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Northwestern Talk:
In November, I had the chance to speak at Northwestern’s School of Engineering and Entrepreneurship. I shared my journey at a high level - the non-linear path, the pattern recognition, and how years of watching teams under pressure ultimately clarified what I’m building now.
What surprised me most was how quickly the conversation gravitated to psychological safety - not as a “nice-to-have,” but as a practical requirement for performance.
One student described it as being able to “share any ideas or difficult concerns… without feeling like” you’ll get punished for it. Another added a version of the real test: whether you can fail, ask, try, and not get crushed for it.
That’s the heart of it, and it matches what I’ve repeatedly witnessed in executive leadership environments: under pressure, people start withholding. Then you get “meetings before meetings,” “meetings after meetings,” and the endless spiral of “what did they mean by that?” When I’ve asked people across industries how much time gets burned by this per week, the spontaneous answer I kept hearing was: about 10 hours.
We also talked about the art of it - how to speak up and still read the room. One student asked how you balance being visible and advancing your career, versus staying quiet and not making waves. My honest answer: it comes down to the fluid nature of observation and regulation, your ability to scan an environment clearly without your physiology hijacking your judgment. That’s not just mindset. It’s body + context + practice.
This is where Google’s research becomes useful. In their work on team effectiveness (Project Aristotle), Google found that psychological safety was a key differentiator of high-performing teams - less about who’s on the team, more about whether people feel safe taking interpersonal risks.
I’m grateful to Professor Jen Baker for the invitation and the chance to have such an engaged, thoughtful conversation at Northwestern.
A note from the coast
I recently spent a few weeks back in San Diego, near the ocean—close to where I grew up and spent most of my life.
What stayed with me wasn’t nostalgia as much as sensation. The warmth of the sun, tempered by a steady breeze. The rhythmic sound of waves—present, but not demanding. Over time, my body seemed to synchronize with the environment. My nervous system settled into a steady state without effort or instruction.
What struck me was how unearned that steadiness felt. I wasn’t trying to regulate myself. The conditions simply made it easier.
That contrast sharpened when I thought about Chicago—city life, momentum, stimulation, pressure. These places are often framed as opposites, but living in both reminded me that neither is better. They simply bring out different qualities: clarity in one place, edge in another. Calm here. Drive there.
You can’t really understand either without experiencing its polarity opposite.
While I was there, I happened to reopen The Obstacle Is the Way and landed on Theodore Roosevelt’s reflections on nerve control - not as suppression, but as self-mastery. Real strength, he argued, isn’t the absence of stress, but the ability to remain steady and deliberate within it.
That landed differently this time.
Reading it while experiencing what a supported nervous system actually feels like made the contrast hard to ignore. The steadiness I felt wasn’t discipline or virtue—it was an outcome. A byproduct of an environment that reduced friction rather than constantly adding it.
It clarified something that’s become central to my work.
Most people aren’t failing at self-regulation. They’re operating inside systems that continually tax it. We ask for composure, presence, and good judgment-while navigating conditions that quietly undermine all three.
That kind of steadiness doesn’t come from motivation. It comes from awareness: noticing what’s happening in the body and responding without judgment.
This is the feeling I want Contextual North to convey-not calm as a command, not correction, but situational awareness, offered in the moments people need it most.
One last pic from a street with so many memories growing up
Product update
Early conceptual design of the CN Watch experience.
This week, while testing an updated build of the app, I had one of those moments that made me pause.
We all carry a lot- inputs, expectations, unfinished thoughts. Our minds are wired for pattern recognition, which is incredibly useful… until it isn’t. The same neural pathways repeat because they’re familiar, not because they’re healthy. Over time, those loops can turn into default narratives-quiet heuristics we fall into when attention is low and dopamine-driven distractions are high.
That’s often when our best intentions slip. Not dramatically - just subtly enough that we show up a little less present than we’d like.
As I was testing the app, my mind drifted into a familiar loop: Am I good enough? I’m not a “real” tech founder. I’ve never done this before. It wasn’t loud or panicked-just that steady, well-worn groove.
And then my watch nudged me.
Not as an instruction. Not as a correction. Just a signal.
In that split second, I noticed what was happening-in my body, not just my head. And that pause gave me a choice: continue the story I’ve told myself before, or write a different one that’s more aligned with where I actually want to go.
That’s when it clicked for me.
It worked - not by forcing a positive thought, but by creating awareness at the exact moment the pattern was taking hold. I was able to course-correct toward something more productive, more honest, and more intentional.
That’s the experience we’re testing for.
Not motivation. Not affirmation. Just timely awareness that helps people bring more of themselves into the moments that matter.
We’re now preparing to begin alpha testing with a small group of people who are willing to use the app in real-world conditions and share thoughtful feedback. From there, we’ll expand access more broadly as we learn and refine.
If this resonates and you’re curious to help shape what this becomes, just reply to this email and I’ll reach out to you. No commitment, just a conversation.
Early access will be limited and rolled out gradually.
If you’re curious about the neuroscience behind automatic thought patterns and heuristics, Daniel Kahneman’s work on “fast thinking” provides a clear foundation:
Thanks for taking the time to read and follow along. I’m moving carefully and intentionally with this work, and I appreciate the thoughtfulness and curiosity of those who’ve chosen to stay connected.
More soon.
-Jesse
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