Getting paid for your passion can make you hate it

Jack Raines, who writes the Young Money newsletter about money and careers in your 20s, was heading into his second year of business school when he got the offer he thought he wanted. Robinhood wanted him to help build a media startup, Sherwood News. He loved financial markets, he loved writing, and his audience was growing, so going all in on content felt like the right move.

The background was pure hobby. His first job after college had been in corporate finance, work he found pretty boring, during the pandemic. For fun, he started a travel blog about backpacking in Europe with friends, and an investing blog about the wild markets, and put both on Substack. Readers showed up. He doubled down during business school, working for a finance meme page and newsletter called Liquidity.

Then came the turn. Inside a structured company, where his paycheck depended on churning out columns, writing stopped being fun. He also could not see the long term income and career progression he wanted in a traditional media job.

Galloway and Raines both argue that chasing a passion for pay can backfire. Pursuing your passion is a bad plan, Scott Galloway said, because the thing you love probably will not pay well, and trying to “draw blood from a rock” can make you stop enjoying it. Raines put it more bluntly, saying “pursue your passion is just like rich people tell people to do that once they already have money.”

Raines did not quit writing. He quit trying to get rich from it. Raines said he had "built a good network from writing," along with a platform, and he could apply both in a more lucrative industry.

He now works for a venture capital fund, a job he found equally intellectually stimulating, with higher earnings and more future options. Raines said “venture capital is a deal flow game,” and his years of blogging gave him access to founders starting companies and a public record of how he thinks. The advice he gives now is to keep the passion in your free time, and use the skills and audience it gave you to get work people pay for.