The case against side hustles

The only thing Millennials love more than avocado toast? Side hustles.

Of course, working a side job is nothing new. Millennials didn’t invent that. However, the term “side hustle” and the need to monetize every hobby in order to live an Instagram-worthy lifestyle? That started with Millennials and it’s spilling over into Gen Z.

The problem is, that approach is frustrating; it’s more likely to kill your creativity than make you rich.

It’s hard to monetize your passion. And what’s more, if you can’t monetize it, it’s easy to become resentful and frustrated. From there, it’s a quick slide into disillusionment. I’ve seen so many artists lose their love of the work because they didn’t get a record deal or a gallery spot.
As a musician and a financial advisor, I take a different approach to creativity. Let’s be clear: I’m not against making money from your passion. Far from it. But I do think we need to stop thinking in terms of side hustles and start thinking in terms of purpose.

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You vs. the headlines

An earlier version of this post appeared on my Retire on Purpose substack. I revised it and am resharing it here in light of the market corrections we’re seeing in March 2025.

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