I read these kinds of threads with a lot of interest. I have a son on the way (August!) and my wife and I end up talking about things like this all the time. We were both raised in completely different kinds of households, so it will take some work for us to find our own direction that incorporates the best of both of them, where possible. How much we want to push achievement, academic or otherwise, is a subject that comes up constantly.
But I can at least tell you this much from my own experience. I graduated college right into the dot-bomb. I didn’t major in computer science like everyone else, so I was spared the indignity of walking down Park Ave with placards that said WILL CODE FOR FOOD. But I more or less went for all the little brass rings just because I thought it would be a shame not to achieve something that I could achieve. In college, I actually thought it might make a difference in a tough job market. Hell, I went to an Ivy League school. Once upon a time, that was a meal ticket by itself.
I have revised my views quite a bit since then.
All of my little Lebowski achievements just made my “quarter life crisis” worse. Stupendously worse. I wasn’t the world’s most entitled kid: I worked through college, paid my own rent in the city as soon as I graduated, and had no financial support from my parents save for some emergencies over the years. I was always employed full-time. I didn’t go to my college graduation because my job had already started and I couldn’t take days off in the first week of work.
This period of my life was really shitty and took a few years to get over. In retrospect, I would love some of the time back that I wasted on accomplishments I see in retrospect are pointless and self-aggrandizing. I could have been napping or learning how to be something other than a slightly monomaniacal jerk.
The content and rigor of my education has paid for itself thousandfold. I do work that I absolutely love. I happen to love learning, so my life is a good fit for me. But I would be no worse off if I hadn’t bothered to amass a shelf of plastic trophies and other achievement-related paraphernalia. Those all went in the trash over a decade ago.

- I simply desired opinions WRT the situation. I’m continually impressed at how - no matter how you plan and prepare, as a parent you continually have to react to novel situations. And wee muddle through as best we can, but occasionally I appreciate a sounding board. In this case, after receiving 50+ responses, I was more comfortable than before as to the appropriateness of how we handled the situation.