How do you know whether to quit your job or grind it out and hope it pays off?

I’ve worked at my job for almost 2.5 years. I found the job through an old family friend, he isn’t the owner of our company, but he is a board member/ executive. He essentially told me, you have to start at the bottom if you wanna make it to the top of this business.

So when I accepted the position, I was overqualified and underpaid, but believed his promise that it would pay off. And his promise was kept. Within two years I was promoted, and I was making about 33% more than when I started. The job didn’t seem that hard, my bosses were pretty cool, and despite working LONG hours, it wasn’t a bad gig.

However, the last few months have been AWFUL. One of my bosses got promoted and the one that’s left can be a hardass, everything could always be better, you’re never working hard enough, and I always have to do the stuff he doesn’t want to do.

We’ve also had multiple employees quit, which has left us short handed. We have about 25% less employees than when I started. This means more work for everyone, particularly me because I can do everybody else’s position.

Because I’m doing more work, I feel like I should get paid more, despite already getting a couple raises. I’m so stressed at work that I’m miserable while I’m there, and a lot of my coworkers/employees aren’t happy either. Which makes our workplace somewhat depressing.
I have a college degree, from a very reputable university, and I know I could find another job. But I’m not sure if this is a sign to get out, or if this is a test, and if I get through it I’ll be rewarded.

How do you know whether to quit your job or grind it out and hope it pays off?
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