I am by nature a pessimist. I would make a terrible salesman or businessman, unless I were a liquidator. Most things that people buy, I never would have thought anyone would want. Socially, I have to hide this aspect of myself or wouldn't have any friends. Too much of a downer. My alltime favorite song is Blind Lemon Jefferson's "See That My Grave Is Kept Clean".
But this unpleasant, unAmerican habit of mind turns out to be well suited to investing in stocks, though probably not so much in real estate. I have never had the nerve to buy an expensive house, hoping it would appreciate before I lost my job and lost the house. I have lived in the same house ever since I bought it in my mid-thirties.
My only real esate profits were from oddities, like buying raw land from a logger who just wanted to buy another treed tract, and short-platting to sell as mini-farms. It took some work, but no optimism
I now have invested assets considerably greater than my total lifetime earned income. There were even a few years when my kids were young that I qualified for the earned income credit.
My pessimism and wariness has helped me avoid some quagmires. The cost of course is that I have never participated in the absolute boom stage of a market; I have sold by then.
Pessimism has not kept me from being at times as much as 120% long equities, with essentially no fixed income other than checking needs. But only at times when things are so stupidly cheap that it would be really hard to lose. Also, now, at my age, I wouldn't repeat that. I always hated jobs, but I knew I could get one. It's different with some age onboard-- who wants a 63 year old pessimistic misanthrope?
In fact, what employer wants a 63 year old with the world's sweetest personality?
Now, before y'all commit suicide, JUST KIDDING
Mikey