I did a similar thing a few years back, but rather than simplifying, I focused on getting rid of hacky DIY things that needed maintenance.

I got rid of almost all the customized software in my life, and the few projects I decided to keep, I aggressively modernized, getting rid of thousands of lines of original code and adding many times more tests than I'd ever had before.

It very significantly improved my life and career to not have a second part time job maintaining a note taking app.