How to Travel Time and Ensure a Better Future: Get Older Friends

Age-gap friendships can enrich your life.

Let’s start with the problem all of us have, no matter our race, age, or culture:

We suck at predicting the future.

According to Daniel Gilbert, Ph.D., Harvard psychology professor and author of Stumbling on Happiness:

“Most of us have a tough time imagining a tomorrow that is terribly different from today, and we find it particularly difficult to imagine that we will ever think, want, or feel differently than we do now.”

And because of that, we tend to make short-sided decisions that might hurt us in the long-term and lead to regret.

But there’s one easy way to avoid this blind spot and make smarter choices in all areas of your life: Get friends from older generations. Because they’ve already lived through it, they can guide you and explain how you’ll most likely feel in those moments—it’s kind of like hopping into a time machine and going into the future to see how everything turned out.

Unfortunately, Millennials are far less likely than Gen Xers or Baby Boomers to have a close friend from an older generation. So let’s fix that. I’ll explain the key benefits of having good friends who are much older than you — and how you can start finding them today.

You’ll be more ready for life-changing events

When you’re in your 20s and 30s, you’ll go through some big life events: Buying a home, getting married, starting a family, starting a new career, etc.

To help you make the best decisions (and avoid the worst ones), it’s important to know what you’re getting into and what’s at stake. For example, it’s one thing to read a book about raising kids while running a company; it’s another thing to talk to a friend who actually lived through it.

“The best part about being my age is knowing how my life worked out.”

— Scott Adams

Getting advice from older friends you respect and admire can help you sidestep many issues or, at the very least, prepare you so you’re not “caught off guard” when they happen. They’ll tell you what it’s really like, what they learned, and how they used those experiences to make themselves better.

But if you only have friends with people your age — people who’ve never gone through those struggles (or are too young to know how they turned out)— you won’t have that knowledge.

You’ll get the truth your parents will never tell you

What’s the difference between asking your parents for advice versus asking for a friend who’s the same age as your parents?

Your parents won’t always tell you everything in explicit detail. Hell, in some cultures, it’s damn-near taboo for parents to open up. (Like mine.) But thankfully, my older friends tell me the honest truth. They give me no-holds-barred stories about what certain situations are really like that few parents would tell their kids.

Also, there’s a chance that you don’t get along with your parents or you don’t want to live the life they lived. In that case, their advice would be “bad advice” because it would be so off from what you want to achieve. Instead, get feedback from older friends who you admire, which will push you in the right direction.

You can see how your decisions work in the future

Whenever I have a life decision in front of me, I like to do my research and consider the pros and cons. But after that, I always ask my older friends. Because whether it’s their experiences, regrets, or even length of life, they can give me a perspective I would never have from my life or from friends my age.

Two years ago, I had an itch to sell everything, leave the US, and go to Europe to travel and find a new home. I knew the benefits, sure, but I had a few nagging doubts—specifically about “missing out” on life back at home.

But when I asked my older friends, they put things in perspective. They thought it was a great idea to spend several years of my life in my early 30s to explore the world. And they assured me I wouldn’t miss anything.

In this example, I hopped in my “time machine,” went to the future, got guidance, and made the best choice I could. And a few months later, I went on my trip and never looked back—and it turns out they were right.

You’ll make the most of the time you have now

It’s easy to think you’ve learned a lot about life and that life will pretty much be how it is now if you’re 26 and all your friends are 26.

But when you talk to a 45-year-old, don’t be shocked if they smack some sense into you.

“In my practice, I notice that many twentysomethings — especially those who surround themselves with other twentysomethings — have trouble anticipating life… They need something to remind them that life is going to continue on past their twenties, and that it might even be great.”

— Dr. Meg Jay, “The Defining Decade”

They’ll remind you there’s still so much to experience—and even though you think you know a lot now, wait 2 years and you’ll realize you knew nothing 2 years ago.

At the same time, they also remind you of the importance of making the most of your life. Of not taking anything for granted. Of not waiting too long to get started.

I have friends in their late-70s that always remind me how important it is to live your life now. Because even if you take great care of your body and health, things change as you age. Joints don’t work as well. Your endurance isn’t as great. And it’s all the more reason to take advantage while you have the physical abilities to do all the things you want.

One of the biggest lessons I learned when I was in my 20s was that youth doesn’t last forever. But back then, I noticed many people my age seemed to be ignorant about that and ended up wasting the prime of their life. But once I realized time was fleeting, it fired me up to make the most of it—and it made all the difference in my life.

The future is here: How to get started

Start simple. Talk to your neighbors who might be in a different generation. Talk to people in your company who are older than you. Hang out with older members in your clubs or organizations.

In my experience, people from different generations are often thrilled and honored to help younger people. Be curious about the things they’ve done and seen. And more importantly, be humble and open-minded when you ask for their wisdom and advice.

There are countless stories of how age-gap friendships can enrich your life.

And it can help create a future better than you could’ve ever imagined.

The Mini Post-Grad Survival Guide

A 5-day email course with tips on budgeting, investing, and productivity for 20-somethings. Sign up for free.

Featured in Esquire & GQ. Founder. Full-time traveler. Ready to upgrade your life? Get my 5 life hacks to boost your results here →

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store