F500 Corp Finance -> Sell Side?

About me: 32 y/o. Decade of work experience in Corp Finance at a couple of large packaged food firms. Now: Finance/Corp Dev Director at family owned food company ($1B revenues) making $180K base + 30% bonus.

Have a passion for the markets and stock picking, but not while I was in college and interviewing for jobs. Didn’t even know what ER was back then. Work is pretty chill now and I post write ups occasionally to SeekingAlpha and Microcapclub (similar to VIC but for microcaps). Also passed CFA L1.

Im interested in making a career transition to ER in order to get “real world experience” with the eventual goal of being a full time investor down the road. However, I’m afraid I am too old and/or make too much for a career change to make sense. I have networked with SS analysts who have covered the companies I’ve worked at in the past. It’s helped me get in the door but I didn’t get an interview because my salary expectations were too high.

Should I continue to do what I’m doing (chill day job + part time investing/analysis) and stack paper in the personal account? Or seriously try to make a change into ER to gain skills?

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