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How 'Failing Up' Actually Helps Your Reputation
Students & Youth

Why career education should include conversations about failure

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Career education often aims to equip students with the tools to succeed, such as resumes that shine, interview tips that impress and pathways that promise upward mobility. But in a world where uncertainty is the only constant, focusing exclusively on “success” does students a disservice. To truly prepare young people for the realities of work and life, career education must also include open, honest conversations about failure. 

A learning experience, not a life sentence  

For many students, especially those under pressure to “figure it all out” early, failure is a loaded word with a lot of fear attached to it. A failed exam, an unsuccessful job interview or dropping out of a program can feel like a permanent roadblock rather than a temporary detour. But failure is not the opposite of success; it’s often the foundation of it. By normalizing the idea that failure is a part of every career journey, educators can reduce the shame and anxiety students often feel when they fall short of expectations.  

Career paths are rarely linear  

Very few people follow a straight line from education to career to retirement. People change majors, shift industries, start over after layoffs or take detours to care for family. Yet in secondary school students are often taught by teachers, guidance counsellors and the career curriculum to just envision a singular, idealized path. Anything outside of that is seen as falling behind. Including stories of “failure” or redirection in career education helps students understand that change isn’t just possible; it’s common.  

Conversations about failure build resilience  

Resilience is the ability to bounce back from challenges and it’s one of the most valuable skills a person can develop. And yet, it’s rarely taught explicitly in school. When career educators talk openly about failure, they model how to handle disappointment, reassess goals and move forward with self-compassion. These are lessons that stick far beyond the classroom or a single career coaching session.  

Acknowledging systemic barriers  

Importantly, not all failure is individual. Sometimes, setbacks stem from inequitable systems like a professional denied a job due to ableism, a newcomer excluded from networking opportunities or a student unable to take on unpaid internships because they need to pay rent. Conversations about failure should also include an awareness of these systematic barriers. Career education should empower students to reflect critically on their experiences rather than blaming themselves for outcomes shaped by injustice, life setbacks and factors outside of our control.  

Supporting neurodivergent and non-traditional learners  

As a neurodivergent learner myself, I’ve experienced what it feels like to be out of step with systems that prioritize a narrow definition of success. Students who don’t thrive in traditional academic environments often carry labels like “unmotivated” or “disorganized” when, in fact, they may simply need different supports or have different ways of processing the world. Career education that embraces diverse paths and acknowledges struggle can help these students feel seen, capable and hopeful.  

What educators and career professionals can do 
  • Model vulnerability: Share your own career detours or moments of failure and what you learned  
  • Highlight non-linear success stories: Invite guest speakers who’ve changed paths, bounced back from setbacks or taken unconventional routes  
  • Encourage reflection not perfection: Ask students what they learned from mistakes or challenging experiences, rather than focusing only on achievements  
  • Create safe spaces: Ensure students feel supported in discussing challenges without fear of judgment or punishment  
  • Name the systems: Don’t shy away from discussing how racism, ableism, classism and other forms of exclusion affect career outcomes 

By including conversations about failure in career education, we foster resilience, authenticity and adaptability, which are traits that are far more valuable than any one job title. When students learn that failure is part of life’s journey, they’re better equipped to navigate the twists and turns that lie ahead with confidence, self-awareness and a belief that they can always begin again.  

Asritha is a marketing and communications professional passionate about education, writing, and career development. With experience creating impactful content and fostering community engagement, she is now pursuing her goal of attending teacher’s college to inspire and empower future learners.
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Asritha is a marketing and communications professional passionate about education, writing, and career development. With experience creating impactful content and fostering community engagement, she is now pursuing her goal of attending teacher’s college to inspire and empower future learners.
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