Jerry Colonna’s advice to aspiring coaches is stark: “If you think you have a choice, don’t do it.” The real calling isn’t a career pivot or a Plan B after a startup fails. It’s a deep inkling that won’t leave you alone — the thing you couldn’t refuse even if you tried.
All three speakers in the conversation would refuse $100 million to never coach again. That’s the bar. Not interest, not passion, not “I think I’d be good at this” — but an undeniable pull that persists through years of resistance, spousal pushback, and practical objections.
Jerry’s own story: he came home from a Reboot VC boot camp and told his wife he wanted to coach. She said do it later when you retire. Two years later he quit his VC career and followed the path anyway. The inkling never left.
The distinction matters because coaching from a career-choice mindset versus a vocational calling produces fundamentally different work. From a choice, you’re trying to help from an empty vessel. From a calling, you’re answering something that uses your whole life as preparation.
“Whatever vocation calls you is not the alternate to the original plan.”
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