The Dollar Bill Game: What You’d Do if Money Were No Object Says a Lot About You

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

Did people ask you 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. We call it 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 the Dollar Bill Game 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.

Now we’re going to go through the methodology and analyze some common answers!

The questions in the Dollar Bill Game

“If someone handed you a single dollar bill, right now, with no strings attached—what would you do with it?”

For most people, the answer is “nothing”—slip it into their pocket and forget about it. Which is perfectly fine. This leads us to the second question.

“How about if it were a ten dollar bill?”

Often the answer is still some variation on “nothing.” Perhaps a small purchase—a coffee, or their next bus ticket. Nothing that would substantially alter someone’s life… yet.

“How about if it were a hundred dollars? A thousand dollars?”

Each step of the game jumps the dollar amount up tenfold. At this level, most people start to think about their medium-term issues: paying rent, paying bills, socking a little money away for the future, shopping for something you’d already decided you wanted. The next level is where things start to get really interesting.

“What if it were ten thousand dollars?”

A very interesting question. Ten thousand dollars opens up many possibilities that weren’t available in previous tiers. For most people (let’s be honest: if you’re reading our blog, this you, baby), ten thousand dollars is several months worth of paychecks—yet it’s small enough that it can be blown on a single vacation or big-ticket purchase. So what would you do with it?

“A hundred thousand dollars? One million dollars?”

We’re not at full Richard Branson yet. This sum of money isn’t quite so much that you never need to worry about money again. But we’re getting damn close. If you’re contemplating big-ticket purchases like cars and houses, it can be gobbled up surprisingly quickly. It’s an enormous sum of money, true—but you should still consider it carefully.

“Ten million dollars? One billion dollars?”

How did Ludacris put it? “Lifestyle so rich and famous / Robin Leach will get jealous”?

Okay, the pie is now well and truly in the sky. (You can turn the dial up to eleven, if you wish, and go to ten billion if you come up with some truly inventive extravagances.) This is the realm of pure wish-fulfillment. If money can buy it, it shall be yours! Where past answers have been ethical and practical in nature, this one is more creative/imaginative. What kind of sick, foolish shit can you dream up? What kind of irrational dreams would you follow? What’s left to pursue?

In other words: “What would you do if money were no object?”, the question we were originally too baffled to answer.

The answers to the Dollar Bill Game

I’ve played this game with many people over the years. Here are some common themes and what they might mean. (Everyone’s situation is different, so your mileage may vary.)

If everything you did was for yourself…

At a certain point, did it occur to you to pay off your parents’ home? Your brother’s student loans? Did certain causes or charities make themselves priorities? Or were you too busy selecting your fourth yacht for your legions of yorkiepoos?

If this was you, you need to look deep inside yourself. Maybe this means you have a very clear and ambitious vision. More likely, it means you need to work harder to cultivate empathy. No matter how little money you have, remember that someone you love surely has less.

If nothing you did was for yourself…

It’s awesome to be loyal and empathetic.

But if you used your imaginary windfall to pour money into the needs and wishes of your family, friends, and community and left none for yourself… you have a problem.

Consider that money has the power to destroy relationships. It can spoil children, make friendships awkward and family bitter.

It’s possible to get this result out of a genuine sense of adoration for the people around you. But more likely, there is something holding you back from a healthy sense of self-care. Maybe being a caretaker or a helper is your only real passion. Maybe your identity is too tied up in other people. Don’t pat yourself on the back and congratulate yourself on your selflessness—this is not healthy! I’ll tell you why.

If the only thing that makes you feel fulfilled and happy is taking care of others, you probably subconsciously don’t actually want those people to become independent. If they’re strong enough, stable enough, or mature enough not to need your help all the time, you just lost your primary identity. This may lead to a codependent relationship with the people you perceive to “need you.” You may sabotage their success, or lash out at them, or become depressed when they move on, because when they succeed, it hurts you and deprives you of your sense of purpose.

Remember: there is only one you. There are reasons you’re here on this planet that aren’t tied to the parents you cared for, the children you raised, or the partner you fell in love with. Caretaking is a beautiful human experience, but it can’t take the place of a healthy sense of self.

If you ran out of ideas…

You probably haven’t interrogated yourself thoroughly enough to know what you want out of life. There isn’t anything wrong with you, but you might be setting yourself up for one hell of a midlife crisis when you realize you have a stack of unexpressed, unacknowledged dreams and goals.

Dig deep and ask yourself what you would regret leaving undone on your deathbed. What brings you a sense of pride? What activities rejuvenate you emotionally? And what scares you, yet also attracts you? Wake the dragon sleeping within your tiny bunny’s heart.

Alternatively, you may just be someone who’s very content with their lot in life, and there isn’t much you want that money can buy. In which case, holy shit you’re well-adjusted! Congratulations. I’m sure you’ll be beatified any day now.

If some (or all) of your key life goals are missing…

I’ve always wanted to write a novel, and I’ve always maintained the reason I don’t is I’m too busy working (i.e., making money). But the first time I played the Dollar Bill Game, guess what didn’t appear anywhere in my fantasy of wealth? That’s right—I still didn’t write a novel, even in the tiers where I had long since quit my job to live full-time on my sprawling ranch of blind rescue horses.

It made me realize money wasn’t what kept me from writing—it was fear of failure. And money can’t buy a cure for that fear.

You may tell yourself money is the reason you don’t follow your dreams—but that’s not always the case. Sometimes money is just an excuse and there’s something else holding you back.

And that’s okay! It’s okay to be afraid of your own goals. That’s proof of how precious they are to you. It’s not something you need to work through all at once, but you owe it to yourself to be honest about obstacles you face.

Money is so often the reason we don’t do things that it becomes an easy scapegoat. In my case, knowing what kept me back was fear (not money) kicked my ass in exactly the way I needed it to be kicked. I started to work on a crappy young-adult novel during my lunch breaks at work. I’m nowhere near finished, but I’ve done more work in the last year than I did in the previous ten.

Alternatively: Some dreams are better off as fantasies. And there’s absolutely nothing wrong with that.

You may say you like the idea of retiring to a cabin to fish every weekend more than you like the reality of it. The last “fishing trip” I went on was with Piggy. We didn’t exactly “fish,” so much as “scarf three blocks of expensive cheese in the freezing rain before giving up and hightailing it to the local hot springs.” Life is an adventure, and you must be free to follow whims over plans!

If you got lots of tangible goods…

Were most of your purchases things like… mansions? Boats? Cars? Clothes? Jewels? DID YOU BEDAZZLE YOUR BOATS WITH JEWELS?! You did, didn’t you?

If you have a million bucks to throw around, yes, by all means: live a little. But if most of the things you want fall into the category of expensive toys, you can never and should never be wealthy, because the things you want aren’t really worth getting. The dopamine you get from acquiring nice things is short-lived; you kill the planet with your mindless consumption; and your accumulation of status symbols will not attract the kind of people with whom you want to fill your life.

You need to go back to the beginning and ask yourself “What is the point of money?” (Hint: the answer is not “more money” and it is also not “jet skis.”)

If you immediately dropped big chunks of your life…

Did you quit your job, divorce your partner, or move away as soon as possible? Maybe around the thousand or ten-thousand dollar mark? It means those things are making you so unhappy that you’re in emotional debt.

To whatever extent you are able, don’t use money as your excuse. Start planning and implementing your escape now. Today, in fact. If some part of your life is so wrong and so bad that you would use a windfall just to get it the hell away from you, you’re probably too emotionally exhausted and unhappy to enjoy everything that’s going right.

We’ve got a whole workshop to help with this part, by the way. Even if you just suspect you’re burned out enough to run screaming for the hills the moment it’s possible to escape from your job or responsibilities, look into our Burnout Workshop. It might make a few things crystal clear!

You saved or invested on every round…

We are huge advocates of both of these things, but human beings are irrational animals who gain happiness—to some degree—through frivolity. Travel, even if you’ll gain nothing from it. Donate, even though you aren’t totally financially comfortable. Take risks because you can.

The serial-saver may incorrectly feel that money can insulate them from uncertainty. Money dulls the edges of a lot of life’s trials, but a vast savings account will not keep you from dying! That’s right: when you’re sucked down to hell, your sweet money will remain here on earth and pass into the hands of future generations of assholes. Some great grand-niece will use your hard-earned fortune to pay for out-of-state tuition at a liberal arts college, and she’ll take out loans without comparing interest rates, and she will pay minimum-payments only, and she will take seven years to graduate.

In other words: it’s your life. It’s now or never. You ain’t gonna live forever! You should just want to live while you’re alive.

And keep your heart open… like an open highway…

(God I hate this song. Who the fuck are all the people he’s talking about? Who’s Frankie? Who’s Gina? Who is the kid in the music video being paid to pretend he likes Bon Jovi enough to risk being hit by a truck for the privilege of seeing him perform? Is he Frankie???)

How did you answer the juiciest questions in the Dollar Bill Game? Tell us all about it with a comment!

An earlier version of this post was published in January, 2017.