Gretchen Rubin decided to override her “ought to” self when she said, “I’ve come to a point where I’d rather fail as a writer than succeed as a lawyer, and I need to try and fail or try and succeed, but I need to do it.”68 Rubin attended Yale Law School, clerked for Sandra Day O’Connor on the Supreme Court, and was at the start of a high‑paying and promising law career. Yet, she understood that if she kept going and never took a chance on becoming a writer, she would regret it.
