Bill Carlson’s Journey: From Stockbroker to Self-Discovery Behind Bars

When you work your way to the American dream and it crumbles around you, how do you survive? Bill Carlson found out the hard way that success can create dangerous blind spots.

I had the chance to sit down with Bill Carlson, and I’ll tell you, his story hit close to home. Bill started as a stockbroker in 1986, worked his way up, and by 2004 had established his own investment firm named after his grandfather. He had everything - kids in private schools, affluent neighborhood, vacation home. The whole American dream package.

But as Bill shared with me, the allure of recognition and material possessions clouded the true essence of his achievements. In 2017, everything caught up to him when he was sentenced to federal prison for mail fraud.

Growing Up in Chicago: The Foundation

Bill grew up about a mile from what we still call Comiskey Park, living in a three-flat with his grandparents, aunts, and his family on the second floor. “I had parents that were always there. I went to Catholic grade school, Catholic high school, got to go away for college. So it was, you know, I grew up with every blessing you could have as a child,” he told me.

What struck me about Bill’s background was how normal it all was - no childhood trauma, no strikes against him. As he put it: “I wish there was something in my background that I can say, well, that was kind of the catalyst for this. But you and I, as we’ve talked in our conversations, we’ve met so many guys that were born with two strikes against them, right? And they had to overcome so many obstacles. And you and I had every opportunity and we end up wearing the same crappy green uniforms."

"Dad, What Were You Thinking?”

The turning point in Bill’s story came from an unexpected source - his daughter. He was taking money from client accounts, justifying it as temporary moves for business ventures that would pay everything back. But when those ventures failed, he kept doubling down instead of having the courage to tell his family they needed to change their lifestyle.

The moment everything unraveled was devastating. Bill called both his kids while standing in a grocery store parking lot on a snowy February day. “I said, you know, here’s what I’ve been doing, taking money from client accounts. I’ve been indicted, I’m mostly likely going to prison. My son swore at me and hung up. My daughter just started crying and hung up.”

The next day, she sent a text that changed everything: “Dad, what the hell were you thinking?”

That question became the catalyst for Bill’s profound journey of self-discovery behind bars. As he explained: “That was that life-changing moment.”

Finding Purpose in a Federal Prison Camp

Bill served 55 months, and instead of letting prison break him down, he chose to stay busy and find meaning. For 16 months, he taught GED classes to fellow inmates. “It’s like raising my children. It’s really some of the most rewarding work in my life,” he said.

The students were mostly guys from the west side and south side of Chicago - people Bill would never have crossed paths with in his former life. “You get a guy that’s been trying to pass his GED for years and you help him, and his eyes light up. Now he’s gonna send that diploma to his mother or his daughter.”

During his time inside, Bill also developed what he calls a “gratitude practice” - writing down three things every day he was grateful for, even in the lowest moments. This simple practice became the foundation for everything that followed.

What really opened Bill’s eyes was realizing that “I was happier having less in that locker than when I had all the stuff that I could have wanted. And that’s when it really dawned on me as I started to do that introspection and research - that happiness wasn’t coming from things. It was coming from within.”

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