I love my boomer parents, but I just can’t understand why they can’t let go of these 7 outdated habits

Look, I love my parents. I really do.

But sometimes I sit at their kitchen table, watching my dad struggle to send a simple text message or listening to my mom insist that “kids these days” don’t know the value of hard work, and I can’t help but feel like we’re living in completely different worlds.

It’s not that I don’t respect everything they’ve accomplished or the wisdom they’ve gained over the years. They raised me, supported me through my degree, and cheered me on when I started my own business. I’m grateful for all of it.

But here’s the thing—some of their habits feel so stuck in the past that it’s almost painful to watch. They cling to ways of thinking and doing things that just don’t make sense anymore, and no amount of gentle suggestions or logical explanations seems to help.

If this sounds familiar, you’re probably dealing with the same generational clash I am. Let’s dive into the habits I just can’t wrap my head around.

1. Refusing to embrace technology that would make their lives easier

This one drives me absolutely crazy.

My dad will spend twenty minutes looking up a phone number in an actual phone book when he could Google it in ten seconds. My mom still pays cash at the grocery store while a line of people waits behind her, even though she has a perfectly good debit card in her wallet.

It’s not that they can’t learn—they’re both incredibly intelligent people. But there’s this weird pride in doing things “the old way” even when the new way is objectively better and faster.

I’ve offered to teach them countless times. I’ve shown them how online banking works, how GPS can save them from getting lost, how texting is actually easier than playing phone tag.

But they just won’t budge.

2. Believing that loyalty to one company guarantees job security

This mindset honestly breaks my heart a little.

My parents genuinely believe that if you work hard, show up every day, and stay loyal to your employer for decades, the company will take care of you until retirement. They talk about their careers like it’s still 1985.

I’ve watched my dad get passed over for promotions while less experienced external hires got the roles he deserved. I’ve seen my mom’s company “restructure” and eliminate positions of people who’d been there for twenty years.

Yet they still think job hopping makes you look unreliable. They cringe when I tell them about switching roles to advance my career or negotiate better pay.

The reality is that company loyalty is largely a one-way street now. The most successful people I know—including in my own journey—understand that you have to advocate for yourself and be willing to move when opportunities arise.

But try explaining that to someone who thinks a gold watch after thirty years is the ultimate career achievement.

3. Insisting that “face-to-face” is always better than digital communication

My mom will literally drive across town to have a five-minute conversation that could have been a text message.

Don’t get me wrong—I value in-person connection. But there’s this absolute refusal to acknowledge that sometimes digital communication is not only more efficient, it’s actually more considerate.

My parents act like sending an email or text is somehow impersonal or rude. They’ll call at the worst possible times instead of sending a quick message I could respond to when convenient. They’ll insist on scheduling face-to-face meetings for things that could be handled in two minutes over the phone.

I’ve tried explaining that different situations call for different communication methods. Sometimes a quick text to confirm dinner plans is perfect. Sometimes a video call works better than driving an hour for coffee.

But they’re stuck in this mindset that anything less than sitting across from each other is somehow lazy or disrespectful.

It’s exhausting, and frankly, it makes them less accessible, not more.

4. Hoarding physical items “just in case” they might need them someday

Walk into my parents’ garage and you’ll find twenty years’ worth of “useful” stuff that hasn’t been touched once.

Old computers that stopped working in 2005. Boxes of cables for devices that don’t exist anymore. Magazines from the 90s because “there might be something important in there.” Don’t even get me started on the closet full of clothes they haven’t worn since I was in high school.

When I suggest donating or throwing things away, I get the same response every time: “But what if we need it someday?”

Here’s the thing—they never need it. Ever. That broken printer they’ve been storing for five years? Still broken. Those VHS tapes of movies they can now stream online? Still collecting dust.

I’ve embraced minimalism in my own life, and the freedom that comes with owning less is incredible. But they look at me like I’m crazy when I tell them I donated a perfectly good jacket I hadn’t worn in two years.

They’re drowning in stuff they don’t use, yet they can’t let go of any of it.

5. Thinking that working longer hours automatically equals better results

This one hits close to home because I used to fall into this trap too.

My parents genuinely believe that if you’re not suffering a little bit—staying late, working weekends, sacrificing personal time—then you’re not working hard enough. They wear exhaustion like a badge of honor.

I’ve watched my dad stay at the office until 7 PM not because he had urgent work, but because leaving earlier somehow felt wrong. My mom will brag about not taking all her vacation days as if that makes her a better employee.

When I tell them about productivity techniques I’ve learned, or how I sometimes get more done in four focused hours than they do in eight distracted ones, they look skeptical. The idea that working smarter beats working harder just doesn’t compute.

I’ve talked about this before, but embracing efficiency and setting boundaries actually made me more successful, not less. Yet they still think my generation is lazy because we value work-life balance.

It’s like they’re stuck in this work ethic mindset that equates hours with value, regardless of actual output.

6. Refusing to adapt their communication style to different generations

My parents talk to my 25-year-old cousin the same way they talk to their 70-year-old neighbors, then wonder why the conversation falls flat.

They’ll use outdated references that nobody under 40 understands. They’ll explain technology in ways that show they fundamentally don’t get it. They’ll make assumptions about what younger people want or think without actually asking.

But here’s what really gets me—when the conversation doesn’t flow naturally, they blame the other person for being rude or disinterested.

I’ve watched them interact with my friends, employees at stores, or service workers, and there’s this invisible wall that goes up. It’s not malicious, but they’re completely unwilling to meet people where they are communicatively.

When I adjust how I explain things based on who I’m talking to, or use references that resonate with different age groups, they act like I’m being fake. But that’s not fake—that’s emotional intelligence.

Learning to communicate effectively across generations isn’t selling out. It’s a skill.

7. Believing that asking for help is a sign of weakness

This might be the most frustrating one of all.

My parents would rather spend three hours struggling with something than admit they don’t know how to do it. Whether it’s assembling furniture, figuring out a new app, or even asking for directions when they’re lost.

I’ve offered to help with everything from setting up their streaming service to organizing their finances. The response is always the same: “We can figure it out ourselves.” Spoiler alert—they usually can’t, or it takes ten times longer than it should.

There’s this deeply ingrained belief that needing help means you’re incompetent or weak. But in my entrepreneurial journey, I’ve learned that the most successful people are the ones who aren’t afraid to ask questions, hire experts, or admit when they’re out of their depth.

They see asking for help as admitting defeat. I see it as being resourceful and smart with my time.

It’s like they’d rather suffer in silence than risk looking like they don’t have all the answers.

Final words

Here’s what I want to be clear about—this isn’t really about my parents being wrong and me being right.

It’s about how hard it can be to watch people you love get stuck in patterns that seem to make their lives more difficult than they need to be. These habits worked for them in a different world, during a different time, and I genuinely respect that.

But the world has changed. The way we work, communicate, and live has evolved dramatically, and some of these old approaches just don’t serve anyone anymore.

I’m not writing this to bash boomers or claim my generation has it all figured out. Trust me, we have our own blind spots and outdated thinking that the next generation will probably roll their eyes at.

What I am saying is that staying curious, being willing to adapt, and recognizing when old habits are holding you back—those are timeless qualities that serve people well regardless of when they were born.

Maybe the real lesson here isn’t about generational differences at all. Maybe it’s about staying open to growth and change, no matter what stage of life you’re in.

Because if there’s one thing I’ve learned from studying human behavior and psychology, it’s that we’re all works in progress—parents, kids, and everyone in between.