In speaking about Lucille Ball, Osborne says:
While Osborne was an actor under contract with Lucille Ball and Desi Arnaz, it was Lucy who encouraged him to become a writer. I asked if he could speak a bit about her and why it was he heeded her advice?
Though Lucy was famous for her comedy, Osborne described her as a very serious business woman who suffered a bit for not thinking she was smart, even though she had major street smarts. After interacting with Osborne for a while and noting his great interest in Hollywood history, she suggested he shift into writing because—while there were plenty of actors to go around—there were not as many writers. Further, she wasn't confident that Robert had the necessary street smarts to deal with auditions. There were so many aggressive young actors who could do nothing else with whom Osborne would be competing and Lucy felt he should explore his other talents. He could write. He had a passion for Hollywood's film history. Osborne took Lucy's advice and has never regretted it. To this day he has not seen a play or a movie where he felt he should have played the part. Lucy remained his friend over the years, checking in at least annually to see what he was doing, who he was socializing with, and frequently inviting him over for dinner.