Written by Chuck Rubin Sept. 3, 2008

F-You Money:

For the past five weeks I have driven by a large Lottery billboard just off rte 128. It reads Lottery Jackpot: $114 Million. Every time I see this sign, I run through the same scenario in my mind. “If I won the lottery what would I do first?” It has become almost typical for lottery winners to be quoted as saying “Well the money is nice, but my life is going to stay the same, I am going to keep working.” To those who truly believe that, I have one thing to say: “What!!!!????”

If I won the Lottery, I would go back to work for exactly one more day. A day I call, “The Day of Truth.” On this day I would shut off the edit function of my brain and just let my inner voice go hog wild. I would tell everybody exactly what I was thinking. I would also do things that I have always wanted to do, but would likely be fired for. Things like, asking a fundamentally more interesting set of questions in a hiring interview. We all know the questions you are supposed to ask. Where do you see yourself in five years? What are your biggest strengths and weaknesses? But here are a few questions and challenges I would like to try out on a candidate to determine if they are the “right fit.”

• Nice to meet you, please make yourself comfortable. So….do you think you are better than me?
• For women: On a scale of one to ten, how attractive do you find me?
  • Follow-up question: If we were both single, would you go out with me?
• For men: If we fought to the death, who would win?
• Your favorite Star Trek series is? (Anyone who says Enterprise is out. Anyone who says Next Generation gets an immediate call back and a follow-up question)
  • How do you resolve the conundrum of the Borg being converted to an individualistic society in Next Generation only to return as a more deadly hive-force in Voyager? (If you can explain your answer in the context of the show without resorting to “the writers did it” you get an offer on the spot)
• Are you comfortable doing my laundry?
• Would you rather ride on a roller coaster continuously for one whole year or have a 3ft inoperable thumb for the rest of your life?
• Have you ever stolen something? If so, can I have it? If not, would you steal something and give it to me?
• As the candidate entered my office I would close the door behind them and say the following: “You now have five minutes to try and get out of this office.”

I would also like to go to an interview and respond to wrote questions with unfiltered answers. I would first set the mood by stating the following: “Is it ok if I respond to your questions with appropriate and pithy movie dialogue” Then the Q and A would go like this:

• Q: What is your biggest weakness? (The right answer is that “I work too hard,” it’s the backdoor method of avoiding a real weakness by bringing up a strength.
• A: I tend to form instant and unshakable opinions about people based on the first thing they say to me. Like now. My opinion is that you are an idiot. Sorry, that’s forever.
• AA: (Alternative answer): I am lazy and I steal things. Hire me and it won’t be long before you notice things missing from the office.

• Q: Where do you see yourself in five years? (The right answer is to describe a wildly successful person in their company)
• A: “Well I can tell you this, if I am still working here in 5 years, I will blow my brains out. You should make a note and call in sick that day.”

• Q: Tell me about a challenging management situation that you faced and how you resolved it.
• A: I once really pissed off a client by not delivering any of the things they contracted for. I am resolving it by looking for a new job. Right now.

• Q: (Consulting Specific) Why do you like consulting? (The right answer is “I like solving hard problems and working with a wide variety of people”)
• A: I like the money and whoring is illegal.

The value of an absurd amount of money is that it buys you the freedom to escape from cultural norms and behavioral standards. You don’t have to rely on anyone because you don’t need anyone to get what you want. You have the money! There is no longer a need to maintain a “network.” M-O-N-E-Y spells the end of shallow, meaningless relationships that you maintain because “someday you might need that person to help you.” In fact, the impact of a sweepstakes explains exactly why everyone can’t have tons of wealth. If we did, there would be anarchy, at least for a little while. However, over time, we would all find a series of meaningful relationships and ways to spend our time that are divorced from the requirement of earning a living.

I don’t blame people like Paris Hilton for making Internet sex videos. I don’t blame Hugh Hefner for living his life alternating between the smoking jacket and the grotto. I understand why the Sultan of Brunei owns 234 Rolls Royces (well maybe people who got the $$$ through the exploitation of an underclass should not be so free) Why not? You have got the cash to give the big “F-You!” to everyone else’s moral judgment.

Ultimately, the value of a winning lottery ticket is that it would eliminate the “have to” component of my life. Never having to respond to a voice mail or email, an end to computer solitaire, an end to conference rooms, an end to eating airport yogurt parfait whose contents are questionable, but it’s the only thing to eat while you wait for a plane that has a chance of being good for you. And finally, an end to sitting in traffic concocting absurd fantasies about what you would do with $114 million dollars.