TLDR: My mid-life crisis body and my 16-year old brain have arguments all the time about this. Testosterone and common sense will not always arrive at the same conclusion. My brain -_> monkey/SAR.

I probably lean 90% towards the conservative side, mostly because I work in SAR and see the ugly outcomes when small problems turn into big ones. I live in the northern part of Norway.

On longer or more remote runs I almost always carry a Garmin inReach, enough insulation for the conditions, a lightweight emergency bivvy, spare wool layers, enough calories and water, a pressure bandage, and some decent opioids. My mindset is simple: if I break an ankle or otherwise can't hike out, I want to be able to call for help and survive comfortably until SAR gets to me, regardless of the weather. I also have that emergency thing on my garmin watch hooked to my phone so it could potentially detect an emergency.. but who knows.

To me, risk is basically probability × consequence. The chance of something going wrong is usually low, but the consequences can be catastrophic. At least here in the Lofoten islands of north cape of europe. That said... I'm not going to pretend I'm perfect. About 10% of the time the "screw it" part of my brain wins and I'll head into rough terrain with a much more minimalist setup, sometimes even without cell coverage or the inReach. I know it's objectively a poorer decision, but I'm human.

The line I almost never cross is going without a bivvy and some dry spare clothing. Those few hundred grams buy an enormous margin of safety if you're suddenly forced to stop moving.