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  1. Blog
  2. Culture & Professionalism
  3. October 22, 2025

The Generational Career Gap: How to Talk to Your Parents About Your Career & Job Search

A guide on constructive, forward-thinking conversations

family sitting at a table eating
Photo courtesy of Markus Winkler

Gone are the days where you could walk into an office, hand your resume to the hiring manager, and wait for a call back for an interview. The job market today looks and feels entirely different. That’s why the majority of women in our audience (71 percent) say their workforce experience differs from that of their parents. 

When we asked them to describe those differences, their responses painted a clear picture of a generational divide:

“They stayed in one job for most of their career, and they made enough money to support a family/buy a house/etc.”

“The hiring process is more competitive and time-intensive now. Additionally, loyalty is no longer rewarded in the same way as it was in my parent's generation.”

“They apply the logic of 40 years ago to present conditions.”

“They don't understand today's job market and how difficult it is to get a job.”

“They still picture you sitting at a desk with a typewriter.”

Many women find themselves receiving well-intentioned but outdated career advice, rooted in workplace norms of the past. That advice can feel limiting, or even discouraging, when navigating an uncertain and competitive job market. 

Here’s a guide on how to have constructive, forward-thinking conversations with your parents about career paths, job searching, and modern work realities. Explore more outdated career advice our audience thinks should disappear here

Read more: Scared of Making the Wrong Choice? These 4 Steps Will Safeguard Your Job Search

How have careers and job-searching tactics evolved over time?

The workplace your parents entered looked very different from the one most women navigate today. For many of them, the path was clear-cut: you chose a company, stayed for decades, and climbed the ladder through loyalty and tenure. Raises, promotions, and retirement benefits often came automatically with time served.

That model has largely disappeared. Job hopping every few years to build new skills, pursue flexibility, and find better pay is the new norm. Instead of being rewarded for longevity, workers are often rewarded for adaptability and transferable skills. “Change is good,” one survey respondent wrote in, “Their career advice always told us risk-taking was career suicide. These days, starting a business, trying something new, working for a startup, moving to gain new skills and tech know-how is how you survive.”

Plus, remote and hybrid work have replaced the traditional office for many roles, and digital tools have made it possible to collaborate more easily across time zones. This change means success isn’t always measured by how many hours you clock in, but more so by the impact of your work.

Another change that’s come with that shift: more boundaries between work and life. “I think there's [been] a tendency to give off the impression at work that you're open and willing to work on anything and everything your manager asks for,” another respondent said. “I think it should always be encouraged that to be a professional is to be able to define expectations from your manager to you and from you to your manager. It's ok to say you can't do it all.”

Parents’ advice—“stay loyal to your company,” “be seen in the office,” “follow the ladder”—comes from a time when stability and visibility were cornerstones of career growth. Those values have merit, but the systems that once rewarded them have evolved. Recognizing these differences is the first step to having constructive, empathetic conversations that actually help you move forward.

Read more: How to Feel More Confident & Secure in Your Job While Working Remotely

How to frame your non-linear or nontraditional career path your parents

Your career might not follow a predictable path. Maybe you’ve switched industries, taken on side projects, or explored freelance work as a way to skill-build, boost income, and dabble in more passions.  

When talking about this kind of career path with your parents, focus on growth and purpose rather than the number of jobs you’ve held. For example, you might say:

“I moved from marketing to product management because I wanted to expand my skills in strategy and analytics. These experiences are helping me reach my long-term goal of leading a team.” 

Framing your journey through the lens of goals shows that each step is intentional and strategic, not haphazard. 

You can also draw parallels to what your parents know: 

“You learned a mix of tasks in your first role that built your expertise over time. My career growth works similarly, just in a different structure.” 

Using concrete examples of projects, skills, and accomplishments makes your choices more tangible and relatable.

When chatting with your parents, acknowledge that your path may look unconventional to them, but that doesn’t make it less valid. Non-linear careers are the norm today, and learning to articulate your trajectory clearly helps your parents to better understand and support your decisions.

Here’s some example language to use when explaining a non-linear career path:

  • “I know it looks different that I’ve moved between roles, but each step is helping me build skills for my long-term goals.”

  • “These days, people often switch jobs or industries to gain experience, similar to how you learned a mix of skills early in your career.”

  • “I’m focusing on personal and professional growth and impact rather than just titles or tenure. Projects and skills matter more nowadays than staying at one company forever.”

How to frame your job search to your parents

When talking about job searching, it’s important to explain that today’s search relies heavily on networking, online applications, and even personal branding. Most roles are found through connections. Informational interviews, LinkedIn outreach, and mentorship often open doors before an application is ever submitted.

Framing the process strategically rather than as a simple checklist can help parents understand your approach. For example, you might say:

“I’m focusing on building connections with people in my field and sharing my work online, in addition to applying for positions. It’s a different approach than you might have used, but it works well in today’s market.” 

Here’s some example language to use:

  • “Most opportunities today come from networking and connections, not just sending a resume. That’s why I’m spending time building relationships in my field.”

  • “Employers now look at portfolios and online profiles in addition to resumes, so I’m making sure my skills and projects are visible.”

  • “I’m approaching my job search strategically, targeting roles, networking, and building my online presence. It’s different from what you might have done, but it works well today.”

You can also normalize some of the challenges of the current market. Ghosting is common, but rejection doesn’t reflect your abilities. 

You might explain it to your parents like this: 

“Even if a job seems perfect, it might take multiple applications before I hear back. This is normal today.” 

At the end of the day, most parents want to see their kids happy, stable, and successful. They just might define those things differently. If you approach these conversations with context and patience, you can help your parents see how work has evolved and why your choices make sense. Your perspective might even change the way they think about their career, too.

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