If I could pick my friends careers:
RD: Owner of tiny vineyard that produces like 250 bottles of hand-crafted (whatever that means) wine a year. She would also paint all the labels on by hand.
B: Something excrutiatingly detail-oriented like wedding planner. Although wedding planner seems almost too common. Caterer maybe.
Sis: Football Statician
R: Organic Flower shop owner in Italy
Zakk: Comic book store owner
The Canadian: Private investigator
BB: Fashion PR person
Cloudy: Vintage clothes store owner
MM: Italian cook
NG: Commander of a ship (this answer is flawed by my desire to see him in uniform)
Giselle: Hand made invitations designer
C: Kindergarten teacher
Bro: Model or video game designer
CeCe: Party planner
D: Business exec or stay-at-home mom
E: coffee shop musician/organic farmer with KH. They own a shop somewhere. KH makes the vegan bars and new orleans style coffee. E plays the tunes…or they both play the tunes.
KH: organic farmer. See above.