Tech hires fast and churns faster. After 30-plus years in tech PR, I made a change, recently becoming a rookie high school teacher at age 55. It was the career upgrade I needed (I hope), and it’s giving me a front-row seat to the one skill this rising generation has that I’m still learning: radical self-trust.
It’s late July, and I’m sitting in a training session with and for high school teachers and instructional coaches and I am stress sweating like a champ. I have the least amount of classroom experience and yet I’m the only greybeard in the room. Nobody here knows or cares what I’ve built over the past thirty years. Nobody knows the campaigns, the clients, the career. My journey as I built a PR agency, tore it down, and built it again. To the teachers in this training, I’m a beginner, a new teacher.
And I can’t help thinking about how, in tech, invisibility has a way of creeping up on you. You get older. Fewer people know your name. Sometimes it feels like you’re slowly aging out of the room.
But then another thought hits me.
My bio got me in the door, but it won’t teach this class. I’m here to learn what comes next. As a beginner, a new guy, I don’t own the room like other, more experienced teachers do. This is the best kind of invisibility: defined by what’s ahead of me, not what’s behind.
Bad invisibility. Good invisibility. They can show up in the same room, on the same day, and feel almost nothing alike.
The assignment was simple enough: teach a ten-minute lesson to the rest of the room. Standing up there, I realized I wasn’t even sure I had ten minutes of material. I fumbled. I sweated. But I watched the teachers who went before and after me: how they held a room, how they recovered when something didn’t land, how generously they coached each other through it. I was a foreign body, though, dropped into a world that runs on techniques and craft I hadn’t yet learned. And somewhere in that discomfort, watching people who do this so well, the good invisibility stopped being a nice idea and started being real.
None of this was part of my plan two weeks ago. In mid July, I mentioned to an old friend that I’d thought about teaching someday. Three days later, after an intense interview process, I received an offer to teach Financial Literacy and Entrepreneurship at DSST: College View High School. I had already earned my CTE certification from the state of Colorado, but I thought it would be a year or two longer before I used it. A few days after my interview, I was talking to my business partner about him taking over our agency, and now I was sitting in teacher training wondering if I’d completely lost my mind.
The decision to join DSST (founded as the Denver School of Science and Technology) Public Schools feels right. The mission is clear: through a STEM-focused curriculum, eliminate educational inequity while preparing every student for college and the 21st century. I’ve already seen the seriousness behind that mission in training, teachers coaching each other through a rough lesson, offering feedback without ego, trading what’s worked for them over years in the classroom. The network now serves more than 7,500 students through 16 schools across Denver and Aurora. Every graduating senior leaves with a plan: a trade, community college, military service, CU Boulder, Harvard, anything in between. This year, more than 900 seniors walked across the stage at the celebratory Senior Signing Day.
I hope I can bring something real to the classroom: years of business experience, a network of people willing to talk to a room full of teenagers about what work actually looks like, and a real respect for the tested curriculum DSST’s teachers have already built and refined. But I’m afraid, too. Afraid of not being enough. Every veteran teacher I’ve talked to has told me the same thing: don’t quit in year one. Year one is a challenge for everyone. That fear and that hope live in the same place, and I don’t think one cancels the other out.
In technology, I was often hired in days and expected to prove my value in weeks. Clients could walk with 30 days’ notice. Teaching hired me just as fast, but then told me the opposite: it might take three years to become exceptional at this, and that’s fine. Expected, even. Business hires fast and judges faster (CMOs in tech average just 1.8 years in the role). Teaching is giving me patience along with an expectation of growth.
Spending time around Gen Z kids energizes me. In a world of relentlessly negative news and shifting opportunities, they often possess a quiet, solid confidence. This year’s Deloitte Global Gen Z and Millennial Survey backs that up: more than half of Gen Zs say the cost of living and housing affordability are actively reshaping their career choices, yet 53% still expect their own financial situation to improve within the next year. They may not trust the systems around them, but they trust themselves. I’m beginning to really appreciate that.
Not long after my training in July, a room full of teenagers walked into my classroom. They are writing their own stories, discovering their own superpowers. Their languages, experiences, and ways of learning are strengths to build on. With or without me, these students are going to build the future. And I am here for it.
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