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What was your dream job/career as a kid? Was it anything remotely realistic?
I remember I wanted to help terraform Mars at NASA because I was a massive sci-fi nerd. I even went into environmental science and wanted to go for that sort of thing, until I realized everyone in environmental science was a depressed dweeb who lied about their stats.
Anyway, now my big dream is to become a writer some day, even if not a great one.
When I was very young, an actor or journalist, and when I was a teenager, a philosopher or occasionally a psychologist (variably academic or practicing). I did want to do a degree (MA, maybe then PhD) in philosophy after my undergraduate degree before going back into finance but I had a crisis of confidence when I struggled with trying to teach myself formal logic (in all fairness, it was at least partially laziness) and so abandoned it.
I’m still not sure whether most good academic analytic philosophers are much more intelligent than me or just hide the relative banality of their ideas behind a tradition of overwrought language and an emphasis on ‘rigor’ that usually just means structuring arguments in a needlessly complex way.
You're not missing much from philosophy imo. I did a minor (1 course away from major but I would've had to do an extra semester) and especially as I've gotten older, I'm less and less impressed with philosophy. It's great for signaling high intelligence/status and talking your way around people, but in terms of actually leading a good, satisfying life, philosophy is a remarkably poor guide.
Which is sad, because that's ostensibly the whole point of the enterprise.
Well... not really?
Philosophy started as a comprehensive rational inquiry into the nature of reality. It was math, science, and metaphysics all wrapped up into one. Knowing how to live a good life might be part of that inquiry, insofar as it's a prominent feature of our reality that we observe people making good decisions and poor decisions, and we want to know what the difference between them is - but it's only one component.
The surviving texts we have from the pre-Socratics are heavy on theoretical speculation about metaphysics, logic, and mathematics, but they contain relatively little in the way of practical life advice. When Plato considered ethical questions, it was typically done as a pretext to introduce broader theoretical issues (e.g. the moral dilemma in the Euthyphro turns into an inquiry into the metaphysical status of moral facts as such). Certainly by the time we get to Descartes, we have a model of a theoretical philosopher who focuses solely on metaphysics and epistemology and pays no attention to ethics at all. So the situation you bemoan has been commonplace for at least 400 years now.
That being said, there are philosophers who make "living life" their main focus, and you'll mainly find them in the continental tradition: Nietzsche, Kierkegaard, Sartre, Lacan, etc.
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