Many will immediately think of the basics - housing, food, transportation, a job, help with psychological and medical problems, stigma, dealing with a parole officer, etc. Those basics are true , but as a prison doctor who watched one out of three return to prison I believe that their greatest hurdle to overcome is their mindset. The mindset where they consciously, or unconsciously think of themselves as a victim.
A victim looks at problems as happening to them and complains. A non-victim looks at themselves, accepts that the world isn’t fair and makes the choices that gives them the best chance for success. They are the type who prepare themselves in prison for who they need to become and what they need to learn to succeed when they re-enter society. They also choose a peer and support group that aligns with those values and is willing to help them succeed.
If they have the mindset of a victim, they are ill-prepared and have a higher risk of not persevering when they face the many hurdles that are set in front of them. Re-entering society after years or decades and staying out, and becoming responsible for one’s success is not easy. It’s my opinion that the greatest hurdle they face is their mindset. Victim or Victor.