@Lazo - There hasn't really been much of any progression. I never treated insurance like rocket science (unlike taxes or financial planning). Basically, I've been able to come up with $5000 for an emergency since I was 24, so insurance plans reflect that (deductible). I'm mostly concerned about liability and tort-reform. Umbrella was added for that reason since our NW began to exceed the liability on other insurances. In the US, it seems that people can sue the bejesus out of you and win outrageous sums for the silliest(*) of reasons, e.g. they tripped over your dog, then stumped their toe on your sidewalk, you served them coffee without warning them that it was very hot, ... Behaviorally, my focus is just naturally (since forever) on what could possibly go wrong rather than the more common combination of obliviousness or "don't worry, be happy".
(*) Relative to the mindset of other countries.
@Did/RealPerson - Yeah, just to clarify my long rant: There's clearly a scale of job-enthusiasm that goes somewhere from "can't wait to go work tomorrow" to "I like my work" to "I don't really mind it, but it could be better" to
brownout and then to burnout, which is similar to clinical depression meaning that there's actual "medical damage". The closer one gets to the right hand side of the scale, the more the present and long-term costs go up, so add these into the income to get the "real income". If "real income" is still high, by all means keep drawing it. What we're seeing in this thread is likely different experiences along that scale.
The other thing I wanted to say is that I'm not sure whether it's really a binary choice between either that high-income job or focusing on side-gigs. There's probably a scale for that too going somewhere from "I just show up at work and do just enough" (e.g. Gervais type loser) to "I spend all of my time and energy at my work; I even sleep under my desk". Some professions may lean more to the right in terms of work-life balance that there's no life left. If there is life left (in my case, there's always been 1-2 hours per day and sometimes up to 6 or 8), that's where I've focused my side-gig effort. Also here I haven't thought of the side-gig as an investment. However, I have considered it under the constraint that it should be able to become one. For example, for many years, I've thought about getting into machining. However, I haven't done so for the reason that startup costs are large ($3000); the time investment is equally large (before you can make anything beyond a toy cannon); and it's generally not very useful. Whereas something like bike repair scales all the way up. This just means spending spare-time deliberately on something that could be useful and doing it in such a way that it keeps developing. E.g. if you're a software engineer making $100k, why not try dabbling on Mech Turk just to try even if it's only $4/hr or something. I'd do that just to verify that I could. It's the verification and the potential that's important. Not the money per se.
