I haven't made a fortune 'being' pessimistic. Being pessimistic enables you to see risks and problems more clearly. You simply avoid them where you can and pick the eyes out of the opportunities that present themselves. For me that's business not property.
This is where most here misunderstand me. I'm pessimistic about the future but optimistic about my chances. Property is a long slow grind with very low annualised returns. Using mega leverage and arbitraging market spreads is high risk in most areas of investment. While volatility is considered low (hence perceived lower risk) exiting a position is often laborious and time consuming effectively neutralising the low volatility advantage.
Business is much more fun and the returns are magnitudes higher with much faster turnaround. The difference though is I use little if any leverage (low to no risk) so total amounts may not compare to property over time.
Would you consider yourself a Pessimist or a Realist Freckle?