Can you be successful in life by focusing on personal happiness rather than traditional milestones like marriage?

Why do people often overestimate their chances of winning in sports betting or casino games?
Why does my mom keep showing me pictures of me before pregnancy to now? She keeps saying I don’t look like that anymore. Well obviously I had three kids back to back. What’s the point?
What if I'm just stupid and naive for my past huge mistakes setup and need to forgive myself to move on to concurred ground to be more disciplined and confident finally breaking free from the prison of the mind and setting myself free by myself?