For me, two points:
(dating myself here) Minimum wage used to be $5.75 when I was in high school. I worked my ass off for an entire summer. I fuckin hated it, but we all gotta hustle. Around my last shift, I came out to the parking lot, and someone had done my car dirty with a hit'n'run. No note, no CCTV, nothing. The damage was in the neighborhood of $2k, which is exactly everything I had saved up that summer.
I worked my ass off 300 hours to break even. It might as well just have been some community service work release program. Fuck capitalism.
The other is when I was older, post-grad. I had a shitty job where I had to pony up for own health insurance plan with high deductibles. I started having random tingling in my joints, so I did the responsible thing and had it checked out. I got sent to several specialists who ran a battery of tests. I'm already in the hole, $3k out of pocket, and all I got was, "We're not sure what's wrong."
The tingling lingered, and I started looking up information for myself on alternative, holistic sites. Someone had listed similar symptoms and said it was just a vitamin deficiency. That couldn't be it, right? Well I ordered some supplements, and within a month, the tingling was gone.
$3k down the hole. Fuck capitalism.
Graduating college and entering the career market for the first time. I had worked multiple service jobs in college and assumed that things would get better when I had a degree. I believed that being paid shit wages in college was "all part of the college experience". You know the stereotypes: Instant ramen, pirating everything, asking friends with meal tickets for free food, wearing old clothes, ect. Turns out the value of a generic 4 year degree disintegrated after the 2008 crash and never recovered.
But honestly I'm kind of grateful. If I had gone straight from college to a cushy salaried corporate job like I was told to expect all my childhood I would have never become a leftist. I think my overall empathy would still be near zero because I was raised by petite bourgeois, so I'm really glad I regained some basic fucking humanity that I was taught to ignore when I was a kid. :improve-society: