Obstacles Different Generations Face in Their Job Search

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The struggle is real when it comes to landing a job — no matter if you’re a product of Generation Z or you belong to the baby boomer generation. And unfortunately, some of that struggle comes from widespread misconceptions that each generation can’t seem to shake.

“What every generation has in common is the obstacle of combatting stereotypes since it’s in our nature to want to put labels on things to help make sense of them,” said Lisa Downs, president of New Aspect Coaching.

Read: The Best Money Experts for Each Generation

But not all of the obstacles different generations face as they seek jobs are due to the perpetuation of stereotypes. Some of them are due to valid concerns within each generation. Either way, here’s a breakdown — from baby boomers to Generation Zers — of the obstacles faced in their job searches. See if any of these ring true for you, and find out how to overcome them.

Baby Boomers

Born: 1946-1964

Obstacle 1: Difficulty in Locking Down New Career Opportunities

Nadia Ibrahim-Taney, owner of Beyond Discovery Coaching, believes that employers are less apt to consider boomers for traditional job roles. “The boomer generation is increasingly finding challenge in exploring their ‘second act’ or a career pivot,” Ibrahim-Taney said. “Since boomers have been working in a particular field or industry the longest in the job market, many employers want to tap them as more of an advisor or content expert in the space they know best — their past experience. But many boomers are ready for something new, something different than what they have been doing for 25 years.”

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See: Surprising Ways Gen X and Boomers Are Worlds Apart Financially

Ibrahim-Taney offers this advice to overcome this obstacle: “I would advise boomers leverage the transferable skill set they developed in one industry and practice effectively articulating how this skill set is transferrable to the future industry or role they wish to go into,” she said. “How do you learn, how do you face the challenge of the unknown? And how can you bring a beginner’s mindset and energy to a new role or industry?”

Obstacle 2: Overcoming the Perception That They Are Short-Term Employees

It’s understandable that employers look at baby boomers and have their doubts that the members of this generation are going to stick around for a while. After all, in 2021, the youngest baby boomers are 57 and the oldest are 75.

Lynn Berger, a career counselor and coach, offered this advice to overcome this obstacle: “A baby boomer needs to exude enthusiasm and interest in growing/advancing in the position.”

Discover: How Each Generation Has Been Affected Financially By the Pandemic

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Additionally, it can’t hurt to explain why you are interested in working longer than you originally planned to before retiring, such as if you were furloughed, laid off, suffered a pay cut or had your work hours reduced during the pandemic.

Generation X

Born: 1965-1980

Obstacle 1: The Possibility of Being Overlooked

“Gen Xers are frequently overlooked in contemporary workplaces and face unique struggles in their job searches as a result,” said George Santos, director of talent delivery and head of marketing for 180 Engineering. “They are often underrepresented in discussions and, as backed by findings published in the Harvard Business Review, overlooked for promotions. They are likely to have worked in jobs without much career progression, which can hurt their chances of landing higher positions in their future job searches.”

More: What Gen X Can Learn From Boomers’ Money Mistakes

To avoid being overlooked, aim to stand out, both on paper and in person. Actions like tailoring your resume and asking unique questions during the interview can help you break free from your status as a career wallflower.

Obstacle 2: Juggling External Pressures

“People born in this generation face significant challenges as a consequence of being the middle child in American culture,” said Santos. “Tasked with looking after their parents and raising their children, Gen X candidates may not have the financial or personal resources available to change career paths or develop extracurricular experience. This can especially prove consequential when workplaces search for candidates with practical knowledge in emerging fields that Gen X candidates have not had an opportunity to get involved with.”

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Read: The Top Money Moves To Make for Each Generation

If taking care of your children and your parents is making it difficult for you to pursue any additional training that could help you land a better-paying job or act as a catalyst for changing your career path, ask for help. Look to your spouse, your relatives or your friends to take over for a little while so you can focus on getting ahead.


Born: 1981-1996

Obstacle 1: Career Interruptions

“Millennials have (…) had their careers interrupted by multiple economic recessions, first in 2008, then again due to COVID,” said Jon Hill, chairman and CEO of The Energists. “This meant many started their career later than they wanted to or were forced to work in jobs outside their specialty because of these difficulties, putting them behind where they ‘should be’ in terms of career progress.”

See: Boomers vs. Millennials: A Look at the Financial Gap Between Generations

Hill acknowledged that you can’t magically create career progress you haven’t made, but also had this advice if you lack progress in your career: “The best thing you can do is target your search to companies that are owned and run by sympathetic and likeminded individuals who will understand these struggles rather than holding them against you,” he said.

Obstacle 2: A Pattern of Job Hopping

While you may consider job-hopping a stereotypical label for millennials, the reasons why millennials are known for their restlessness may surprise you. Millennials do job-hop, but generally not because they feel entitled. According to Gallup, it’s because they are “uninspired, unmotivated and emotionally disconnected from their workplace.”

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Find Out: The Best Expert Money Advice for Millennials

To keep job-hopping from ruining your resume — and your chances to get hired — Daniel Hale, director of Pulse Recruitment, had this advice:

“The solution is always to pad your resume with enough information to overcome any such objections,” said Hale. “In the case of millennials, it’s essential to state why you left each role and, in the summary, why are you looking for a long-term position now. Your resume is your voice, so you need to make sure you use this voice to explain why you fit the role that you are applying for in a way that overcomes any perceived weaknesses in your application.”

Generation Z

Born: 1997-2012

Obstacle 1: Facing a Lack of Entry-Level Jobs

“Gen Z is also bearing a large brunt of the COVID impact on their shoulders,” said Pablo Listingart, career expert and founder of ComIT. “Traditionally, this is the time in which Gen Z workers would be introduced to the industry through entry-level jobs. But entry-level positions were some of the first to be shed in the pandemic-related job loss, and for many organizations, they’ll be some of the last-positioned to be recovered. This will prove challenging for early-stage professionals, who might see increased competition for beginner roles or miss out on the industry experience that they’re expected to have at this point.”

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More: A Look at Gen Z’s Financial Habits, From Spending to Saving and More

Listingart offered this advice to help overcome this obstacle:

“Luckily, every Gen Z is in the same boat, and having been through it all together, recruitment professionals should understand any COVID-era gap in employment,” he said. “To make the most of this strange market moment, Gen Z professionals should look for other ways to earn experience. Affordable (or free) training programs, shadowing opportunities, mentorship relationships or extended internships; all of these are valuable ways to avoid losing any time as the job economy regains stability.”

Obstacle 2: Overcoming the Perception That They Lack Social Skills

Another obstacle Generation Z faces, according to Downs, is the stereotype that they have no social skills due to an addiction to technology. Social skills are also soft skills and include things like effective communication, empathy, active listening and conflict resolution. As a Generation Zer, the best way to combat an employer’s preconceived notion about lack of social skills is to show them otherwise. Some suggestions are to incorporate those relevant buzzwords into your resume and then dazzle your interviewers with your stellar soft skills when you meet.

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