9 careers Boomers pushed their kids into that are now completely obsolete or underpaid

Remember those career fairs in high school? I do. My parents dragged me to every single one, pointing enthusiastically at booths for accounting firms, law schools, and banks. "These are stable careers," they'd say. "You'll always have work."

Fast forward to today, and I'm watching friends from my economics program struggle with careers that barely pay the bills or, worse, don't even exist anymore. After spending nearly 20 years as a financial analyst myself, I've seen firsthand how the "safe" career paths our Boomer parents championed have crumbled.

The world changed. Technology exploded. And many of those "guaranteed" careers? They're either automated, outsourced, or paying wages that haven't kept up with the cost of living.

Let's talk about the careers that Boomers swore would set us up for life, but instead left many of us scrambling to pivot in our thirties and forties.

1. Travel agent

"People will always need help booking vacations!" I can still hear my friend's mom saying this back in 1995. She ran a successful travel agency and was convinced her daughter should follow in her footsteps.

Today? Most travel agents have been replaced by Expedia, Kayak, and a dozen other booking sites. Sure, luxury travel advisors still exist, but the neighborhood travel agency where you'd book your family trip to Disney? Gone.

Travel agent employment dropped approximately 70% between 2000 and 2021, according to the Bureau of Labor Statistics. The median salary sits around $48,450, and while the BLS projects modest 2% growth from 2024 to 2034, it's significantly slower than the average for all occupations. Not exactly the thriving career it once was.

2. Bank teller

Banking was supposed to be recession-proof, right? My college roommate's dad worked at a bank for 40 years and retired with a full pension. He pushed all three of his kids into banking.

But ATMs, online banking, and mobile apps have decimated teller positions. When I worked in finance, I watched entire branches close as customers shifted to digital banking.

Employment of tellers has declined nearly 30% since 2010, and the BLS projects a 13% decline from 2024 to 2034. Today's bank tellers earn a median of $39,340 annually, barely above minimum wage in many cities. And those positions that remain? They're increasingly part-time with no benefits.

3. Print journalist

"Get into newspapers," they said. "It's a noble profession with job security."

The newspaper industry has been devastated. Newsroom employment fell 26% from 2008 to 2020, dropping from about 114,000 jobs to approximately 85,000. Even more dramatic: newspaper newsroom employment alone plummeted 57% between 2008 and 2020, from roughly 71,000 jobs to about 31,000.

Local papers have shuttered across the country, and even major publications struggle to stay afloat. A journalist friend of mine started at $28,000 a year after getting her master's degree. She's now freelancing and barely scraping by, competing with content mills that pay pennies per word.

4. Middle management

Here's one that hits close to home. During my finance days, I watched layer after layer of middle management get eliminated. Companies realized they could flatten their organizational structures and save millions.

The data is stark: research by Gartner predicts that by 2024, robo-bosses will replace almost 69% of the manager's workload, and in a global survey by Pega, 78% of executives believe AI and robots will dramatically reduce middle management ranks.

Those comfortable middle management positions with corner offices and company cars? They've been replaced by "team leads" who do twice the work for half the recognition.

A 2025 Gusto report analyzing 8,500 small businesses found that the ratio of individual contributors to a single manager has nearly doubled in five years, with managers now juggling twice as many employees as they did five years ago.

5. Data entry clerk

My neighbor's son was pushed into data entry in the early 2000s. "Computers are the future," his parents said. "Learn to type fast and you'll always have work."

Automation killed this career faster than you can say "optical character recognition." Middle-skill jobs, which include data entry, declined from 58% of U.S. employment in 1981 to 44% in 2011, primarily due to automation.

Software now does in seconds what used to take humans hours. The positions that still exist pay minimum wage and are often shipped overseas. It's become the definition of a dead-end job.

6. Retail store manager

Running a retail store used to mean a solid middle-class income, benefits, and respect in the community. Boomers saw it as entrepreneurship without the risk.

Today's retail managers? They're working 60-hour weeks for around $40,000 a year, dealing with skeleton crews and impossible sales targets.

With stores closing left and right thanks to Amazon and online shopping, even these underpaid positions are disappearing. A former colleague left finance to manage a clothing store, thinking it would be less stressful. She lasted six months.

7. Toll booth operator

Okay, this one might seem obvious now, but I knew several people whose parents thought toll booth jobs were golden tickets. Government job, benefits, pension, sitting in a booth all day? What could go wrong?

E-ZPass and automated toll systems answered that question. In Northern California, the California Department of Transportation laid off roughly 250 Bay Area toll workers permanently as it transitioned to digital toll collection.

These jobs have virtually vanished, and the workers who held them often struggled to transition to new careers. It's a perfect example of how quickly technology can make an entire profession obsolete.

8. Paralegal

"If you can't be a lawyer, be a paralegal!" How many of us heard that one?

While paralegals still exist, the profession has been squeezed from both sides. Law firms now use AI for document review and legal research that used to take paralegals hours.

Meanwhile, the field has become oversaturated with graduates from paralegal programs that promised easy job placement. The median salary has stagnated around $52,000 while the cost of living has soared.

9. Traditional accountant

This one hurts because it was my backup plan. Accounting was supposed to be bulletproof. Death and taxes, right?

But tax software like TurboTax and QuickBooks have eliminated the need for basic accounting services. Small businesses that once hired accountants now do their books with apps. Even in larger firms, automation has reduced the need for entry-level accountants.

The positions that remain require constant upskilling and certifications just to stay relevant. Starting salaries haven't budged much in 20 years while everything else has gotten more expensive.

Final thoughts

Looking back at my own journey, leaving that "stable" finance job at 37 was terrifying. But staying in a career that no longer served me would have been worse. The irony? My parents still introduce me as "my daughter who worked in finance" rather than "my daughter the writer," as if my old career somehow carries more weight.

The truth is, our Boomer parents gave us the best advice they had based on their experience. They couldn't have predicted how technology would reshape everything or how the gig economy would replace traditional employment for millions.

So what do we do with this information? First, stop feeling guilty if you've pivoted away from the career path your parents envisioned. Second, embrace continuous learning because no career is truly safe anymore. And finally, maybe think twice before pushing the next generation into any "guaranteed" career path.

By 2030, 30% of current U.S. jobs could be fully automated, while 60% will see significant task-level changes due to AI integration. The world is changing too fast for guarantees. Sometimes the riskiest thing you can do is play it safe.