The Dollar Bill Game, Part 1: If Money Were No Object

“If money were no object, what would you do with your life?”

Did you get asked this hypothetical question a lot? Especially around high school and college graduation? I did. And it was frustrating as hell, because I was so overwhelmed by my choices that I had no idea how to answer.

This question requires you to have a deep knowledge of yourself and your place in the world—deeper than many young people will have adequate experiences to inform.

The Dollar Bill Game

I have a different way of thinking about this conundrum. It’s called the Dollar Bill Game. Answer the following series of ten questions and you will likely arrive at a more nuanced and interesting answer. Be as specific as you can in your answers.

  1. If someone handed you a single dollar bill, right now, with no strings attached—what would you do with it?
  2. What if it were a ten dollar bill?
  3. What if it were a one hundred dollar bill?
  4. One thousand dollars?
  5. Ten thousand dollars?
  6. One hundred thousand dollars?
  7. One million dollars?
  8. Ten million dollars?
  9. One hundred million dollars?
  10. What if it were one billion dollars?

The reason this works

The “if money were no object” question is as open as the English countryside. It’s really hard for your brain to process the difference between zero money and infinite money.

But the Dollar Bill Game is much easier to wrap your head around because it breaks the hypothetical options into graduating tiers. You may not know what to do with limitless resources, but you certainly know what you’d do if you had just a little bit more.

So ask yourself these ten questions next time you’re in the shower or about to take a long drive. Then look them over and see if you can discern a pattern.

Then come back for our guided tour of some common responses and what they might reveal about you:

The Dollar Bill Game, Part Two

In the meantime, here’s some more Bitchy wisdom on what to do with a nice fat stack of cash:

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