If you’re reading this, chances are you’re trying to find work, move forward, and do right by yourself and your future. But maybe you’ve got a record, and that label is making things feel impossible. We want you to know something right from the start: You are not alone, and you are not the only one walking this path.
We work with people every week who feel like giving up. Some have done time, some have broken marriages, and so forth. They’ve made mistakes. And now they’re doing everything they can to turn their lives around but the world doesn’t always make it easy. Still, they keep showing up. You’re showing up. And that’s where the journey begins.
Let’s walk through this together, step by step.
Step 1: Let’s Acknowledge the Truth
Finding a job with a criminal record is harder. That’s the reality. Employers can be hesitant. Background checks can feel like barriers. And you might start to wonder, “Why even try?”
We get it and you’re allowed to feel that way. But don’t let that feeling stop you.
What you can’t do is stay stuck there. Because your story isn’t over. Your past doesn’t have to dictate your future. And right here in Orlando, there are people who believe in second chances. We know because we’re one of them.
Step 2: You Don’t Have to Do This Alone
The job search is hard for everyone but when you’ve got a felony or any kind of record, it can feel isolating. Like no one wants to give you a chance. That’s where Cornerstone Connections becomes a lifeline.
We’re based right here in Orlando, and we exist to walk alongside individuals who are rebuilding after incarceration. No judgment. No shame. Just real tools, real guidance, and real relationships.
If you need help writing or fixing your resume…
If you want to practice for interviews and build confidence…
If you need help with getting access to a computer…
If you’re looking for connections to local employers who believe in second chances…
Or even if you just need someone to remind you that you’re not a lost cause…
That’s what we’re here for.
Our Employment Connections program is designed specifically for people in your shoes. We’ll support you through every step of the process, from job readiness training to placement opportunities and mentorship that keeps you grounded.
Step 3: Understand the Playing Field
The good news is that Orlando has jobs. As of spring 2025, our city’s unemployment rate was around 3.3% (source). That means there’s work out there. But the challenge for many returning citizens isn’t availability, it’s access.
That’s where strategy comes in. Here’s how we coach people to approach it:
Focus on industries that tend to be more open to second chances. Jobs in warehousing, logistics, food service, construction, janitorial services, and general labor are often more willing to look past a record if you’re ready to show up and work hard. These roles may not be forever but they’re a real and honest place to start.
Step 4: Telling Your Story Without Getting Stuck In It
One of the biggest challenges is how to talk about your past in interviews. It can feel scary. But here’s the truth: your story matters but how you tell it matters even more.
The key is to be honest, keep it short, and focus on growth.
Here’s a simple starting point:
“I’ve made some mistakes in the past. I’ve served my time and used it as a turning point. Since then, I’ve taken steps to grow through training, volunteering, and staying committed to building a better future. I’m looking for an opportunity to prove what I’m capable of now.”
You need to practice that saying, and say it with confidence. Because your past is part of your story but it is not your whole story.
Step 5: Build a Resume That Tells Employers Who You Really Are
We’ve heard so many people say, “But I don’t have anything to put on a resume.” And to that we say yes, you do.
You may have worked in the kitchen, on a maintenance crew, or handled laundry duties while inside and that’s real work experience. If you earned your GED, took vocational training, or helped others learn, that’s education and leadership. And if you’ve volunteered, been involved in your community, or held any kind of job since your release, that shows commitment, effort, and growth.
All of it matters. And we’ll help you put it together into a resume that tells your story with honesty and strength—so employers can see who you are now, not just where you’ve been.
Step 6: When You Feel Like Quitting—Don’t
There will be days when the job search wears you down. You’ll hear “no.” You’ll get ghosted. You’ll feel like nothing is working.
But please, don’t give up.
Every application you submit is a seed planted. Some won’t grow. But others will. And when that door finally opens, all those hard days will have been worth it.
You are not your charges. You are not your worst moment. You are someone who’s still here, still trying, still pushing for better and that is worth everything. That’s who we see every day at Cornerstone Connections. And that’s exactly who we’re here to serve.
Let’s Take the Next Step Together
If you’re ready to start over or try again, we’re ready to walk with you. We work with individuals from across Orlando and the surrounding areas: Apopka, Pine Hills, Winter Park, and beyond. It doesn’t matter where you’ve been. What matters is where you want to go.
Please visit our Employment Connections program page and contact us via the contact form or directly by phone to see how we can help you in your time of need: https://cornerstoneconnections.org/employment-connections
We want to start by saying this: we see you. We hear your frustration. We understand what it feels like to be stuck, to want a fresh start, but feel like doors keep slamming shut because of your past. If you’re sitting here thinking, “No one will hire me because of my record,” please know that you’re not alone and you are definitely not without options.
We’re here to walk with you through this. We want to offer honest, real advice, the kind you’d get from people who believe in second chances and believe in you.
Step 1: Understand What You’re Up Against
It’s tough out there. Employers often conduct background checks. And in Florida, there are a number of laws and licensing restrictions that make it harder for people with records to get into certain careers.
But here’s a truth we want you to hold on to: many employers DO want to give people second chances but they just want to know that you’re ready, responsible, and serious about moving forward. The stigma around a criminal record is real, but it’s not the whole story and it certainly doesn’t define who you are today.
Step 2: Get Help From People Who Know the Way
Trying to figure this out alone is like walking through a maze without a map. That’s exactly why we exist. At Cornerstone Connections, we help people with records gain the skills, confidence, and support they need to land a job and keep it.
Through our Employment Connections program, we walk with you through the process of:
- Building your resume so it highlights your strengths — not just your past.
- Preparing for interviews, including how to talk about your record honestly and professionally.
- Connecting with employers in Central Florida who are open to hiring people with criminal backgrounds.
If you’re ready to break the cycle and take the next step forward, we’re here and ready to help.
Step 3: Be Honest
When it comes to your background, honesty matters. But so does how you tell your story. Don’t let your past become the center of your narrative. Focus instead on:
- What you’ve learned since then.
- The steps you’re taking to build a better future.
- How ready and reliable you are as an employee.
This is something we help people practice all the time. With support and preparation, you can share your story in a way that communicates accountability and hope, not defeat.
Step 4: Invest in Yourself
We know it can feel like your past limits your future. But that’s not the full picture. You can build new skills. You can earn certifications. You can go back and finish your GED. All of these steps show employers that you're serious about growth.
Right here in Orlando, there are industries like hospitality, construction, logistics, and healthcare that are actively hiring. Ask yourself: what kind of training could help you qualify for a role in those fields?
If you’re not sure where to start, we can help. We work closely with local training programs and can connect you to opportunities that align with your goals and in some cases, help you access funding or scholarship programs.
Step 5: Build Your Network
Here’s something most people don’t realize: many jobs don’t come from online applications. They come from relationships. Having people in your corner — mentors, community leaders, program coordinators can open doors you never expected.
That’s why we don’t just train you — we walk with you. We introduce you to a community in Orlando and the surrounding areas who will root for you, speak up for you, and support your growth.
Step 6: Know Your Rights
You deserve to know what’s fair and what’s not. In Florida, certain laws like “Ban the Box” mean that public employers can’t ask about your criminal history until later in the hiring process. And depending on your situation, you might even qualify to have your record sealed or expunged.
We can connect you with legal resources to help you figure out what steps you can take. Knowing your rights gives you the confidence to advocate for yourself — and that matters in every interview and opportunity.
Step 7: Start Somewhere
Your first job after a conviction might not be your dream job and that’s okay. What matters is getting your foot in the door. Entry-level or temporary jobs are an important stepping stone. They help you show up, build trust, earn a reference, and keep moving forward.
Over time, history builds momentum and momentum changes everything.
Step 8: Stay Patient and Keep Going
We’re not going to sugarcoat it: this road takes time. You might face rejection. You might feel like you’re spinning your wheels. But we’ve walked this road with many people before you and we know that persistence pays off.
Every “no” you hear is one step closer to a “yes.” Keep learning. Keep growing. Keep showing up. And lean on us whenever you need to.
Final Thoughts
We know this journey is heavy sometimes. But please remember this: your record does not define you. You are more than your past. You have value. You have potential. And with the right support — like the kind you’ll find here at Cornerstone Connections — you can move forward.
We’re here to help you take that first step. Please visit https://cornerstoneconnections.org/employment-connections and submit the contact form with how we can be of aid to you and provide any questions that you may have.
If you'd like to read another article that would help you, check out https://www.cornerstoneconnections.org/career-support/from-prison-to-paycheck-how-to-get-a-job-as-a-felon/.
Reentering the workforce after incarceration can be challenging, but absolutely achievable. With targeted strategies, community support, and the right tools, formerly incarcerated Floridians can successfully transition from prison to paycheck. This guide is tailored to Florida and optimized to help your audience find meaningful work post-release.
1. Understand the Challenges — and How to Overcome Them
We want you to know that you're not alone in facing the road ahead. Reentering the workforce after incarceration comes with unique challenges, and it's important to name them so we can plan how to overcome them together.
- Stigma & background checks: One of the first hurdles many face is the stigma attached to a criminal record. When you apply for jobs, background checks can feel like a door slamming shut. But here's the truth: many employers today are open to giving second chances. They appreciate loyalty, strong work ethic, and dependability—all traits that you ought to aspire toward. We'll work together on how to tell your story in a way that shows growth, accountability, and value.
- Limited job readiness skills: Maybe you've never written a resume, or it's been years since you've been in an interview. You may feel unsure about how to communicate your strengths or how to use job search platforms. That’s normal. Through our workshops, mock interviews, and hands-on coaching, you’ll build the confidence and practical skills needed to thrive in today’s workforce. Whether it's how to answer tough questions or how to dress for success, we’re here for every step.
- Logistical hurdles: Life after incarceration often brings additional challenges like finding stable housing, reliable transportation, or consistent internet access. You may feel overwhelmed, but you don't have to navigate this alone. At Cornerstone Connections, we help address these barriers by connecting you with resources and support. Whether it’s getting to an interview, printing your resume, or accessing a computer, we’ll help you problem-solve your way the best we can.
Identifying these obstacles isn’t about dwelling on the past, but about making a clear plan for your future. We're not just preparing you for a job; we're preparing you for long-term stability and success.
2. Tap into Florida-Specific Reentry & Job‑Readiness Programs
Cornerstone Connections: Employment Connections Program
We specialize in helping Floridians get job-ready through our Employment Connections program. Learn more at cornerstoneconnections.org/employment-connections.
Our program offers:
- Job Readiness Workshops: Focused on resume writing, interview preparation, and workplace behavior.
- Vocational Assessments: Helping participants discover their strengths and align with career opportunities.
- Mock Interviews: To build communication skills and boost confidence.
- Job Placement Assistance: We connect you with employers who believe in second chances.
- Supportive Services: Assistance with transportation, clothing, and other job-related needs.
- Ongoing Case Management: Personalized employment plans, accountability, and regular check-ins to support long-term success.
3. Federal Incentives That Benefit You—and Employers
We want to equip you with every possible advantage during your job search, including knowledge about federal incentive programs. These programs are not part of Cornerstone Connections, but we believe it's important you know they exist. When you understand these tools, you can walk into job interviews with greater confidence and even help educate potential employers who may not be aware of them.
Federal Bonding Program
This program provides free fidelity bonds to employers who hire individuals with criminal records. It’s essentially an insurance policy that protects the employer against potential loss, giving them peace of mind in hiring someone who is rebuilding their life. You can mention this in interviews to help reduce any hesitation an employer may have.
Work Opportunity Tax Credit (WOTC)
The WOTC gives a federal tax credit to employers who hire from certain target groups—including people with felony convictions. That means you could be a financial benefit to the company simply by being hired.
While we don't manage these programs ourselves, we make sure you're aware of them and know how to use them to your advantage. When you're informed and prepared, you become a solution.
4. Level Up Your Job‑Search Skills
Many returning citizens feel left behind when it comes to technology, but you don’t have to stay stuck. We offer resume workshops that walk you step-by-step through creating a professional resume—even if you don’t have much prior job history. Our computer labs are available to help you get comfortable with basic digital tasks like setting up an email, searching and applying for jobs online, and using Microsoft Word or Google Docs. Through our digital literacy classes, you’ll also learn how to navigate today’s tech-driven job market with confidence.
An interview is your moment to tell your story and show who you are today—not who you were. We help you prepare with various workshops and trainings we offer, including mock interviews that simulate real-life scenarios. You’ll get practical feedback on your responses, body language, and communication. Our coaching sessions also cover critical soft skills like time management, conflict resolution, workplace behavior, and how to work on a team. These are the skills employers look for that make you not just employable, but promotable.
5. Know Your Rights on Resumes, Interviews & Privacy
- Record sealing & expungement: Florida offers limited opportunities for record sealing and expungement, which could potentially remove or hide parts of your criminal record from background checks. This can significantly improve your chances of landing a job, especially with employers who might otherwise hesitate. It's worth researching if your offense qualifies under Florida law. Speak with a licensed attorney or contact a legal aid organization to explore whether you’re eligible. The more informed you are about your options, the more control you have over how your past affects your future.
- Disclosure tips: When applying for jobs, it's essential to know your rights and obligations around disclosing a criminal record. Some applications ask directly about convictions, while others do not. In interviews, be honest when disclosure is required, but focus on how you've grown. Explain the positive steps you've taken since your release—like job training, community service, or personal development. Keep your message clear and future-focused. Employers appreciate honesty and accountability when it’s paired with progress.
- Digital clean‑up: Employers today often search for candidates online before interviews. That means your digital footprint matters. Review your social media accounts and remove anything unprofessional or misleading. If your name appears in mugshots or outdated arrest records online, you might be able to contact the website or take steps to have them removed. Consider creating a LinkedIn profile to highlight your new skills, training, and career goals. Taking charge of your online presence helps control the narrative about who you are today.
6. Building Your Plan — A Step-by-Step Blueprint
Creating a clear, realistic plan is one of the most important things you can do to move forward after incarceration. Whether you're still inside or recently released, having structure gives you control and confidence. Here’s what a sound plan might look like—and remember, each step should be tailored to your needs and pace:
- Pre-release preparation: If you're still incarcerated, start thinking about your goals and gather documents you’ll need (ID, Social Security card, etc.). Identify what type of work you want to pursue and what steps it will take to get there. Some facilities offer programs or release planning services—take advantage of those if available.
- Build a support system: Your transition will be easier if you're surrounded by people who believe in your success. Whether it's family, a mentor, a reentry support group, or a local church, lean into positive relationships. This can also include reaching out to organizations like Cornerstone Connections to explore programs that match your goals.
- Skill-building and learning: Spend time developing skills that will make you more employable. This can include resume writing, digital literacy, soft skills, or vocational training. Many of these resources are available for free in your community.
- Plan your job search: Know where to look and how to apply. Create a resume, set up an email account, and make a list of places you’d like to apply. Stay organized by tracking your applications and following up.
- Prepare for interviews: Practice how you'll speak about your past honestly and confidently. Learn how to talk about the positive changes you've made, what you've learned, and how you're ready to work. Prepare your outfit, practice good posture, and work on making a strong first impression.
- Stay focused on growth: Once you land a job, don’t stop there. Keep growing. Show up on time, work hard, and ask for feedback. Learn new skills on the job and think about where you want to be in a year.
Remember, a good plan isn’t perfect—it’s practical. Life will throw curveballs, but if you have direction and purpose, you'll be more likely to stay on track. And if you ever feel overwhelmed or unsure, reach out to us. We're here to walk with you, one step at a time.
Final Thoughts
Transitioning from prison to paycheck is more than obtaining a job—it’s restoring dignity, supporting families, and reducing recidivism. Florida’s range of dedicated programs and federal incentives is there to support your journey.
Partnering with Cornerstone Connections gives you a guided roadmap, personal support, and employment opportunities to turn your story into one of transformation.
Ready to start?
Visit cornerstoneconnections.org/employment-connections to connect with your case manager, find workshops, and begin building your new future.
As we move deeper into 2024, the landscape of the job market continues to evolve, emphasizing the need for continuous skill development to stay competitive. Whether you're looking to secure a better salary, advance in your career, or ensure job security, acquiring specific high-income skills can significantly enhance your marketability. At Cornerstone Connections, our Care Connections program provides you with free wifi and computers to help you toward these skills. Here are the top skills you should consider mastering this year:
Data Analysis
The ability to understand and interpret data is more crucial than ever. Data analysis skills enable you to provide valuable insights that can drive business strategies and improve outcomes. Whether you are in management, tech, or even marketing, being able to analyze and leverage data effectively is a key asset. With most jobs being virtual, you have the added benefit of being able to do all of this from home.
UX/UI Design
As the digital landscape expands, so does the need for skilled UX/UI designers. This role is critical in creating engaging and functional digital experiences for billions of internet users worldwide. A career in UX/UI design not only offers great income potential but also high job satisfaction from improving user interactions. Due to UX/UI applying across mobile devices, tablets, desktops, as well as new devices such as the Apple Vision Pro (and much more), this is a space worth exploring. Websites like www.dribbble.com can aid you with inspiration to help your skillset grow.
Digital Marketing
From content creation to social media strategy and beyond, digital marketing encompasses a broad set of skills that are highly sought after in any sector that benefits from online presence. Specializing in niche areas like SEO or video marketing can further increase your desirability to employers. In a Social Media world with lots of content needing to be made, you could get ahead of the curve by supplying content creation services to businesses in need of spreading brand awareness. Certifications online available such as Google Ads and Meta Business Suite also make it accessibly for freelancers to learn how to create and run effective ads.
Prompt Engineering in Artificial Intelligence (AI)
AI continues to be a transformative force in multiple sectors. Understanding how to apply AI techniques can improve efficiency and innovation within any role. While becoming an AI specialist might require intensive study, familiarizing yourself with its applications can enhance your job performance significantly. Learning how to properly create a prompt for AI tools such as ChatGPT to precisely cater to your question is the key to maximizing your performance in your career or entrepreneurship venture. Many solopreneurs are taking advantage of these tools to create web applications that they otherwise would have been unable to build without the advent of AI.
Web Development
As the backbone of the internet, web developers create the platforms we use every day. This skill set is not only in high demand but also offers the flexibility of freelance work, making it both lucrative and versatile. With most websites being made on open-source platforms like WordPress, as well as other existing platforms like Wix and Squarespace, you're just a few YouTube videos away from learning about these platforms to help you be on track for assisting people with their website needs.
Websites such as www.awwwards.com feature great websites created by people across the globe to help you in honing your website development skills.
Sales
Sales skills are invaluable, with potential earnings going beyond just a base salary to include commissions and bonuses. Enhancing your sales techniques, like improving negotiation skills or learning new sales software, can catapult your earning potential, especially when applying it towards any of the above skillsets as a freelancer, entrepreneur, or worker in the sales department of your job.
Continuing Your Development with Cornerstone Connections
At Cornerstone Connections, we understand the importance of keeping your skills sharp and relevant. That's why we offer programs such as our Care Connections program offers free access to WiFi, computers, and a range of resources to help you develop these high-income skills. We also offer Connecting H.O.P.E. to help you land work that will help you to be able to pay for a child support order that you've been given.
Investing time in acquiring these skills will not only enhance your resume but also equip you with the capabilities to thrive in a rapidly changing job market. Remember, developing high-income skills is an investment in your future, and at Cornerstone Connections, we're here to help you achieve that.