The Trojan Horse That Inspired Contextual North

The Trojan Horse That Inspired Contextual North

At one point in my career, I moved from an outward-facing role-focused on customers and partners-into a more internal, cross-functional seat inside a large organization.

In one of my first conversations with a senior leader, after we wrapped up the usual introductions, rapport building, and agenda topics, he held up a pen on his desk.

It was a Montblanc 2018 Writers Edition “Homage to Homer” design inspired by the Trojan Horse. (+$1,000 pen)

 He explained that he kept it as a reminder: inside organizations, things aren’t always what they appear. Motives can be misunderstood. Trust takes time. And systems-especially complex ones-can create dynamics that feel very different from the outside world.

I remember initially absorbing that moment as something personal, like I needed to prove I belonged or trustworthy.

But over time, and through deeper study of organizational behavior, I came to see it differently.

It wasn’t a warning about me.

It was a quiet truth about how humans navigate uncertainty, incentives, and perception inside modern workplaces.

That’s part of what led to Contextual North: building tools that help people stay grounded, emotionally clear, and psychologically safe-especially in the moments when the environment feels ambiguous.

Because most people don’t need another productivity app.

They need a steadier internal compass.

If you’ve ever felt this… Hit reply, I’d love to hear about it.

Over the past several weeks, we’ve been hard at work refining Contextual North -  improving the core experience, tightening the design, and continuing to build the features that make the app feel genuinely supportive in real time.

We’ve also begun a very small round of early external testing with a leader inside real world organization environments. The feedback from our first tester so far has been incredibly encouraging and insightful to the work needed to enhance the experience, and very soon we will expand access to a broader group of testers.

If we’ve spoken one-on-one over the past few months and you expressed interest in trying the app, expect me to reach out directly soon to get you set up.

And if you’d like to be part of the early testing group, simply reply to this email and let me know - I’ll add you to the list and make sure you’re included as we open things up further.

One more exciting milestone: we’ve submitted the Contextual North App to Apple for App Store review, and we’re expecting approval shortly. While we’ll continue refining the user experience before a full public launch, we’re getting closer to being live in the App Store.

Thank you again for all the support, encouragement, and curiosity along the way. This project has always been about building something of real value for people as they navigate through ever changing modern day workplace - tools that help us stay grounded, steady, and clear-minded inside environments that can sometimes feel ambiguous or hard to navigate.

If you have thoughts, questions, or stories of your own, I’d genuinely love to hear from you.

Just hit reply:

What would help you feel more grounded at work? Where do you wish you had a steadier internal compass?

We’re building this together.

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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