Skillful Steps Frequently Asked Questions (FAQs)
Where does Skillful Steps operate?
What are the challenges with reentry?
Reentry can be overwhelming without the right support. Many individuals face hurdles like:
- Being released with very little money and limited options for safe housing.
- Struggling to find stable employment that pays a livable wage.
- Lacking access to necessary identification documents.
- Navigating pressure from past environments while trying to stay focused on building a new life.
Skillful Steps was created to break through these barriers and offer a fresh path forward.
How does Skillful Steps help with reentry?
We surround every participant with real, hands-on support from day one:
- Identity Documents: If you’re missing a birth certificate, ID, or Social Security card, we assist you in obtaining them.
- Transportation: We partner with Uber to provide free rides to your classes and appointments if needed.
- Financial Support: We offer financial assistance during training, helping cover testing fees and small stipends to support your success.
- Career Placement: We connect you to high-paying CDL careers and continue helping you grow professionally for up to 5 years after graduation.
At Skillful Steps, we’re here to walk alongside you — not just for today, but for your future.
How does the program work, and when can I start?
Here’s how to get started with Skillful Steps:
- Submit an Application: Our team reviews applications quickly — typically within 1-2 business days.
- Identity Support: If you need help with identity documents, we step in right away.
- Permit Training: We help you prepare and cover costs for your CDL permit exams.
- School Enrollment: Once your permit is secured, we match you with a trucking school near you.
- Financial Stipend: You receive a stipend while attending school to help with personal expenses.
- Job Placement: After graduation, we assist you in finding your first CDL job and continue supporting your career growth for 5 years.
Why trucking?
In 2025, the trucking industry continues to face a critical shortage of drivers, offering stable opportunities for individuals seeking a fresh start. According to national statistics:
- The average entry-level CDL driver earns between $55,000 and $65,000 annually — often with opportunities for bonuses and quick advancement.
- Trucking offers one of the fastest career pathways for justice-impacted individuals to rebuild their lives with dignity and financial independence.
At Skillful Steps, trucking isn’t just a job — it’s a career pathway to prosperity.
This sounds amazing. What’s the catch?
There’s no catch — but there is a commitment. We expect you to:
- Show up on time.
- Work hard and stay focused.
- Be honest, open, and willing to grow.
When you bring your best, we bring ours. Together, we can change lives and strengthen communities.