I think about that episode a lot in perspective of my life. I actually lived my life like Picard reliving his life. What really hit home was when he was transported back to the present and was questioned Troi and Riker about getting into command. They pretty much laughed at him. To me that really opened my eyes about who I am as a person. I liked being wise even young that it almost has created a retroactive effect my future prospects simply because of it. I've often been told "are you an old man?" by many adults when I was younger and in hindsight now I understand why. However I find it very stupid that human culture (or just western values) find that as a negative. For some reason were supposed to waste our youth and engage in risky behaviors. I just never saw it that way.

You aren’t “supposed” waste your youth. Those who waste can’t stand seeing others doing it differently.

It does not mean that you live right, but people’s opinions are often reflections of their own insecurities.

Whilst I enjoyed that episode, it was fictional. Did Picard really need to be stabbed in the heart, just to learn his lesson? (And, his 'unremarkable career' seemed to be a bigger criticism of Starfleet/the Federation than we normally see - what's wrong with an ordinary life?)

I would be happy to remove the trauma that I experienced in my past. I'd take the risk of being a different person - with different good qualities.

This is Q we're talking about. He's not the kind of character who would sit down with Picard over a cup of tea and talk him through why changing his past would change who he is. Humbling Picard by showing him the folly of his wish to change the past, while he lay on his deathbed, by making him choose to get stabbed through the heart is definitely more his style.

Also, I don't believe they portrayed Picard's "unremarkable" career negatively, except in Picard's own view (and Q's I guess).

I always like to do new and different things. It is the main reason I migrated several times and changed job many times. Currently I am doing my own startup. Sometimes I wonder what life would be if I live a simple boring life? Will I be more successful? or end up like Captain Picard in his alternate universe?

I watched said episode, and it does make you think.