The other day, I was having coffee with my old neighbor Bob when he started venting about his thirty-something son. “He’s got a perfectly good job,” Bob said, shaking his head, “but he’s talking about switching careers again. And don’t get me started on the sharing. I know more about his therapy sessions than I ever wanted to.”

I couldn’t help but chuckle. After raising three kids of my own, Sarah, Michael, and Emma, and now watching my grandchildren grow up, I’ve witnessed firsthand how different generations see the world. And while I deeply love my millennial children, there are certain habits that make me, well, quietly roll my eyes from time to time.

Now, before anyone gets defensive, let me be clear: this isn’t about one generation being better than another. Research actually suggests that many perceived generational differences are more about life stage than anything inherently wrong with younger folks. But that doesn’t mean we older folks don’t occasionally scratch our heads at certain behaviors.

So, in the spirit of good-natured reflection, here are nine things millennials do that tend to make their boomer parents raise an eyebrow or two.

1) Treating job loyalty like an outdated concept

When I started my career in insurance, I expected to be there for the long haul. And I was, for 35 years. The idea of leaving a stable job just because it wasn’t “fulfilling enough” would have seemed almost reckless to folks in my generation.

But millennials see things differently. According to Gallup research, 21% of millennials changed jobs within a single year, more than three times the rate of older workers. They’re not necessarily disloyal; they’re searching for something that feels worthwhile. Half of millennials don’t strongly agree they’ll still be at their current company a year from now.

What’s interesting is that when you dig deeper, millennials actually want job security. Research shows nearly 90% would stay at a company for a decade if they knew they’d receive regular raises and growth opportunities. The issue isn’t commitment; it’s that they’re unwilling to stay somewhere that doesn’t invest in them.

Still, to a boomer who spent decades building a career at one company, all that job-hopping can look a bit like restlessness.

2) Prioritizing experiences over building wealth

Here’s one that really gets the older generation talking: millennials would rather spend money on a trip to Bali than save for a house deposit.

Research from Eventbrite found that 72% of millennials say they’d like to increase their spending on experiences rather than physical things. They’re collecting memories, not possessions. Travel, concerts, festivals, fancy brunches. These are the things that light them up.

Now, I understand the appeal. Some of my best memories involve experiences rather than stuff I’ve bought. But as someone who grew up watching my parents scrimp and save for their first home, it can be hard to watch younger folks prioritize a weekend getaway over their retirement fund.

That said, research from Georgetown University suggests experiential purchases do tend to provide more lasting happiness than material ones. So maybe they’re onto something. But try telling that to a boomer who worked double shifts to afford a mortgage.

3) Sharing every aspect of their lives online

If you’ve been on social media lately, you’ll know what I mean here.

Millennials document everything. What they ate for breakfast. Their relationship struggles. Their workout routines. Their mental health journeys. For those of us who grew up valuing privacy, this level of openness can feel, well, a bit much.

Research from Psychology Today highlights that this constant sharing can actually reduce a person’s control over their personal information, which has implications for stress and mental wellbeing. The ability to regulate what others know about us is, apparently, a strong moderator of stress.

I’ve mentioned this before, but there’s something to be said for keeping certain things close to the chest. Not everything needs to be broadcast to the world. But to millennials, sharing is connecting. It’s building community. It’s just a fundamentally different way of relating to others.

4) Being very public about therapy and mental health

Speaking of sharing, millennials have completely transformed how we talk about mental health. They discuss therapy the way my generation might discuss a doctor’s appointment for a bad knee.

According to survey data, more than half of millennials have gone to therapy or are currently attending sessions. And 83% of those in therapy openly tell others about it. Compare that to my generation, where admitting you saw a therapist might have raised eyebrows.

On one hand, this openness has done wonders for reducing stigma. Mental health matters, and getting help shouldn’t be shameful. But to many boomers, there’s a sense that some things should remain private. We dealt with our struggles quietly, often through sheer willpower or leaning on close family.

The millennial approach is different. They believe in talking it out, processing emotions openly, and normalizing the conversation. It’s admirable, really. It just takes some getting used to.

5) Questioning traditional life milestones

Get married by 25. Buy a house by 30. Have kids before 35. That was the roadmap for many in my generation.

Millennials have torn that roadmap to shreds.

According to research from the Urban Institute, the millennial homeownership rate is about 8 percentage points lower than previous generations at the same age. They’re getting married later. Having children later. Some are questioning whether they want these milestones at all.

Now, some of this is economic. Student debt, stagnant wages, and sky-high housing costs have made traditional paths harder to follow. But there’s also a values shift happening. Millennials aren’t just delayed; many are actively questioning whether the old milestones even define success.

A study from Stanford found that millennials actually want to achieve these goals at similar ages to previous generations. The difference is, they’re less likely to get there. For boomers who followed the traditional script, watching their kids forge completely different paths can be confusing.

6) Demanding work-life balance above all else

“Work hard now, enjoy life later.” That was the mantra for many in my generation. We put in the hours, climbed the ladder, and trusted that the rewards would come eventually.

Millennials flipped that script.

According to Deloitte’s global survey, work-life balance remains the top consideration when millennials choose employers. Only 6% say their primary career goal is reaching a leadership position. They want flexibility, meaning, and time for the things that matter outside of work.

I’ll admit, when my son turned down a promotion because it would have meant less time with his family, I didn’t fully understand. But watching my grandchildren now, I see the wisdom in it. Those Sunday pancake mornings and nature walks mean more than any corner office ever could.

Still, there’s part of me that wonders whether this generation might regret not pushing harder when they had the energy.

7) Expecting constant feedback and recognition

This one might ruffle some feathers, but it’s worth mentioning.

Millennials grew up receiving participation trophies and regular praise. As adults, they often expect the same level of feedback in the workplace.

Research suggests millennials want to feel valued and appreciated, not just compensated. They want regular check-ins, ongoing recognition, and to know their work matters. When that doesn’t happen, disengagement follows quickly.

For boomers who grew up expecting to put their heads down and work without fanfare, this can seem, well, a bit needy. My father worked double shifts at a factory and never expected anyone to tell him he was doing a good job. The paycheck was the feedback.

But times have changed. Millennials want to know they’re making a difference, and honestly, there’s something healthy about that expectation, even if it makes the rest of us roll our eyes occasionally.

8) Being skeptical about institutions and traditions

Whether it’s organized religion, traditional marriage, corporate loyalty, or even the diamond industry, millennials approach institutions with a healthy dose of skepticism.

Research shows millennials are less likely to identify with traditional religious institutions and more likely to question long-held customs. They ask “why” before accepting “that’s just how it’s done.”

Having spent 35 years navigating corporate culture, I understand both sides. Institutions aren’t perfect, and questioning them can lead to positive change. But there’s also wisdom embedded in traditions that shouldn’t be discarded too quickly.

The challenge is finding balance, honoring what works while being willing to evolve what doesn’t.

9) Blurring the lines between work and personal life

Finally, there’s the way millennials blend their professional and personal identities.

Unlike boomers who typically kept clear boundaries between office life and home life, millennials integrate everything. They check emails at 10 p.m. but also handle personal errands during work hours. They bring their whole selves to the office, expecting workplaces to accommodate their values, mental health needs, and life circumstances.

This integration isn’t necessarily bad. It offers flexibility and authenticity. But for those of us who learned to leave work at work and home at home, it can look a bit chaotic.

Final thoughts

Look, every generation has its quirks. Boomers were criticized by our parents for rock and roll, long hair, and questioning authority. Now we’re the ones raising eyebrows at the generation after us.

The truth is, millennials aren’t doing anything wrong. They’re just doing things differently. And maybe, just maybe, they’ve figured out some things we missed along the way.

So yes, we might quietly roll our eyes from time to time. But deep down, I think most of us are pretty proud of the thoughtful, values-driven adults our kids have become.

What habits of younger generations make you scratch your head?