The Power of Second Chances
A Skilled AF podcast conversation with Brad Henderson
“When you have a past, you have to rise above it. The expectation is higher for us. And it’s an unfortunate situation, but that’s the way it is.”
Brad Henderson — who has quickly become a sought-after expert in right-sizing the operational ship across different trades companies while building a second-chance pipeline — said that to me in episode 22 of the Skilled AF podcast.
He’s someone who got caught up in the opioid epidemic after a baseball injury, battled addiction for years and found himself in a prison cell. The HVAC trades became a landing ground to rebuild his life after leaving prison only a short five years ago.
This statement was something I had personally never thought about before. How someone who has a record, done the wrong thing in the past, has more to prove to society. The expectations are higher and seemingly stacked against them.
There’s a sense of trust that needs to be built back up. Established. Gained. Earned. Trust with an employer, their colleagues, their families and friends. But most importantly, trust and belief in themselves. That their past doesn’t define their future. That they can truly see something through. That they can change. They can provide. That they are worthy of a beautiful life.
And when that happens, when that person is given an opportunity and they can see, albeit it can be slow, these actions stack up, confidence comes back, trust and belief in oneself comes back, and that’s when everything changes. Their circumstances no longer define them, they define their circumstances.
But you can’t do this in isolation. It would be like throwing someone into the deep end who doesn’t know how to swim, and doesn’t have a life raft.
Roughly 37% of people released from state prison are arrested again within that first year.
Source: Bureau of Justice Statistics, 2021
Brad and I talk about this at length in the interview — how that first year out of prison is make or break. It’s the single highest-risk stretch of the whole journey, steeper than any year that follows because the actions that first year compound. And the water is roughest right when someone has the least structure in their life. No steady paycheck yet, stable housing is questionable, and there’s no proof that they will succeed.
So Brad took it upon himself to build his own life raft, because “the system is not going to change for Brad Henderson.” He surrounded himself with the right people. With people who he only dreamt of being connected with. They became his mentors. His team. A group of people holding him accountable with no judgement attached. People who saw Brad for who he was — a good person, a smart person, a father trying to leave a better legacy for his daughter, a husband trying to show up for his wife, and someone taking total ownership for his past. They never let him lose sight of where he was headed when the hard days crashed down. And oh they crashed down. The work isn’t easy. These are physically demanding, high stress jobs and he was coming in at the lowest rung of the totem pole.
But here he is, out on the other side, on a mission to share his life raft with people who’ve been in his shoes. Individuals hungry for a second chance. Who just need support on their journey to swimming on their own.


