If you could ask a question of yourself, 20 years in the future, what would it be?

future-self

It sounds like one of those stupid party games, right? In the same ballpark as “which 10 albums would you take with you to a desert island?” It’s an entertaining conundrum when you’ve had too many cocktails, but in a sober moment, who cares?

Well, you might not think that after watching this 4-minute teaser for a new documentary (yet to be completed) called Later That Same Life.

Here’s the basic premise: In 1977, a 18 year old guy named Peter Emshwiller filmed himself asking a bunch of questions of his future self. Almost four decades later, an older and ostensibly wiser Emshwiller finally responds.

The younger him asks some unsurprising questions, like “Are you exceedingly rich?” Exactly what you’d think an 18 year old would want to know.

But then comes a moment that’s like a sucker punch to the heart, when the young Emshwiller asks about his parents.

“I don’t know what I should tell you,” the elder Emshwiller says, his face grimacing. “You should spend as much time as you can with them, okay? Spend more time with dad.”

If you’ve lost a parent, this exchange is especially difficult to watch. Because there’s probably a part of you that wishes you could go back in time, find the younger you, and tell him, “Stop being such a self-obsessed asshole and call your damn dad!”

But of course you can’t. And neither can you interview your future self and ask him, “What should I be preparing for? Should I start hoarding canned goods? Is the next 20 years going to be awesome or awful?”

“One of the biggest sources of anxiety in life is uncertainty about the future,” says Art Markman, Ph.D, a professor of psychology at the University of Texas at Austin and the author of Smart Change. “We want to know that things will work out for us. I often say that the narrative of our lives is only clear looking back on it.”

So why bother with this little parlor game at all? Why ask questions of somebody who’s unable to answer them, or more depressingly, who’ll only be able to answer when it’s too late to do anything about it?

You should bother because if you ask the right questions, it might actually make a difference to the future you.

I decided to try an experiment. I reached out my friends, on social media and otherwise, and gave them this challenge: You’re able to ask one question to the future you, 20 years down the line. What do you ask?

I got dozens of responses, and I started to notice some patterns. All of their questions fell into one of four very different categories.

First, there were questions that assumed the person’s future happiness depended on their making the most lucrative financial investment . . .

David P: “What stocks should I buy, and when should I sell?”

Michael J: “Why didn’t you buy any of that Zuckerberg-Weyland-Yutani stock when it was still just Facebook, you dumbass?”

Jed R: “What was the largest Mega Millions jackpot of the last 20 years and what were the winning numbers?”

Second, the tongue-in-cheek predictions of a dystopian future . . .

Tom M: “With the total advent of digital and virtual reality, will people have to leave their homes for anything?”

Jeff S: “When will the zombies come for me?”

Brendan B: “If you could do it all over again, would you really clone yourself so many times?”

Christopher K: “What kills us most? Climate change? Virus? Or nuclear war?”

Third, the questions that revealed regrets about how they’re pretty sure they’ll be screwing up their lives in the coming two decades . . .

Corey L: “What was the biggest mistake I made as a dad?”

JM: “Was all of that job stress worth it, huh dumbass?”

Stephanie K: “Why were you always so anxious?”

Allison B: “Was it a good choice to watch ALL THE TV?”

Eric G: “What self-sustaining measures have you made in preparation of dying alone?”

And then a fourth category, which was by far the most revealing. These questions weren’t as jokey, and no attempts were made to predict what would happen in the future. Instead, they seemed genuinely curious, and hinted at more than a little yearning.

Gary R: “Do you think you’ve created your best thing yet?”

Emma K: “Did you fight for yourself?”

Christopher M: “What did you do to survive the odds on the diagnosis that should have had you dead by now?”

Thom K: “Did you ever finish it, or did you keep putting it off?”

Mike J: “Is there something you didn’t do that makes you sad?”

Diane S: “Aren’t you glad you kept telling yourself ‘It’s never too late’”?

I shared all the questions with Hal Hershfield, Ph.D., a social psychologist at UCLA, and he agreed that the fourth category demonstrated how these sorts of exercises can be worthwhile.

Hershfield has studied the complex relationship between who we are now and who we’re hoping to become in the future.

Most notably in 2009, when Hershfield and his then colleagues at Stanford took a closer look at how and why people felt a connection to their “future self.”

What he found is that people who “have a stronger emotional connection to their future selves are more likely to make sacrifices today for better outcomes down the road.”

Meaning, if your future self isn’t just some random abstract idea, but a flesh and blood human being that you can visualize and empathize with, you’re more likely to do things like save money and not eat an entire pie in one sitting.

But that’s not really where this gets interesting. Sure, if you’re a smoker, it might be helpful to imagine interviewing the future you, and asking him a question like, “How many chemo treatments do we have left?”

But what if we framed the questions not in terms of what we shouldn’t have done, but what we could still do?

Gary S’s question is the one that gave me pause.

“Do you think you’ve created your best thing yet?”

Doesn’t matter what field you’re in, or what you’ve devoted your life to doing, that’s a question you want your future self to answer with a big, confident smile, and not just stare sheepishly at his feet and hope somebody changes the subject.

What will he say? How the hell should we know? We don’t have a damn time machine. And that’s not the point.

Asking these questions of your future self have nothing to do with how your future self answers them. By the time he shows up for the interview, you’ll both know how it turned out anyway.

The question is really for you. Present day you. It’s a way to remind yourself that time is fleeting, and 20 years goes by faster than you think.

What are you doing today to make sure those decades don’t disappear with nothing to show for it?

Forget asking questions like, “Did we get rich?” or “Did I become famous?” or “Did I buy a moon condo?”

Ask questions like, “Did you write that novel?” or “Did you end up running in the New York City marathon?” or “Did you finally quit the job that’s eating your soul and find something that makes you happy?”

This isn’t wish fulfillment. Asking “Did I buy the perfect stock at the perfect time and now I live in a 9 bedroom mansion with a moat?” won’t tell you anything (other than that you apparently think money buys happiness.)

But a question like, “Did I finally figure out how to start my own stock portfolio?”, well, that’s like giving yourself a gentle nudge in your own back.

If being rich really is the ultimate goal, that’s fine. But don’t let the future you get away with a yes or no answer, says John D. Mayer, Ph.D, a psychologist at the University of New Hampshire.

“A better question than, ‘Did you get rich?’ or ‘Did you actually finish that novel?’ would be ‘How did you get rich?” and ‘How did you stop procrastinating and write that novel?’,” he says.

Consider this a personal challenge for the final weeks of 2015. Take a few minutes and think about the future you, 20 years from today. What are you gonna ask him?

How are you going to become what you hope he is?

What’s your version of, “Do you think you’ve created your best thing yet?”

Because your best thing isn’t going to build itself.

(This story originally appeared, in a slightly different form, in Men’s Health.)