Of course, each of us is responsible for our own level of aggressiveness, and we should not let pressure from online or groups affect our choices in that there is nothing wrong with being aggressive as long as we do not end up overdoing it. If we overdo it, then we have to suffer the consequences, and it might be 10 years down the road that we realize that we cannot turn back the clock an hopefully we did what we were able to do without overdoing it and taking ourselves out of the game due to our own overly aggressive screw up(s).
if I may ask, how does someone really decide where to draw the line between being aggressive enough to see good gains and being too aggressive to the point it turns risky?
You should draw a limit based on your financial situation. For example, you can invest $50, if you invest $100 there, then you are making a wrong decision. Because the remaining $50 is taken from your emergency fund. If you need this money, where will you get it from? Then you will have to sell your holdings. So you should continue buying based on your financial situation.
Your investment can be at risk only through your wrong financial management. For example, if you invest the money you need to invest. Then after a while you will need that amount of money. Then where will you get your money. Then you may have to sell your holdings or take a loan from somewhere. Invest with the amount of money that you can afford to lose or the amount of money that you can keep for the long term.