How Content Can Land You a Job: From Layoff to WorkOS with Michael Chan

In this episode of Guidance Counselor 2.0, host Taylor Desseyn spoke with Michael Chan, a developer educator at WorkOS who exemplifies how authentic content creation can transform a career setback into new opportunities. Michael's journey from unexpected layoff to landing his ideal role demonstrates the power of storytelling, vulnerability, and strategic content creation in today's job market.

The Human Reality of Getting Laid Off

Michael's story begins with a jarring reality check that many professionals face but rarely discuss openly. In January, he was laid off from his role at Chromatic, where he had been creating Storybook content. Despite feeling good about his work and seeing positive sentiment shifts in the community, the layoff came as a shock.

"It sucks," Michael said bluntly about the experience. "I work for money. I would just be a nerd writing docs for myself if that wasn't the case." This honest admission cuts through the typical career advice narrative that suggests layoffs are simply opportunities in disguise.

The emotional impact was significant, even for someone with an established audience and financial runway. "There's this shame in it, too, that you're feeling. Shame around getting laid off of like, 'oh, I guess I couldn't hack it or whatever,'" he explained. This shame often prevents people from creating content precisely when it could be most valuable.

Michael's experience highlights an important truth: having a successful podcast (React Podcast) and established audience doesn't eliminate the human emotions that come with job loss. The difference lies in how you process and channel those emotions.

Content as a Trust-Building Machine

Rather than retreating during this difficult period, Michael chose to document his job search journey through a YouTube series. This decision wasn't driven by a calculated content strategy, but by his natural curiosity and desire to help others navigate similar situations.

"Content is a machine for building trust with people," he explained. "You're creating a space where you're having an honest conversation about what it looks like to find work and continue to market yourself as a professional."

This perspective reframes content creation from self-promotion to service. Instead of trying to convince people he was qualified, Michael focused on sharing his authentic experience and lessons learned. This approach resonated with both his audience and potential employers.

Michael Greenwich, CEO of WorkOS, specifically cited this authenticity when explaining why they hired Michael: "Trust is the most important thing when building a brand, building a company, making content. You are a person that people trust because you open up and you talk honestly about a thing."

The Strategic Value of Public Applications

One of the most innovative aspects of Michael's job search was making his applications public. He created detailed videos for companies like Netflix, explaining why he thought he'd be a good fit and demonstrating his thought process.

For Netflix, he made a video identifying a specific team and explaining his qualifications. While he ultimately determined the role wasn't a good fit, the application video generated significant attention and led to interviews. "I would not have gotten that interview if I did not make a video for them," he noted.

This approach works because it demonstrates several valuable qualities simultaneously:

• Initiative: Going beyond traditional application methods

• Communication Skills: Articulating complex ideas clearly

• Production Quality: Showing actual work output rather than just describing it

• Confidence: Being willing to put yourself out there publicly

The key insight is that most opportunities remain unexplored not because they're impossible, but because people aren't willing to stand out. "It's so easy to get attention just by being willing to stand out," Michael observed. "Everything hasn't already been done."

Video Production as Developer Skill

A particularly valuable aspect of Michael's story is how video production skills enhanced his technical career rather than replacing it. Despite being hired as a developer educator, he estimates his current role is "90% editing."

This trend reflects broader changes in how companies approach developer marketing. Traditional marketing approaches are failing, and companies increasingly need people who can combine technical expertise with content creation skills.

"There are way more companies that need people who can tell stories about what they've built than there are people who can do that," Michael explained. For developers struggling to find traditional engineering roles, this represents a significant opportunity.

The combination is particularly powerful because technical people understand the complexity and nuances of what they're explaining. They can create content that resonates with other developers while being accessible to non-technical stakeholders.

The Entrepreneurial Developer Mindset

Throughout the conversation, Michael emphasized the importance of thinking entrepreneurially regardless of your role. This doesn't mean starting a company, but rather understanding market trends and adapting your skills accordingly.

"The people who have the best sustained careers are the people who think like entrepreneurs, no matter what field you're in," he noted. This requires looking beyond narrow technical specialization to understand how your skills connect to business value.

For developers, this often means developing communication and storytelling abilities alongside technical skills. "If you can't sell some feature that you built, there's no way you're going to be able to sit in an interview and sell yourself," Michael pointed out.

The Power of Self-Awareness

One of the most impressive aspects of Michael's job search was his willingness to turn down opportunities that weren't good fits. When Netflix's role turned out to require rapid execution rather than the thoughtful, architectural approach he preferred, he told them it wasn't a match.

"I have slow twitch muscles when it comes to development, not fast twitch," he explained. This self-awareness allowed him to focus on opportunities that aligned with his strengths rather than trying to force fit into roles that would be frustrating for everyone involved.

This level of confidence requires both experience and financial stability, but it demonstrates the value of understanding your own work style and preferences. The ability to articulate what you're good at (and what you're not) becomes increasingly valuable as you advance in your career.

Content Creation for Career Development

For professionals considering content creation as a career strategy, Michael's experience offers several practical insights:

Start with Curiosity: The best content comes from genuine interest in learning and sharing knowledge. Michael's love of writing guides and documentation reflects his natural inclination to help others understand complex topics.

Embrace Vulnerability: Authentic content requires being honest about challenges and failures. Michael's layoff series worked because he didn't pretend everything was fine.

Focus on Service: Rather than promoting yourself, focus on helping others. Trust and opportunities follow naturally from genuine value creation.

Build Consistently: Michael had been creating content through his podcast and other projects long before his layoff. This foundation made it possible to leverage content creation during his job search.

Document Learning: Even if you're not an expert, sharing what you're learning provides value to others at similar stages.

The Future of Developer Careers

Michael's story reflects broader trends in how technical careers are evolving. As markets become more competitive and traditional marketing approaches lose effectiveness, the ability to communicate and create content becomes increasingly valuable.

"As markets collapse, everything ends in individuals," he observed. This means professionals need to develop personal brands and direct relationships rather than relying solely on company credentials or technical skills.

The combination of technical expertise and communication ability creates unique value that's difficult to replicate. Companies need people who can bridge the gap between complex technical concepts and business stakeholders or customer audiences.

Storytelling as Universal Skill

Perhaps the most important takeaway from Michael's experience is the universal value of storytelling ability. "Find a way to figure out how to tell stories throughout your whole career - it's everything," he advised.

This applies far beyond content creation:

• Interviews: Articulating your experience and qualifications

• Performance Reviews: Communicating your contributions and impact

• Team Collaboration: Explaining technical decisions and trade-offs

• Career Advancement: Making the case for promotions and raises

"Nobody gives a care about the thing that you're doing," Michael noted bluntly. "Everyone's trying to survive and figure out their own stuff. So you have to figure out how to tell a story that helps other people."

Practical Steps for Getting Started

For professionals inspired by Michael's approach but unsure where to begin, the conversation offers several actionable strategies:

Leverage Existing Platforms: You don't need sophisticated video production to start. Michael emphasized that authenticity matters more than polish.

Document Your Process: Share what you're learning, building, or solving. The learning process itself provides value to others.

Connect with Community: Use content creation as an excuse to network and build relationships with peers and industry leaders.

Focus on Teaching: Even as a beginner, you can help others who are earlier in their journey.

Be Consistent: Regular creation builds trust and audience over time, even if individual pieces don't get much attention initially.

Conclusion

Michael Chan's journey from layoff to WorkOS demonstrates that content creation is more than a marketing tactic - it's a career development strategy that builds trust, demonstrates skills, and creates opportunities that traditional job search methods miss.

His success came not from having the most followers or the most polished content, but from being authentic, helpful, and consistently showing up. By treating his job search as a learning opportunity and sharing that journey with others, he created value for his audience while demonstrating his capabilities to potential employers.

Most importantly, his story shows that career setbacks don't have to be purely negative experiences. With the right mindset and approach, challenging periods can become catalysts for growth, new connections, and better opportunities.

For professionals navigating their own career transitions, Michael's example provides both inspiration and practical guidance. The key is starting where you are, being authentic about your journey, and focusing on helping others rather than promoting yourself. The opportunities will follow naturally from genuine value creation and relationship building.

This blog post summarizes insights from Guidance Counselor 2.0, a live streaming show hosted by Taylor Desseyn that explores career development in the tech industry. Find more episodes here: Guidance Counselor 2.0