Bad outcomes do not say much about you or the processes you use. Luck matters too.
Your brain is lazy. Be a little skeptical of what it tells you.
Would you accept a $5,000,00 risk for $2,350?
Be careful over-applying old experience.
You can get satisfactory outcomes without being lucky
There is a cost to do nothing and there is a cost to doing things yourself. Be sure you know that cost.
Probability doesn’t matter. You cannot be 90% alive. You have to insure as if you could be 100% dead.