity

As Jack worked hard to adjust to his new life. He grew within Goodwill and encountered colleagues that would grow to be part of his support system. He shared, “I was blessed by going back [to the Goodwill warehouse] because there are so many nice people back there that are caring. Greg and Bill and all the guys are just awesome people back there. I could talk to them when I had a problem or when I couldn’t make a decision on something.”

Jack was also positively impacted by the kind customers at each store he worked at. He shared that the daily conversations he had with customers and those who would go out of their way to say hello to him meant the world to him. These conversations helped normalize his life and helped him feel accepted. Kind conversations like these eased his once worried mind that everyone was looking at him for the wrong reasons. 

Jack stands proud of his improvement after re-entering society.

Goodwill gives you an opportunity to change who you are. They gave me a chance to have a job and life that nobody else wanted to give me. And I met a lot of good people here. And I’ve learned a lot here. It goes to show that you can change no matter what. You just have to have the will to do so. It took all these years that I was bad and it’s not going to be all good now. It’s going to take me awhile, but it’s what I’m going to make of it. The choices that I make today are going to be different than the choices that I made back then. It took me 62 years to get where I’m at. But I’m happy today.

When asked what the opportunity with Goodwill meant to him, Jack shared, “I’m happy to have a job. I’m happy to have insurance. I feel good about myself. I’ve been out for a while now. I’m living on my own. I got my own place. I got a motorcycle. I’m just happy for the second chance.  I was thinking one day and thought ‘you know what, I don’t know why I’m so sad or so depressed and think that I should be further than I am today. I’ve come a long way. I can understand people that have done time and would rather be back in prison because it’s the easier alternative. But that’s not going to be me. I’m never going back again. I’m never going back.”


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