


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.




Prosperity Paths
Trucking offers second chances—and real careers.


Here’s why we chose trucking:
The U.S. has a nationwide shortage of commercial drivers—meaning jobs are waiting for skilled, committed workers



Who We Serve

- Justice in-volved Individuals

- Reentry Candidates & Returning Citizens

- System-Impacted Jobseeker
The Experience That Powers Skillful Steps

Cage H.
CDL Success
OTR Truck Driver
I feel happy to see that there are people in the world willing to help out people that are in need of a second chanc

Norris L.
CDL Success
OTR Truck Driver
Because of the support I received, I finally have the opportunity to rebuild my life and create a future I’m proud of.

Brennisha W.
CDL Success
OTR Truck Driver
This program didn’t just give me a second chance—it gave me the hope and tools to succeed against all odds
Our founding team brings decades of combined experience in CDL training, workforce development, and reentry support. As we grow, we are building a passionate team committed to empowering second chances.