Entrepreneur Max Anderson reflects on his New York pastor and friend’s teaching on the Prodigal Son

Read: The Prodigal God.

Listen: 2005 Sermon on The Prodigal Sons (YouTube)

The Prodigal God came out in 2008. It wasn’t Tim’s first book, but it’s the one that for me best captures one of the most powerful ideas I gleaned from Tim’s preaching when I first moved to New York.


When I left Princeton I planned to move to New York to join McKinsey as a junior consultant. A friend of mine said I needed to check out a church called Redeemer Presbyterian because of a pastor there named Tim Keller.

By that point in the early 2000s Tim was preaching multiple times a day on both the Upper East Side and the Upper West Side of Manhattan. What I heard in those early days forever re-shaped my understanding of faith, who Jesus is and what we call “the gospel”. 

Tim preached a sermon about Jesus’ parable of the prodigal son, you know the one who asks his father for his share of the inheritance, takes it and squanders it on women and wine and ends up living among pigs? Then the son returns home, head low in shame, and his father, seeing him in the distance, strips off his robes and runs to him. Embraces him. He calls his servants to prepare a feast.

I knew that story. I got that it was about God’s generous love toward us who were lost. But Tim points out there are actually two sons in the story. Not only is there the “bad” younger brother who takes the money and runs. There’s also the “good” older brother, one who doesn’t spurn his father and skip town but who stays, sacrifices and does “the right thing”. When the older brother sees the younger brother return home, he doesn’t celebrate with the father. He sulks outside complaining that he never got a feast, despite being the “good” one.


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Tim suggested that Jesus told that story not only to teach about God’s radical, forgiving love, but to say there are two ways to be lost. One is through selfish self-discovery (the younger brother), the other is through pious moralism (the older brother).

In reality, as Tim explains: “Neither son loved the father for himself. They were both using the father for their own self-centred ends rather than loving, enjoying and serving him for his own sake…You can rebel against God and be alienated from him either by breaking his rules or by keeping all of them diligently.”

The picture of wholeness in the story is to be close to the father, but at the end the righteous son (or let’s call him the self-righteous son) is more lost than the “sinner” son.

I had never considered that you could be lost through moralism just as much as you could be lost through being immoral. I had always been the “good kid” who got good grades, went to an Ivy League school, got a job with a brand name company in the city. I attended church.

While I hope I wouldn’t have ever been thought of as judgmental or self-righteous, I wasn’t radically grateful to be in the presence of the father. I was, unbeknownst to myself, trying to be good enough that I didn’t really feel a deep need for a saviour. I didn’t fully appreciate my own lostness.

What I was missing, and what Tim helped unlock for me, was a radical new dynamic for personal growth: “The more you see your own flaws and sins, the more precious, electrifying and amazing God’s grace appears to you. But on the other hand, the more aware you are of God’s grace and acceptance in Christ, the more able you are to drop your denials and self-defences and admit the true dimensions and character of your sin…“This leads to deep humility and deep confidence at the same time. It undermines both swaggering and snivelling. I cannot feel superior to anyone, and yet I have nothing to prove to anyone. I do not think more of myself nor less of myself. Instead, I think of myself less.”


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The truth, as Tim so often articulated it, is that we’re more flawed than we dare admit, but we’re more loved and accepted than we’d ever dream, at the same time. Therefore, we don’t need to live for God to win his favour. We live for him because we already have it. If there is only one book I could recommend or only one sermon, it would be ones I listed above that explain this deep story of two brothers and the father who loved them.

In those early days when I first got to New York, after the evening service on the Upper West Side, I would annoyingly run up to Tim at the end of the service and ask follow-up questions about what I’d heard him preach. I was hungry to know more. He was patient and kind, and didn’t seem to mind talking.

But I was often aware there was a queue forming behind me and I couldn’t stay as long as I wanted. I supposed that’s why I eventually left McKinsey and applied to study with him full-time.


Max Anderson is an entrepreneur and author. He is founder of Stagecoach Ventures and author of The Weekend Reader, a deep thinker’s guide to modern culture. He is author of Modern Meditations: Reflections from the Mid-Point of the Second Decade of the Twenty-first Century. Max is founder and CEO of The Lift Seminar - a personal accelerator for entrepreneurs, and a platform for teaching MBAs at the world’s top business schools the secrets of massive personal productivity.