"Pull yourself up by your bootstraps" and other cringey phrases boomers repeat like a broken record

Ever sat through a family dinner where your well-meaning relatives dish out advice that makes you want to crawl under the table?

You know the drill. "Just work harder and you'll get ahead!" or "Back in my day, we didn't complain about rent prices!"

Look, I love my parents dearly, and I've worked alongside some brilliant older colleagues who've taught me a ton. But there's this collection of phrases that seem to get passed down like vintage furniture – except nobody really wants them anymore.

The thing is, these sayings weren't always empty platitudes. They made sense in a different economic reality. But when you're facing student loans that could buy a house, healthcare costs that rival a luxury car payment, and a job market that demands a degree for entry-level positions, suddenly "pull yourself up by your bootstraps" feels less like motivation and more like a cruel joke.

Let's unpack some of these well-intentioned phrases and talk about why they miss the mark so spectacularly.

1. Pull yourself up by your bootstraps

This one's the granddaddy of them all, isn't it?

Here's the irony that always gets me: the phrase was originally meant to describe something impossible. You literally cannot pull yourself up by your own bootstraps – it's physically impossible. Yet somehow it morphed into this rallying cry for self-reliance.

My dad used to say this whenever I complained about anything career-related in my twenties. Sweet guy, but he landed his first real job when a handshake and showing up on time were basically your entire resume.

The numbers tell a different story today. The middle class' share of national income has plummeted—from 62% in 1970 to just 43% today. Is it that none of us are willing to pull up our bootstraps? I doubt it. 

2. Just buy a house instead of wasting money on rent

This gem usually comes right after you mention your monthly rent payment, followed by a dramatic gasp and some variation of "For that much, you could have a mortgage!"

Sure, Karen. Let me just dig into my spare $100,000 for a down payment.

I remember a former colleague telling me I was "throwing money away" on my apartment. When I explained that houses in my area started at half a million, he genuinely seemed shocked. He'd bought his place for what sounded like lunch money.

The reality check? Homes had a median value of $47,200 in 1980. Adjust that for inflation and compare it to today's market, and you'll see why this advice feels like being told to "just buy a unicorn."

The down payment alone on many homes today exceeds what entire houses used to cost. But sure, let me just stop buying avocado toast and I'll have that saved up in no time.

3. Get a job with good benefits and stay there for 30 years

Ah yes, the old "company loyalty will take care of you" speech. This usually comes with stories about gold watches and generous pensions that sound like fairy tales from a bygone era.

I've mentioned this before, but the disconnect here is staggering. These days, staying at one company for 30 years isn't loyalty – it's career suicide. Many companies don't even offer pensions anymore, and "good benefits" often means you only go slightly bankrupt if you get seriously ill.

The advice made sense when companies actually invested in their employees long-term. Now? You're more likely to get laid off via Slack message than receive a gold watch. Job hopping isn't disloyalty – it's economic survival.

4. Just walk in and ask to speak to the manager

This one makes me physically cringe every time I hear it. Usually delivered with the confidence of someone who got their last job during the Carter administration.

"Don't apply online," they'll say. "Show some initiative! March right in there and demand to speak to someone in charge!"

Right. Because nothing says "hire me" like ignoring a company's established application process and interrupting someone's workday unannounced.

I watched my mom try to give this advice to a barista once, suggesting she bypass the online application for a corporate position. The poor kid just stared at her like she'd suggested communicating via smoke signals.

Here's what actually happens when you "show initiative" this way: security gets called, or you get politely redirected to the website you were trying to avoid. Most hiring managers aren't even in the building during regular hours, and the ones who are definitely don't want surprise visits from random job seekers.

The whole approach screams "I don't understand how modern workplaces function."

5. Money doesn't buy happiness

This philosophical nugget usually drops right after you mention struggling with student loans, rent, or medical bills. As if your stress about making ends meet is just a character flaw that needs some folksy wisdom to fix.

I love how this one often comes from people who've never had to choose between groceries and gas money.

Don't get me wrong – there's research showing that beyond a certain point, more money doesn't dramatically increase happiness. But that "certain point" is usually described as having your basic needs covered plus some breathing room. You know, the stuff that actually costs money.

What they're really saying is "stop complaining about being poor," which is about as helpful as telling someone with a broken leg to "walk it off."

The bottom line

Look, I'm not trying to bash an entire generation here. My parents and their peers lived through their own challenges, and many of their core values – hard work, persistence, treating people with respect – are timeless.

But context matters. The economic landscape has shifted so dramatically that advice from 40 years ago can feel not just outdated, but insulting. When someone making minimum wage today has less purchasing power than their 1980 counterpart, "just work harder" isn't wisdom – it's tone-deaf.

The real issue isn't the people saying these things. It's that we're all navigating a world that changed faster than our advice could keep up.

Maybe instead of recycling phrases that made sense in a different era, we could start with "Tell me what you're dealing with" and actually listen to the answer. That's advice that works in any decade.