Twenty Questions

Recently, our nephew from New Hampshire, having just turned 14 and deemed old enough for the long solo flight, came to visit. We hadn’t seen him in two years and were amazed at the four extra inches, the dropped voice, the same funny gait. He was excited (but couldn’t possibly show that) and nervous (which he couldn’t possibly hide). We were excited (which adults and little kids don’t think to hide) and nervous (which nobody can hide).

Over lunch the first day, there was awkward silence; it had been so long we were all at a loss. I proposed the question game, a game I invented to get to know the little kids I used to babysit, and he thought it sounded stupid. He didn’t actually say that, but his blank face said “that sounds really stupid.” The stupidity factor was raised by the excitement of his 6 and 8 year-old nieces.

The game isn’t twenty questions, where you decide on something and then have someone deduce what you are thinking by asking if it is bigger than a toaster or if it barks. Instead, you ask questions and from the answers try to deduce the person.

The rules:

  1. Whoever asks the questions is in charge.
  2. Whoever answers the questions must choose between one of the two options, even if it is difficult or even impossible to choose between the two.
  3. The respondent cannot launch into long explanations about his choice. He must simply choose.
  4. The one in charge must similarly not launch into long explanations about the question, nor make obvious judgments about the answer (except for having fun, which much be had, see italics).


  1. What do you like better, cookies or cake? Cookies.
  2. Trains or planes? I’ve never been on a train. OK, train.
  3. Chocolate or vanilla? Depends. OK, vanilla.   

Beaches or mountains? Swimming in the lake or the ocean? Mexican or Chinese food? Red or green? Blue or yellow? Mounds or Almond Joy? Cats or dogs? Rats or hamsters? Broccoli or spinach?  Hydropower or nuclear power? Coal or gas?

With only two choices, there is little room for nuance which the respondent always wants to add, which adds to the fun.

There are myriad variations of this game, and the following you should play at least once. Repeat if you find the questions difficult or impossible to answer. This version explores your relationship to your finances. (You knew it was coming, this is a money blog.)

  1. Do you have an emergency fund or a vacation fund?
  2. Do you like risk or do you crave safety?
  3. Does risk make you think of thrill or danger?
  4. Do you wait to have money to create an investment plan or do you plan how you are going to get money to invest?
  5. Does interest work for you or against you?
  6. Do you have term life insurance or I-hope-I-don’t-die insurance?
  7. Is it too late to save for retirement or too late to save for college?
  8. Can you risk $100 or $10,000?
  9. Is it too late or too early for asset allocation?
  10. What will produce the greatest return, college or retiement saving?

It isn’t as much fun as cookies vs. cake, but these are the questions that most people put off or avoid altogether until worry begins to creep up as their kids approach college – and then they put off the questions again because they are ashamed they put off the questions in the first place. Then their kids go to college on loans anyway. Then their kids put off the questions until they think they can work themselves out of their loan burdens. Most people think financial planning is portfolio-driven, which leads to not planning until you have a portfolio, which means, well, the portfolio is a long time coming.

Avoid all that by a DIY financial checkup in which you make sure you have basic estate plans (like wills), basic insurance (car, health, life), a savings plan (emergency first, then retirement, then college or other big goal), and most importantly, don’t spend as much as you make. Every year, repeat. Every year it will become a tiny bit more complicated as you begin building, but, by then, you can move on to more interesting questions — Do you like scones or muffins? Apples or oranges? Camping or hotels?