Do you have younger mentors?

When learning something new and hard, here's a case for heeding the cubs.

Warmup

We’re keeping up with the kids this week. So this N2L post is going out Sunday to give us an early start.

And speaking of being able to keep up, Spartan Race, the world’s largest obstacle course racing company, right now is offering a FREE RACE of any length in 2024 or 2025 to people who purchase a copy of my new book, NOT TOO LATE.

This offer is good even if you bought the book months ago. And if obstacle course racing isn’t your jam, give the code to someone who might like to give it a go!

(Click button below to get your code; available while supplies last.)

Summary

Reverse mentoring — where a younger person instructs the older one — gained traction in the 1990s as a way to translate fast-moving technology skills between generations. General Electric CEO Jack Welch specifically championed the idea. (Source: BBC)

The concept picked up steam in the workplace during the pandemic. Hybrid working. Social equality issues. Figuring out Zoom and TikTok. All of these things required knowledge-sharing between the generations in new ways.

And now, there’s Generative AI. Enough said.

Today, I’m going to make the case for why listening to younger people can be pivotal to helping you master something new and hard — at work or in your personal life.

After a weekend of difficult news where we've been reminded of what divides us, this is one small idea about how to unite us — at least generationally.

Let’s get it done.

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The first time I laid eyes on Cali Schweikhart, pictured with me above, she was a blaze of red hair running around the local high school track in my hometown.

I sort of knew who she was. I’d completed a couple of obstacle course races at that point. Local lore had it that she was a 20-something wunderkind in the sport, having won her first Elite race on a brutal course in New Jersey.

For months, I studied her respectfully from afar. I looked at …

• What brand hydration vest she used.

• How she placed her feet as she ran.

• The degree to which she leaned forward when pulling a tire around the track. (The tire was attached to a vest she wore.)

One day, we started running on the track at the same time. I kept up with her for the first lap. Then, like a thoroughbred, she looked over her shoulder, grinned and was gone.

Cali was young enough to be my daughter. I wanted her to be my teacher.

The failure email

I networked around town. Got an email introduction. I was worried she wouldn’t write back. But she did.

We had coffee. I was definitely a little nervous at first. I’d never done the reverse mentor thing. But Cali was everything you’d want a teacher to be.

Gracious.

Kind.

Instructive.

Confident.

Not condescending.

We discussed obstacle course racing techniques. We shared our other passions (Harry Potter among them; she has a lightening bolt tattoo on her wrist.) I talked some.

But mostly, I listened.

There was a race that weekend in New Jersey. Both of us attended. It was my sixth race and first attempt at a half-marathon length. Things took a very bad turn. The weather was cold. I was wearing all the wrong clothing. Once I got wet at a water obstacle, my body seized up. I couldn’t stop shaking.

At Mile 8, I quit the race.

This might have been the end of my obstacle course racing journey. For 24 hours I wallowed in misery doomscrolling through my Instagram feed looking at photos of finishers. Doubt pounced: maybe I was too old for this sport.

Then, I noticed my young mentor had DMed me on Instagram.

“How did it go today?”

I wrote her back confessing my DNF (Did Not Finish) scenario. I was embarrassed not to have finished. But I also wanted comfort from someone who’d been there. (She finished #3 in the women’s Elite category)

Instead, I got something better back from Cali.

Information.

Information on the proper material of clothing to wear. On the right gloves to buy (these big neoprene mitts). On how to carry a windbreaker in a plastic baggie to have something dry to put on after a cold water obstacle. A recommendation of two other young women who would eventually become my formal coaches.

Without Cali’s mentorship that day, I’m not sure you’d be reading this.

Recently, she flew from Colorado to speak with me on stage here in New York for my book launch event. For an hour, the audience got to hear give-and-take from a 52-year-old and her (almost) 28-year-old teacher.

I learned even more from Cali that day. Everyone there did too.

The choice

As we age, there’s a moment where we go from being the youngest person in the room to the oldest. It’s not really a “moment,” but it feels like it.

One day, you just notice.

There are two options: fight it or love it.

If you fight, you’ll be that person constantly telling old war stories trying to establish your dominancy. The one who younger people patiently humor while hoping it will wrap up soon so they can get back to whatever they were doing.

It’s not that war stories are bad. But you want someone to ASK you to tell them.

If you fight, you’ll also miss out because you aren’t listening to younger people. And if you aren’t listening, you aren’t learning. And if you aren’t learning, you aren’t getting better. And if you aren’t getting better, you are becoming obsolete.

You cannot pursue new challenging things with any success if you aren’t open to learning, unlearning and relearning.

But if you instead love being around younger people and respect their energy, differences and fresh thinking, it will change you. For the better.

Will you sometimes feel frustrated? Sure. There will be that Millennial who can’t stop talking about himself; the hot-headed Gen Z kid with all the answers (none of them remotely correct), the occasional piece of advice you just know is boneheaded.

Mostly though, you’ll stay current and not get left behind. In technology. Your speech. Your attire. Your open-mindedness. Your physical training — particularly if you pair yourself with the best younger people.

Sure, your children and grandchildren also can help you stay current. But there’s something unique about a non-familial reverse mentorship that can transcend the natural power dynamic that exists with our relatives.

The ripple effect

Once you’ve got one younger mentor, chances are, you’ll add others.

Two years ago, I left a pretty secure job as the Chief Content Officer at a well-known media brand: Consumer Reports. At 51 years old, I joined a tech start-up called SmartNews, which is a Tokyo-based news aggregator.

I’m one of the oldest people working at the company. My boss and the CEO are younger than I am. Every day, I’ve got a cadre of 20-, 30- and 40-something year-old employees teaching me about engineering, Generative AI and product development.

A few have become personal mentors. One young man spent an hour giving me a Substack tutorial. A 30-something woman who now works at Facebook wrote me a 19-page primer after I asked her how younger people are thinking about the Israel-Gaza war.

It’s not a one-way street. Some of them come to me for advice on how to navigate managerial complexities, politics, salary negotiations, and yep — even their love life. (Ok to share this photo on my dating app?) Experiences isn’t everything, but it does count for something.

Speaking of experience, last year, I took a group of 10 SmartNews employees (I was the oldest) on a Spartan Race in Monterey, Calif. and shared my knowledge about climbing a 17-foot rope and throwing a spear.

That’s us above. The kids did great. :)

(Note: if you download the free SmartNews app, heads up that we’re testing a new, highly-polished version that you’ll start to see in the weeks to come.)

Cooldown

Before we close out, if you are now thinking about introducing some young blood into your life, here’s some additional food for thought.

Shorter read: Some great tips here about how not to screw up a mentor/mentee relationship on either end from Harvard Business Review. Alert: There’s actually something called “mentorship malpractice.”

Medium listen: Are you worried you might look foolish to a younger mentor? In a thoughtful discussion on the Stubbornly Young podcast this week, the host Dave Tabor and I get into the shackles this mindset can bring.

That’s it. As always, find something you love. Dig in. Stick with it when things get hard. Find some younger mentors. Listen to them, learn, and get better.

Wendy