For me, it really helped that I sat down for two weeks with nothing to distract me except my own thoughts, and thought about life really really hard. I went through the whole emotional roller coaster, starting from "oh shit, I'm going to have to do this?!" and ending with "this is what I need to do to get there."

The thing about a lot of these major life events is they're somewhat predictable - you know, to some degree of certainty, that you're going to get married, have kids (or not) and, if so, whether or not you want to send them to college. You know you're going to need transportation and housing, you know they're going to depreciate and require ongoing maintenance, and you know there will come a time when the accumulated damage is just so much you have to replace them entirely. More grimly, you know that there is a good chance that your parents will fall ill - more likely to be a chronic illness these days - and, depending on your value set, you may have to assume the caregiving role (and all that entails).

It was really an iterative process of laying down the life events, taking time to accept that this will happen, and then planning for it.

In my case, it was a really good thing that I did it too because, in the process, I concluded I needed to sell out of some illiquid investments and prepare a $75,000 catastrophic illness fund in case my aging parents needed it. True enough, two years later, my dad was diagnosed with cancer, and having that fund available in a savings account eliminated one huge source of worry in what was already an immensely stressful time.

Actually, Jessie, it's funny that you've written this article now because I've submitted an article answering this very question (well, partially anyway) in a lot more detail!