In this day and age, skepticism is arguably less of a virtue and more so a tool of sorts to poke holes in anything that threatens the status quo.
My mind has this stereotypical image of a skeptic as the person in a group who drags everyone else down to Earth whenever they dream of reaching the stars, so to speak.
I think this was developed via observing that there's always a naysayer in the room, hence assigning them the role of a skeptic makes total sense.
But digging a layer deep, I try to know where the skepticism is coming from, whether it's founded or not. People have a subtle way of projecting their own FUDs onto other people's plans, which could be a blend of both genuine concern and personal limitation.
Don't even realize they're doing it for the most part. They think they're being helpful, rational, protecting you from making a mistake. But what they're really doing is protecting themselves from having to confront their own choices.
If you succeed at something they were too afraid to try, it holds up a mirror they'd rather not look into. So the skepticism becomes a defense mechanism dressed up as wisdom.
The tricky part is separating useful caution from borrowed doubt.
The one who tried and failed will either warn you away from their mistakes or simply assume you'll repeat them. Where as someone who's never taken a risk will unsurprisingly see risk everywhere.
But there's a third type too, the person who never tried at all but has convinced themselves they already know the outcome and these are often the loudest skeptics because they have the most to prove, mostly to themselves.
Moral high ground
I've noticed this pattern play out in different contexts. Some of those who've gone the conventional path like my cousin always have subtle and not so subtle ways at jabbing into my unconventional path.
I get the part about having visible rewards to parade as a form of achievement/success but then examining the foundation from which such a built gives me the impression that he's only a few economic hiccups away from the same uncertainty he mocks me for embracing.
It's rarely about the specific situation.
Good judgement, in this context, is me trying to filter these voices without dismissing them entirely.
There's also the matter of timing and context. Some skepticism comes from a different era entirely, from people applying rules and lessons from a world that doesn't exist anymore.
Old-school investors who missed the tech boom often become the loudest skeptics of anything that sounds too new or different.
The hard part is doing this filtering work without becoming arrogant of sorts with making your point across.
Every now and then, the skeptics can be right. Sometimes you are missing something obvious or confidence is just inexperience in disguise.
It's a balance that only comes from repeatedly making calls, seeing them play out, and honestly examining what you got right and what you got wrong. Then, iterate on the process itself, fine tuning for the better.
Good judgement basically comes from experience, a ton of it, and the willingness to actually learn from it in all its variations.
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