I have one major mistake from my teens and early twenties. I could chalk it up to youthful stupidity, but it had the potential to be a grave situation:
I would never glorify being "gangsta" or street life.
As a youngster I watched crime movies vociferously and listened to nothing but gangster rap. I would pour over the lyrics, obsessing over which rapper had "cred" based on how many crimes they had committed in the past.
This was such a stupid mentality for a variety of reasons.
When I grew up, I saw other wannabe criminals in my neighborhood get "cred" for selling drugs and fighting, and I respected the fear and aura around them. In reality, any sort of criminal element or gang influence for a white dude in my town was from rap music and not the local minority gangs/dealers. I was only aligning my respect to them based on what I had heard from rap music.
As I grew up and began a successful white collar career, I see these guys on social media and what losers they are. In and out of rehab/jail, crashing at their parents place in between stints, getting lucky with a 4 once in a while. Their lives went nowhere while the people who didn't emphasize being "gangsta" went out to live happy and normal lives.
Growing up I also didn't get the opportunity to meet real deal career criminals. Had this happened to me I would have seen how stupid this lifestyle is, ending up in a 5x5 prison cell getting no pussy or shot dead on the street. I would also see what lowlife types of guys they are, never getting a job, being an absent father, risking their personal safety for some peasant "street code."
Fortunately the opportunity to be a real gangster didn't offer up it's opportunity to me because I'm honestly not sure which direction I would have floated in.
I understand why I did it, I wasn't a great athlete, slightly socially awkward with my father not living up to my idea of masculinity. I was looking to flex my muscles and be respected as a warrior in some way, by identifying myself as a survivor of the streets. In reality, I was nothing close. It was just my fragile ego as a man desperately revolving my life around "cred."
I think it's important for a young male to have an outlet to harness his masculine urges. I should have become obsessed with a combat sport like boxing, so I could feel superior and more masculine than these bullies with "cred."
If I could pose one question to my younger self, I'd say: who is the real tough guy in life, the real king of the jungle? Is it a lowlife hoodlum who people fear because he carries a gun and won't hesitate to use it? Or is it a man who gets up every day and battles people in the boardroom, climbing his way to the top of the business world, coming home to his mansion after benching 315 and fucking his hot wife?
Coming from a rough and tumble background is acceptable. What's not acceptable is becoming like those same guys that made your background rough and tumble instead of taking the opportunities to have an awesome, legitimate life.
I'd laugh at re-entering any of my mini-conflicts from that period of my life. This guy called me a fake pussy? What the hell do I care? I have a top job in a top city, flying all over the world for vacation, dating young beautiful women and I could handle myself in a fight.