Skillful Steps

We Don’t Just Talk Second Chances — We Train Them.

At Skillful Steps, we go beyond promises — we deliver transformation. We support justice-impacted individuals with fully funded CDL training, weekly stipends, and wraparound support that continues beyond graduation. Our approach restores purpose, reduces recidivism, and opens the door to real career paths — not just jobs. Every comeback we build is powered by opportunity, accountability, and community. We don't just prepare people to reenter society. We prepare them to succeed in it.

Why We Exist

Trucking offers second chances—and real careers.

The commercial trucking industry is one of the most accessible and high-demand fields for people with justice-involved backgrounds. It doesn’t require a college degree, offers livable wages, and is filled with employers willing to give individuals a fresh start.

Here’s why we chose trucking:

It’s a direct path to economic independence. With high demand and a fast-track training process, our participants can launch careers in 45–60 days. The U.S. has more than 3.5 million trucking job opportunities. New drivers can earn $55,000–$65,000 their first year—and over $100,000 after 2–3 years of experience. This isn’t just training—it’s transformation.

The U.S. has a nationwide shortage of commercial drivers—meaning jobs are waiting for skilled, committed workers

Most students can complete CDL training and be job-ready in just 4–6 weeks

Entry-level CDL drivers can earn $45,000–$60,000 per year, with potential to grow into six figures

Many employers in trucking are open to hiring individuals with criminal records, especially those who’ve completed formal training

A CDL opens the door to more than just driving—it’s a ticket to financial independence and long-term stability

How It Works

Skillful Steps makes it simple to start your new career in trucking—at no cost to you. We’ve designed a step-by-step process that supports you from the moment you apply through job placement and beyond.