As someone who came from a fairly poor background (not half as as bad as the OP to be fair) and who has managed to "break out" I can say for sure that looking back I had a ton of lucky breaks - but, and this to me is crucial, only after I stopped worrying about what might go wrong and focus on what I could do right. If I had predicated my success on somehow getting lucky I don't think I would have made it.
So to me - and not wanting to speak for the OP of course - but the way I look at this is that the simple encouragement of "I made it and you can too" is more motivating than "I made it but then again looking back I had a ton of lucky coincidences that you probably won't have so, sure, try it, but don't expect success" :)
I only think of it as “failure is understandable and doesn’t reflect on you as a person” - but you bring up a good point. I have no patience for people who say “because I made it everyone else can too” which is a really common attitude. People play up their adversity (understandable; it’s the adversity one has had) and downplay their advantages. Lack of empathy and help for those struggling is unacceptable to me. As people succeed they tend to stop congregating around those that don’t, and I think that’s fine but to sit around those successful and vote against policies to help those not succeeding is to me a moral failing.
For those struggling through poverty - one must know that one CAN succeed, or else you end up in a psychological hole waiting for the next nibble of luck. A tempered balance of both optimism and also a real social safety net seems like the best of both worlds to me.
So to me - and not wanting to speak for the OP of course - but the way I look at this is that the simple encouragement of "I made it and you can too" is more motivating than "I made it but then again looking back I had a ton of lucky coincidences that you probably won't have so, sure, try it, but don't expect success" :)