[123pie123]

I get called out by others for overthinking - until the risks I've pointed out become reality

It's all relative - one person can be thought of overthinking and the other person can be thought of as a 'cowboy' and just winging it

[andrewksl]

I guess the difference between an overthinker and having foresight is the rate of false positives?

[xyzelement]

That's a great way to put it.

There right balance of action and caution is the thing that enables you to move forward quickly without blowing up.

It also "takes all kinds" on a team since different people have a knack for one or the other. The problem happens because most people fall in love with their preference and are blind to its downsides.

A quick tell is - whenever someone's justification for something blowing up is "oh but I have a bias for action" -- they are basically oblivious to their recklessness and underthinking. Whenever someone says "oh but I am much more cautious and thoughtful than these cowboys" they are oblivious to how little they do (vs could be doing) because they are paralyzed by overthinking.

The person I like to work with is the one who says "man, I have a bias for over/under thinking but I try to catch myself in situations where it's not appropriate"

[phnofive]

I am an overthinker, and I know that ideas are cheap; they're driven as much by emotion as thought, and if my observations are not received in the intended spirit, it's not necessarily worth it to keep pushing.

What has consistently helped in winning trust when providing feedback is pairing any concern with either a qualification (blocker/aesthetic/security), a solution, or both. Then, you not only expose the thought process behind your perspective that they've missed something - with which your audience may not agree, but can judge in earnestness - but also your intention to help and support their vision.