The Healthiest Conversation You’ll Ever Have

Instead of comparing yourself to others, have a conversation with your former selves. It’ll be a healthy measurement of where you’re at in your life.

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A few months ago, I joined a friend for a drink.

I sit down in the chair next to him at the end of the bar. He’s a fashionable guy. He’s wearing a loose gray t-shirt that I could never pull off. A half-full bottle of High Life rests in front of him on the bar. We have a mutual friend who recently moved to New York. Without our connection, though, we see each other less.

Recalling Our Dreams

We catch up with each other’s lives for the next forty minutes or so. Then, we discuss dreams—not our life’s aspirations—our actual dreams. He tells me he has the same dream two to three times a year.

“What?” I smile. I’m curious. I don’t remember my dreams much.

“Yeah,” he nods, “I’m in this enormous airport hangar.” He stretched his arms wide. “It’s empty.” I take a sip of my cocktail and rest my elbow on the bar. He points across the room. “And way over on the other side are a bunch of people standing around. So I skateboard closer to them.” His eyes widen. “And I realize that they’re all my former selves, and I’m the oldest one.”

My jaw drops. “That’s crazy! And you have this exact dream at least two times a year?” I ask. He nods again.

“They ask me what life is like for me now at my age. They want to know how things turned out.”

Remarkable, I thought. It stuck with me since we left the bar. It’s turned into a personal philosophy for me and applying it has made me happier. I’m more relaxed. I wonder how my former self would react to things I tell them. Sometimes I feel I take living in Chicago for granted. It crosses my mind every now and then. I think about my teenage self. He would be amazed. It makes me smile, and I suddenly discover an energy boost.

I think we compare ourselves to others too much. We measure our standing and success based on what we see from other people within our age group: grades, jobs, money, family, travels, activities. It’s natural. Social media can escalate this process. We can often feel behind or inadequate. Or jealous.

Comparing ourselves to others is immensely problematic because we lack information. The better thing to do is measure ourselves to our former selves. You have all the available information you need. You know what you’re most passionate about. You know what your dreams are and were. You know what experiences impacted you. You know the resources you had. And you know what unique advice you’d give to your former selves.

Have a conversation with your former selves. It’s the healthiest conversation you’ll have. You may be surprised when you see how much you’ve grown—or maybe you need a kick in the butt. This is your life. How are you living it?

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A Conversation with My Former Selves

I’ll demonstrate. This is what a brief conversation with my former selves might look like. For clarity’s sake, I’ll combine myself into age groups. I wouldn’t be skateboarding in an airport hangar, though. I’d fall. Instead, I’d walk towards my former selves.

“Hey guys! What’s up?” I ask. My former selves gather around me.

Teenage Rich, wearing Dad’s oversized suit, asks, “So what’s life like at 29? How’re we doing?” Each locks eyes on me, awaiting my response.

“Uh. Well, things are getting better. We have a book coming out in October,” I explain. Their faces beam. Smiles stretch across their faces. It’s impressive to them. “So what kind of questions do you have for me?” Each former self raises their hand. (I was always a good participant in class—as well as a brown-noser). I point to kid Rich.

“Um. I saw you have a lot of pictures of dinosaurs,” he says bashfully. He happens to be wearing a dinosaur shirt.

“What’s that bud?” I lean toward the ground. Teenage Rich nudges college Rich.

“We still have bad hearing,” he jokes. I look up to them with narrowed eyes.

“I heard that!” I point to teenage Rich. “You know it’s your fault, right? Did you really have to listen to music that loud on your headphones?” I shake my head. “You couldn’t just wear noise-canceling headphones when you’re mowing the lawn or on the tractor?” I wear a slight smile.

“I need to be inspired,” he replies with classic typically teenage sarcasm. “It’s my thinking time. Besides, those look dumb.” I roll my eyes and bend toward the ground again.

“Now, what did you say? Dinosaurs?” Kid Rich nods his head. “Yeah! Super awesome, right?” Kid Rich nods again with a smile. (He won the 1994 Wisconsin State Fair Smile contest with that same smile). “What you’re going to realize is that if you’re interested in something, you don’t have to wait to learn about it. You can just go do it. Or read a book about it. Or go watch something about it. You don’t have to spend all of English class dreaming about what you’re going to learn in History class. You can just go learn on your own.” My former selves bobble their heads up and down. “Oh, by the way, pay more attention in your English classes. It would save your future self a lot of headaches.” They smile.

“So what kind of cool things have we done lately?” college Rich asks. He has no style. He wears jeans and whatever free shirt DePaul gave him.

“We go to Spain! And Asia! And we take some trips out west!” I answer.

“Whoa!” teenage Rich shouts. “So we’re a millionaire? I knew we would be!” He spins in a circle (I used to think only people with money could travel out of the country). I bend over laughing, then gasping for air. “What’s so funny?”

“We’re far from it,” I say. Teenage Rich’s face becomes pale. He looks like he just had a heart attack. He was a student of Donald Trump’s How to Get Rich book. “You’re going to be crafty.” I wink to college Rich. “But seriously, the world is going to be so much more open. Traveling costs will actually be pretty reasonable for you.”

“So how was Spain?” college Rich cocks his head. I look up to the rafters and smile.

“It was amazing. It’s the first time you leave the U.S. And it was only a year ago. You’re going to look out at the Mediterranean Sea and just cry. We finally did it. We visited another country after spending our entire life dreaming about it.”

“That sounds really cool,” says college Rich. It’s still hard for him to visualize, though.

I continue, “Traveling outside the country is exactly what you thought it’d be—and all you want to do is travel again. You realize there’s more than just one way to look at life. You can learn about other people and cultures just by simply walking around.”

Each Rich nods and smiles, but they don’t really understand. Kid Rich has a hard time following the conversation, especially. Maybe I’m too boring for him. He probably just wants to talk about Teenage Mutant Ninja Turtles, dinosaurs, and sports.

College Rich steps forward. “So what advice—like life advice—would you give us?”

“Hmm.” I twist my face and look up to the rafters again. After a couple seconds, I look back at them. “I would say, continue to be open-minded and willing to follow your curiosity. It’s going to take you to some odd places, but it’ll work out. Keep people watching too.”

“People watching?” teenage Rich raises an eyebrow.

I laugh. “I know. But observing others will tell you a lot. You can try and understand their emotions. It’ll make you a better person.”

“He’s right,” murmurs mid-twenties Rich. All my other former selves whip their heads around.

“Were you here the whole time?” asks teenage Rich. Mid-twenties Rich smiles to one side and then looks at me. I match his smile and give him a nod.

College Rich looks back to me. “Wait. So what’s 30-year-old us going to be like?”

“Oh, I think we’re going to like him.” I give every Rich a high-five.

Have you had conversations like this before? Have you found it beneficial? What emotions do you experience?