This was posted recently - the 1st quote in reference to a particularly poor outcome, whilst the 2nd was referring to an earlier stage in the investment journey. I would guess that both felt v. similar in the earlier stages of their journey - they both felt they had education, did research and consulted with trusted and apparently expert individuals. So the question is.... How do you know if you are still unconsciously incompetent ? I would say, it's a lot more than just education.... It's the right education - ie a broad education from multiple unrelated sources It's running simulations or scenarios - spreadsheets of both the good & bad possibilities, likely & unlikely. It have an idea of what might happen in the future. It's experience - either others or your own. But be very careful of small samples - someone else's anecdote is completely irrelevant to anyone's future but their own. It's critical thinking - Ask many secondary questions like.... Why does that happen? What are 2nd & 3rd level effects ? How will 'the herd' behave ? It's knowing what happened last time. It won't necessarily be the same this time, but it will broaden your outlook to the possibilities It's discounting (but not completely ignoring) anyone with a relevant bias - and everyone has biases of some sort It's asking the right questions. However, knowing what the right questions are is hard for absolute beginners, so a poor substitute is asking any questions of many participants. You'll gravitate towards the right questions & the right people eventually It's looking at the bigger picture - don't get fixated on a particular course of action without understanding how it fits in with the economy It's being especially wary of anyone who exhibits Illusory Superiority - it's often the case that they are unconsciously incompetent or have their own biases or self interests It's mitigating risk - run scenarios like 'if X happened then it would be OK because I will do Y & Z', and thinking of all risks, not just the obvious ones It's thinking about where you feel your standing is amongst both a range of other participants (your peers, subject specialists, those N years ahead or behind you on the journey), and also yourself N months ago. Are you the patsy ? It's knowing what you don't know - once you know a little, you find a few details you don't know, and upon investigation an avalanche of minutiae (think tax, legal or even depreciation schedules) - do you know just enough to be dangerous ? So next time you take action, first ask yourself if this is a topic where you are still incompetent.