Re-entering society after incarceration is no small feat—every step forward can feel like climbing a mountain while carrying the weight of societal judgment and self-doubt. When I walked out of federal prison and into Springfield, MO, in 2010, the odds seemed to stack up against me. The label of "felon" felt crushing, and the path ahead appeared riddled with insurmountable obstacles.
Yet, it was the small wins—the tiny victories that many overlook—that became the building blocks for a new beginning. Every step mattered, no matter how small. Each one whispered the promise of progress and freedom. Here, I’m sharing my story to encourage you to take your own steps, no matter how daunting life feels right now.
The First Job After Prison: A Beacon of Hope
It all started with a "yes" after hearing countless "no’s." Finding work with a criminal record isn’t easy—rejection after rejection can chip away at your hope. But then a telemarketing company gave me a shot. They didn’t see me as a label; they saw someone who could make sales and contribute.
That job wasn’t glamorous, but it was everything to me. It was my very first win. Every single sale became a moment of career growth, a symbol of resilience, and proof that I could begin again.
What this taught me:
- Your first opportunity might not be your dream job, but it’s a chance to prove your worth—to yourself and others.
- Small wins show you that moving forward is possible, even if the progress feels modest at first.
Riding the Bus, Riding the Wave of Change
For the next chapter of my rehabilitation journey, I endured a grueling three-hour bus ride to and from work every single day. I'll be honest—it wasn’t fun. But each ride represented something bigger than discomfort; it was movement. It was me taking action, refusing to stay stuck in one place.
Eventually, I saved enough money to buy a bicycle. That bike, though far from luxurious, was another win. It shortened my commute and gave me a newfound sense of independence. Every pedal forward represented personal growth and my commitment to rewriting my story.
What this taught me:
- Progress isn’t always glamorous. Sometimes, it’s simply about showing up and doing hard things because they lead you closer to your goals.
- Celebrate every step—you’re moving forward, not backward.
From Laundry to CNA: The Power of Incremental Promotions
Next, I landed a position in the laundry department at a nursing home. Folding clothes and sheets may not sound like much, but it was honest work. It showed me that small victories can lead to larger opportunities.
When I was promoted to janitor, it wasn’t just about cleaning rooms—it was about cleaning up my life.
That promotion was a spark, one that encouraged me to dream a little bigger. Why stop here? Why not see what else I could achieve? With the nursing home’s support, I became a Certified Nursing Assistant (CNA). Each new role was a tangible reminder of my capacity to grow and overcome challenges.
What this taught me:
- Progress happens step by step. Each milestone—no matter how small—lays the groundwork for something greater.
- Sometimes, others will see potential in you before you see it in yourself. Lean into their belief.
The "Why Not?" Moments
All the small wins—jobs, promotions, commutes—added up. They brought me to a mindset that I call the "Why Not?" mindset.
- Why not apply for that better-paying job?
- Why not go back to school?
- Why not believe that I could be more than my record?
When my wife and I decided to go to truck driving school together, it was a culmination of all the small victories that came before. It was one more "Why not?" moment that changed the course of my life.
What this taught me:
- Each win builds confidence and opens the door to possibilities you might have once dismissed.
- Asking "Why not?" helps you overcome fear and take action toward what you truly want.
The Life-Changing Impact of Small Wins
Looking back, those small wins weren’t small at all. They were revolutionary.
Here’s how they helped me transform my life after prison:
- Building Momentum: Every tiny achievement gave me the courage to tackle the next challenge.
- Reinstating Self-Worth: For too long, I had been reduced to a number in the system. Small wins reminded me of my value as a person and as a contributor to society.
- Encouraging Persistence: Success rarely happens overnight. It’s the accumulation of consistent effort that creates meaningful change.
- Challenging Stigma: Every win served as visible proof that I was more than my criminal record—I was someone capable of growth, resilience, and contributions to my community.
Why Small Wins Matter to Your Rehabilitation Journey
My story isn’t special—it’s universal. Small wins aren’t just a part of overcoming challenges after prison; they’re central to any transformation.
For you, those wins might look like:
- Preparing your resume and landing your first interview.
- Showing up to appointments, support groups, or therapy consistently.
- Saving a little money each week for a future goal.
- Reading a new book or learning a skill that inspires you.
Whatever your wins look like, celebrate them. Recognize their importance. Step by step, they will carry you closer to the freedom, success, and growth you deserve. Because the only thing more powerful than asking "Why not?" is actually acting on it.
Ready to Rewrite Your Story?
If you’re on your own re-entry success path—or considering starting it—remember this: You don’t need huge leaps to change your life. You just need small steps forward.
Ask yourself today, "Why not take the first step?" You’ll be surprised at what you’re capable of achieving.
Why not rewrite your story?
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