I’ve seen the analysis paralysis happen as well, but I think the key is to also assign likelihoods/severities upside downside to the analysis, you can usually quickly triage what to focus on from there (or as I often find the nice you’ve bounded the range of likely outcomes, pick the one one that fits your risk tolerance (e.g. do I take the train for an almost guaranteed 3hr trip, or do I try and outsmart the traffic and either be right and have a 2hr trip, or be wrong and have a 4hr trip)

This. I've received consistent feedback (from mentor, from family, etc) to do less second-order analysis. It can be very productive in some specific scenarios, especially when I used to do initial architecture; but these days, it's a complete analysis paralysis. Moving from technological architecture to people leadership / client relationship management, second order thinking brings up so many pros and cons for each action, with insufficient data to weigh the balancing.

I've taken to using a sort of internal version of "disagree and commit" - I have the little mental debate with myself, arrive at an ambiguous juncture, then pick an option (at random if necessary) and go all-in on it. If it turns out I was wrong there's usually still time to course-correct.

Delaying or not making a decision is a choice itself, one that is almost always inferior to the options you're stuck between.

Yep, fail fast is often going to have a superior resolution time than time spent in deep analysis.

Plus you get more experience making decisions, more experience making quick decisions, and more problem-solving experience that way.

I agree. I believe it is not that second-order thinking is unhelpful, but rather that it is only useful when applied wisely. The challenge is knowing when and how to apply it, and of course having the tool kit necessary to do this kind of thinking.

Leveled thinking is common in competitive games, for obvious reasons. There's no better illustration of what you're talking about than the poison scene in Princess Bride:

https://www.youtube.com/watch?v=rMz7JBRbmNo

The way I've heard most competitive gamers talk about the line between leveling and tail-chasing is to play at level 2:

Level 1: The obvious strategy

Level 2: Strategy that beats the obvious strategy <-- Default to this level

Level 3: Strategy that beats level 1

The problem is, if you're playing in a competitive environment, everyone knows about leveling, so you may actually gain more edge by picking a strategy randomly. I've heard competitive Magic player Huey Jensen would make random plays when he was behind on the chance he could throw his opponent off and trap them in leveling second-guessing.

I think it requires balance. Seems to me like the more you can consider the better decision you can reach, but there is a point where thinking more is negative value, and you must decide.

“The instant of decision is madness”

-Kierkegaard

You can use a mind mapping tool and limit your expansion radius. I've had some success with that.

or the opposite - in ML terms more brain will likely just introduce overfitting - while less brain makes way for some neat generalization that is quick and works just good enough ;)