Many of the pain points listed have a common trait: the decision would seem easier with less information. For example, the PhD decision is easier if you didn't know about the costs which have been sunk, the identity decisions are easier if you're not sure of your own identity, cached thought problems are easier without having that thought cached, etc...

But we know that information should never have negative value. So why not highlight that dissonance? Imagine the following exercise:

Handout: "You spent the last 3 years working toward a PhD. You passed up a $90k job to stay in the program. Now you have 2 years left, and another $90k job offer has come your way. Do you take it?" (I don't know much about PhD programs, so feel free to imagine more plausible numbers here and add narrative).

Exercise 1: Is there any information you would prefer to not know? Exercise 2: How much would you pay to not know it?

If you really want to have fun, give people monopoly money and let them bid to remove information from a range of scenarios. Note that we're not offering to change the facts, just to not know them.

Personally, I think this would be a lot easier if I could just forget about all that time spent in the PhD program.

At least in this case, the exercise highlights the difference between consequentialist and non-consequentialist reasons/excuses for doing things. The "how much would you pay to not know it" is especially handy, since it puts a number on that mental pain. Then we can ask whether the mental pain is worth all the money you'd lose by, in this example, staying in the PhD program.