coaching a client on failure

What do you tell a client that says all the major things that were important to him that he attempted to give his best effort to in life didn’t work out, so he feels like he isn’t good at achieving his goals/isn’t creating great things/isn’t learning the lessons he needs to learn and keeps repeating this pattern. (This is a nearly 60 year old). My thoughts are coaching on why he wants to make it mean these things, how its keeping him stuck, what he wants to do about it now, how can he truly give his “best effort” so he succeeds, or redefine what success or “working out” means. But would love to hear your thoughts. Mostly because as I was thinking about it after the call I got in the pool noticing my Dad feels this way about his life and is sad and makes me sad and I want to feel this sadness now and then continue out of the pool on the next call. These were things that didn’t work out for him: Being in business with my dad (a big dream of mine)
Creating and sustaining my marriage to my first wife
Being the kind of dad to my kids that would mean having a life-long good relationship with both of them and their kids
Creating a career that would be meaningful and rewarding and that I could now look back on with a sense of accomplishment
Taking great care of my health such that I would be able to be as active as I want to be