Q put it best:
"This is the man you are today. And you should be happy! You have a real heart beating in your chest, and you get to live out the rest of your life in safety: running tests, making analyses, and carrying reports to your superiors."
But he was comparing it with his own previously lived dreams, ambitions, and experience. As someone who doesn't aspire to be famous, wealthy, a leader of many, etc., I don't feel it's a knock on me. I'm quite deliberate in choosing the life I have, particularly my family life. It's worth noting that Picard never had a traditional family life, which for some people gives life meaning. He gave that up for the life he did have.
Regrets over which he struggled with in Family, and which bring him to tears later, in Generations. The writing was aware of the contradictions, which also elevated it.