Breaking Down the Seven Biggest Barriers

It’s time to Get Started
Your release date is coming. It might feel distant, or it might be just around the corner. Either way, now is the time to start preparing for the real challenges you’ll face when you walk out those gates. The barriers to successful reentry don’t surprise you when you plan ahead—they break you when they blindside you.
This guide walks you through the seven biggest concerns you’ll face and concrete steps you can take right now, from your cell or your housing unit, to build a stronger foundation for your return.
1. Employment and Financial Stability
The Reality: Finding work with a felony conviction is genuinely hard. Many employers run background checks. Some industries won’t touch you. But people with records do find work—the difference is whether you prepared.
Plan Now:
- Take every educational opportunity available. GED classes, vocational training, certification programs—these matter. An employer hiring someone with a record will look for evidence that you’re serious about changing. Certifications in trades (electrical, plumbing, HVAC, welding) often pay well and have more flexible hiring practices.
- Document your prison jobs and skills. If you’ve worked in prison—kitchen, maintenance, yard crew, library—keep records of what you did. These are real work experience.
- Network inside. Talk to corrections officers, chaplains, program instructors, and other inmates who’ve been released. Ask them what worked. Some may know employers who hire people with records.
- Research ban-the-box employers. Some major companies have policies against automatic disqualification based on convictions. Start learning which industries and employers are more receptive.
- Start thinking about self-employment. Small gigs (day labor, landscaping, handyman work) may be easier entry points than traditional employment.
Financial Goal: Before release, understand your basic living costs. How much do you need for rent, food, transportation? Set a realistic timeline for achieving financial independence.
2. Housing
The Reality: Landlords can legally deny you based on your record. Deposits and first month’s rent are expensive. Homelessness nearly guarantees you’ll end up back inside.
Plan Now:
- Research housing resources. Many cities have reentry housing programs, halfway houses, or nonprofits that help formerly incarcerated people find housing. Ask your counselor or case manager for referrals. Start learning the names of these organizations now.
- Contact your family. If you have family support, start these conversations now. Can you stay with them temporarily? Be honest about your situation and realistic about their boundaries.
- Look into transitional housing. Many reentry programs offer 3-6 months of housing as part of their support. Getting into one of these programs before you’re released gives you stability while you find permanent housing.
- Understand your rights. Learn what you can and cannot be denied housing for. Some convictions disqualify you from public housing; others don’t. Know the rules in your state and the city you’re moving to.
- Plan your location. Where will you go when you’re released? Staying in the same environment where you got in trouble is statistically risky. If possible, consider moving somewhere with better opportunities and fewer old connections.
Housing Goal: Have the name of at least one organization that helps with reentry housing. Have a preliminary plan—family, halfway house, or nonprofit program—before your release date.
3. Parole and Probation Compliance
The Reality: One mistake—missing an appointment, failing a test, being in the wrong place—and you’re back in a cell. This isn’t about second chances; it’s about strict rules, and you have to follow them perfectly.
Plan Now:
- Get clarification on your conditions now. Before you’re released, meet with your counselor to get a written copy of your release conditions. If they’re unclear, ask questions now, not after you’re out. Ignorance won’t save you.
- Understand your officer’s expectations. Some probation officers are more flexible than others. You don’t know who you’ll get, but understand that your job is to be reliable, consistent, and transparent.
- Set reminders and routines. You’ll have reporting requirements, drug tests, possibly curfews. The moment you’re released, establish a system—phone alarms, written calendars, routines—that ensures you never miss an appointment.
- Know your violations. What happens if you miss a meeting? A failed test? An arrest for something minor? Understand the consequences and whether they’re negotiable or automatic.
- Plan for substance testing. If drug testing is part of your conditions, commit now to staying clean. This isn’t just about passing tests—it’s about rebuilding your life. Test positive, and everything unravels.
Compliance Goal: Have a written copy of your release conditions and a clear plan for how you’ll meet every single requirement without fail.
4. Family Relationships
The Reality: Prison damages family relationships. Some family members may not be ready to welcome you back. Others may be, but rebuilding trust takes time. Isolation makes reentry much harder.
Plan Now:
- Start communicating now. Write letters, make calls, use video visits if available. Be honest about where you are emotionally and what you’re working on. Don’t promise things you can’t deliver.
- Take responsibility. Don’t blame others for your incarceration. Family members may need to hear that you recognize what you’ve put them through. That doesn’t mean self-flagellation—it means honest accountability.
- Set realistic expectations. Things have changed. Family dynamics are different. Life moved on while you were away. Don’t expect to pick up where you left off.
- If you have children, be especially intentional. Child support, custody, visitation—these are complicated. Find out your legal obligations and your realistic options now. Start having conversations with your children’s mother or guardians.
- Connect with family counseling resources. Some prisons offer family programs. Some nonprofits provide free counseling for people re-establishing family connections. Use these resources.
- Have a backup plan. If family support falls through, who else can you lean on? Mentors, faith communities, program facilitators?
Family Goal: Have at least one solid family or quasi-family relationship you can count on for support, whether that’s emotional, financial, or just having someone who cares whether you succeed.
5. Substance Abuse and Mental Health
The Reality: A significant percentage of people in prison struggled with addiction or mental health issues that weren’t addressed or were made worse by incarceration. Without treatment, you’re at high risk of relapse or crisis.
Plan Now:
- Be honest about your history. Whether it’s addiction, depression, PTSD, or trauma—get clear about what you’re dealing with. Honesty is the foundation of getting help.
- Engage with prison mental health services. Therapy, support groups, medication management—use whatever is available inside. Build the habit of talking to someone about what you’re going through.
- Research treatment options on the outside. Medication-assisted treatment (MAT) for opioid addiction, outpatient counseling, 12-step programs, faith-based recovery communities—know what’s available in your area.
- Get connected before you’re released. Your reentry program, parole officer, or counselor can often connect you with mental health services before your release date. Walking out with an appointment already scheduled is huge.
- Tell your probation officer and treatment providers the truth. Confidentiality protections mean they can help you without judgment. Lying about your struggles just sets you up to fail.
- Build your support network. Identify people who understand addiction or mental health—people who won’t judge you if you’re struggling.
Mental Health Goal: Have a concrete plan for ongoing mental health care or substance abuse treatment, including the name of a counselor or program, an appointment date if possible, and a 24-hour crisis contact.
6. Social Stigma and Discrimination
The Reality: People will judge you based on your record. Some employers will discriminate. Some landlords will refuse you. Some people will never trust you again. This is unfair, but it’s real.
Plan Now:
- Work on yourself. The best antidote to stigma is becoming someone worth believing in. Your actions, reliability, and character will eventually speak louder than your record.
- Develop a narrative. You don’t have to tell everyone your story, but when you need to—job interviews, housing applications, new relationships—have a clear, honest, brief explanation. Own what happened. Explain what you’ve learned. Talk about your plan forward.
- Find your community. Connect with others who’ve been through reentry. Support groups, mentorship programs, faith communities—these places understand and don’t judge. This is lifesaving.
- Know your legal rights. In many places, you can have your record sealed or expunged after a certain period. Learn the rules in your jurisdiction. Understanding your legal options reduces the sense of permanent condemnation.
- Build new relationships carefully. Dating, friendships, professional relationships—you get to decide who knows your history and when. Start fresh in some areas if that helps you move forward.
- Surround yourself with people who believe in change. Not everyone will give you a chance, and that’s okay. Your job is to find the people who do.
Stigma Goal: Before release, identify at least one community (support group, faith organization, mentorship program, or reentry program) where you’ll be welcomed without judgment.
7. Identity, Purpose, and Direction
The Reality: Prison time steals years from you. It can make you feel small, powerless, and defined by your worst moments. Walking out without a sense of who you are now and where you’re going is walking out lost.
Plan Now:
- Do real reflection. Use your time inside to genuinely think about who you want to be. What are your strengths? What do you care about? What kind of life do you actually want? Not what people expect—what do you want?
- Develop skills and interests. Take classes. Learn a trade. Read. Write. Create. Develop hobbies and skills that will matter to you on the outside and that you can build a life around.
- Identify your “why.” Why do you want to succeed? Is it your children? Redemption? A specific dream? A better life than you had before? Connect with something deeper than just “staying out of prison.”
- Set realistic goals. By six months out, I want stable housing and a job. By one year, I want to reconnect with my kids or take a training course. By five years, I want X. Write these down.
- Find mentorship. Is there someone inside—a counselor, an officer, an older inmate who’s been through reentry—who believes in you? Cultivate that relationship. On the outside, actively seek mentors who have the kind of life you want.
- Connect to something bigger than yourself. Whether it’s faith, service, community activism, or family—having a purpose beyond just surviving makes the difference between going through the motions and actually building a life.
Purpose Goal: Before your release, have a written statement about who you want to become and at least three concrete goals for your first year out.
Final Thoughts: It Starts Now
The men who successfully reenter the community aren’t the ones who got lucky. They’re the ones who planned. They’re the ones who used their time inside to prepare, to learn, to build relationships, and to develop a realistic vision for their lives on the outside.
You have time right now. Whether it’s months or years, use it. Talk to program staff, mentors, and other inmates who’ve been released. Read. Take classes. Start writing letters to your family. Get connected with reentry organizations. Work on your GED or trade certification. Go to support groups.
The barriers you’ll face are real. But they’re not insurmountable. Thousands of people with records have reintegrated into their communities, found jobs, rebuilt families, and created lives worth living. You can too—but only if you start preparing now.
Your release date isn’t the start of your reentry. It’s the graduation day. The real reentry work happens between now and then.
Start today.

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