Show Notes

In this episode, I talk with Stephen Guerriero, a former 6th-grade social studies teacher who, after 20 years in the classroom, built a new "mini portfolio" career. Stephen’s entry into teaching was "accidental," but his passion for ancient history and his students kept him there for two decades. When he finally decided to explore new paths, he used his voice and expertise to build an authentic presence online.

Stephen shares how his current edtech role as Chief Learning Officer for Litmus Learn found him—all because of his authentic activity on LinkedIn. We talk about the unique fears veteran teachers face when considering a change, why you should never hire someone to write your resume, and why you must stop saying "I'm just a teacher."

• The 20-Year Accidental Teacher: Stephen shares his "accidental road" into teaching, a job he fell in love with and promised to keep only as long as it was fun (which turned out to be over 20 years!).
• Getting Found on LinkedIn: How did he land an edtech leadership role with a company in India? They found him on LinkedIn. He explains why the platform is a "powerful tool" for teachers when you're "earnest" and authentic.
• Building a "Mini Portfolio": Instead of jumping from one linear job to another, Stephen "built a mini portfolio of things," combining his work as a Chief Learning Officer with his passion for ancient Greece at a nonprofit.
• The Veteran Teacher's Fear: Stephen speaks to the "very scary" feeling of leaving a 20-year career—walking away from the top of the salary scale, a pension, and a well-established reputation.
• Write Your Own Resume: His number one piece of advice: do not hire a resume writer. He explains why the process of reflecting and writing it yourself is the most valuable part of a transition.

Episode Article

After more than 20 years in the classroom, my guest Stephen Guerriero had built an incredible career. His path to teaching was "accidental," a detour he took while waiting for a job in the Foreign Service. He fell in love with the work and spent 16 years as a 6th-grade social studies teacher, geeking out about ancient history—a personal passion he'd even pursued with archaeological digs in Greece and Italy. He always told himself he’d stay as long as it was fun, and for two decades, it was.

But like many veteran educators, the pandemic era made him rethink his path. He got involved in education policy, which "opened his mind to this education world outside of the classroom". Instead of a single leap, Stephen "built a mini portfolio of things". Today, he’s the Educational Director for a nonprofit that takes teachers to Greece and the Chief Learning Officer for Litmus Learn, an edtech startup in India.

The most fascinating part? Litmus Learn found him. The co-founders, who had no education background, saw his posts on LinkedIn and reached out. Stephen’s story is a testament to the power of using the platform authentically. He avoids the bland, ChatGPT-like "LinkedIn language" and instead uses it as a "professional portfolio"—a place to share his real voice, vulnerability, and unique perspective. "It feels a little bit like sending your thoughts out into the ether," he says, "but the more you put yourself... out there, the more people respond to that".

He is especially passionate about helping other veteran teachers navigate this transition, acknowledging the "very scary thing" it is to leave after 15 or 20 years. You're not just leaving a job; you're leaving a high salary, a pension, and an identity. His most practical advice is to write your own resume. "Don't hire someone to write it," he insists, "because it's not just about the product, it's about you looking back and reflecting on all the accomplishments... you need to be able to do that".

Ultimately, Stephen’s journey is a powerful reminder to never say, "I'm just a teacher". That phrase, he says, "is discounting all that expertise that so many other people don't have". As a teacher, your stock in trade is your communication ability, your skill in preparation, and your experience making "thousands of micro-decisions every day". By owning that expertise and sharing it authentically, you open yourself up to a world of new possibilities.