Inspired by @BWN_7
  1. When my parents sat me down and said: "We can't afford two kids going to Ivy League schools. Would you please consider going to University of Oregon?"
    I said: "Yes", and I never regretted that decision ever. Best years of my life.
  2. When I decided to go to a law school all the way across the country versus a California or Massachusetts law school.
    They offered me more money. I regretted nothing, save the weather.
  3. When I realized that, after years of putting up with a lot of emotional abuse, I had to get out of marrying "Miss Emotionally Severe Ohio Beauty Queen." I wanted things to work out between us, but I knew that something bad was going to ultimately happen. Two weeks later, it did.
    I was driving on the streets of San Francisco, thinking about her, the bullshit, how unsure that I was about our relationship, and a line from a Lemonheads song sprang in my head: "He'd rather be alone than pretend." At that point, I just knew.
  4. When my college roommate and best friend bet me $10.00 that I would get into Oxford if I just sent in the damn scholarship application.
    Easily, the best $10.00 I ever lost.
  5. When I decided to quit my job at a insane, severally emotionally tumultuous worker's compensation law firm. I immediately started working at Macy's. I regretted nothing.
    I was broke. I had a wedding that didn't end up happening and massive amounts of credit card debt to pay off. My willingness to be exploited was understandable. I just didn't anticipate it would last so long.
  6. When I decided to open a law firm at 32 with only borrowed money, some office supplies, and no idea what was in store for us.