Upon returning home, making money became McCloskey's career plan. After earning a master's degree in international business and returning to Japan as a well-paid consultant, he eventually settled in New York City to try a Wall Street job, followed by a stint as a management consultant at Hay Group in Philadelphia. He quickly realized it was a poor fit. Concerned about the meaning of his career and his reluctance to commit to marriage, McCloskey sought direction through religion.
He returned to Philadelphia, where he told only one person about the pull of faith - the Reverend Richard Streeter, who was minister of Paoli Presbyterian Church. Streeter's preaching "compelled one to serve others, and the only person I had been serving was myself," McCloskey recalls. His epiphany arrived when he decided the corporate life felt exploitative.
"If I was going to be exploited by anybody, I wanted to be exploited by God, not by a corporation," he says. McCloskey began exploring entry into the ministry. Some moments, he says, "I thought I was crazy. Me, in the ministry? If my friends and family ever discovered that, they'd think I was a fool, and a hypocrite." When he gave notice at his consulting firm, his boss said, "Gee, Jim, I didn't even know you went to church."
At age 37, McCloskey entered the Master of Divinity program at Princeton Theological Seminary. Required to undertake his field education in a church, a nursing home, or a prison, he recalled an interesting luncheon talk years earlier by a prison chaplain. For no better reason than that, McCloskey asked for an available student chaplaincy. His assignment: Trenton State Prison. There, in 1980, he met Jorge De Los Santos, a convicted murderer proclaiming his innocence.