When AI Gets Personal:
Grief, Growth, and the Inner Trail

I’ve been building TrailGuide for the last three months while working a full-time job.

I’ve been thinking, designing, writing, mapping, questioning—early mornings, late nights, in stolen moments and long internal monologues. Not because I had endless time or resources, but because something about this felt urgent, necessary, and strangely… possible.

Two weeks ago, my dad died.

For this and other painful reasons, this has been a season of personal heartbreak, challenge, and stress that feels as though it’s shaped every hour of my life. The truth is: I’m walking through the most difficult season I’ve ever known—by any objective measure.

And I’ve been using AI this entire time.

Not as an escape. Not as a replacement for real presence. But as a tool that met me, strangely, in the fog. Sometimes to help me write when I couldn’t find the words. Sometimes to help me think when my thoughts felt scattered. Sometimes just to move something forward when I didn’t have the energy to start from zero.

At its best, it’s helped me reach toward something imaginative, strategic, useful. To make something. To keep building.

But that’s not the whole story.

Because this has also been one of the most connected seasons of my life.

The people around me—the ones who’ve listened, challenged, encouraged, and stayed close—have shaped how I’m thinking about all of this. About AI, about work, about calling. And what I’ve discovered is: the more I’ve engaged with this technology, the more I’ve wanted to share it. To ask questions about it. To bring it into relationship.

That’s how it has to be.

Because after everything—after all this—I’ve realized something important about this project:

It’s not just about how organizations use AI.
It’s about how people do.

Change is organizational.
AI is personal.

And that changes everything.

When I first created the Trail Map, it was designed to help organizations find their way through AI adoption. It offered structure—four key dimensions (Applications, People, Principles, and Strategy), each mapped across five stages of maturity. It was a tool for teams to reflect, assess, and grow together, without losing their values in the process.

But recently, I’ve been thinking:

What if individuals had their own trail?

Not a professional development rubric. Not a gamified skill tracker. But a way of being—a set of postures a person might hold as they navigate their own relationship with AI.

Because while organizations are the ones that change systems, individuals are the ones interacting with these tools. Prompting them. Responding to them. Deciding what to automate and what to hold sacred. And if the work of organizational transformation is communal, then the work of individual AI maturity is personal, ethical, and deeply human.

So here’s what I’m beginning to sketch: The Inner Trail.

It shares the same four dimensions as the original Trail Map—but instead of stages of advancement, it offers postures. Five postures per dimension. Ways of showing up, holding tension, and moving with integrity. Not sequential. Not hierarchical. Just real.

Let me give you a taste:

These aren’t stages to climb. They’re ways of being to notice. They can change day to day, moment to moment.

🧰 Applications → Practical Agency

• Curiosity: I allow myself to explore without shame.
• Discernment: I choose tools on purpose, not impulse.
• Iteration: I treat AI as a partner in process, not a vending machine.
• Ownership: I remain the author of what I create.
• Constraint-setting: I decide what not to automate, and why.

This isn’t about tech fluency—it’s about self-awareness in action. Knowing not just what you can do, but what you should do.

🫂 People → Relational Integrity

• Transparency: I share what I’m using and how it shapes my work.
• Relational awareness: I notice how AI shifts the dynamics of trust and presence.
• Empathic imagination: I consider who benefits, and who doesn’t.
• Generosity: I document and teach, not just hoard and scale.
• Boundaried presence: I stay human, even when it’s easier not to.

Because even when you’re prompting alone, you’re not actually alone. These tools ripple outward.

Each of the other dimensions—Principles (Ethics) and Strategy (Orientation)—has its own set of postures too. Things like Accountability, Justice-seeking, Reverence, Foresight, and Modeling.

None of them require a certification. Just a willingness to be present, curious, and honest.

This is not about mastering AI.
It’s about self-mastery.

And if the outer Trail Map helps organizations move forward together, then the Inner Trail is here to help individuals move forward with wholeness. So that how we use these tools actually matches who we want to be—inside our orgs, and outside of them.

I’ll be sharing more soon. But for now, maybe just sit with the question:

🧭 What posture are you holding today?

This work isn’t for everyone. And I’m okay with that.

If you’re here because you want to use AI to cut corners, replace your staff, or scale faster than your values can follow—you’re going to be disappointed.

If you’re looking for a plug-and-play content funnel, or a brand strategy that smooths over the hard stuff in service of performance—I’m not your person.

If you see AI as a tool to dominate your space rather than deepen your presence, I can’t help you.

Because this isn’t just a framework or a consultancy or a digital product.
It’s a stance.

And it’s built for people who feel the tension. Who want to do more, yes—but not at the cost of who they are or why they began.

This is for the comms director asking, “Can we use GPT without losing our voice?”
For the fundraiser wondering, “Will this help us reach people—or just reach quota?”
For the ED who stays up late quietly testing things before bringing it to the board.
For the community organizer who wants to move toward technology—but only if it moves with them.

It’s for people who are smart enough to know AI is powerful, and human enough to know that power isn’t the goal.

I’m building this for the curious. The discerning. The slightly wary but still open. For people who want tools that match their integrity. Who want to think out loud without being made to feel behind.

If that’s you, welcome.
You’re not late. You’re just on the inner trail now.

This project isn’t finished. Neither am I.

I’m still listening, still learning, still stumbling into the next right thing. But if anything in this letter rang true—if something opened up in you while reading—I hope you’ll keep walking with me.

In the coming weeks, I’ll be sharing more about the Inner Trail: reflection tools, ways to use the posture cards in your own work, and how they’ll shape upcoming cohorts and workshops. I’ll also be lifting up the stories of real people using AI in quiet, meaningful ways— like the comms lead who stopped burning out once she started prompting differently.

You’ll see more about the systems side of this work, too. Strategy. Fundraising. Organizational use cases. That thread is still strong.

But so is this one: the human, the present, the in-process.

Because even if AI is moving fast, we don’t have to.
We can go with care. Together.