I won't say having a teenage boy was easy, but we think our son turned out (IMO) very well is because we gave him VERY strict boundaries until he was ready for his boundaries to be expanded. My wife and I watched and discussed alone which boundaries and when were to be expanded. This process was dependent on him and his personal journey in our world.

The world to a kid can be terrifyingly complex (to adults, too). Having no rules, aka "The Cool Parent," ends up being no favor to the kid. They are completely unprepared for being an adult if they spend their youth with no rules. The exception is if you are in the 0.1%, where there are few rules even for being an adult (refer Musk, Elon, et al).