How to Share Wisdom and Overcome Ageism in a Youth-Obsessed Culture

The Wisdom Paradox

Here's something that's been bothering me for years.

We live in a culture that's completely obsessed with youth. Young entrepreneurs are celebrated. Young leaders are praised for "fresh thinking." Young workers are assumed to be more innovative, more tech-savvy, more in touch with current trends.

Meanwhile, those of us who've accumulated actual wisdom over decades of living and working? We're increasingly treated like we're past our expiration date.

It's a weird paradox. On one hand, we supposedly value experience and expertise. On the other hand, if you're over 60 in most industries, you're seen as out of touch, behind the times, maybe even a liability.

I've spent 40+ years building businesses, making mistakes, learning from them, and figuring out what actually works. I've seen economic cycles, market crashes, technological disruptions, and business trends that were supposed to change everything (but mostly didn't). I've accumulated the kind of wisdom that only comes from actually living through stuff.

And yet, there's this pervasive sense that this accumulated experience is somehow less valuable than the "fresh perspective" of someone who's been in the workforce for five years.

It's frustrating. And it's also wrong.

Because here's what I've learned: wisdom matters. Experience counts. And the perspective that comes from decades of living is actually more valuable now than ever – we just need to figure out how to share it in ways that actually get heard.

Why Ageism Is Different (And Harder to Fight)

Let's be clear about what we're dealing with.

Ageism is one of the last socially acceptable forms of discrimination. You can't openly discriminate based on race, gender, or sexual orientation anymore – at least not without serious consequences. But age? People make jokes about "boomers" being out of touch. They talk about older workers "not getting it." They assume anyone over 60 can't possibly understand technology or current culture.

And here's what makes it particularly insidious: it's often internalized.

You start believing the narrative yourself. You apologize for your age. You try to hide it. You downplay your experience because you're worried it makes you seem old and irrelevant. You stop offering your perspective because you assume nobody wants to hear from someone your age.

I've caught myself doing this. Starting sentences with "Back in my day..." and then immediately cringing because I know how it sounds. Holding back advice because I don't want to be "that old guy" who thinks he knows everything.

But here's the thing: holding back your wisdom doesn't make you more relevant. It just deprives people of the insight they actually need.

What Wisdom Actually Is (And Isn't)

Before we talk about sharing wisdom, let's get clear about what wisdom actually is.

Wisdom isn't just knowledge. Any 25-year-old with internet access can accumulate knowledge.

Wisdom isn't just expertise in a specific domain. You can be an expert in your field and still lack wisdom.

Wisdom is pattern recognition across contexts and time. It's the ability to see what matters versus what's noise. It's understanding that most "revolutionary new ideas" are actually old ideas repackaged. It's knowing which battles are worth fighting and which ones aren't.

Wisdom comes from making mistakes and learning from them. From seeing cycles repeat. From understanding human nature doesn't change even when technology does. From knowing that some truths are timeless, even when the surface details shift.

Here's an example: Young entrepreneurs often think they need to reinvent everything. They dismiss what came before as "the old way" and assume their approach will be completely different.

Wisdom says: the fundamentals of business haven't changed. You still need to create value for customers. You still need to manage cash flow. You still need to build relationships and trust. The tools change. The packaging changes. But the core principles? Those are the same as they were 50 years ago.

That's not being resistant to change. That's understanding what actually changes and what doesn't.

The Ways We Inadvertently Make Ourselves Irrelevant

Here's some hard truths: sometimes we contribute to our own irrelevance.

We tell stories that start with "back in my day." This immediately positions us as out of touch with current reality. Even if the story has a valuable lesson, framing it this way makes people tune out.

We dismiss new approaches because "we tried that before." Maybe you did. But maybe the timing is different now, or the technology has changed, or the market conditions are different. When we automatically dismiss new ideas because they seem familiar, we lose credibility.

We complain about "kids these days." Every generation thinks the next one is soft, entitled, or doing it wrong. Every generation is also wrong about this. Complaining about younger generations just makes us sound bitter and out of touch.

We resist learning new tools or platforms. Look, I get it. I don't love having to learn new software every few years. But when we refuse to adapt at all, we reinforce the stereotype that older people can't keep up.

We position our experience as superior rather than complementary. When we act like our way is the only right way and younger people just need to listen to their elders, we create resistance instead of connection.

All of these patterns undermine our ability to share wisdom effectively. Not because our wisdom isn't valuable, but because we're packaging it in ways that make people defensive or dismissive.

How to Share Wisdom That Actually Gets Heard

So how do we share what we've learned in ways that create value rather than resentment?

Frame your experience as a perspective, not a prescription. Instead of "Here's what you should do," try "Here's what I've seen work in similar situations." Instead of "You're doing it wrong," try "Here's a pattern I've noticed that might be relevant."

The goal isn't to tell people what to do. It's to offer a perspective they might not have considered because they haven't lived through it yet.

Connect wisdom to the current context. Don't start with "back in my day." Start with the current situation and then bring in relevant experience. "I'm seeing some similarities between what you're facing now and what happened in 2008. Here's what we learned then that might apply now."

Ask questions instead of giving answers. Sometimes the best way to share wisdom is through Socratic questioning. "Have you thought about X?" "What would happen if Y?" "How does this connect to Z?" Questions make people think rather than resist.

Share your mistakes, not just your successes. Younger people don't need another person telling them how great they were. They need to hear about the mistakes you made and what you learned from them. That's where the real wisdom is. Learning to be vulnerable is a crucial skill here.

Be curious about new approaches. Show genuine interest in how younger people are doing things. Ask questions. Learn from them. This creates reciprocity – when you're genuinely curious about their perspective, they become more open to yours.

Know when to speak and when to listen. You don't need to weigh in on everything. Sometimes the most valuable thing you can offer is your attention and support, not your advice.

Bridging the Generational Gap

One of the biggest challenges in sharing wisdom is the generational divide.

Different generations have different communication styles, different values, and different assumptions about how work should happen. These differences can create friction that makes wisdom-sharing harder. For me, the hard lesson was that my children text and hate talking on the phone.

But here's what I've learned: the differences are smaller than we think.

Yeah, millennials and Gen Z communicate differently than boomers. They're more comfortable with technology, more skeptical of traditional institutions, and more focused on work-life balance and purpose.

But fundamentally? They're dealing with the same human challenges we all dealt with. Building careers. Figuring out relationships. Navigating uncertainty. Trying to make a meaningful contribution. Dealing with failure and setbacks.

The surface looks different. The core is the same.

When you can connect your wisdom to their actual challenges – not the challenges you think they should have, but the ones they actually face – that's when they listen.

This means:

Stop comparing their experience to yours. "When I was your age, I worked 80-hour weeks and never complained" doesn't help anyone. It just creates resentment.

Understand their context. The economic reality they face is different. The social expectations are different. The tools available are different. Your wisdom needs to account for those differences.

Find common ground. What challenges are universal? What fears or hopes connect across generations? Start there.

Positioning Your Experience as Valuable

Here's the strategic piece: you need to actively position your experience as valuable rather than assuming people will recognize it.

Don't apologize for your age or experience. Stop starting sentences with "I know I'm old but..." Just share your perspective confidently.

Translate your experience into frameworks. Don't just tell stories. Extract the principles. Create frameworks that help people understand the patterns you've seen. This makes your wisdom more portable and applicable.

Focus on timeless principles, not outdated tactics. The specific tactics you used 20 years ago might not work now. But the principles behind them probably do. Focus on the principles. This means being strategic, not tactical.

Be selective. You don't need to share everything you know. Share what's relevant, valuable, and timely. Quality over quantity.

Create spaces for wisdom-sharing. This might be through writing, mentoring, teaching, speaking, or advising. Don't wait for people to come ask for your wisdom. Create channels where it can flow naturally.

The Mentoring Relationship Done Right

One of the best ways to share wisdom is through mentoring. But most mentoring relationships fail because they're set up wrong.

Bad mentoring: The older person positions themselves as the sage with all the answers. They tell the younger person what to do. They talk about how things were in their day. They expect the mentee to implement their advice without question.

Good mentoring: It's a two-way relationship. The mentor shares experience and perspective. The mentee shares current context and challenges. Both parties learn from each other. The mentor asks more questions than they give answers.

I've been on both sides of mentoring relationships. The ones that worked were always the ones where I approached it with genuine curiosity about the other person's situation, rather than assuming I knew what they needed to hear.

What Gets Better With Age (And How to Leverage It)

Let's talk about what actually improves with age, because there's plenty:

Pattern recognition. You've seen enough situations play out that you can often predict what's coming before it arrives. This is valuable.

Perspective on what matters. You've lived long enough to know what's actually important versus what just seems urgent. This helps prioritize.

Emotional regulation. Most of us get better at managing our emotions and not overreacting to temporary setbacks. This is wisdom younger people desperately need.

Understanding of human nature. You've dealt with enough people in enough situations that you understand what drives human behavior. This doesn't change with technology.

Long-term thinking. You've seen short-term thinking blow up enough times that you naturally think in longer timeframes. This balances out the tendency toward immediate results.

These are real advantages. Don't downplay them. Don't apologize for them. Leverage them.

Creating Value Without Becoming a Burden

Here's a delicate balance: you want to share your wisdom without becoming the person everyone avoids because they're always "sharing wisdom."

Nobody likes the person who's constantly offering unsolicited advice or telling stories about the old days. That's not sharing wisdom – that's being insufferable.

The key is invitation and timing.

Share when asked. Offer when it's clearly needed. Ask permission before diving into a long story or piece of advice. Read the room and know when people are open to hearing from you and when they're not.

And remember: sometimes the most valuable thing you can offer isn't your wisdom at all. Sometimes it's your time, your attention, your encouragement, or your belief in someone's potential.

Start Where You Are

You don't need to write a book or give speeches or become some kind of guru to share wisdom.

Start small. Start local. Start with the people right in front of you.

Have real conversations with younger colleagues, this could even be your children, but if you choose this, be careful. What you think is mentoring can be seen as meddling.

Mentor someone who's facing challenges you've navigated. Share your experience when it's relevant. Write down the lessons you've learned for your kids or grandkids. Teach someone a skill you've mastered.

Your wisdom has value. Your experience matters. Your age doesn't diminish that – it's precisely why you have wisdom to share in the first place.

Don't let our youth-obsessed culture convince you otherwise.

And don't wait until you're "ready" or until someone explicitly asks. Start sharing now. In small ways. In natural ways. In ways that create value without demanding recognition.

That's how we overcome ageism – not by fighting it directly, but by demonstrating so much value that age becomes irrelevant.

Let's figure out how to do this together. Are you curious about how you can be seen once you hit 60? Let’s have a conversation about this.