Growing up as a millennial meant growing up with Britney Spears and Justin Timberlake (N’SYNC). They were the couple to watch. To this day, die hard fans still fantasize about the two getting back together.
When asked what advice she’d give to her younger self, Britney said:
“Never get married is number one. That’s probably the best advice I could give myself.” – Britney Spears
Contrast that with Justin Timberlake, who said:
“If you only make bad decisions – for the rest of your life, (and) you made one really good decision…marry your best friend.” – Justin Timberlake
As reality would have it, one has been divorced three times, the other is happily married.
This article is how most most advice for young people is unreliable. And of course I have some magic solution to this (keep reading), because I’m an ultra spiritual1 guru.
The scenario: my friend was collecting advice from “older” folks (me) to give to her cousin. Young blood’s about to graduate high school. This is the prompt I was challenged to answer:
What is the ONE piece of advice you’d give your younger self?
This exercise made me realize how hard it is to give fair advice with as little personal bias as possible.
I wanted to give advice that…
- has the maximum positive impact
- is the fairest for younger, more impressionable youth
- doesn’t seem obvious and cliche
After much deliberation, this is what I landed on:
Diversify your experiences.
That’s it.
Diversifying one’s experiences acts as a catch-all, meta-level advice that affects everything else…especially for young people.
What might diversifying one’s experience look like?
- Meet & date different people.
- Work a variety of jobs.
- Pick up weird skills & hobbies.
- Get involved in projects and ventures
- Travel the world.
Basically, my advice boils down to try lots of things.
All this sound great and agreeable to most people. But why is this diversity of experiences especially important, the younger you are2?
Maximizing the advantage of reckless youth
On a trip to Costa Rica, I met two Dutch travelers. They’ve been on the road for 3 months and were only halfway through their Latin America trip. They were broke, and couldn’t be happier. Oh yeah, they were seventeen.
Compare that to many well-to-do, even affluent twenty & thirty-somethings I know back home. We would share our bucket list items, and invariably, world travel or some kind of sabbatical would come up. But they could never pull the trigger3. “Maybe next year,” they’d say.
When you’re young, you’ll have less experiences, resources and responsibilities than when you’re older4.
And it can be the ultimate hidden advantage.
Loss aversion is real. And when you don’t have as much to lose, you have the freedom to take bigger risks:

If you have a well paying career, house with a mortgage, or spouse w/kids, those are all things you can lose. There’s higher risk involved, and your circle of concern often extends beyond your own life.
Those of you reading this with soul-crushing-jobs-but-cushy-paychecks know all too well the term “golden handcuffs.”
It’s an illusion that “things will get better/easier” as life goes on. You and I both know that life looks more like the game Katamari Damacy – we trend towards picking up more responsibility over the span of our lives:
Because the effects of sunk cost fallacy and loss aversion become stronger the older we get, I believe this is the easiest time of your life to take risks:

You might be young and poor, but you have the luxury of being untethered by responsibilities other than to expand the self.
And if you fuck up? You can start over again. Many times.
Maximize your naïveté. Maximize the advantage of reckless youth.
Experiences over things.
I chose to give the advice diversify your experiences in hopes of being as unbiased as possible.
If I’m a scientist, I’m advising you to conduct many experiments5, not which experiment to do. (Unlike Britney, I’m not telling you that marriage is a mistake.)
But to be honest, I do have an agenda:
Promote the idea that experiences are not only what makes life worth living, but that they are more important than material things.
Instead of buying the nicest clothes, spend time with people who don’t care what clothes you wear.
Instead of saving for an overpriced luxury car, use that money to travel the world. Cars break down, but memories are forever.
What is life, but what we remember? So go out and make as many new, good memories as you can.
- https://www.youtube.com/results?search_query=jp+sears+ultra+spiritual ↩
- I’m using youth as a proxy for lack of responsibility. You can be a young twenty something but 3 baby momma’s to answer to – that’s a lot of responsibility, and you’re excluded from what I’m generalizing as “young” in this article. ↩
- Surprisingly, most of these acquaintances have the means to travel; little debt, plenty of savings, many even with six-figure salaries. ↩
- Millionaire teenage app makers and trust fund babies need not apply. ↩
- By the way, a companion piece of advice I have for “diversify your experiences,” is, like a scientist, to journal, reflect, and record your own observations as you go through these experiences. This helps you figure out yourself and life patterns. There’s a time to experience, and there’s a time to reflect. ↩