How to evaluate decisions is a good question, NT. As you say, to decide between two things it helps to have a common standard to compare them to. You use time, which is a great system. When I was young, I used an aspirational purchase I liked to make: magic cards. Purchases could be conceptualized in terms of how many packs of magic cards it was equivalent to. That number was always far more visceral for me than an abstract number of dollars, as I think time is for you, and so it made the decision more tangible.
A limitation I’ve found with time is that I find value in doing things myself. I could spend money to have someone paint my house, for example, but I like doing it myself. I learn a new skill and I find more satisfaction in a job well done then just seeing someone else do it for me. That particularly applies when it is something I haven’t done before, or might not feel comfortable doing. For that reason, sometimes I find it useful not to follow my analysis–whether based on time or magic cards–too closely.
Explore vs. Exploit – The Case for Randomness
When I’m faced with a few options, I often do try to find a common baseline to make the comparison. But I also try to introduce some randomness. If it’s something I haven’t done before, maybe I do it even if it seems like the worse option, so I can learn if it’s for me. If doing it will teach me a new skill, that might add a few points too.
When I get invited to attend an event, for example, I try to err on the side of accepting. They have a cost in time, but there is always a stimulating element of randomness because I’m forced out of my routine and to talk and interact with new people. Sometimes the event is good, sometimes it is bad, but I usually learn something, especially if it isn’t the kind of event I would normally attend.
Your advice, to include the non-quantifiable, seek asymmetry, and protect your downside, is good. I would add one more: accept randomness. Seek new things. Err on the side of the new, not the old. It’s too easy to stagnate and get stuck in ruts. If you always optimize the same way, you’ll likely always reach the same optimum. If you try something new, you might find you like it even more. I meet too many people who seem to just do what they’ve always done, stuck part way along the path of self-improvement without realizing it.