Will I regret it if I take over the family business out of obligation instead of choice?

Almost certainly yes, and the cost compounds for decades. Kris Kluver, in The Dysfunctional Family Office, tells the story of a Texas ranch family where the youngest son turned down a top marine biology program to work the family business out of obligation. Fifteen years later, he was running a division he hated. Three marriages. Self-medicating to get through the daily dissatisfaction. Deep resentment toward the family for making him feel obligated. The business hadn't taken his time. It had taken his life. The pattern is consistent across UHNW families. Heirs who join out of obligation rarely thrive. They usually erode quietly, sometimes for decades, before either breaking down or breaking out. The hard conversation about whether you actually want the role costs less than fifteen years of suppression.