Rebuilding Careers

Why Employment Matters

Work anchors reentry. A job restores structure, stabilizes finances, and signals progress to judges, probation officers, and employers. The labor market is shifting under the pressure of automation and AI; roles that were once reliable are changing or disappearing. That reality raises the standard for anyone with a conviction. The response is preparation that starts now—well before release—and continues through the first year back. It’s never too early and never too late to start preparing; the earlier you begin, the more options you create.

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Plan Early, Aim Ahead

Great leaders taught me to focus on outcomes and work backward. Wayne Gretzky’s point—skate to where the puck is going—applies to reentry. Decide what kind of work you intend to do and study where that field is moving. Build skills that match the future market, not yesterday’s. Write a plan that fits your stage of life, sentence length, and resources. Break time into segments with specific targets for 30, 90, and 180 days after release. Execute daily. I make three promises: I won’t lie to you; I won’t ask you to do anything I didn’t do; and I won’t charge you for the educational content at PrisonProfessors.org. Without a plan, the system pushes you toward housing instability and more friction. Write the plan now and work it daily.

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Build a Resume That Reflects Growth

A post-incarceration resume is a record of skills, results, and reliability.

• Use a functional (skills-based) format when there are long gaps. Group competencies—operations, logistics, kitchen/food service, facilities, maintenance, safety, tutoring, customer support—and list measurable outcomes under each.
• Translate prison work into professional language. Example: “Food Service Worker — Managed preparation and sanitation for 200+ individuals daily; coordinated with inventory for on-time distribution; completed ServSafe coursework.”
• Include education and credentials earned inside: GED, college credits, OSHA, ServSafe, forklift, welding, facilities maintenance, computer applications.
• Add leadership and service (mentoring new arrivals, tutoring GED, facilitating groups). These show initiative, responsibility, and follow-through.
• Keep it factual. No exaggerating to cover gaps; no minimizing real progress.

Create a one-page version for online applications and a fuller version for interviews. Maintain a one-sheet project list pairing tasks with outcomes (units completed, on-time delivery rate, zero safety incidents, customer or supervisor feedback).

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Address the Conviction and Move to Value

Expect background questions. Prepare an answer that is honest, brief, responsible, and focused on what you offer.

“Yes. I have a felony conviction from [year]. I took responsibility and completed my sentence. During that time I completed [training/education], worked in [role], and built a strong record for reliability. I’m ready to contribute the same discipline to this job.”

Deliver it calmly. No excuses. Then shift to the employer’s needs—attendance, safety, teamwork, quality, and output—and how you will meet them.

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Prepare for a Changing Market

Automation and AI are reshaping entry-level and mid-skill roles. Durable demand persists in skilled trades, logistics, CDL, maintenance, healthcare support, construction, food production, and manufacturing leadership—fields that reward certifications and a clean safety record. Technology-enabled roles in warehousing, dispatch, data work, and customer support value accuracy and process discipline. Entrepreneurship remains viable for those who build trust, document results, and keep clean books. Choose a direction that fits your strengths and build credentials and a portfolio that prove you can deliver.

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Licensing and Legal Hurdles

Some careers require a license (healthcare, finance, real estate, law, security, transportation). Boards often ask about convictions; many still grant approval when rehabilitation is well documented.

A practical sequence:

1. Research state rules for the license you want, including look-back periods and disclosure requirements.
2. Collect documentation: completion certificates, transcripts, restitution history, employer evaluations, service records.
3. Secure letters from supervisors, mentors, faith leaders, and community partners who know your current work.
4. Prepare a short statement that admits the past, outlines the steps you’ve taken, and explains how you will meet the profession’s standards.
5. Map adjacent roles that use the same skills where licensure is limited (e.g., property management instead of brokerage; healthcare support roles instead of clinical licensure; assistant or technician roles on a path to later licensing).

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Manage the Online Record

The Department of Justice publishes press releases that rank high in search results and remain online for years. Do not let those define your name. Build your own public record that reflects who you are now—education, service, employment, writing, and a clear plan. When someone searches you, give them verified evidence of growth. 

After my release, the record I published—books, articles, projects, and business results—shaped how employers and partners evaluated me. The same approach is available to you.

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Practical Job Search Tips

• Target reentry-friendly employers in construction, manufacturing, logistics, hospitality, facilities, food production, and nonprofits.
• Network through family, faith communities, mentors, unions, and community colleges. Make specific requests: “I’m pursuing [role]; do you know a hiring manager in [company/industry] I can contact?”
• Use public resources: America’s Job Centers, state vocational rehabilitation, community college career services, workforce boards, and reentry organizations.
• Accept a stepping-stone role and rebuild credibility through safety, attendance, learning the system, and steady output. Promotions tend to follow documented reliability.
• Track results—on-time rates, safety records, units completed, customer satisfaction—so you can present numbers in interviews.

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Entrepreneurship: A Parallel Track

Some will build future income through self-employment or by combining W-2 work with a side business. Treat it professionally: define the product or service, document delivery, price it transparently, collect testimonials, and keep clean accounting. 

Raising capital and winning enterprise customers is harder with a conviction unless you present a current, verifiable record that reduces risk. Build that record before you ask for the opportunity.

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Be the CEO of Your Life 

Specialized guidance is a personal decision, but no vendor replaces the daily work of skill-building, documentation, and consistent employment. You don’t need to pay for advice from people whose only experience is serving a year or two in a camp. They generally have no understanding of judicial history or familiarity with BOP operations at different levels of custody, and no substantial body of published work to establish expertise. What they offer is narrow and shallow.

Use PrisonProfessors.org to learn the process at no cost. For live Q&A, join the weekly webinars hosted by Justin Paperny at WhiteCollarAdvice.com/Nonprofit.

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Profiles: Make Your Record Visible

Use your Profile on PrisonProfessors.org to organize a portfolio employers, boards, and partners can verify. Family or a trusted supporter can help keep it updated while you are inside, and the aggregated progress across Profiles strengthens our advocacy with agencies, employers, and the media.

• Biography — Explain who you are beyond the conviction and the direction you are building toward in work and service.
• Journals — Record weekly progress—training hours, credentials earned, applications submitted, interviews completed, and lessons learned.
• Book Reports — For each title, note why you chose it, what you learned, and how those insights support reentry into today’s labor market.
• Release Plan — Present a practical roadmap—housing, lawful work, education, transportation—so reviewers see preparedness rather than wishful thinking.
• Testimonials — Add short statements from supervisors, mentors, and community leaders who can speak to your reliability and character.

Update your Profile regularly and consistently so progress is ongoing, timestamped, and verifiable.

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Key Takeaways

Employment after custody is built, not granted. A functional resume that translates prison work into professional language earns a fair look. Speak plainly about the conviction and move to the value you bring. Licensing requires disclosure and proof; many boards still approve when rehabilitation is clear. 

• Manage your online narrative by publishing current work. 
• Accept stepping-stone roles, 
• Keep score with real numbers, and 
• Earn credentials that match where the market is going. 
• Use your Profile to make your record easy to validate.

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Self-Directed Exercise

Publish a workforce packet to your Profile:

• Biography: a 10–12 sentence update on skills, purpose, and the roles you are pursuing.
• Journals: one entry each week for four weeks capturing job leads, applications, training completed, interviews, and lessons learned.
• Book Report: a title on resumes, interviewing, second-chance hiring, or entrepreneurship; explain why you chose it, what you learned, and how it will change your approach this month.
• Release Plan: a 90-day employment plan—target roles, certifications in progress, transportation, and schedule.

Testimonials: one note from a supervisor or mentor and one from a community member who can speak to your current work and character.