Let’s be honest for a second.

Even though we like to think of ourselves as adaptable, open-minded Boomers who’ve seen it all, there are still certain things that make us squirm a little.

We’ve lived through recessions, dial-up internet, and shoulder pads, for crying out loud.

We’ve adjusted to smartphones, social media, and even streaming TV without commercials.

But deep down, there are moments when our middle-class roots and those unspoken social codes we grew up with still poke through.

I’m talking about the little everyday things that younger generations breeze through, but that still leave us with a faint sense of unease.

You’ll probably recognize a few of these.

Let’s dive in.

1) Talking openly about money

Growing up middle-class in the 1960s and 1970s, money was a private matter.

You didn’t ask someone what they earned, and you certainly didn’t tell anyone what you paid for your car or house.

These days, people share their salaries online, negotiate raises out loud, and even discuss financial “transparency” in workplaces.

And while that’s healthy in many ways, I’ll admit it still makes my palms a little sweaty.

When I first retired and joined a local writing group, one of the younger members casually mentioned how much he made freelancing.

I remember thinking, Wow, that’s bold.

It wasn’t judgment, it was discomfort.

My upbringing wired me to think that talking about money was almost impolite.

Old habits die hard.

2) Not dressing “properly” for certain situations

You can take the man out of the office, but you can’t quite take the “dress appropriately” mindset out of him.

I still can’t bring myself to wear shorts on a plane or a hoodie to a nice restaurant.

My grandkids tease me for “overdressing,” but I grew up believing that appearance showed respect for yourself and for others.

I remember my father polishing his shoes every Sunday evening for work the next day.

That ritual stuck with me.

Even now, if I’m heading to a doctor’s appointment or a coffee with a friend, I’ll tuck in my shirt without even thinking.

It’s not vanity. It’s comfort in tradition.

But in a world that now values comfort over formality, we can feel a little out of place.

3) Asking for help (especially with technology)

Here’s one that really humbles us.

For most of our working lives, we were the ones teaching others.

We trained new hires, mentored juniors, and explained how to fix the printer jam.

But now we’re the ones saying, “Can you show me how to get this app on my phone?”

Even though my kids are patient, there’s still a sting of pride when I have to ask.

I suspect it’s not about the technology itself, but about how independence used to define success.

In our generation, competence was everything.

If you didn’t know how to do something, you figured it out quietly.

Admitting confusion publicly, especially about something as “basic” as an iPad, still feels like losing ground.

But here’s the funny part.

When I finally let go of that pride, I actually learned faster.

Maybe discomfort really is the first step toward growth.

4) Splurging on ourselves

Middle-class Boomers were raised with an internal voice that says, Do you really need that?

Even now, with grown kids and a bit of savings, I hesitate to buy something just for me.

A new gadget? “Too expensive.” Dinner at a nice restaurant? “Let’s just cook at home.”

That frugality got us through the mortgage years and college tuition, but it can also rob us of joy in later life.

I recently read a book called Your Money or Your Life, an old classic written back when budgeting meant a checkbook ledger, and it reminded me that money is only useful when it aligns with what makes life meaningful.

So yes, I finally booked that weekend trip by the coast.

Did I overthink it for days? Absolutely.

Did I enjoy every minute once I got there? You bet I did.

Sometimes it’s okay to be a little irresponsible with your own happiness.

5) Public displays of emotion

This one runs deep.

Our parents came from a generation that didn’t talk much about feelings.

You worked hard, kept your chin up, and didn’t make a scene.

Emotions were something to manage quietly, not express publicly.

But today’s world is built on openness. People post about their anxiety, hug freely, and say “I love you” outside of family gatherings.

Wonderful, right?

And yet, many of us still freeze up when someone tears up mid-conversation or tells us they’re proud of us.

I remember when a close friend of mine gave me a long, emotional thank-you speech at his retirement dinner.

My instinct was to wave it off with a joke.

I wasn’t used to sitting in that kind of vulnerability.

It’s not that we don’t feel deeply, we do.

We were just taught to keep the lid on tight.

These days, I’m learning to let it loosen a bit.

6) Using first names with authority figures

This might seem small, but it says a lot about how we were raised.

When I grew up, you called teachers “Mr.” or “Mrs.,” and even into adulthood, you addressed your boss as “Sir” or “Ma’am.”

Now, everyone from CEOs to doctors says, “Please, call me Dave.”

Even after decades in the workforce, I still hesitate.

There’s a voice in my head saying, That’s disrespectful!

I once slipped and called my doctor “Doctor Reynolds” even after he’d insisted, several times, on “just Jim.”

He laughed, of course, but I couldn’t bring myself to do it.

For us, titles were about respect and boundaries.

These days, the lines are more relaxed, but the conditioning remains.

Old-school politeness might be outdated, but it still feels right in my bones.

7) Being on the receiving end of generosity

It’s strange how hard it can be to accept kindness.

When a neighbor insists on helping me carry groceries or a friend refuses to let me pay for lunch, my first instinct is to argue. “No, no, I’ve got it.”

That’s the middle-class Boomer way: don’t owe anyone, don’t impose, don’t be a burden.

But there’s humility and even connection in accepting help gracefully.

A while back, my granddaughter baked me a small cake after I’d had a rough week.

My gut reaction was to say, “You shouldn’t have gone to the trouble.”

Thankfully, I caught myself and simply said, “Thank you.”

The smile on her face reminded me that generosity isn’t about money.

It’s about letting people show love in their way.

If there’s one lesson I keep relearning in retirement, it’s that sometimes giving others the joy of helping us is its own act of generosity.

8) Talking openly about aging and mortality

Now here’s the big one.

For many Boomers, getting older is something we acknowledge jokingly, not seriously.

We’ll laugh about “senior moments” or thinning hair, but deep, honest talk about mortality?

That’s still a tough one.

Maybe it’s because we were the “forever young” generation.

Rock and roll, rebellion, idealism—we were defined by youth.

So now, as our bodies slow and our friends start facing health issues, we struggle to reconcile that identity.

Even discussing wills or end-of-life wishes can feel taboo, as if saying it out loud might tempt fate.

But avoiding the subject doesn’t make it go away.

A few years ago, I lost an old friend, someone I’d known since my twenties.

After the funeral, his daughter told me how grateful she was that he’d planned everything down to the music.

“He made it easier for us,” she said.

That conversation stuck with me.

Talking about aging and death doesn’t diminish life.

It deepens it. It makes the present more precious.

A final thought

We Boomers pride ourselves on resilience.

We’ve adapted to more social and technological change than any generation before us. But that doesn’t mean old discomforts disappear completely.

The truth is, many of these feelings about money, manners, and vulnerability aren’t weaknesses.

They’re remnants of a value system built on modesty, self-reliance, and respect.

The trick is knowing when those values serve us and when they hold us back.

So the next time you feel a little uneasy in a world that’s changing faster than ever, don’t scold yourself.

Smile, take a breath, and maybe ask, Is this discomfort trying to teach me something?

Because more often than not, it is.