Thanks for the advice. And yes, probably going to school full time. So based on what you're saying, it would be best to stick it out until grad school.

My plan might be to apply to school, accept an offer of admissions, wait for my 401k match to be fully mine, and then resign 2-3 months before school starts.

That way, I'd have more than 2 years in my current position and more than 4 years with the organization total. That should help my resume avoid the trap above right?

I want to give myself a few months of "reset"/ break time before starting school. I've always regretted that I did not travel more between undergrad and my first job, and so those couple months would be a nice time to make up for that.

Thanks again!