In retrospect, I should've been more aggressive and risk taking with life decisions in my early teens and early twenties. Now with two small kids and a mortgage

In retrospect, I should've been more aggressive and risk taking with life decisions in my early teens and early twenties. Now with two small kids and a mortgage, I no longer have the flexibility to take massive risks. All the risky moves that I made so far in life ended up being ok. Stressful, terrifying, but I always came out ok somehow. Couple of examples: - Moved to a lesser developed country at 19 to be with a girl. - Bought two homes at the same time, was broke for a while. - Moved back to my home country & bought a house in a crazy market. - Joined a startup as the third employee.