8 work habits boomers have that make zero sense to younger generations

You’ve probably heard the jokes (or complaints) about “boomers” and their old-fashioned work habits.

But beyond the stereotypes, there really are certain behaviors, especially in professional settings, that feel totally bizarre to many of us in younger generations.

I’ve seen this firsthand in startups I ran in my twenties.

Sure, some traditions have stood the test of time for good reason—good manners and solid work ethic will always be valuable.

But there are practices that leave younger folks scratching their heads, wondering, “Why are we still doing this?”

Before we jump into it, I want to make it clear: this isn’t a knock on boomers personally.

A lot of these habits started in a different era of business, back when technology wasn’t what it is now, and remote work was basically science fiction.

Still, times change.

Let’s explore eight boomer-favored work habits that feel wildly outdated—and even frustrating—to many of us in younger generations.

1) They refuse to embrace remote work

For better or worse, remote work is here to stay.

Younger people often see it as the logical evolution of how we get things done—why endure a commute if your job can be done just as effectively from home or a shared workspace?

Many boomers, though, still hold the idea that “being at the office” is the only true way to work.

I remember talking with a friend who was forced to move back to the city because his boss insisted on physical presence.

Yet his work was fully digital, and he had been doing it seamlessly from another state for months.

Studies like the 2019 Gallup poll found that around 54% of employees would leave their current job for one that offers flexible work time.

That’s a stat many boomers might ignore, but younger professionals see it as a non-negotiable.

A few decades ago, remote work was nearly impossible.

Today, we have high-speed internet, Slack, Zoom, project management software—everything you need to collaborate effectively.

This is why Tim Ferriss famously said, “Focus on being productive instead of busy.” Younger generations have taken that to heart. If the job is getting done well, does it really matter where it’s done from?

2) They rely heavily on physical paperwork

“Print it out and file it.” It’s a sentence that still makes me cringe.

If I need to keep something, it’s going in the cloud, not a manila folder in a metal cabinet.

Yet I’ve noticed many older colleagues still find a certain comfort in paper trails.

In a world that’s racing toward digital solutions, younger employees tend to see piles of paperwork as both an environmental burden and a productivity killer.

Greg McKeown wrote, “If you don’t prioritize your life, someone else will.”

One of the best ways I’ve found to prioritize is to keep everything searchable and accessible in digital form.

Digging through physical files is just inefficient.

At Small Biz Technology, we often talk about the benefits of automation and cloud storage for entrepreneurs who want to streamline operations.

Still, some workplaces have managers who insist on real, printed forms. That might have been necessary years ago, but now it’s mostly just extra work—especially if you’re going to scan it later, anyway.

3) They hold onto rigid hierarchies

There’s something about older generations that makes them love titles, corner offices, and departmental silos.

Hierarchies served a purpose in old corporate structures, but many younger professionals prefer flatter organizations where everyone feels comfortable sharing ideas.

If you’ve worked in a creative startup environment, you know what I’m talking about.

Titles matter less than who has the best idea.

Younger generations often value making a difference over climbing the corporate ladder.

Rigid hierarchies can block that sense of collaboration and contribution. There’s more hunger among younger workers for open communication and feedback, not just top-down directives.

4) They equate time at the desk with productivity

You come into the office at 7 A.M. and leave at 7 P.M. That means you’re a star employee, right?

Not necessarily.

Younger generations usually measure success by output or results, not the number of hours spent warming a chair.

I’ve mentioned this before but it bears repeating: looking busy isn’t the same as getting real work done.

James Clear famously wrote, “We don’t rise to the level of our goals; we fall to the level of our systems.”

Younger pros tend to optimize their systems—focused bursts of work, flexible schedules, and the intelligent use of technology to automate tasks.

Boomers often come from a culture where face time in the office was the gold standard.

But if you can do the same work in five hours that others do in ten, shouldn’t you be encouraged to go home instead of sitting around for show?

5) They stick to formal dress codes

Do ties and suits really make sense for every job? Some boomer-era workplaces think so.

It used to be that a suit signaled respectability, authority, and competence.

Now, in many fields—especially tech or creative industries—a suit can appear out of place or even stifling.

Younger generations often equate competence with skill, not with how starched your collar is.

Jordan Peterson has said, “If you fulfill your obligations every day you don’t need to worry about the future.” I interpret that as focusing on what matters: your responsibilities and results, not whether you’re wearing the “right” outfit.

Obviously, some industries like finance or law still keep dress codes for client-facing reasons.

But if your job is to code or design from your couch, wearing sweatpants shouldn’t be shocking. Younger workers tend to value comfort and authenticity over stuffy traditions that don’t add any real value.

6) They prefer phone calls and voicemails

There’s nothing quite like that moment when you see a voicemail notification and think, “Couldn’t this have been a text?”

For many boomers, the phone call is still the go-to. It’s personal, immediate, and in their eyes, more professional.

But younger generations—who grew up with texting, instant messaging, and Slack—often find phone calls intrusive and time-consuming for quick updates or questions.

It’s not that younger people hate talking; we just prefer asynchronous communication for routine stuff.

This way, we can respond when we have the bandwidth. It’s more efficient.

As workplace technology advanced, written communication became faster, simpler, and more convenient. Voicemails, on the other hand, feel like relics of a time when we had no alternative.

7) They want loyalty to one company

Work a decade (or two, or three) for the same employer, get that gold watch, retire.

That was the dream for many boomers, and back in the day, it sometimes worked out great.

But times changed.

Younger employees typically job-hop in search of better pay, a more meaningful role, or simply to explore new industries.

Loyalty for loyalty’s sake makes little sense if career progression stalls or the role becomes stale.

“As you might know,” older bosses often say, “job-hopping looks bad on a résumé.”

But that perspective doesn’t carry the same weight it once did.

Employers now expect that younger employees will have shorter stints at companies.

The workforce is more dynamic, startups rise and fall quickly, and technology evolves at breakneck speed. The idea of staying in one place for half your working life might seem stifling. It’s not about disloyalty; it’s about adaptability and growth.

8) They insist on in-person meetings for small issues

Ah, the dreaded “We need to talk—let’s schedule a meeting.” You walk in and realize it’s something that could have been resolved with a quick Slack message.

Granted, sometimes face-to-face is important—sensitive topics, brainstorming sessions, forging deeper connections.

But many younger folks see the endless string of in-person meetings as a colossal time drain.

We live in an era of Zoom, chat apps, and collaborative docs.

Quick decisions can be made asynchronously, no need for an hour-long sit-down.

It’s not about dismissing human interaction; it’s about using it wisely.

When you gather a bunch of people in a room, you’re essentially hitting pause on everyone’s productive flow. If the meeting is important and strategic, that’s great. But if it’s to discuss something trivial, it can feel pointless and inefficient.

Wrapping things up

Those are eight boomer-driven habits that, in all honesty, make zero sense to younger professionals.

The workplace is evolving, and while some traditions are worth preserving, others are better left in the past. I’m not saying boomers are clueless—far from it.

They bring a wealth of experience and wisdom.

But as technology advances and workforce values shift, clinging to outdated practices can hurt morale and productivity.

Some of these habits might be rooted in nostalgia or the notion of “that’s just how it’s always been done.”

Younger generations, though, have grown up in a very different world—rapid innovation, greater emphasis on work-life balance, and a preference for agile, flexible work environments.

And that’s okay.

Each generation has something valuable to bring to the table.