It's Nearly Impossible To Read The Label On The Jar You're Sitting In
Why EdTech leaders stay stuck despite smart teams and proven solutions—and how pattern recognition creates breakthrough.
As an EdTech leader, you're too close to see the patterns keeping you stuck. And it's nearly impossible to read the label of the jar you're in on your own—even with smart teams, proven solutions, and years of success behind you.

I’ve rowed uphill far too often that most of what I know for certain are lessons learned the hard way — failures that knocked the smirk clean off my face. This experience has taught me more than a decade of success ever did.
After several years of branding and UX work, I found myself trapped in a pattern I couldn't see. Clients would come to me asking for design work—a new logo, website redesign, marketing materials. I'd ask difficult questions: "What's the real problem we're going to solve? What about solving it today is important?" They'd get frustrated.
I felt stuck between two not so great choices: deliver what they asked for (and then defend the initial idea) or keep pushing back (and let ego get in the way). I thought this was a creative industry problem. I thought difficult clients were the issue.
Then I realized: I was the problem. I'd positioned myself as someone who would do whatever design work clients requested, even when I wasn't sure it would be beneficial. Meanwhile, clients were stuck in their own pattern—asking for tactical fixes to strategic problems, hoping for different outcomes.
We were both sitting in our respective jars, unable to see that the real problem wasn't the creative work. It was how we thought about the problems the creative work was supposed to solve.
Bridging the gap

This exact pattern blindness shows up everywhere in EdTech. EdTech faces a unique challenge to bridge the gap between not just building products but transforming how people learn and teach. The pressure to get this right while tiptoeing through traditional pressures makes it even harder to step outside your jar and see what's actually happening.
After working with EdTech leaders for several years, I see a few of the same patterns over and over again:
- You get in your own way: Smart, successful EdTech executives find themselves drowning in their own decision-making. You have options, experienced staff, and solid data—but every strategic choice feels overwhelming. What you can't see from inside your jar is how trying to make perfect decisions creates aimlessness and anxiety. You have to move in a direction, even if uncertain, and a good place to start is to work at the ONE thing that’s standing in your way right now.
- You're too smart for your own good: Your deep expertise in education becomes a liability in business growth. You understand learning theory, pedagogy, and student outcomes better than anyone—and you probably overcomplicate some aspects of your business. From inside your jar, sophisticated solutions feel more credible. Yet, you're frustrating yourself trying to work harder and faster rather than slowing down to eliminate what doesn't work while focusing more on what does.
- Everything to everyone...or no one: You're trying to satisfy students, teachers, administrators, parents, and investors all at once, hoping that casting the widest possible net will help you win. The very attempt to serve everyone prevents you from being essential to anyone. What you can't see from inside your jar is that trying to serve everyone prevents you from being essential to anyone. Choosing your audience requires courage, but it's where the most valuable insights often emerge.
a peek behind the curtain
The last thing you want is another consultant or advisor to analyze your business and tell you what you're doing wrong. You've probably sat through presentations or been handed a 50-page report where someone explains your problems back to you using your own data.
How did that feel? Even if they could be right, did you find yourself thinking, "I'm not sure they really understood what I'm actually dealing with."
Here's what I've learned: Whose advice are you more willing to take—mine or yours? Think back to a significant moment in your past where you felt completely stuck. Did you confide in someone? Did that person help you see something you couldn't see before or tell you what they think you should do?
I'm guessing that moment isn't significant because of someone else's brilliant advice. It's when you finally were able to see your own patterns clearly.
That's what pattern recognition work actually is—an outside perspective willing to listen carefully to help you read the label on the jar you're in and ask targeted questions to strip everything else away so you can see clearly. When you see the pattern yourself, you see what needs to happen and you have the conviction to act on it.
proven impact

"I feel like I need some kind of cheat sheet to finish...?", one participant said during testing. University of Oregon's research team had three years of development and sophisticated expertise—but teachers couldn't even create accounts. The breakthrough came when they painfully watched users struggle and finally saw what was invisible from inside their jar: they'd built for researchers, not teachers. That moment changed everything.

A cybersecurity company was caught in a contradiction—declining sales while customers requested new offerings. When they finally stepped outside their jar, what became visible wasn't a product problem—it was a workflow problem. Customers weren't asking for more features; they were signaling that current tools didn't fit how they actually worked. Revenue doubled in 36 months.

An EdTech founder was paralyzed. Every option felt both right and overwhelming. The pattern she couldn't see: she was optimizing for theoretical potential instead of readiness to act. When that became clear, the decision was obvious—and breakthrough followed naturally.
The pattern is always the same: when you can finally read the label on your own jar, what needs to happen becomes clear.