“Living the dream?” the dean asked.

Actually, yes. My son, Jack, and his band, Vulfpeck, are living the dream. Last fall they were on “The Late Show with Stephen Colbert,” next month they’re performing at Bonnaroo, and in August they’ll play at Lockn’, another huge festival, on the same bill as the legendary jam band Phish.

I’m a proud dad, but along the way to embracing my son’s music career, I faced the same dilemma other parents face: Do you tell your kid to go for it — live the dream — or play it safe?

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Even though I’m a musician myself, I didn’t steer Jack toward music. I thought real estate, my day job, might be a good fit. Medicine would be fine, too. (Maybe a doctor who specializes in musical injuries?) All three of my children took music lessons — went to Hebrew school, played sports, etc. — but I never nagged them to practice any of it, and they often didn’t. When it came to Jack’s drumming, though, he had sitzfleisch — the ability to sit and focus for hours. That was a talent.

So I wasn’t surprised when Vulfpeck’s music caught on.

In 2011, Jack’s band started posting videos on the Internet. They hadn’t even played a gig, but the clips went viral. Fans knew about Vulfpeck through YouTube and Facebook even before the band hit town to do a show.

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Joe Dart, Vulfpeck’s bass player, said he knew the band had made it when they reached 40,000 “likes” on Facebook a few months ago. “That’s a legit number,” he said. My rabbi’s 23-year-old son, Jared, said Vulfpeck made it when the band became headliners at Brooklyn Bowl. I knew the band was on its way when Jack no longer had to sleep on friends’ floors and could afford his inflated Los Angeles rent on his own.

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Jared and I talk funk at kiddushes. His father sometimes joins in, but he’s a little too old to know what’s going on — he’s a Kinks fan. Of course, I’m even older — 65 — I’m a Paul Butterfield fan. I was in the studio audience for the Colbert taping, and afterward Jack and I walked along Broadway, recapping. Jack explained that 20-somethings don’t watch TV, but they do check out clips on the Internet the next day. And he was right: Vulfpeck became a lot more popular about a day after the broadcast.

So how did Jack get so lucky? Talent is cheap, and everywhere. But he worked hard. He met other talented musicians at music school, and he’s a nice guy. (I’m biased, but it’s true.) Still, to make a solid living at pop music, the odds are pretty long. I know, because I’ve led a Cleveland-based klezmer group for 28 years. I know about luck, and the lack thereof, in the music game. My band’s biggest break was six nights at a retirement community in South Florida in 2002, then back to playing bar mitzvahs in Ohio.

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In the ’70s at the University of Michigan, my English professor, Donald Hall, who later became poet laureate of the United States, encouraged me to go into the arts. “What you are going to do,” he asked, “go back to Cleveland and sell insurance?” Well, yes. I went into my dad’s property management business. My dad was the anti-poet: “The arts is one big ego trip,” he said. Which hurt. And still does. I said to him, “Give me five more years.” He said “fine” and waited me out. Five years later I was full time. I’ve been doing real estate for 40 years. Nothing wrong with that, but it’s the job of real estate and the joy of music.

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I’m glad Jack and his bandmates stuck with music as a career — it’s more than 10,000 hours of practice, for sure. I’m glad I didn’t pester my son to join the family business.

Jack is not a rock star. (Do people say “rock star” anymore?) Other than Beyoncé and Taylor Swift, maybe there are only sort-of rock stars now. Universities crank out thousands of music-school grads, but there are only so many gigs for oboe players, dancers in the “Hamilton” chorus and bands waiting to “blow up,” which, in today’s parlance, means “hit it big.”

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This summer Vulfpeck is flying to gigs. Jack said: “We’re not schlepping gear in a van. We get backline [amplifiers and instruments supplied by the venue]. Ultimately, I want to tour in a Speedo.”

That certainly would be traveling light.