Expire, Don’t Retire: Stephen Dickson

When Stephen Dickson retired in 2016 after fifteen years in public accounting, followed by 17 years as the chief accounting officer for a Fortune 500 company, he didn't picture his days the way they look now. He pictured something quieter. But as his pastor liked to say, "The Bible talks about expiring, not retiring." Stephen took that seriously. Today, at 65, he's been married to Louise for 41 years, a father of three, a grandfather of four, and one of the most engaged volunteers and supporters at JUMPSTART SC.

We sat down with Stephen to talk about how a career in numbers turned into a calling for people, what he's learned from the men and women inside, and why he believes generosity is less about wealth than obedience.

A career built on integrity

Stephen spent his working life keeping the books for a publicly traded company, and during a stretch when the investing world viewed his industry with deep skepticism, he became the face investors and regulators looked to for the truth.

"Integrity mattered to me very, very highly," he says. "I wanted people to look at me and hear me and say, 'If he said it, he's going to follow through. It's true.'"

That commitment didn't come from nowhere. Stephen grew up in Wisconsin in a family that lived by a simple conviction his pastor would later put into words: "I came from God, and I will meet God when I die, so I should live my life for God."

That sentence has driven Stephen's work, his marriage, his fatherhood, and now his retirement.

Expiring, not retiring

When Stephen left corporate life, he started volunteering in prison ministry, long before he ever heard of JUMPSTART. For about four years he taught classes inside, eventually teaching as many as eight men at a time. He didn't have a background in addiction recovery or criminal justice. He just kept showing up. “I remember the shock and hearing what you guys were doing, and it was very, very impressive...”

"You're not just helping them spiritually. You're giving them a real path to success," he says. Through his work on a county prison reentry committee alongside people from SCDC and other community organizations, his eyes opened to just how steep the climb is for returning citizens. Driver's licenses. Housing. Employment. Community. "Society writes these men and women off. And there's a huge opportunity here that almost no one is taking."

A great-great-grandfather's sermons

One of the more remarkable threads in Stephen's story reaches back generations. His great-great-grandfather and great-grandfather were both missionaries to Turkey.

Years ago, Stephen learned that his great-great-grandfather Joseph Kingsbury Greene's sermons were archived at a college in New York City. He tracked them down. One sermon, on 2 Corinthians, "the love of Christ compels us," has stayed with him ever since.

"He explains what the love of God really is. Christ came down from heaven out of incredible love. And when you really understand that, when it lands in your heart, you can't help being compelled by it. The Greek word for 'compels' there is the same word used for soldiers marching under orders. Once God has your heart, nothing else gets a vote."

That, Stephen says, is what drove him out of a comfortable retirement and into the work he does now.

What he wishes more people understood about prison

Stephen is direct about the stereotypes. "People think everyone in prison is a hardened criminal. They're not."

He talks about Michael, a man he met while teaching inside. Michael grew up in a tough part of New York City, the oldest of many children, with an abusive father. His mother, only a teenager when he was born, sent him to live with his grandparents. As a young adult, Michael was carrying a gun when an incident involving his brother-in-law ended in tragedy. He panicked. He was 25.

"If he'd been wealthy and white, with a good attorney, the outcome would have been very different. But he was poor and Black, and that was that."

Inside, Stephen watched Michael grow as a man of faith and become someone other inmates looked up to. When Michael came up for parole, Stephen wrote on his behalf. "Most of these guys weren't born hardened. They were born into terrible situations and were trying to survive. The question I ask myself is: if I'd been born into that family, into that neighborhood, where would I be?"

That question keeps him humble. It also keeps him generous.

A note on giving: "Just be obedient"

Stephen is careful about how he talks about money. He doesn't want to be praised for what he gives, and he doesn't believe generosity is about hitting a percentage.

The word, obedient, comes up over and over. So does the verse from 1 Timothy 6 about those who are rich in this present world: be generous, willing to share, and store up treasures in heaven.

From a practical giving standpoint, Stephen also points to something the U.S. tax code currently makes possible that most other countries do not: donating appreciated stock. "My broker got me into Nvidia. Something I paid $50,000 for is now worth far more. If I'd sold it, I'd owe capital gains. If I give it directly to Jumpstart, neither of us pays, and the full value goes to the mission. People with appreciated assets should really look at this. It's a unique opportunity.”

His broader counsel to people with means is gentler than a pitch: figure out what you actually need, and consider what God might be asking you to do with the rest. "When you're doing what God has given you to do, it's a passion. It starts inside. And then you look up and see. There are people without food, people without homes, people coming out of prison with nothing. The world is full of places to put your hands."

Trust in the Lord

Stephen quotes Jesus's parable of the sower, the seed that fell among thorns and was choked out by "the deceitfulness of wealth." It's the line he wants to put in front of people.

"I see a lot of people worshiping their stuff. My house here, my house there, my kids, my retirement. And I'm not saying don't enjoy what God has given you. But ask yourself honestly: is it consuming you? Because if it is, you're missing what life is actually for."

His own life verses have changed over the years. One has been Philippians 3: forgetting what is behind and pressing on toward the goal. Another is Proverbs 3:5-6: Trust in the Lord with all your heart, and do not lean on your own understanding. In all your ways acknowledge him, and he will make straight your paths, a verse his grandmother loved, and one that has become a theme for him throughout his life.

"Trust Him. That's it. That's the whole thing."

Two kinds of birds

Stephen laughs when he describes his hobbies in retirement. "Birds and jailbirds. That's what I do."

He watches the literal birds with Louise. Songbirds, hawks, and herons. And he invests his time, his treasure, and his attention in the men he calls his other birds: those coming home, learning to fly again, getting honest about their addictions and their God.

"When you focus on kingdom work, you never have to worry about asking for money. The men and women who get serious about it, God takes care of them. He's always taken care of me."

Asked what he'd say to other retirees on the fence about getting involved, Stephen smiles.

"You probably have ten, twenty years on the horizon. That's not nothing, but it's not everything either. We were made for eternity. So, get right with God. Look at what He's doing in the world. And get yourself in the middle of it. You'll be more blessed than the people you serve. I promise."

Watch the Full Interview here:

Stephen Dickson serves as a volunteer at JUMPSTART SC and regularly works with men in the reentry program. To learn more about JUMPSTART’s work in South Carolina, visit us at: https://jumpstartsc.org/transition-programs/