The rational thing to do with ESPP is immediately sell and collect the discount from market value. So if you were fully rational, at best this would have gained you a couple extra thousand per year.
Ok, sure, itβs great to have an extra couple thousand a year. But I assumed someone saying it was a regret meant they regretted not piling into their employers stock years ago which is now worth 10x or whatever. So just commenting that even if you used it, the rational choice would not have resulted in a windfall.