“When I was your age” and other annoying phrases boomers use lecture younger generations

We’ve all been there. You’re venting about student loans, the impossible housing market, or the fact that entry-level jobs now require five years of experience, and suddenly Uncle Bob chimes in with “When I was your age, I pulled up my bootstraps and worked my way up from the mailroom.”

Cue the internal eye roll.

Look, I get it. Every generation has faced challenges, and older folks often share these stories because they genuinely want to help. My own parents have dropped a few of these gems over the years, and I know they mean well.

But here’s the thing—some of these phrases can feel pretty tone-deaf, especially when they ignore how much the world has changed. Whether it’s dismissing technology, oversimplifying complex problems, or making sweeping generalizations about “kids these days,” these well-intentioned comments often miss the mark.

Today, we’re diving into some of the most cringe-worthy phrases that get thrown around, and why they might not be as helpful as intended.

1. “When I was your age…”

I remember complaining to a family friend about rent prices, and he launched into this exact story. He genuinely couldn’t understand why I didn’t just “save up and buy” like he did in his twenties.

This hits different when you’re staring down a $500,000 starter home that would’ve cost $50,000 or even less in 1980.

Here’s the reality check: what cost $15,000 in 1975 would cost about $90,000 today when adjusted for inflation. But actual home prices? They’ve skyrocketed way beyond that.

According to some sources, the median home price has increased roughly 121% since 1960, while household income has grown less than 30%. 

The math just doesn’t add up the same way anymore.

2. “Just walk into the office and ask to speak to the manager”

My dad actually said this to me when I was job hunting after university. He meant well, but I had to gently explain that showing up unannounced would probably get me escorted out by security, not hired.

The job application process has completely transformed. Most companies don’t even accept paper resumes anymore—everything goes through online portals, applicant tracking systems, and multiple rounds of interviews.

Walking into an office today without an appointment is more likely to annoy the receptionist than impress a hiring manager. Plus, the person at the front desk probably has zero influence over hiring decisions anyway.

I’ve got colleagues who’ve tried the “show up in person” approach, and it almost always backfires. Companies have structured processes now, and bypassing them doesn’t show initiative—it shows you can’t follow basic instructions.

The modern job hunt requires navigating LinkedIn, crafting ATS-friendly resumes, and mastering video interviews. It’s a different game entirely.

3. “Back in my day, we didn’t need participation trophies”

This one always makes me chuckle because, plot twist: boomers were the ones handing out those participation trophies in the first place.

I’ve heard this from relatives at family gatherings, usually while complaining about how “soft” younger generations have become. But here’s the thing—eight-year-old me didn’t march into the trophy shop and demand recognition for showing up to soccer practice.

The adults made those decisions. They organized the leagues, bought the trophies, and handed them out at the end-of-season pizza parties.

Now those same adults are criticizing us for receiving what they gave us. It’s like blaming a kid for eating too much candy after you filled their Halloween bag.

The irony is that most of us who got participation trophies knew they weren’t real achievements. We could tell the difference between the plastic trophy everyone got and the shiny one that went to the actual winners.

But somehow we’re the entitled ones for accepting what the previous generation created and distributed.

4. “You just need to work harder”

This phrase drives me up the wall, especially when it comes from someone who landed their career-defining job through a college buddy’s dad’s connection.

A colleague of mine works two jobs, freelances on weekends, and still can’t afford to move out of her parents’ house. When her uncle suggested she just “wasn’t working hard enough,” I watched her face go completely blank.

The idea that success is purely a function of effort ignores so many factors that have shifted over the decades. Healthcare costs, education expenses, and housing prices have all outpaced wage growth dramatically.

Previous generations could often support a family on one income. Today, dual-income households are struggling to afford what single earners could manage thirty years ago.

Don’t get me wrong—hard work absolutely matters. But acting like it’s the only variable in the success equation is just willfully ignorant of economic reality.

When someone’s already grinding 60+ hours a week and still can’t get ahead, maybe the problem isn’t their work ethic.

5. “Kids these days are always on their phones”

I hear this one constantly, usually from people who spend their evenings glued to cable news or scrolling Facebook for hours.

Here’s what older folks often miss: our phones aren’t just entertainment devices. They’re our cameras, maps, books, notebooks, banking systems, and primary way of staying connected with friends and work. When you see a young person on their phone, they might be paying bills, checking work emails, or video-calling a friend across the country.

Meanwhile, the same people criticizing phone use will spend three hours watching cable TV without seeing the irony. At least our screen time is often interactive and social.

The real difference is that our digital lives are more visible. When someone reads a physical newspaper for an hour, nobody bats an eye. But scroll through news on your phone for ten minutes? Suddenly you’re addicted to technology.

It’s the same behavior, just different tools.

Final words

Look, I want to be clear about something—most of the time, these phrases come from a place of love and genuine concern.

When my relatives share their “back in my day” stories, they’re not trying to be dismissive. They’re sharing what worked for them, hoping it might help. The problem is that the world has fundamentally changed in ways that aren’t always obvious if you’re not living through them as a young adult.

Housing costs, job markets, technology, and social structures have all shifted dramatically. What worked in 1980 might not work in 2024, and that’s not anyone’s fault—it’s just reality.

Instead of getting frustrated (though trust me, I still do sometimes), I’ve started approaching these conversations differently. When someone drops one of these phrases, I try to share specific examples of how things have changed rather than just rolling my eyes.

Sometimes it leads to genuinely interesting discussions about how different our experiences really are.

The key is recognizing that every generation faces unique challenges. Boomers dealt with their own struggles, just like we’re dealing with ours. Maybe instead of lecturing each other, we could try listening and learning from our different perspectives.

After all, we’re all just trying to figure this life thing out.