7 times working-class boomers mean well but come off judgmental without realizing it

Ever notice how the people who love us most can sometimes make us feel the smallest without even trying?

Last weekend, I was at a family barbecue when my uncle cornered me near the potato salad. "Still doing that writing thing?" he asked, eyebrows raised. "You know, your cousin just got promoted to regional manager. Real stability there." He meant well, genuinely concerned about my wellbeing, but his words stung in that familiar way.

If you grew up in a working-class boomer household like I did, you probably know exactly what I mean. These are the folks who worked their fingers to the bone, valued a steady paycheck above all else, and genuinely believe they're helping when they share their "wisdom." My mother still introduces me as "my daughter who worked in finance" rather than "my daughter the writer," even though I left that career path years ago.

The thing is, they really do mean well. But sometimes their well-meaning advice and comments can feel like judgment, leaving us feeling misunderstood or even inadequate. Here are seven times this happens, and why understanding the pattern can help us respond with compassion rather than frustration.

1. When they question your career choices

"But you had such a good job!"

Sound familiar? Working-class boomers often equate success with traditional employment: benefits, pension, the whole nine yards. When I made the difficult decision to leave a six-figure salary at 37 to pursue writing full-time, you'd think I'd announced I was joining the circus.

They're not trying to crush your dreams. For many of them, a stable job was the difference between putting food on the table and going hungry. They learned that security meant survival, and when they see you taking risks, their protective instincts kick in. What sounds like criticism is often fear dressed up as concern.

The problem? Their comments can make you second-guess yourself, especially when you're already navigating uncertainty. You start wondering if maybe they're right, if you're being foolish or irresponsible.

2. How they talk about money and spending

"Must be nice to afford organic vegetables."

"Forty dollars for running shoes? Mine cost twelve at Walmart."

These comments aren't really about your shopping habits. Growing up, many boomers watched every penny because they had to. When they see younger generations spending money on things they consider luxuries, like gym memberships or quality coffee, they can't help but comment.

I learned that my parents expressed love through concern about financial security. Every question about my spending was their way of trying to protect me from the financial struggles they faced. But it often came across as judgment about my choices and values, especially when I chose to prioritize things like healthy food or experiences over saving every possible dollar.

3. Their views on education and its value

Here's a fun contradiction: they pushed us to go to college because "education is the key to success," but then question why we're still paying off student loans or why our degree didn't guarantee us a corner office.

"In my day, you could work your way through college with a summer job."

Yeah, well, in your day, college cost about the same as a used car, not a small house. I took on significant student loan debt that took me until age 35 to pay off. When older relatives made comments about how I should have "been smarter" about it, they genuinely didn't understand how the economics had changed.

They see our struggles with student debt and underemployment as personal failures rather than systemic issues, not because they're cruel, but because their frame of reference is completely different.

4. Comments about relationship and family timing

"When I was your age, I already had three kids and a mortgage."

"You're not getting any younger, you know."

"Who's going to take care of you when you're old?"

These gems usually come out at holiday gatherings, birthdays, or any time you dare to show up somewhere alone. Working-class boomers often married young, had kids young, and built their entire identity around family structures. When they see us delaying or opting out of these milestones, they genuinely worry we're missing out on what gave their lives meaning.

What they don't realize is how their comments can feel like pressure or judgment about deeply personal choices. They're projecting their own fears about loneliness or regret onto us, wrapped in what they think is helpful advice.

5. Their take on mental health and self-care

"Therapy? We just dealt with our problems."

"Self-care? That's just being selfish."

"Depression? Have you tried going for a walk?"

For a generation that lived through actual hardship, the concept of prioritizing mental health can seem indulgent. They pushed through, sucked it up, and got on with it because that's what you did. When they minimize mental health struggles, they're not trying to be dismissive. They literally don't have the framework to understand it differently.

But when you're genuinely struggling and hear these responses, it feels like they're saying your problems aren't real or valid. Their bootstrap mentality, while it served them in their context, can feel incredibly isolating when you need support, not a pep talk about toughening up.

6. Assumptions about technology and modern work

"Working from home isn't real work."

"You're always on that computer."

"In my day, work meant getting your hands dirty."

Try explaining to someone who worked in a factory for forty years that you're exhausted from back-to-back Zoom meetings, and watch their eyes glaze over. They associate work with physical labor, commutes, and time clocks. When they see us working from our couches in pajama bottoms, they can't quite square it with their definition of "real work."

Their comments about our work habits or career paths often stem from genuinely not understanding how the economy has shifted. When they question whether what we do is "real work," it's not meant to diminish our efforts, but it sure can feel that way.

7. Lifestyle choices and generational values

"Veganism is just a phase."

"Why do you rent when you could buy?"

"You'll understand when you're older."

That last one might be the most frustrating. It dismisses our choices as immature rather than different. Whether it's choosing not to eat meat, deciding to rent instead of buy, or prioritizing experiences over possessions, working-class boomers often see these as rebellious phases rather than legitimate lifestyle choices.

They came from a world where there was one path to success and happiness: steady job, marriage, house, kids, retirement. When we deviate from that script, they interpret it as confusion or rebellion rather than conscious choice.

Moving forward with compassion

Here's what I've learned after years of navigating these interactions and finally confronting my parents' disappointment to realize I couldn't live for their approval: they're scared for us. Every comment that feels like judgment usually comes from a place of love filtered through fear.

Understanding this doesn't make the comments less frustrating, but it does help us respond with more grace. They're operating from their own experiences and traumas, just as we are. The world they prepared us for no longer exists, and that's not their fault.

The next time your working-class boomer relative makes a comment that stings, try to hear the fear behind it. Set boundaries when you need to, but remember they're usually just trying to protect you the only way they know how. Their judgment isn't really about you. It's about a changing world they don't quite recognize anymore, and their deep desire to see you safe and secure in it.