I spend most of my time bouncing between coffee meetings with Gen Z marketers, Zoom calls with millennial editors, and the occasional lunch with older investors who cut their teeth in the pre-digital era. The conversations are usually great—until a few well-worn boomer catch-phrases slip out and the room’s energy drops faster than a phone battery on 3G.

The words themselves aren’t evil. They just carry hidden messages that rub younger ears the wrong way: you’re lazy, you’re entitled, you don’t understand how the world really works. When that sub-text leaks through, collaboration stalls. More importantly, no one feels heard.

Below are the nine repeat offenders I keep hearing, why they grind everyone’s gears, and what could be said instead. If you’re a boomer who wants to connect across generations—or you have a beloved boomer in your life—this list is pure gold. Let’s dive in.

1. “Back in my day…”

Nothing triggers an eye-roll faster than this nostalgia opener. It usually leads to a long story about walking ten miles to school or surviving without Wi-Fi.

Why it annoys people

• It frames the present as inferior before the conversation even starts.

• It shuts down any discussion about today’s challenges because “the old days” are suddenly the gold standard.

• Younger listeners feel lectured, not included.

A better swap
Try “Here’s what worked for me when I was starting out—does any of that feel useful?” Same story, but now it invites dialogue instead of dismissing modern reality.

2. “Kids these days don’t know the value of hard work”

Translation: You’re lazy. It’s a blanket judgment that ignores the fact that gig work, endless side-hustles, and always-on email can be exhausting in brand-new ways.

Why it annoys people

• It erases the brutal hours many millennials and Gen Zers already log just to stay afloat.

• It comes off as self-congratulation masked as social commentary.

A better swap
Ask, “What does hard work look like for you right now?” You might learn about 60-hour coding sprints or night shifts at two jobs. Respect follows.

3. “When I was your age, I already owned a house”

Boomers bought property when a suburban three-bed cost the same as a modern city’s annual rent. Quoting that milestone now sounds tone-deaf.

Why it annoys people

• It ignores the wage-to-housing-cost gap that’s tripled since the 1980s.

• It implies failure if someone hasn’t hit a completely different economic benchmark.

A better swap
Share the principle, not the purchase: “One big financial move that helped me early on was building equity—what kind of long-term assets interest you?” Now you’re offering guidance, not bragging.

4. “Because I said so”

This phrase leaks out of boardrooms and family dinners alike, shutting down curiosity in a single swipe.

Why it annoys people

• It kills trust. Adults don’t respond well to parental ultimatums.

• It suggests hierarchy matters more than logic, which scuttles innovation.

A better swap
Say, “Here’s my reasoning—let me know where I’m off base.” You still lead, but you keep brains switched on around you.

5. “That’s just the way things are”

Also known as the progress killer. Every disruptive company I’ve built thrived on asking “but why?” This phrase slams the door on that question.

Why it annoys people

• It paints systemic problems as immovable, which frustrates anyone trying to improve them.

• It signals you’re unwilling to rethink outdated norms.

A better swap
Try, “The system works like this right now—how could we tweak it?” Suddenly you’re an ally, not a gatekeeper.

6. “You’ve got it so easy with all this technology”

Sure, smartphones eliminate paper maps. They also introduce constant notifications, algorithmic anxiety, and the joy of troubleshooting Zoom five minutes before a pitch.

Why it annoys people

• It dismisses modern stressors as convenience.

• It suggests achievements earned with tech are somehow less legitimate.

A better swap
Ask, “Which tech tool saves you the most time? I’m curious.” You’ll learn something—and maybe modernize your workflow.

7. “Money doesn’t grow on trees”

We know. Gen Z watches their bank app like a hawk. Saying this implies they’re careless, even when they’re living paycheck to paycheck amid record inflation.

Why it annoys people

• It feels patronizing, as though basic budgeting is a new concept.

• It can sting when someone’s already hustling multiple gigs to cover rent.

A better swap
Offer specifics: “When cash felt tight for me, I tracked every expense for 30 days. Want me to walk you through that process?” Practical beats preachy every time.

8. “If it ain’t broke, don’t fix it”

Great for grandfather clocks, terrible for business models in a fast-moving world.

Why it annoys people

• It stalls experimentation, which younger teams view as oxygen.

• It signals comfort over growth, dampening motivation.

A better swap
Say, “Let’s stress-test what’s working—maybe we’ll uncover tweaks that make it even better.” Now the door to improvement stays open.

9. “We didn’t need participation trophies”

The classic dig at younger generations’ self-esteem culture. Ironically, plenty of boomers were the parents handing out those trophies in the first place.

Why it annoys people

• It belittles anyone who values recognition for effort, not just victory.

• It reduces nuanced conversations about mental health to a cheap punch-line.

A better swap
Frame the underlying lesson: “Focusing on growth over instant praise helped me—how do you stay motivated after setbacks?” Shared experience beats shaming.

The bigger picture

Each of these phrases shares a common flaw: they build a wall instead of a bridge. The speaker signals “I’ve figured it out—you haven’t,” which guarantees the listener stops listening. In start-ups and families alike, that dynamic kills momentum.

I learned this the hard way. Early in my career I caught myself saying “that’s just the way things are” to a twenty-something developer who wanted to rewrite our entire content pipeline in Python. He pushed back, we debated, and three months later his new script cut our publishing time in half. I retired the phrase on the spot.

How to check yourself

1. Pause before you preach. Ask, “Is this story actually helpful, or does it just make me sound superior?”

2. Lead with curiosity. One genuine question can replace any of the nine phrases above.

3. Share context, not judgment. Offer the lesson you learned, then invite feedback.

4. Update your scripts. Language evolves. So should we.

Final thoughts

Boomers, millennials, Gen Z—we’re all playing on the same field now. Markets move too fast, and problems are too complex for generational turf wars. Ditching these nine phrases won’t solve every conflict, but it will keep conversations flowing, ideas surfacing, and relationships intact.

And if you catch me slipping back into “that’s just the way things are,” feel free to call me out. After all, entrepreneurship—and life—is one long lesson in unlearning what no longer works.