I read once that optimization is a sign of anxiety and boy howdy do I see this over and over.

If you find yourself always trying to figure out the best way to do things and you spend a lot of time considering different options, especially for things that aren't that high stakes, I highly recommend working on figuring out why you're so scared of a low stakes negative outcome like "took my friend to a mediocre sushi restaurant." Or why is it harder to sit with the uncertainty of a low stakes outcome than to spend hours deciding between basically equivalent events?

It can be really hard to interact with folks who have this pattern - every little thing you do together can turn into extremely long conversations with flow charts of decisions and extreme over-complication and over-explanation.

Most people with this pattern that I interact with don't see it as coming from a place of anxiety, but I've found that understanding to help me be more compassionate and productive.

If you have a friend or a co-worker who's like this, it is actually counterproductive to engage in the optimizing process and doing so reinforces their anxiety.

Be kind, but don't participate. Don't ask open ended questions, but offer just two options, set time limits (we've been talking about this for 5 minutes, that's long enough), and normalize “good enough.” They will try to pull you back in with what-ifs and you can refuse - "it'll be good enough."

If you have to work closely with them, create defaults for recurring things so you’re not renegotiating every time. You might have to have a conversation with them about how the long decision cycles are draining and using time that could be used for more important things.

Remember, you are not helping them or being kind by participating in their anxiety. You're making their anxiety worse and wasting your time.